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  • The brief
  • Start here
  • Idea portfolio
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  • This week · 6
  • This quarter · 9
  • Big bets · 3
  • Wildcards · 3
  • How we can help
Generated Oct 18, 2026
  1. Programmable
  2. Playbooks
  3. Canopy Connect
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growth playbook · Oct 18, 2026

usecanopy.com (opens in a new tab)

Canopy Connect growth playbook

Diagnosis

Canopy Connect is moving up-market. Its new hires are two enterprise AEs, one for automotive software and one for real estate software, reporting to a Head of GTM, plus its first SDR team for insurance agencies and more carrier integration engineers.

That says the agency product is a base to sell from, and the growth bet is six-figure, multi-year platform deals in verticals where insurance has to be checked at the point of sale.

Canopy has strong proof (400 carriers, 10M policies, the Easterns results, deep agency and lending integrations), but the site has no real estate page, no comparison pages, no carrier pages and no security packet, and its proof numbers do not match from page to page. This playbook gives the AEs the pages, packets, pilots and target lists to start selling, and gives the SDRs a warmer list.

Growth Score

7/10

Biggest Opportunity

Become the insurance check inside the software dealers, landlords and lenders already use, starting with a real estate page, a fixed pilot and platform deals reached through the integrations Canopy already has.

Biggest Risk

Axle and MeasureOne are pitching the same verification to the same platforms, with Axle now in renters insurance, so slow enterprise cycles could let a rival become the default integration first.

01

Start here

The three moves to make first. Each one is written up in full below.

  1. 1

    Publish a real estate page before the Real Estate AE takes their first call

    List the four real estate workflows the page will cover and pick the proof point for each from existing pages.

    High impact First result in 2 weeks
  2. 2

    A security and procurement packet the enterprise AEs can send on day one

    Collect the last three security questionnaires Canopy answered and merge them into one master answer set.

    High impact First result in 1 month
  3. 3

    Turn the Easterns numbers into a business case calculator for dealer groups and auto platforms

    Build the spreadsheet with the Easterns inputs as the default values.

    High impact First result in 2 weeks

02

Your idea portfolio

21 ideas, grouped by when to run them. Open any idea for how to run it: the steps, who to approach, copy you can use, and how to measure it.

  • 8 ideas are marked Unexpected: plays you are unlikely to have tried.

    2 of these are things Programmable can build and run for you.

Every idea placed by the effort it takes against the impact it could have. Quick wins sit top left; select a number to open that idea. The filters below narrow the list by status, timing, category and what Programmable can build.

Effort vs impactEach number is an idea. Select one to open it.
Impact →
Quick wins · 4Big bets · 8Fill-ins · 5Reconsider · 4
Effort →

Showing 21 of 21 ideas

This week 6

Quick wins with a clear first action.

  • 01

    Canopy is hiring an enterprise AE just for real estate software, but the site has pages for mortgage, loan servicing, rental cars and dealerships and none for property managers or the software they run on. The first thing a proptech buyer does after a cold email is look for their own use case, and Axle has just launched renters insurance verification aimed at exactly that buyer.

    High impactLow effort First result in 2 weeks VP of Marketing

    First action

    List the four real estate workflows the page will cover and pick the proof point for each from existing pages.

    How to measure it

    Real estate demo requests

    Now
    –
    Target
    8 a month
    By
    90 days

    Steps

    1. 1

      Pick the workflows

      Renters insurance at move-in, ongoing monitoring, single-family rental, and closing or title.

      VP of Marketing 2 hours

    2. 2

      Reuse the proof

      Carrier coverage, speed and policies shared from the dealerships page, plus any real estate customer that will be named.

      VP of Marketing 2 hours

    3. 3

      Write the page

      Problem, how the link or API works, data fields that matter to a landlord, monitoring, security.

      VP of Marketing 1 day

    4. 4

      Build it in Webflow

      Clone the dealerships template so it ships this week.

      VP of Marketing 1 day

    5. 5

      Route the form

      A HubSpot form whose vertical field sends the lead to the Real Estate AE.

      Head of GTM 2 hours

    6. 6

      Add it to the navigation

      Under Solutions, next to Mortgage Lenders and Loan Servicing.

      VP of Marketing 30 minutes

    7. 7

      Hand it to sales

      A two-line description and the URL for the AE's outbound sequences.

      Real Estate SaaS Enterprise AE 30 minutes

    First result
    2 weeks
    Cost
    $0
    Owner
    VP of Marketing

    Smallest test

    Publish the page with a single workflow (renters insurance at move-in) and send it in ten outbound emails.

    Why it works

    A solution page for real estate platforms: renters insurance verification at move-in, continuous monitoring with lapse alerts, the landlord named as interested party, homeowners coverage for single-family rental and closing workflows, by API or a branded link. It uses the same layout as the dealerships page, with the proof Canopy already has (400 carriers, 5.6 seconds, 10M policies) and a demo form that goes straight to the Real Estate AE.

    An enterprise AE with a quota needs somewhere to send people. The page also makes Canopy show up in the comparison a proptech product manager makes once Axle and MeasureOne both claim renters insurance.

    Risks and how to handle them

    • No real estate logo to show yet

      Lead with carrier coverage and speed; add a named customer as soon as one agrees.

    • Promising features that are not live

      Check every workflow with Product before it goes on the page.

    Evidence

    • HiringReal Estate SaaS Enterprise Account Executive: the same enterprise new-business role, written for real estate software buyers, with the same hubs, travel, pilots, business cases and multi-year agreements; an Enterprise Account Management team takes over growth after the handoff.Source
    • Your websiteSitemap: 361 URLs, including about 200 blog posts, 24 integration pages, 21 webinars, 15 solution pages, 10 customer stories and about 35 co-branded partner landing pages for agency networks and carrier groups (Big I, SIAA, Smart Choice, TWFG, MarshBerry, RPOA, Country Financial and more). There is no real estate or property management solution page, no comparison page against another verification vendor, and no page per insurance carrier.Source
    • Competitor researchAxle sells insurance verification and monitoring to rental car, loaner car, dealership sales, loan servicing and mortgage teams and has just added renters insurance "to instantly verify renters policies" for tenant onboarding. MeasureOne verifies insurance, income, employment and education data, with renters and homeowners insurance verification for lending, automotive and property. Covie offers policy Access and Monitor for tracking and enforcement.Source
    • Your websiteDealerships page: dealers risk "fines for releasing uninsured vehicles" and liability for accidents; 400 carrier integrations covering more than 95% of the market; "96% Auto Insurance Market Coverage", "5.6 Seconds to Transfer Policy Data", "10M Policies Shared", "6,000 Business Use Canopy Connect"; Cox Automotive Ecommerce is the featured integration; cross-selling insurance is pitched as new revenue.Source
  • 02

    Both new AEs are told they will "navigate Security, Privacy, Legal, Procurement" on six-figure, multi-year deals. Canopy has a security page, SOC 2 and an "Is Canopy safe?" page, but no single packet an enterprise reviewer can download, so every deal starts that work from scratch.

    High impactLow effort First result in 1 month Head of GTM

    First action

    Collect the last three security questionnaires Canopy answered and merge them into one master answer set.

    How to measure it

    Security review time

    Now
    –
    Target
    Under 15 business days
    By
    2 quarters

    Steps

    1. 1

      Gather past answers

      Every questionnaire answered in the last year.

      Head of GTM 1 day

    2. 2

      Write the master set

      One answer per common question, owned by engineering.

      Principal/Sr Staff Engineer 3 days

    3. 3

      Add the data flow

      A one-page diagram of what the consumer shares, where it goes and how long it stays.

      Backend Engineer, Carrier Integrations 1 day

    4. 4

      Package it

      PDF plus a pre-filled standard questionnaire file.

      Head of GTM 1 day

    5. 5

      Gate it

      A request form on the security page with an NDA click-through.

      VP of Marketing 2 hours

    6. 6

      Train the AEs

      When to send it: at the first technical call, not at procurement.

      Head of GTM 1 hour

    7. 7

      Track it

      A deal field for when security started and finished.

      Head of GTM 1 hour

    First result
    1 month
    Cost
    Staff time only
    Owner
    Head of GTM

    Smallest test

    Send the draft packet to one active enterprise prospect and time their review.

    Why it works

    One packet: SOC 2 summary and how to request the report, data flow for consumer-permissioned sharing, data retention options from the Enterprise plan, subprocessors, SSO, the SLA in the MSA, and a pre-filled standard security questionnaire. A request form on the security page sends it after an NDA.

    Security review is where enterprise deals sit for weeks. Having answers ready shortens the cycle, and it tells the buyer Canopy has done this before.

    Ready to use

    ChecklistSecurity packet contents

    [ ] SOC 2 summary and how to get the report
[ ] Consumer-permissioned data flow diagram
[ ] Data retention and deletion options
[ ] Subprocessor list
[ ] SSO and access controls
[ ] Uptime SLA and support terms from the MSA
[ ] Incident response summary
[ ] Pre-filled standard security questionnaire

    Risks and how to handle them

    • Answers drift from reality

      Review the packet every quarter with engineering and date it.

