growth playbook · Oct 18, 2026

Hospitable growth playbook

Hospitable is hiring two kinds of sellers. On the software side, an AE, an SDR for mid-market and enterprise managers, and a Customer Success Manager with a revenue quota show a push upmarket and deeper into the base. On the insurance side, a Sales Manager and an AE for Align, its own licensed brokerage, show a bet that insurance becomes a second business, sold to the 25,000 customers "from day one" and then to the open market.

Add a first CFO and a first Head of Design, and the picture is a profitable company getting ready to scale. The strongest move is to join the two sides: offer cover at the moments the software sees (a new property, a damage alert, a rule change, a closing), make insurance a front door for new customers, and use the data Hospitable holds to pay claims faster than anyone.

Alongside that, the playbook gives the software sellers a migration service, a mid-market list, an upgrade story built on Hospitable's own research and conference meetings booked in advance.

Growth Score

Biggest Opportunity

Turn Align into the reason hosts choose Hospitable: insurance offered at the exact moments the software sees, sold beyond the customer base, and backed by a claims promise only a company with the reservation data can make.

Biggest Risk

Insurance is regulated state by state and depends on carriers; a misstep in referral rules, default options or claim handling could damage trust in the software too.

Start here

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

A free 24-hour policy review for the 25,000 customers: upload your declarations page, get your gaps back
Write the gap report template against the four Align components.
High impact First result in 3 weeks
An annual-plan campaign for monthly customers after their third paid month
Build the list of monthly customers past their third paid month.
High impact First result in 2 weeks
Ask for an App Store rating right after a host gets a five-star guest review
Find the event that fires when a five-star guest review syncs.
Medium impact First result in 1 month

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.

7 ideas are marked Unexpected: plays you are unlikely to have tried.
3 of these are things Programmable can build and run for you.

This week 6

Quick wins with a clear first action.