    Evidence

    • HiringAutomotive SaaS Enterprise Account Executive (remote, preferred hubs Dallas, Denver, Chicago, the Bay Area and New York, about 25% travel, reports to the Head of GTM): win net-new ARR in named enterprise accounts, build quantified business cases, lead technical evaluations and pilots, navigate Security, Privacy, Legal and Procurement, and close six-figure multi-year deals. Canopy says its customers "span insurance, automotive, lending, fintech, real estate".Source
    • HiringReal Estate SaaS Enterprise Account Executive: the same enterprise new-business role, written for real estate software buyers, with the same hubs, travel, pilots, business cases and multi-year agreements; an Enterprise Account Management team takes over growth after the handoff.Source
    • Your websiteAPI plans: a free API Sandbox, an API Production Pilot "for startups and companies with lower or uncertain volume", and API Enterprise Scale with volume discounts on pre-committed spend, an MSA with SLA, custom data retention, a dedicated integration engineer and single sign-on.Source
    • programmable.infoSite scan: Webflow with Google Tag Manager and HubSpot; no live chat; SOC 2; YouTube channel with 224 videos, 435 subscribers and about 587,000 views; a Facebook community called the Canopy Connectors; a podcast, Connected Conversations in Insurance, hosted by the VP of Marketing and the Customer and Partner Marketing Manager; an "AI information" page written for chatbots, last updated April 10, 2026. A year ago the site showed one "Enterprise" plan from $99.Source
  • 03

    The AE role asks for "quantified Business Cases tied to meaningful customer outcomes". Easterns already gave Canopy the inputs: 90 minutes saved per deal, 40% of verifications automated and 20-minute digital deals. The agency ROI calculator exists, but nothing comparable exists for automotive.

    High impactLow effort First result in 2 weeks Automotive SaaS Enterprise AE

    First action

    Build the spreadsheet with the Easterns inputs as the default values.

    How to measure it

    Automotive opportunities with a business case

    Now
    –
    Target
    80%
    By
    1 quarter

    Steps

    1. 1

      Set the inputs

      Deals per month, online share, minutes per verification, hourly cost, locations.

      Automotive SaaS Enterprise AE 2 hours

    2. 2

      Use Easterns as the default

      90 minutes per deal, 40% automated, 30% online.

      Automotive SaaS Enterprise AE 1 hour

    3. 3

      Add the risk line

      Uninsured releases avoided, framed as risk rather than a promise.

      Automotive SaaS Enterprise AE 1 hour

    4. 4

      Check with Easterns

      Confirm the numbers can be shown to prospects.

      Customer and Partner Marketing Manager 3 days

    5. 5

      Use it in discovery

      Fill it live in the second call.

      Automotive SaaS Enterprise AE Ongoing

    6. 6

      Publish a page version

      A simple calculator page linked from the dealerships page.

      VP of Marketing 1 week

    First result
    2 weeks
    Cost
    $0
    Owner
    Automotive SaaS Enterprise AE

    Smallest test

    Use the spreadsheet in the next three automotive discovery calls.

    Why it works

    A spreadsheet, later a page, where a dealer group or platform enters monthly deals, share started online, and staff cost per hour, and gets hours saved, deals that can close after hours, and the liability of releasing an uninsured car. The AE fills it in during discovery and leaves it behind as the business case.

    Enterprise buyers sign multi-year agreements against a number they can defend internally. A calculator built on a named peer's results is more credible than a generic ROI slide.

    Risks and how to handle them

    • Inflated outputs

      Show a conservative case first, as the agency calculator does.

    Evidence

    • Your websiteEasterns Automotive Group case study: 11 used-car locations around DC, Maryland and Virginia; 40% of insurance verifications automated; 90 minutes saved per deal; full deals in 20 to 25 minutes, even at night; more than 30% of deals start online through Roadster (CDK).Source
    • HiringAutomotive SaaS Enterprise Account Executive (remote, preferred hubs Dallas, Denver, Chicago, the Bay Area and New York, about 25% travel, reports to the Head of GTM): win net-new ARR in named enterprise accounts, build quantified business cases, lead technical evaluations and pilots, navigate Security, Privacy, Legal and Procurement, and close six-figure multi-year deals. Canopy says its customers "span insurance, automotive, lending, fintech, real estate".Source
    • Your websiteROI calculator: "customers report 30 to 50% higher close rates and 30+ minutes saved per quote". Car rental page: most rental companies "simply ask if the customer has insurance"; few verify it. Driver compliance page: manual verification takes 30 minutes on average.Source
    • Your websiteDealerships page: dealers risk "fines for releasing uninsured vehicles" and liability for accidents; 400 carrier integrations covering more than 95% of the market; "96% Auto Insurance Market Coverage", "5.6 Seconds to Transfer Policy Data", "10M Policies Shared", "6,000 Business Use Canopy Connect"; Cox Automotive Ecommerce is the featured integration; cross-selling insurance is pitched as new revenue.Source
  • 04

    Canopy already has co-branded pages and member pricing for about 35 agency networks and carrier groups, but a new SDR team starting from a cold list throws that away. Each network is a list of member agencies who already trust a deal their network negotiated.

    High impactLow effort First result in 2 weeks GTM Associate

    First action

    Export the partner page list and pick the five largest networks for the first week of calls.

    How to measure it

    Meetings per 100 calls to network members

    Now
    –
    Target
    2x non-network
    By
    6 weeks

    Steps

    1. 1

      List the partners

      Every co-branded page and its member offer.

      GTM Associate 2 hours

    2. 2

      Find member agencies

      Member directories, network sites, LinkedIn.

      GTM Associate 2 days

    3. 3

      Load to HubSpot

      Agency, network, offer and page URL as properties.

      GTM Associate 2 hours

    4. 4

      Write the opener

      Name the network and the member offer in the first sentence.

      Customer and Partner Marketing Manager 1 hour

    5. 5

      Run the sequence

      Call, Loom video showing their partner page, email.

      GTM Associate Daily

    6. 6

      Report by network

      Meetings and trials per network each week.

      GTM Associate Weekly

    7. 7

      Feed back to partners

      Share results with the best networks and ask for a member email.

      Customer and Partner Marketing Manager Monthly

    First result
    2 weeks
    Cost
    $0
    Owner
    GTM Associate

    Smallest test

    Call 100 members of one network and compare meetings with 100 cold agencies.

    Run this outreach. The sequence sent for you: addresses found and verified, replies routed to your CRM. Usually live within days.

    Book a working session

    Why it works

    For each partner network, the SDRs get the member agencies they can find, the partner page, the member discount, and a two-line opener ("Your [network] membership includes 12.5% off Canopy"). Calls go to agencies in networks first, and results by network show which partnerships are worth more co-marketing.

    The GTM Associate job asks for strong cold calling and a meetings-booked quota. Calling with a membership benefit is warmer than a cold call, and the partner page is already built.

    Ready to use

    EmailNetwork member opener

    Subject: Your {network} member pricing on Canopy Connect

Hi {first_name},

{network} members get {offer} on Canopy Connect, the link agents send so prospects share their current policies and dec pages in about 20 seconds.

Agencies using it tell us they save 30+ minutes per quote. Here is your member page: {partner_url}

Worth a 15-minute look this week?

{sdr_name}

    Risks and how to handle them

    • Networks dislike vendors calling members

      Ask each network first and offer to co-sign the outreach.

    Evidence

    • HiringGTM Associate: "the first members of our SDR team", selling to insurance agencies by email, phone and social; strong cold calling, HubSpot, LinkedIn, Loom and Gong; competitive analysis; watching job changes, funding rounds and conferences for reasons to reach out; OTE $70K to $100K; SDRs are expected to move into closing roles quickly.Source
    • Your websiteSitemap: 361 URLs, including about 200 blog posts, 24 integration pages, 21 webinars, 15 solution pages, 10 customer stories and about 35 co-branded partner landing pages for agency networks and carrier groups (Big I, SIAA, Smart Choice, TWFG, MarshBerry, RPOA, Country Financial and more). There is no real estate or property management solution page, no comparison page against another verification vendor, and no page per insurance carrier.Source
    • Your websiteAgency pricing: Scratch $100 a month (30 Quote Points, 3 users), Elevate $250 (100 Quote Points, integrations into Applied Epic, EZLynx, PL Rating, AgencyZoom), Peak $500 (300 Quote Points); extra Quote Points $4, $3 or $2; 14-day free trial. Partner pages such as Big I Alliance offer members 12.5% off the first year.Source
  • 05

    The homepage says 6,000 agencies, networks, insurtechs and lenders; the navigation says 24,000 users; the dealerships page says 6,000 businesses; carrier coverage is "more than 95%" in one place and 96% in another. Enterprise buyers check numbers, and the AI information page feeds them to chatbots.

    Medium impactLow effort First result in 1 week VP of Marketing

    First action

    List every number on the site with its page and pick one official value for each.

    How to measure it

    Pages using the official proof numbers

    Now
    –
    Target
    100%
    By
    2 weeks

    Steps

    1. 1

      Inventory the numbers

      Every count and percent on the site.

      VP of Marketing 2 hours

    2. 2

      Pick the official set

      One value and one date for each.

      VP of Marketing 1 hour

    3. 3

      Update Webflow

      Homepage, solution pages and navigation.

      VP of Marketing 3 hours

    4. 4

      Update the AI page

      Same numbers and a new "last updated" date.

      VP of Marketing 1 hour

    5. 5

      Update decks

      Sales and partner decks.

      Customer and Partner Marketing Manager 2 hours

    6. 6

      Set a review date

      Refresh the set every quarter.

      VP of Marketing 15 minutes

    First result
    1 week
    Cost
    $0
    Owner
    VP of Marketing

    Smallest test

    Fix the homepage and AI page first.