The insurance team is told to sell to the existing base "from day one", but "do you want insurance?" is a weak opener. A host who uploads their current policy and gets back a list of gaps (no short-term rental endorsement, no liability for co-hosts, no guest damage layer) has a concrete reason to talk.
High impactLow effort First result in 3 weeks Sales Manager
First action
Write the gap report template against the four Align components.
How to measure it
Policy reviews requested
Now
–
Target
400
By
45 days
Steps
Write the template
Owner's, guest damage, entity, trip insurance, co-host liability: covered, gap, or unknown.
Sales Manager, Insurance Technology 3 hours
Set up the upload
A secure upload form tied to the host's account.
Staff Product Manager 2 days
Write the email
One paragraph, one button, plain about what happens to the document.
Sales Manager, Insurance Technology 1 hour
Add the dashboard banner
In the property protection dashboard for hosts with no Align policy.
Staff Product Manager 1 day
Staff the reviews
Producers return reports within 24 hours.
Account Executive, Insurance Tech ongoing
Book calls on real gaps
Only where the report shows a gap worth fixing.
Account Executive, Insurance Tech ongoing
Track outcomes
Reviews, calls, quotes and bound policies in the pipeline.
Sales Manager, Insurance Technology weekly
First result
3 weeks
Cost
Producer time
Owner
Sales Manager, Insurance Technology
Smallest test
Offer the review to 500 hosts with three or more properties and count uploads in a week.
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
Ready to use
EmailPolicy review email
Risks and how to handle them
Evidence
Annual conversions are named in the Customer Success Manager's quota, and annual billing already saves 12%. Customers who have paid three months in a row have shown they are staying, which is the right moment to ask.
High impactLow effort First result in 2 weeks Customer Success Manager
First action
Build the list of monthly customers past their third paid month.
How to measure it
Monthly customers moved to annual
Now
–
Target
8% of the list
By
60 days
Steps
Build the list
Monthly, three or more paid months, no failed payments.
Customer Success Manager 2 hours
Rank by size
Most properties first.
Customer Success Manager 1 hour
Write the offer
Save 12% plus a setup review.
Customer Success Manager 1 hour
Send in-app and email
Through Intercom.
Customer Success Manager 2 hours
Call the top 100
Personal calls to the largest accounts.
Customer Success Manager 2 weeks
Log upgrades found
Note upgrade or Align chances from each review.
Customer Success Manager ongoing
First result
2 weeks
Cost
$0
Owner
Customer Success Manager
Smallest test
Send the offer to 10% of the list first and compare with a holdout group.
Why it works
Risks and how to handle them
Evidence
The iOS app sits at 3.08 from 112 ratings while G2 and Capterra rate Hospitable highly. Unhappy users rate apps unprompted; happy ones are rarely asked. The best moment to ask a host is when something good just happened.
Medium impactLow effort First result in 1 month Staff Product Manager
First action
Find the event that fires when a five-star guest review syncs.
How to measure it
iOS App Store rating
Now
–
Target
4.3 or higher
By
90 days
Steps
Find the trigger
The five-star review sync event.
Staff Product Manager 2 hours
Add the prompt
Apple's native review request, once per period.
Staff Product Manager 1 day
Add the web ask
A small card linking to G2 or Trustpilot.
Staff Product Manager 1 day
Exclude bad moments
No prompt within a week of a support ticket or failed sync.
Staff Product Manager 2 hours
Design the moment
A short celebration of the guest review first.
Head of Design 1 day
Track the rating
Weekly rating and count.
Staff Product Manager weekly
First result
1 month
Cost
$0
Owner
Staff Product Manager
Smallest test
Turn it on for 20% of iOS users and compare new ratings with the rest.
Why it works
Risks and how to handle them
Evidence
Hospitable now sells insurance and handles payouts, deposits and tax remittance. Its search description still says "Best vacation rental software in 2024 and 2025", and the site scores F on Mozilla Observatory, while a SOC 2 trust center sits unused in the footer.
Medium impactLow effort First result in 1 week Staff Product Manager
First action
Rewrite the homepage meta description.
How to measure it
Mozilla Observatory grade
Now
–
Target
B or better
By
2 weeks
Steps
Rewrite the meta
Title and description without year claims.
Staff Product Manager 1 hour
Audit other years
Find other pages that still say 2024 or 2025.
Staff Product Manager 2 hours
Set headers
Cloudflare transform rules, CSP in report-only first.
Staff Product Manager 1 day
Test the site
Intercom, HubSpot, Segment and Framer still work.
Staff Product Manager 3 hours
Enforce and rescan
Record the new grade.
Staff Product Manager 30 minutes
Link the trust center
From pricing, Align and direct booking pages.
Staff Product Manager 1 hour
First result
1 week
Cost
$0
Owner
Staff Product Manager
Smallest test
Change the meta description alone and watch search click-through for two weeks.
Why it works
Risks and how to handle them
Evidence
The SDR is asked to reach prospects "before and after industry conferences using targeted lists" and to book meetings for Mid-Market and Enterprise AEs. Conference floors are crowded with property management software booths; meetings booked in advance are where the deals come from.
High impactLow effort First result in 3 weeks Sales Development Representat…
First action
Choose the next two conferences and the AEs attending.
How to measure it
Pre-booked meetings held per conference
Now
–
Target
20
By
next conference
Steps
Pick the events
Next two regional or national STR conferences.
Sales Development Representative 1 hour
Build the list
Attendees, exhibitors and local property managers with 20+ listings, via Clay.
Sales Development Representative 2 days
Write the sequence
Email, LinkedIn and call around the switching session.
Sales Development Representative 3 hours
Book the slots
AE calendars for the event days.
Sales Development Representative 1 week
Confirm
SMS two days before.
Sales Development Representative 1 hour
Follow up
Within 24 hours with a migration plan.
Account Executive 2 days
First result
3 weeks
Cost
Conference costs already budgeted
Owner
Sales Development Representative
Smallest test
Invite 100 managers for the next event and count bookings.
Why it works
Risks and how to handle them
Evidence
Hospitable runs public Town Halls on YouTube every two weeks, where customers ask questions and hear the roadmap. That is rare in this market: a live, unscripted look at the company that prospects can attend.
Medium impactLow effort First result in 1 month Sales Development Representat…
First action
Add a registration link that captures email for the next Town Hall.
How to measure it
Prospects attending per Town Hall
Now
–
Target
40
By
60 days
Steps
Add registration
A form for the next Town Hall that captures email and property count.
Sales Development Representative 2 hours
Invite trials and deals
Trial users and open opportunities.
Sales Development Representative 2 hours
Add the newcomer segment
Ten minutes at the end for first-timers.
Founder & CEO 1 hour
Log attendance
Match attendees to HubSpot.
Sales Development Representative 1 hour
Hand off
Attendees with 20+ properties go to an AE the same day.
Sales Development Representative per Town Hall
Clip highlights
Short clips for sequences and social.
Sales Development Representative 2 hours
First result
1 month
Cost
$0
Owner
Sales Development Representative
Smallest test
Invite 50 trial users to one Town Hall and compare their conversion with other trials.
Why it works
Risks and how to handle them
Evidence

This quarter 9

The core plays for the next three months.