    Why it works

    Decide the official numbers (businesses, users, carriers, market coverage, policies shared, seconds to transfer), date them, and use the same wording everywhere: homepage, solution pages, AI information page, decks and the security packet.

    Consistent numbers read as audited; inconsistent ones invite procurement questions. It is also what AI assistants will repeat when a buyer asks about Canopy.

    Risks and how to handle them

    • A smaller number looks worse

      Pick the metric that fits each audience (businesses for enterprise, users for agencies) and label it clearly.

    Evidence

    • Your websiteHomepage: "Collect Verified Insurance Information in Seconds"; "Trusted by 6,000 Agencies, Networks, Insurtechs and Lenders"; Trailhead branded intake pages and Sharing Paths; a link sent by text, email or QR or a widget on the site; 500+ insurance data fields by API; solutions for agencies, carriers, marketplaces, auto finance, mortgage, loan servicing, dealerships, rental cars, fleets, rideshare and employers. The navigation names "A few of our 24,000 users".Source
    • Your websiteDealerships page: dealers risk "fines for releasing uninsured vehicles" and liability for accidents; 400 carrier integrations covering more than 95% of the market; "96% Auto Insurance Market Coverage", "5.6 Seconds to Transfer Policy Data", "10M Policies Shared", "6,000 Business Use Canopy Connect"; Cox Automotive Ecommerce is the featured integration; cross-selling insurance is pitched as new revenue.Source
    • programmable.infoSite scan: Webflow with Google Tag Manager and HubSpot; no live chat; SOC 2; YouTube channel with 224 videos, 435 subscribers and about 587,000 views; a Facebook community called the Canopy Connectors; a podcast, Connected Conversations in Insurance, hosted by the VP of Marketing and the Customer and Partner Marketing Manager; an "AI information" page written for chatbots, last updated April 10, 2026. A year ago the site showed one "Enterprise" plan from $99.Source
  • 06

    Canopy's September post says internet leads "cool off fast" and agents should send the link before they say hello. Canopy's own demo forms (agency, commercial, API) end on a thank-you page with no live chat, and there is no sign of how fast a new enterprise lead gets a reply.

    Medium impactLow effort First result in 2 weeks Head of GTM

    First action

    Pull last quarter's demo requests and measure median time to first reply.

    How to measure it

    Time to first reply

    Now
    –
    Target
    Under 10 minutes in business hours
    By
    1 month

    Steps

    1. 1

      Measure today

      Median and worst reply time per form.

      Head of GTM 2 hours

    2. 2

      Add the vertical field

      One question on every form.

      VP of Marketing 1 hour

    3. 3

      Route by vertical

      HubSpot rotation per vertical owner.

      Head of GTM 2 hours

    4. 4

      Calendar on thank-you pages

      Book a time without waiting for an email.

      VP of Marketing 2 hours

    5. 5

      Instant sandbox for API leads

      The developer-account link on the API thank-you page.

      VP of Marketing 1 hour

    6. 6

      Alert the owner

      Slack alert when a lead lands.

      Head of GTM 1 hour

    7. 7

      Review weekly

      Reply time and booked rate.

      Head of GTM Weekly

    First result
    2 weeks
    Cost
    $0
    Owner
    Head of GTM

    Smallest test

    Put a calendar on the API thank-you page only and compare booking rates for a month.

    Why it works

    Measure time to first reply on every demo form, show a calendar on the thank-you page so a lead can book at once, route by vertical (agency, automotive, real estate, lending) to the right person, and offer an instant sandbox key to API leads.

    Two enterprise AEs and a new SDR team will be judged on pipeline. Booking on the thank-you page is the cheapest pipeline gain there is, and it makes Canopy practise its own pitch.

    Risks and how to handle them

    • Wrong routing annoys buyers

      Default anything unclear to the SDR team for a same-day call.

    Evidence

    • Your websiteBlog, September 2026: "Send the link before you say hello", on agents putting their Canopy link in the first reply because "internet leads cool off fast"; "The real cost of good enough insurance data" names agencies, lenders, rental companies and compliance teams as the buyers.Source
    • programmable.infoSite scan: Webflow with Google Tag Manager and HubSpot; no live chat; SOC 2; YouTube channel with 224 videos, 435 subscribers and about 587,000 views; a Facebook community called the Canopy Connectors; a podcast, Connected Conversations in Insurance, hosted by the VP of Marketing and the Customer and Partner Marketing Manager; an "AI information" page written for chatbots, last updated April 10, 2026. A year ago the site showed one "Enterprise" plan from $99.Source
    • Your websiteAPI plans: a free API Sandbox, an API Production Pilot "for startups and companies with lower or uncertain volume", and API Enterprise Scale with volume discounts on pre-committed spend, an MSA with SLA, custom data retention, a dedicated integration engineer and single sign-on.Source
    • Your websiteSitemap: 361 URLs, including about 200 blog posts, 24 integration pages, 21 webinars, 15 solution pages, 10 customer stories and about 35 co-branded partner landing pages for agency networks and carrier groups (Big I, SIAA, Smart Choice, TWFG, MarshBerry, RPOA, Country Financial and more). There is no real estate or property management solution page, no comparison page against another verification vendor, and no page per insurance carrier.Source

This quarter 9

The core plays for the next three months.

  • 07

    The automotive AE sells to software companies, not single dealers. Canopy already integrates with CDK, Cox Automotive Ecommerce and TSD Rental and has Ford Direct as a named customer, so the next accounts are the platforms beside them: digital retailing, F&I menus, DMS, rental and loaner software, and auto lenders' origination systems.

    High impactMedium effort First result in 1 quarter Automotive SaaS Enterprise AE

    First action

    Draft the 40 platforms in five categories and mark the ten closest to an existing integration.

    How to measure it

    New automotive platform opportunities

    Now
    –
    Target
    10
    By
    1 quarter

    Steps

    1. 1

      Categorise the market

      Digital retailing, DMS, F&I, rental and loaner, lending.

      Automotive SaaS Enterprise AE 1 day

    2. 2

      Score the list

      Fit, size, existing integration nearby, known contact.

      Automotive SaaS Enterprise AE 1 day

    3. 3

      Map stakeholders

      Product, partnerships, compliance and the executive sponsor at each.

      Automotive SaaS Enterprise AE 1 week

    4. 4

      Write a point of view

      One page per category on the insurance step it is missing.

      Automotive SaaS Enterprise AE 1 week

    5. 5

      Ask for intros

      Through CDK, Cox and customer contacts.

      Head of GTM 2 weeks

    6. 6

      Offer a pilot

      The Production Pilot plan with agreed success measures.

      Automotive SaaS Enterprise AE Ongoing

    7. 7

      Review monthly

      Advance or drop each account.

      Head of GTM Monthly

    Who to approach

    • Tekion

      Cloud DMS and digital retail.

    • RouteOne

      F&I and credit application network used by dealers and lenders.

    • Reynolds and Reynolds

      DMS with digital retailing products.

    First result
    1 quarter
    Cost
    Travel at about 25%
    Owner
    Automotive SaaS Enterprise AE

    Smallest test

    Send the category point of view to five platforms and count replies.

    Build the prospect list. The list compiled from public sources, verified, deduplicated and delivered to your CRM. Usually live within days.

    Book a working session

    Why it works

    Build a list of about 40 platforms by category, map which already connect to an integration Canopy has, and approach each with the workflow it is missing (insurance at checkout, loaner agreements, lien holder updates), the Easterns case and a pilot offer.

    Platform deals multiply: one integration reaches every dealer on that platform. The integrations Canopy already has are the credibility a platform product team asks for.

    Risks and how to handle them

    • Long platform cycles

      Run dealer-group deals in parallel so the quarter has closes.

    Evidence

    • HiringAutomotive SaaS Enterprise Account Executive (remote, preferred hubs Dallas, Denver, Chicago, the Bay Area and New York, about 25% travel, reports to the Head of GTM): win net-new ARR in named enterprise accounts, build quantified business cases, lead technical evaluations and pilots, navigate Security, Privacy, Legal and Procurement, and close six-figure multi-year deals. Canopy says its customers "span insurance, automotive, lending, fintech, real estate".Source
    • Your websiteDealerships page: dealers risk "fines for releasing uninsured vehicles" and liability for accidents; 400 carrier integrations covering more than 95% of the market; "96% Auto Insurance Market Coverage", "5.6 Seconds to Transfer Policy Data", "10M Policies Shared", "6,000 Business Use Canopy Connect"; Cox Automotive Ecommerce is the featured integration; cross-selling insurance is pitched as new revenue.Source
    • Your websiteEasterns Automotive Group case study: 11 used-car locations around DC, Maryland and Virginia; 40% of insurance verifications automated; 90 minutes saved per deal; full deals in 20 to 25 minutes, even at night; more than 30% of deals start online through Roadster (CDK).Source
    • Your websiteHomepage: "Collect Verified Insurance Information in Seconds"; "Trusted by 6,000 Agencies, Networks, Insurtechs and Lenders"; Trailhead branded intake pages and Sharing Paths; a link sent by text, email or QR or a widget on the site; 500+ insurance data fields by API; solutions for agencies, carriers, marketplaces, auto finance, mortgage, loan servicing, dealerships, rental cars, fleets, rideshare and employers. The navigation names "A few of our 24,000 users".Source
  • 08

    Canopy already has an API Production Pilot plan for buyers with "uncertain volume". A real estate platform has exactly that uncertainty, and Axle and MeasureOne are pitching the same renters insurance check.

    High impactMedium effort First result in 1 quarter Real Estate SaaS Enterprise AE

    First action

    Write the pilot one-pager: scope, measures, timeline, and the price after.

    How to measure it

    Pilot to contract

    Now
    –
    Target
    60%
    By
    2 quarters

    Steps

    1. 1

      Define the scope

      One portfolio, move-in and monitoring, 60 days.

      Real Estate SaaS Enterprise AE 1 day

    2. 2

      Pick three measures

      Verified share of residents, lapses caught, minutes saved per lease.

      Real Estate SaaS Enterprise AE 1 day

    3. 3

      Agree the price after

      Written into the pilot order form.

      Head of GTM 1 week

    4. 4

      Build the report

      A weekly email from pilot data.

      Backend Engineer, Carrier Integrations 1 week

    5. 5

      Run a kickoff

      Implementation and the platform's product owner.

      Real Estate SaaS Enterprise AE 1 day

    6. 6

      Mid-point review

      Fix problems at day 30.

      Real Estate SaaS Enterprise AE 1 hour

    7. 7

      Close

      Readout and order at day 60.

      Real Estate SaaS Enterprise AE 1 week

    First result
    1 quarter
    Cost
    Implementation time
    Owner
    Real Estate SaaS Enterprise AE

    Smallest test

    Offer the pilot to the first three real estate platforms in active talks.

    Why it works

    A standard pilot: one portfolio, the branded link at move-in, monitoring on, a weekly report of verified policies, lapses caught and staff time saved, and a price for the full rollout agreed before the pilot starts.

    A pilot with an agreed finish line turns into a contract instead of a long trial, and lapse data from a real portfolio is the case study the Real Estate AE needs.

    Risks and how to handle them

    • Pilot never converts

      Pre-agree the price and the decision date.

    Evidence

    • HiringReal Estate SaaS Enterprise Account Executive: the same enterprise new-business role, written for real estate software buyers, with the same hubs, travel, pilots, business cases and multi-year agreements; an Enterprise Account Management team takes over growth after the handoff.Source
    • Your websiteAPI plans: a free API Sandbox, an API Production Pilot "for startups and companies with lower or uncertain volume", and API Enterprise Scale with volume discounts on pre-committed spend, an MSA with SLA, custom data retention, a dedicated integration engineer and single sign-on.Source
    • Competitor researchAxle sells insurance verification and monitoring to rental car, loaner car, dealership sales, loan servicing and mortgage teams and has just added renters insurance "to instantly verify renters policies" for tenant onboarding. MeasureOne verifies insurance, income, employment and education data, with renters and homeowners insurance verification for lending, automotive and property. Covie offers policy Access and Monitor for tracking and enforcement.Source
  • 09

    Canopy connects to about 400 carriers but has no page per carrier. People search for "verify Progressive insurance" or "share my State Farm policy" every day, and Canopy is the tool that answers those questions.

    High impactMedium effort First result in 3 months VP of Marketing

    First action

    Pull the carrier list with the lines supported and pick the top 50.

    How to measure it

    Carrier page visits

    Now
    –
    Target
    5,000 a month
    By
    6 months

    Steps

    1. 1

      Export carrier data

      Lines and fields supported per carrier.

      Backend Engineer, Carrier Integrations 2 days

    2. 2

      Write the template

      Intro, what can be shared, how it works, FAQ, CTA by audience.

      VP of Marketing 2 days

    3. 3

      Legal review

      Trademark wording and no implied endorsement.

      Head of GTM 1 week

    4. 4

      Build in Webflow CMS

      One collection item per carrier.

      VP of Marketing 1 week

    5. 5

      Publish 50

      In two batches.

      VP of Marketing 2 weeks

    6. 6

      Link internally

      From solution pages and the help center.

      VP of Marketing 1 day

    7. 7

      Keep them current

      Sync when an integration changes.

      Backend Engineer, Carrier Integrations Monthly

    First result
    3 months
    Cost
    $0 plus legal review
    Owner
    VP of Marketing

    Smallest test

    Publish five carrier pages and watch impressions in Search Console for a month.

    Why it works

    Pages for the top 50 carriers by market share: what can be shared, how the link works for that carrier, which lines are covered, and a call to action for each audience (agent, dealer, lender, landlord). Data comes from the carrier integration list, so pages stay accurate.

    Carrier names are high-volume, high-intent searches that competitors are not answering. Each page also helps the SDRs and AEs ("do you cover X?").

    Risks and how to handle them

    • Carrier trademark complaints

      Factual wording, a clear "not affiliated" line, and quick takedown on request.

    • Thin pages

      Include real coverage details per carrier, not just the name swapped.

    Evidence

    • Your websiteDealerships page: dealers risk "fines for releasing uninsured vehicles" and liability for accidents; 400 carrier integrations covering more than 95% of the market; "96% Auto Insurance Market Coverage", "5.6 Seconds to Transfer Policy Data", "10M Policies Shared", "6,000 Business Use Canopy Connect"; Cox Automotive Ecommerce is the featured integration; cross-selling insurance is pitched as new revenue.Source
    • Your websiteSitemap: 361 URLs, including about 200 blog posts, 24 integration pages, 21 webinars, 15 solution pages, 10 customer stories and about 35 co-branded partner landing pages for agency networks and carrier groups (Big I, SIAA, Smart Choice, TWFG, MarshBerry, RPOA, Country Financial and more). There is no real estate or property management solution page, no comparison page against another verification vendor, and no page per insurance carrier.Source
    • HiringSix open roles on Greenhouse: the two enterprise AEs, the GTM Associate, a Backend Engineer on the Carrier Integrations team (data aggregation from third-party sites and APIs, Node and AWS), a Principal/Sr Staff Engineer and a general application.Source
  • 10

    Enterprise buyers make a vendor shortlist, and the SDR job asks for competitive analysis, but Canopy has no comparison page. Axle sells to the same rental, dealer and lending teams; MeasureOne and Covie sell verification and monitoring.

    Medium impactMedium effort First result in 2 months VP of Marketing

    First action

    Write the comparison rows and check each competitor's public pages for each row.

    How to measure it

    Demos from comparison pages

    Now
    –
    Target
    6 a month
    By
    1 quarter

    Steps

    1. 1

      Pick the rows

      Coverage, lines, monitoring, consumer flow, agency tools, integrations, pricing model.

      VP of Marketing 1 day

    2. 2

      Research each vendor

      Public pages only, with links.

      GTM Associate 3 days

    3. 3

      Write fairly

      Say where each competitor fits better.

      VP of Marketing 3 days

    4. 4

      Legal review

      Every claim sourced and dated.

      Head of GTM 1 week

    5. 5

      Publish

      With a demo form per page.

      VP of Marketing 1 day

    6. 6

      Make competitor comparisons

      Same content, in Gong and HubSpot.

      GTM Associate 2 days

    7. 7

      Update quarterly

      Recheck every row.

      GTM Associate Quarterly

    Who to approach

    • Axle

      Verification and monitoring for rental, dealer, lending, now renters.

    • MeasureOne

      Consumer-permissioned insurance, income and education data.

    • Covie

      Policy access and monitoring API.

    First result
    2 months
    Cost
    $0
    Owner
    VP of Marketing

    Smallest test

    Publish the manual verification page first; it has no legal risk.

    Why it works

    Four pages: Canopy vs Axle, vs MeasureOne, vs Covie, and vs manual verification. Each compares carrier coverage, lines, monitoring, the branded consumer experience, agency workflows, integrations and pricing model, with sources and a date.

    Comparison searches come from buyers late in the process. A fair page gets Canopy onto shortlists it is missing from and gives the AEs a competitor comparison.

    Risks and how to handle them

    • Claims go stale

      Date each page and review quarterly.

    Evidence

    • Competitor researchAxle sells insurance verification and monitoring to rental car, loaner car, dealership sales, loan servicing and mortgage teams and has just added renters insurance "to instantly verify renters policies" for tenant onboarding. MeasureOne verifies insurance, income, employment and education data, with renters and homeowners insurance verification for lending, automotive and property. Covie offers policy Access and Monitor for tracking and enforcement.Source
    • HiringGTM Associate: "the first members of our SDR team", selling to insurance agencies by email, phone and social; strong cold calling, HubSpot, LinkedIn, Loom and Gong; competitive analysis; watching job changes, funding rounds and conferences for reasons to reach out; OTE $70K to $100K; SDRs are expected to move into closing roles quickly.Source
    • Your websiteDealerships page: dealers risk "fines for releasing uninsured vehicles" and liability for accidents; 400 carrier integrations covering more than 95% of the market; "96% Auto Insurance Market Coverage", "5.6 Seconds to Transfer Policy Data", "10M Policies Shared", "6,000 Business Use Canopy Connect"; Cox Automotive Ecommerce is the featured integration; cross-selling insurance is pitched as new revenue.Source
    • Your websiteSitemap: 361 URLs, including about 200 blog posts, 24 integration pages, 21 webinars, 15 solution pages, 10 customer stories and about 35 co-branded partner landing pages for agency networks and carrier groups (Big I, SIAA, Smart Choice, TWFG, MarshBerry, RPOA, Country Financial and more). There is no real estate or property management solution page, no comparison page against another verification vendor, and no page per insurance carrier.Source
  • 11

    Connected Conversations in Insurance is hosted by Canopy's VP of Marketing and Customer and Partner Marketing Manager and talks mostly to the agency world. The new AEs need a reason for senior people at automotive and real estate software companies to give them an hour.

    Medium impactMedium effort First result in 1 quarter Customer and Partner Marketin…

    First action

    Write the season theme and send ten guest invitations from the AEs' target lists.

    How to measure it

    Guest accounts with an opportunity

    Now
    –
    Target
    30%
    By
    2 quarters

    Steps

    1. 1

      Pick the theme

      Insurance at the point of sale, by vertical.

      Customer and Partner Marketing Manager 1 day

    2. 2

      Choose guests from target lists

      Ten from automotive, ten from real estate.

      Automotive SaaS Enterprise AE 2 days

    3. 3

      Invite

      Personal invitations from the hosts.

      Customer and Partner Marketing Manager 1 week

    4. 4

      Prep with the AE

      Thirty minutes before each recording.

      Real Estate SaaS Enterprise AE 30 minutes each

    5. 5

      Record and publish

      Episode, three clips and a written recap.

      Customer and Partner Marketing Manager Biweekly

    6. 6

      Follow up

      The AE sends the episode to the guest's colleagues.

      Automotive SaaS Enterprise AE Per episode

    7. 7

      Measure

      Meetings and opportunities by guest account.

      Head of GTM Monthly

    First result
    1 quarter
    Cost
    Editing time
    Owner
    Customer and Partner Marketing Manager

    Smallest test

    Record two episodes with target-account guests.

    Why it works

    Dedicate a season to "insurance at the point of sale": product and compliance leaders from dealer platforms, rental software, property management systems and lenders. The AE for that vertical joins the prep call; each episode becomes clips and a written recap.

    An invitation to talk about their work is the warmest way in to a senior buyer, and the conversation is the discovery call.

    Risks and how to handle them

    • Guests feel sold to

      Keep the episode editorial; the business talk happens afterwards.

    Evidence

    • programmable.infoSite scan: Webflow with Google Tag Manager and HubSpot; no live chat; SOC 2; YouTube channel with 224 videos, 435 subscribers and about 587,000 views; a Facebook community called the Canopy Connectors; a podcast, Connected Conversations in Insurance, hosted by the VP of Marketing and the Customer and Partner Marketing Manager; an "AI information" page written for chatbots, last updated April 10, 2026. A year ago the site showed one "Enterprise" plan from $99.Source
    • HiringAutomotive SaaS Enterprise Account Executive (remote, preferred hubs Dallas, Denver, Chicago, the Bay Area and New York, about 25% travel, reports to the Head of GTM): win net-new ARR in named enterprise accounts, build quantified business cases, lead technical evaluations and pilots, navigate Security, Privacy, Legal and Procurement, and close six-figure multi-year deals. Canopy says its customers "span insurance, automotive, lending, fintech, real estate".Source
    • HiringReal Estate SaaS Enterprise Account Executive: the same enterprise new-business role, written for real estate software buyers, with the same hubs, travel, pilots, business cases and multi-year agreements; an Enterprise Account Management team takes over growth after the handoff.Source
  • 12

    Canopy's agency customers insure car dealers, property managers and lenders, the businesses the new AEs are trying to reach. An agent is a trusted advisor to those businesses and benefits when their clients verify coverage faster.

    Medium impactMedium effort First result in 1 quarter Customer and Partner Marketin…

    First action

    Ask ten agency customers which of their commercial clients check insurance at a sale or lease.

    How to measure it

    Agency-referred enterprise opportunities

    Now
    –
    Target
    5 a quarter
    By
    2 quarters

    Steps

    1. 1

      Find agents with the right clients

      Commercial agencies with dealer, rental or property clients.

      Customer and Partner Marketing Manager 1 week

    2. 2

      Design the reward

      Quote Points credit or revenue share.

      Head of GTM 1 week

    3. 3

      Write the terms

      Simple, with licensing and disclosure checked.

      Head of GTM 1 week

    4. 4

      Build the referral form

      HubSpot form inside the agent dashboard.

      VP of Marketing 2 days

    5. 5

      Announce it

      Canopy Connectors group, webinar and email.

      Customer and Partner Marketing Manager 1 week

    6. 6

      Route referrals

      Straight to the AE for that vertical.

      Head of GTM 1 hour

    7. 7

      Report back to agents

      Status of every referral.

      Customer and Partner Marketing Manager Monthly

    First result
    1 quarter
    Cost
    Credits or revenue share
    Owner
    Customer and Partner Marketing Manager

    Smallest test

    Pilot with the five agencies that write the most commercial business.

    Why it works

    A partner referral program: agents introduce a commercial client who needs verification at the point of sale and get account credit or a revenue share; the client gets setup help, and the agent can be the named interested party on the verified policies.

    It turns the base Canopy already has into an enterprise channel, and agent-referred leads arrive with trust attached.

    Risks and how to handle them

    • Insurance referral rules

      Check state rules on referral payments; use account credit if needed.

    Evidence

    • Your websiteHomepage: "Collect Verified Insurance Information in Seconds"; "Trusted by 6,000 Agencies, Networks, Insurtechs and Lenders"; Trailhead branded intake pages and Sharing Paths; a link sent by text, email or QR or a widget on the site; 500+ insurance data fields by API; solutions for agencies, carriers, marketplaces, auto finance, mortgage, loan servicing, dealerships, rental cars, fleets, rideshare and employers. The navigation names "A few of our 24,000 users".Source
    • Your websiteAgency pricing: Scratch $100 a month (30 Quote Points, 3 users), Elevate $250 (100 Quote Points, integrations into Applied Epic, EZLynx, PL Rating, AgencyZoom), Peak $500 (300 Quote Points); extra Quote Points $4, $3 or $2; 14-day free trial. Partner pages such as Big I Alliance offer members 12.5% off the first year.Source
    • HiringAutomotive SaaS Enterprise Account Executive (remote, preferred hubs Dallas, Denver, Chicago, the Bay Area and New York, about 25% travel, reports to the Head of GTM): win net-new ARR in named enterprise accounts, build quantified business cases, lead technical evaluations and pilots, navigate Security, Privacy, Legal and Procurement, and close six-figure multi-year deals. Canopy says its customers "span insurance, automotive, lending, fintech, real estate".Source
    • HiringReal Estate SaaS Enterprise Account Executive: the same enterprise new-business role, written for real estate software buyers, with the same hubs, travel, pilots, business cases and multi-year agreements; an Enterprise Account Management team takes over growth after the handoff.Source
  • 13

    The API Sandbox is free and self-serve, and the Production Pilot is "contact us". Nothing visible connects the two, so a developer who builds a working test can stall there without anyone at Canopy knowing.

    Medium impactMedium effort First result in 6 weeks Head of GTM

    First action

    List the four sandbox events that best predict a real integration.

    How to measure it

    Sandbox to pilot

    Now
    –
    Target
    15%
    By
    2 quarters

    Steps

    1. 1

      Pick the events

      Key created, first pull, webhook, multi-carrier test.

      Backend Engineer, Carrier Integrations 1 day

    2. 2

      Send events to HubSpot

      From the sandbox backend.

      Backend Engineer, Carrier Integrations 1 week

    3. 3

      Write the emails

      One helpful email per event, from an engineer's name.

      VP of Marketing 2 days

    4. 4

      Set the AE trigger

      Threshold creates a task with the account's company.

      Head of GTM 1 day

    5. 5

      Offer office hours

      A weekly integration call.

      Backend Engineer, Carrier Integrations Weekly

    6. 6

      Measure the steps

      Drop-off between events.

      Head of GTM Monthly

    First result
    6 weeks
    Cost
    Engineering time
    Owner
    Head of GTM

    Smallest test

    Manually email the last 30 sandbox sign-ups and see who replies.

    Why it works

    Track sandbox events (first key, first test pull, webhook set up, test pulls across several carriers) and send help at each step: docs, an offer of an integration call, then the pilot offer. A sandbox account that crosses a threshold creates a task for the right AE.

    Developers who have already built something are the best leads Canopy will get, and enterprise AEs need warm technical champions inside accounts.

    Risks and how to handle them

    • Emails feel like tracking

      Keep them useful and few; make them easy to stop.

    Evidence

    • Your websiteAPI plans: a free API Sandbox, an API Production Pilot "for startups and companies with lower or uncertain volume", and API Enterprise Scale with volume discounts on pre-committed spend, an MSA with SLA, custom data retention, a dedicated integration engineer and single sign-on.Source
    • HiringSix open roles on Greenhouse: the two enterprise AEs, the GTM Associate, a Backend Engineer on the Carrier Integrations team (data aggregation from third-party sites and APIs, Node and AWS), a Principal/Sr Staff Engineer and a general application.Source
    • HiringAutomotive SaaS Enterprise Account Executive (remote, preferred hubs Dallas, Denver, Chicago, the Bay Area and New York, about 25% travel, reports to the Head of GTM): win net-new ARR in named enterprise accounts, build quantified business cases, lead technical evaluations and pilots, navigate Security, Privacy, Legal and Procurement, and close six-figure multi-year deals. Canopy says its customers "span insurance, automotive, lending, fintech, real estate".Source
  • 14

    Both AEs are based near hubs and travel about 25% of the time; the SDRs are told to watch conferences for reasons to reach out. Canopy's events today are mostly webinars and agency network gatherings.

    High impactMedium effort First result in 1 quarter Head of GTM

    First action

    Choose two shows per vertical for the next two quarters and list 30 target attendees for the first.

    How to measure it

    Pre-booked meetings per show

    Now
    –
    Target
    12
    By
    2 quarters

    Steps

    1. 1

      Pick the shows

      Two per vertical, chosen by target attendance.

      Head of GTM 1 day

    2. 2

      Build attendee lists

      Speakers, sponsors and target accounts going.

      GTM Associate 1 week

    3. 3

      Book meetings early

      SDR outreach six weeks before.

      GTM Associate 4 weeks

    4. 4

      Host one dinner

      Ten guests per show.

      Automotive SaaS Enterprise AE 1 evening

    5. 5

      Follow up in 48 hours

      Every meeting gets a recap and a next step.

      Real Estate SaaS Enterprise AE 2 days

    6. 6

      Score the show

      Meetings, opportunities and cost.

      Head of GTM 1 week after

    First result
    1 quarter
    Cost
    Travel and dinners
    Owner
    Head of GTM

    Smallest test

    Book meetings for one show without buying a booth.

    Why it works

    Pick a small set of shows per vertical (dealer and auto-finance shows, apartment and property management shows, mortgage technology), book meetings with target accounts six weeks ahead through the SDRs, run one small dinner per show, and judge each show on meetings and pipeline.

    Enterprise relationships are built in person, and pre-booked meetings make a show pay even without a booth.

    Risks and how to handle them

    • Expensive shows with little return

      Attend without a booth first.

    Evidence

    • HiringAutomotive SaaS Enterprise Account Executive (remote, preferred hubs Dallas, Denver, Chicago, the Bay Area and New York, about 25% travel, reports to the Head of GTM): win net-new ARR in named enterprise accounts, build quantified business cases, lead technical evaluations and pilots, navigate Security, Privacy, Legal and Procurement, and close six-figure multi-year deals. Canopy says its customers "span insurance, automotive, lending, fintech, real estate".Source
    • HiringReal Estate SaaS Enterprise Account Executive: the same enterprise new-business role, written for real estate software buyers, with the same hubs, travel, pilots, business cases and multi-year agreements; an Enterprise Account Management team takes over growth after the handoff.Source
    • HiringGTM Associate: "the first members of our SDR team", selling to insurance agencies by email, phone and social; strong cold calling, HubSpot, LinkedIn, Loom and Gong; competitive analysis; watching job changes, funding rounds and conferences for reasons to reach out; OTE $70K to $100K; SDRs are expected to move into closing roles quickly.Source
  • 15

    Loan servicing already promises verifying and monitoring "now and in the future", and the Enterprise plan includes account monitoring. A one-time check is a transaction; monitoring for lapses across a portfolio is a subscription that grows with the portfolio.

    High impactMedium effort First result in 1 quarter Head of GTM

    First action

    Price monitoring per policy per month and add it to the enterprise proposal template.

    How to measure it

    Deals with monitoring

    Now
    –
    Target
    50%
    By
    2 quarters

    Steps

    1. 1

      Set the price

      Per policy per month, by volume tier.

      Head of GTM 1 week

    2. 2

      Build the lapse report

      A monthly summary per customer.

      Backend Engineer, Carrier Integrations 2 weeks

    3. 3

      Update proposals

      Monitoring included by default.

      Head of GTM 1 day

    4. 4

      Train the AEs

      Discovery questions about lapses today.

      Head of GTM 1 hour

    5. 5

      Upsell existing accounts

      Account management offers it to every servicer.

      Head of GTM 1 quarter

    6. 6

      Track the revenue line

      Monitoring ARR in reporting.

      Head of GTM Monthly

    First result
    1 quarter
    Cost
    Engineering for the report
    Owner
    Head of GTM

    Smallest test

    Run monitoring free for one servicer for 30 days and present the lapses found.

    Why it works

    Package monitoring with a per-policy monthly price, a lapse report, and alerts into the customer's system; make it the default proposal for lenders, servicers and real estate accounts, and track it as its own revenue line.

    Recurring revenue per policy is what makes enterprise accounts expand, and lapse data is evidence of value every month.

    Risks and how to handle them

    • Customers see it as an extra cost

      Show lapses found during the pilot as the reason.

    Evidence

    • Your websiteMortgage page: lenders verify a policy "in 30-seconds" from carrier data instead of weeks of documents, check Fannie Mae and lender requirements and edit the mortgagee; it works inside Encompass. Loan servicing: verify and monitor home and auto insurance and update lienholders and mortgagee clauses "in less than a minute".Source
    • Your websiteAPI plans: a free API Sandbox, an API Production Pilot "for startups and companies with lower or uncertain volume", and API Enterprise Scale with volume discounts on pre-committed spend, an MSA with SLA, custom data retention, a dedicated integration engineer and single sign-on.Source
    • Competitor researchAxle sells insurance verification and monitoring to rental car, loaner car, dealership sales, loan servicing and mortgage teams and has just added renters insurance "to instantly verify renters policies" for tenant onboarding. MeasureOne verifies insurance, income, employment and education data, with renters and homeowners insurance verification for lending, automotive and property. Covie offers policy Access and Monitor for tracking and enforcement.Source

Big bets 3

Larger plays that can change the trajectory.

  • 16

    A consumer who shares their policy with a dealer today shares it again with a landlord, a lender and an agent. Canopy sits in all of those flows and is built on consumer-permissioned data, so it could let the consumer reuse one verified profile with their consent.

    High impactHigh effort First result in 3 quarters Head of GTM

    First action

    Measure how many consumers already shared with more than one Canopy business in the last year.

    How to measure it

    Reused-profile verifications

    Now
    –
    Target
    20%
    By
    1 year

    Steps

    1. 1

      Size the overlap

      Consumers who shared with two or more businesses.

      Backend Engineer, Carrier Integrations 1 week

    2. 2

      Design consent

      What is reused, for how long, and how to revoke.

      Principal/Sr Staff Engineer 1 month

    3. 3

      Legal and privacy review

      Consent, retention and state privacy law.

      Head of GTM 1 month

    4. 4

      Build the consumer view

      Who has access and revoke.

      Backend Engineer, Carrier Integrations 1 quarter

    5. 5

      Pilot in one pair of verticals

      Dealer then agent, for example.

      Automotive SaaS Enterprise AE 1 quarter

    6. 6

      Measure speed and completion

      Against first-time shares.

      Head of GTM Monthly

    7. 7

      Decide the rollout

      On completion lift and consumer trust.

      Head of GTM 1 week

    First result
    3 quarters
    Cost
    An engineering team for two quarters
    Owner
    Head of GTM

    Smallest test

    Ask consumers at the end of a share whether they want to save it for next time, and count yes answers.

    Why it works

    A consumer-side profile: after one share, the person can approve the same verified data for the next business in seconds, see who has access, and revoke it. Businesses get a faster flow; Canopy gets a network effect across verticals.

    Every new vertical makes the profile more useful to consumers, which makes Canopy faster than rivals in every vertical. It fits the mission of letting consumers choose how others use their data.

    Risks and how to handle them

    • Privacy concerns

      Opt-in only, clear revocation, short default retention.

    • Carriers object

      Keep data flows consumer-initiated, as today.

    Evidence

    • Your websiteHomepage: "Collect Verified Insurance Information in Seconds"; "Trusted by 6,000 Agencies, Networks, Insurtechs and Lenders"; Trailhead branded intake pages and Sharing Paths; a link sent by text, email or QR or a widget on the site; 500+ insurance data fields by API; solutions for agencies, carriers, marketplaces, auto finance, mortgage, loan servicing, dealerships, rental cars, fleets, rideshare and employers. The navigation names "A few of our 24,000 users".Source
    • programmable.infoSite scan: Webflow with Google Tag Manager and HubSpot; no live chat; SOC 2; YouTube channel with 224 videos, 435 subscribers and about 587,000 views; a Facebook community called the Canopy Connectors; a podcast, Connected Conversations in Insurance, hosted by the VP of Marketing and the Customer and Partner Marketing Manager; an "AI information" page written for chatbots, last updated April 10, 2026. A year ago the site showed one "Enterprise" plan from $99.Source
    • Your websiteDealerships page: dealers risk "fines for releasing uninsured vehicles" and liability for accidents; 400 carrier integrations covering more than 95% of the market; "96% Auto Insurance Market Coverage", "5.6 Seconds to Transfer Policy Data", "10M Policies Shared", "6,000 Business Use Canopy Connect"; Cox Automotive Ecommerce is the featured integration; cross-selling insurance is pitched as new revenue.Source
    • Your websiteMortgage page: lenders verify a policy "in 30-seconds" from carrier data instead of weeks of documents, check Fannie Mae and lender requirements and edit the mortgagee; it works inside Encompass. Loan servicing: verify and monitor home and auto insurance and update lienholders and mortgagee clauses "in less than a minute".Source
  • 17

    Ford Direct is already a named customer, and Cox Automotive Ecommerce uses Canopy for online sales. Automakers and their finance arms run the digital retail and loaner programs their dealers must use, so one program can reach thousands of stores.

    High impactHigh effort First result in 1 year Automotive SaaS Enterprise AE

    First action

    Map the digital retail and captive finance owners at three automakers.

    How to measure it

    OEM or captive finance programs

    Now
    –
    Target
    1 signed
    By
    1 year

    Steps

    1. 1

      Map the programs

      Digital retail, loaner and captive finance owners.

      Automotive SaaS Enterprise AE 1 month

    2. 2

      Use Ford Direct as a reference

      Ask for permission and a contact.

      Automotive SaaS Enterprise AE 2 weeks

    3. 3

      Build the regional case

      Volume, time saved, fraud and liability avoided.

      Automotive SaaS Enterprise AE 1 month

    4. 4

      Propose a regional pilot

      One brand or region.

      Automotive SaaS Enterprise AE 1 quarter

    5. 5

      Clear procurement

      Security packet and the MSA.

      Head of GTM 1 quarter

    6. 6

      Roll out

      Dealer enablement with the OEM.

      Customer and Partner Marketing Manager 1 quarter

    Who to approach

    • Ford Direct

      Already a named Canopy customer.

    First result
    1 year
    Cost
    Travel and a long sales cycle
    Owner
    Automotive SaaS Enterprise AE

    Smallest test

    Get one OEM digital retail meeting through an existing customer.

    Why it works

    Approach OEM digital retail and captive finance teams with the Easterns results, a security packet and a pilot on one region or brand, priced per verification across the network.

    An OEM program is the biggest single source of automotive volume, and the automotive AE role is built for exactly this kind of multi-stakeholder deal.

    Risks and how to handle them

    • Very long cycles

      Run platform and dealer-group deals in parallel.

    Evidence

    • HiringAutomotive SaaS Enterprise Account Executive (remote, preferred hubs Dallas, Denver, Chicago, the Bay Area and New York, about 25% travel, reports to the Head of GTM): win net-new ARR in named enterprise accounts, build quantified business cases, lead technical evaluations and pilots, navigate Security, Privacy, Legal and Procurement, and close six-figure multi-year deals. Canopy says its customers "span insurance, automotive, lending, fintech, real estate".Source
    • Your websiteHomepage: "Collect Verified Insurance Information in Seconds"; "Trusted by 6,000 Agencies, Networks, Insurtechs and Lenders"; Trailhead branded intake pages and Sharing Paths; a link sent by text, email or QR or a widget on the site; 500+ insurance data fields by API; solutions for agencies, carriers, marketplaces, auto finance, mortgage, loan servicing, dealerships, rental cars, fleets, rideshare and employers. The navigation names "A few of our 24,000 users".Source
    • Your websiteEasterns Automotive Group case study: 11 used-car locations around DC, Maryland and Virginia; 40% of insurance verifications automated; 90 minutes saved per deal; full deals in 20 to 25 minutes, even at night; more than 30% of deals start online through Roadster (CDK).Source
    • Your websiteDealerships page: dealers risk "fines for releasing uninsured vehicles" and liability for accidents; 400 carrier integrations covering more than 95% of the market; "96% Auto Insurance Market Coverage", "5.6 Seconds to Transfer Policy Data", "10M Policies Shared", "6,000 Business Use Canopy Connect"; Cox Automotive Ecommerce is the featured integration; cross-selling insurance is pitched as new revenue.Source
  • 18

    Real estate SaaS buyers expect vendors to plug into their property management system. Canopy integrates deeply with agency and lending systems (Applied Epic, EZLynx, Encompass) but lists nothing for property management, where Axle is now pitching renters insurance.

    High impactHigh effort First result in 1 year Real Estate SaaS Enterprise AE

    First action

    Ask the Real Estate AE's first ten prospects which property management system they run.

    How to measure it

    Accounts on the integration

    Now
    –
    Target
    10
    By
    1 year

    Steps

    1. 1

      Pick the system

      By prospects' answers and partner program access.

      Real Estate SaaS Enterprise AE 2 weeks

    2. 2

      Join the partner program

      Contracts and sandbox access.

      Real Estate SaaS Enterprise AE 1 month

    3. 3

      Build the integration

      Resident record, policy status, lapse alerts.

      Backend Engineer, Carrier Integrations 1 quarter

    4. 4

      Certify and list

      Marketplace listing and docs.

      Backend Engineer, Carrier Integrations 1 month

    5. 5

      Launch with one customer

      Joint case study.

      Customer and Partner Marketing Manager 1 month

    6. 6

      Repeat for the next system

      Reuse the data model.

      Backend Engineer, Carrier Integrations 1 quarter

    Who to approach

    • AppFolio

      Property management software with a partner ecosystem.

    • Entrata

      Multifamily property management platform.

    • Yardi

      Property management and investment software.

    First result
    1 year
    Cost
    Partner fees and engineering
    Owner
    Real Estate SaaS Enterprise AE

    Smallest test

    Build a CSV import or export with one system before a full integration.

    Why it works

    Build one deep integration with a leading property management system, list it in that system's partner marketplace, and use it as the reference for the rest. Renters insurance compliance status shows up on the resident ledger.

    Integration listings are how property managers find vendors, and one built integration gives the Real Estate AE a demo that looks like the buyer's own screen.

    Risks and how to handle them

    • Partner program fees or delays

      Start where prospects concentrate and fees are lowest.

    Evidence

    • HiringReal Estate SaaS Enterprise Account Executive: the same enterprise new-business role, written for real estate software buyers, with the same hubs, travel, pilots, business cases and multi-year agreements; an Enterprise Account Management team takes over growth after the handoff.Source
    • Competitor researchAxle sells insurance verification and monitoring to rental car, loaner car, dealership sales, loan servicing and mortgage teams and has just added renters insurance "to instantly verify renters policies" for tenant onboarding. MeasureOne verifies insurance, income, employment and education data, with renters and homeowners insurance verification for lending, automotive and property. Covie offers policy Access and Monitor for tracking and enforcement.Source
    • Your websiteAgency pricing: Scratch $100 a month (30 Quote Points, 3 users), Elevate $250 (100 Quote Points, integrations into Applied Epic, EZLynx, PL Rating, AgencyZoom), Peak $500 (300 Quote Points); extra Quote Points $4, $3 or $2; 14-day free trial. Partner pages such as Big I Alliance offer members 12.5% off the first year.Source
    • Your websiteMortgage page: lenders verify a policy "in 30-seconds" from carrier data instead of weeks of documents, check Fannie Mae and lender requirements and edit the mortgagee; it works inside Encompass. Loan servicing: verify and monitor home and auto insurance and update lienholders and mortgagee clauses "in less than a minute".Source

Wildcards 3

Unexpected experiments, each with a cheap way to test it.

  • 19

    Insurance checks bunch up: dealer month-end and model-year changeovers, peak move-in season for apartments, rental fleets before summer travel, and mortgage rate drops that bring a refinance rush. The SDR job already asks reps to watch for reasons to reach out.

    Medium impactLow effort First result in 1 month GTM Associate

    First action

    Write the peak calendar for automotive, real estate and lending.

    How to measure it

    Reply rate on timed outreach

    Now
    –
    Target
    2x untimed
    By
    1 quarter

    Steps

    1. 1

      Write the calendar

      Peaks per vertical and month.

      GTM Associate 1 day

    2. 2

      Write one message per peak

      With the cost of the peak in staff time.

      Customer and Partner Marketing Manager 1 day

    3. 3

      Schedule sequences

      Four weeks before each peak.

      GTM Associate 2 hours

    4. 4

      Set rate alerts

      For lending accounts.

      GTM Associate 1 hour

    5. 5

      Compare results

      Timed vs evergreen sequences.

      GTM Associate Monthly

    6. 6

      Share with marketing

      Best messages become ads and posts.

      Customer and Partner Marketing Manager Monthly

    First result
    1 month
    Cost
    $0
    Owner
    GTM Associate

    Smallest test

    Run one move-in season sequence to 50 property managers.

    Why it works

    A calendar of these peaks per vertical, with outreach timed a few weeks before each ("move-in season starts in May; here is how much staff time verifying renters insurance costs"), plus alerts on rate moves for lenders.

    Buyers act when the pain is about to arrive, and a well-timed message reads as insight rather than a cold pitch.

    Risks and how to handle them

    • Peaks vary by region

      Adjust per territory.

    Evidence

    • HiringGTM Associate: "the first members of our SDR team", selling to insurance agencies by email, phone and social; strong cold calling, HubSpot, LinkedIn, Loom and Gong; competitive analysis; watching job changes, funding rounds and conferences for reasons to reach out; OTE $70K to $100K; SDRs are expected to move into closing roles quickly.Source
    • Your websiteROI calculator: "customers report 30 to 50% higher close rates and 30+ minutes saved per quote". Car rental page: most rental companies "simply ask if the customer has insurance"; few verify it. Driver compliance page: manual verification takes 30 minutes on average.Source
    • Your websiteMortgage page: lenders verify a policy "in 30-seconds" from carrier data instead of weeks of documents, check Fannie Mae and lender requirements and edit the mortgagee; it works inside Encompass. Loan servicing: verify and monitor home and auto insurance and update lienholders and mortgagee clauses "in less than a minute".Source
    • HiringReal Estate SaaS Enterprise Account Executive: the same enterprise new-business role, written for real estate software buyers, with the same hubs, travel, pilots, business cases and multi-year agreements; an Enterprise Account Management team takes over growth after the handoff.Source
  • 20

    Canopy has 224 YouTube videos, a TikTok and Instagram account, and a Facebook group of agents called the Canopy Connectors, but views are modest (435 YouTube subscribers). Agents trust other agents, and many already make short videos for their own marketing.

    Medium impactLow effort First result in 1 month Customer and Partner Marketin…

    First action

    Post the first challenge in the Canopy Connectors group with a prize.

    How to measure it

    Agent clips

    Now
    –
    Target
    20 a month
    By
    3 months

    Steps

    1. 1

      Write the brief

      Thirty seconds, real lead, link sent.

      Customer and Partner Marketing Manager 1 hour

    2. 2

      Set the prize

      Quote Points and a feature.

      Customer and Partner Marketing Manager 30 minutes

    3. 3

      Launch in the group

      With an example clip.

      Customer and Partner Marketing Manager 1 day

    4. 4

      Collect permissions

      Release for reuse.

      Customer and Partner Marketing Manager Ongoing

    5. 5

      Publish the best

      TikTok, Instagram, YouTube Shorts.

      Customer and Partner Marketing Manager Weekly

    6. 6

      Give clips to SDRs

      For Loom follow-ups.

      GTM Associate Weekly

    First result
    1 month
    Cost
    Prizes
    Owner
    Customer and Partner Marketing Manager

    Smallest test

    Run one month with one prize.

    Why it works

    A monthly challenge in the group: agents post a 30-second clip of how they send their Canopy link to a new lead; the best get Quote Points and a feature on Canopy's channels. Clips become ads and SDR follow-ups.

    Peer clips are more credible than vendor videos and cost almost nothing; they also give the SDRs proof to send.

    Risks and how to handle them

    • Clients' personal data shown

      Require dummy data in every clip.

    Evidence

    • programmable.infoSite scan: Webflow with Google Tag Manager and HubSpot; no live chat; SOC 2; YouTube channel with 224 videos, 435 subscribers and about 587,000 views; a Facebook community called the Canopy Connectors; a podcast, Connected Conversations in Insurance, hosted by the VP of Marketing and the Customer and Partner Marketing Manager; an "AI information" page written for chatbots, last updated April 10, 2026. A year ago the site showed one "Enterprise" plan from $99.Source
    • Your websiteBlog, September 2026: "Send the link before you say hello", on agents putting their Canopy link in the first reply because "internet leads cool off fast"; "The real cost of good enough insurance data" names agencies, lenders, rental companies and compliance teams as the buyers.Source
    • Your websiteHomepage: "Collect Verified Insurance Information in Seconds"; "Trusted by 6,000 Agencies, Networks, Insurtechs and Lenders"; Trailhead branded intake pages and Sharing Paths; a link sent by text, email or QR or a widget on the site; 500+ insurance data fields by API; solutions for agencies, carriers, marketplaces, auto finance, mortgage, loan servicing, dealerships, rental cars, fleets, rideshare and employers. The navigation names "A few of our 24,000 users".Source
  • 21

    Canopy already wrote an AI information page for chatbots, which few companies do. The next step is the questions buyers ask assistants: how dealers verify insurance, how landlords check renters insurance, how lenders confirm a mortgagee clause.

    Medium impactLow effort First result in 2 months VP of Marketing

    First action

    List the ten questions from sales calls and support tickets.

    How to measure it

    Visits from AI assistants

    Now
    –
    Target
    500 a month
    By
    6 months

    Steps

    1. 1

      Collect the questions

      From Gong calls and the help center.

      GTM Associate 1 day

    2. 2

      Write the answers

      Short, factual, sourced.

      VP of Marketing 1 week

    3. 3

      Publish as a hub

      Linked from the AI page.

      VP of Marketing 1 day

    4. 4

      Add FAQ markup

      For each page.

      VP of Marketing 2 hours

    5. 5

      Test in assistants

      Ask the ten questions monthly.

      VP of Marketing 1 hour a month

    6. 6

      Track referrers

      AI assistant traffic in analytics.

      VP of Marketing Monthly

    First result
    2 months
    Cost
    $0
    Owner
    VP of Marketing

    Smallest test

    Write two answers and ask three assistants the questions after a month.

    Why it works

    Write ten short, factual answer pages on those questions (process, rules, what to check, how long it takes), each citing official sources and showing Canopy as one way to do it, and link them from the AI page.

    Assistants cite clear, factual pages. Being the cited source for the process question puts Canopy in front of buyers before they search for vendors.

    Risks and how to handle them

    • Answers read as ads

      Lead with the process; mention Canopy once.

    Evidence

    • programmable.infoSite scan: Webflow with Google Tag Manager and HubSpot; no live chat; SOC 2; YouTube channel with 224 videos, 435 subscribers and about 587,000 views; a Facebook community called the Canopy Connectors; a podcast, Connected Conversations in Insurance, hosted by the VP of Marketing and the Customer and Partner Marketing Manager; an "AI information" page written for chatbots, last updated April 10, 2026. A year ago the site showed one "Enterprise" plan from $99.Source
    • Your websiteDealerships page: dealers risk "fines for releasing uninsured vehicles" and liability for accidents; 400 carrier integrations covering more than 95% of the market; "96% Auto Insurance Market Coverage", "5.6 Seconds to Transfer Policy Data", "10M Policies Shared", "6,000 Business Use Canopy Connect"; Cox Automotive Ecommerce is the featured integration; cross-selling insurance is pitched as new revenue.Source
    • Your websiteMortgage page: lenders verify a policy "in 30-seconds" from carrier data instead of weeks of documents, check Fannie Mae and lender requirements and edit the mortgagee; it works inside Encompass. Loan servicing: verify and monitor home and auto insurance and update lienholders and mortgagee clauses "in less than a minute".Source
    • Your websiteROI calculator: "customers report 30 to 50% higher close rates and 30+ minutes saved per quote". Car rental page: most rental companies "simply ask if the customer has insurance"; few verify it. Driver compliance page: manual verification takes 30 minutes on average.Source

03

How Programmable can help

Where an idea in this playbook is something Programmable builds or runs, it's listed here with what we'd do. Everything else is yours to run.

Have it built

ProgrammableAgency

2 of the 21 ideas are things Programmable builds and runs for its customers: pages, outreach, prospect lists, booking flows and monitors. Pick one, or send the whole list.

Outreach1The sequence sent for you: addresses found and verified, replies routed to your CRM.

Prospect lists1The list compiled from public sources, verified, deduplicated and delivered to your CRM.

A 30-minute session with the engineer who would build it, not a sales call. You leave with a plan whether or not you hire us.

Book a working session

Usually live within days.

Tools for the rest

ProgrammableDigital

Show it, don't just describe it

These ideas need something to show: a demo, a video, an animation, graphics or a deck. Digital turns screenshots or the site into all of them, in the company's own brand.

Make a demo (opens programmable.digital in a new tab)
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See every playbook and website review

Independent research. Programmable wrote this playbook from public sources, as they stood on October 18, 2026, and cites them throughout. Canopy Connect did not commission, review or endorse it, and Programmable is not affiliated with Canopy Connect. Company and product names are trademarks of their owners, used only to identify them. The ideas are suggestions and opinion, not professional, legal or financial advice, and not statements about how Canopy Connect runs its business.

Something wrong, or do you represent Canopy Connect? Email [email protected] and we will correct it or take it down.

30/60/90 roadmap

What to focus on in each month, and the ideas that carry it.

  1. Days 1 to 308 ideas

    The real estate page, the security packet, the automotive business case, the SDR network list, consistent proof numbers and fast demo replies; start the platform list and the sandbox path.

    Programmable can ship 2 of these in days.

  2. Days 31 to 6010 ideas

    The real estate pilot, carrier and comparison pages, the podcast season, agency referrals, the event plan, monitoring, and the three wildcards.

  3. Days 61 to 903 ideas

    Decide the big bets on the first pipeline: the reusable consumer profile, OEM programs and property management integrations.

The research behind the plan

3 research areas, each summarised in a few lines. Open any of them for the full detail.

Customers

What customers say

Customers value verified policy data in seconds instead of chasing documents. The most cited problem: clients cannot find or share proof of insurance.

  • Fewer manual steps for agents, dealers and lenders
  • Manual verification takes about 30 minutes and can be forged
  • In their words: “verified insurance information”

Market

Competitive landscape

4 competitors compared: Axle, MeasureOne, Covie and Manual verification.

  • Gap to exploit: Insurance checks inside property management software
  • Axle: No agency product or agency community
  • MeasureOne: Insurance is one of several products

Hiring signals

Canopy is hiring for an enterprise push: two enterprise AEs (automotive software and real estate software) reporting to a Head of GTM, with business cases, pilots and security reviews in the job (ideas 1, 2, 3, 7, 8…

  • Automotive SaaS Enterprise Account Executive: Six-figure, multi-year platform deals in automotive, with business cases and pilots. Ideas 2, 3, 7…
  • Real Estate SaaS Enterprise Account Executive: A new vertical with no page on the site yet. Ideas 1, 2, 8, 18.
  • GTM Associate (first SDR team): Cold calling insurance agencies, competitive analysis, watching for reasons to reach out. Ideas 4, 10, 19.

From the team that wrote this playbook

All products
  • ProgrammableAgencyWorking AI systems in days, not quarters (opens programmable.agency in a new tab)
  • ProgrammableInfoAn agent that finds, researches and asks first (opens programmable.info in a new tab)
  • ProgrammableDigitalScreenshots in, an animated product demo out (opens programmable.digital in a new tab)
  • ProgrammableWatchKnow the day a supplier falls out of compliance (opens programmable.watch in a new tab)
  • ProgrammableTalkGet registrants for your events, and know who’s coming (opens programmable.talk in a new tab)
  • ProgrammablePageText what you need, your customer gets a page that works (opens programmable.page in a new tab)
  • ProgrammableCommunityForums with labelled AI members, never empty (opens programmable.community in a new tab)
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