Insurance is "built into the core Hospitable product", but a host only thinks about cover at certain moments: when they add a property (a new policy is needed) and when something goes wrong (guest damage). Hospitable sees both events as they happen.
High impactMedium effort First result in 2 months Staff Product Manager
First action
Count how many properties are connected each week and how many guest issue alerts fire.
How to measure it
Quotes started from triggers
Now
–
Target
300 a month
By
1 quarter
Steps
Size the moments
Weekly new properties and guest issue alerts.
Staff Product Manager 1 day
Design the cards
Short, specific to the property, easy to dismiss.
Head of Design 1 week
Build the new-property trigger
Card after a listing connects.
Staff Product Manager 2 weeks
Build the damage trigger
Card after a guest issue alert.
Staff Product Manager 2 weeks
Prefill the application
Property details passed to Align.
Staff Product Manager 1 week
Route to producers
Quote requests to the insurance team with context.
Sales Manager, Insurance Technology 1 day
Measure
Views, quotes, bound policies.
Sales Manager, Insurance Technology weekly
First result
2 months
Cost
Product and design time
Owner
Staff Product Manager
Smallest test
Ship the new-property card first to 20% of accounts and measure quote starts.
Why it works
Risks and how to handle them
Evidence
The SDR books meetings for Mid-Market and Enterprise AEs and already uses Clay. Property managers show their portfolio size in public: host profiles list how many listings they run and their own websites show their properties.
High impactMedium effort First result in 1 quarter Sales Development Representat…
First action
Build a test list of 200 managers in three markets.
How to measure it
Meetings with 20-200-listing managers
Now
–
Target
60 a quarter
By
1 quarter
Steps
Define the segment
US, 20 to 200 listings, professional managers.
Sales Development Representative 1 hour
Build the list
Public listing counts and websites, enriched in Clay.
Sales Development Representative 1 week
Detect current software
Booking engine and PMS signals on their sites.
Sales Development Representative 3 days
Write per-competitor sequences
Guesty, Hostaway, OwnerRez, Lodgify.
Sales Development Representative 3 days
Run the cadence
Calls, email, SMS and LinkedIn over three weeks.
Sales Development Representative ongoing
Hand off
Booked meetings to AEs with the switching notes.
Sales Development Representative ongoing
Review
Reply and meeting rate by competitor.
Sales Development Representative monthly
First result
1 quarter
Cost
Clay credits
Owner
Sales Development Representative
Smallest test
Run one sequence for Guesty Pro users in one market and compare reply rates.
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
Risks and how to handle them
Evidence
Hospitable has 28 comparison pages arguing it is better, but switching software is the real barrier for a manager with 50 properties: calendars, message templates, owner statements and team settings. A comparison page cannot move those.
High impactMedium effort First result in 2 months Account Executive
First action
Write the migration checklist for one competitor.
How to measure it
Accounts switched with the migration service
Now
–
Target
40
By
1 quarter
Steps
Write checklists
One per competitor: what moves and how.
Account Executive 1 week
Set the threshold
Property count where the service is free.
Account Executive 1 hour
Staff it
Onboarding specialists with a runbook.
Customer Success Manager 2 weeks
Add to comparison pages
A migration section and booking link.
Account Executive 1 day
Add to proposals
Migration plan in every mid-market proposal.
Account Executive ongoing
Collect stories
A short case study from each of the first five.
Customer Success Manager ongoing
Who to approach
Guesty
Largest brand; Lite-to-Pro is a product switch.
Hostaway
Popular with growing managers.
OwnerRez
Strong with direct-booking owners.
First result
2 months
Cost
Onboarding staff time
Owner
Account Executive
Smallest test
Offer free migration in five open deals and track close rates.
Why it works
Risks and how to handle them
Evidence
Hospitable's own report found up to 99% of searches never convert, and the Professional plan includes the direct booking website, Google Vacation Rentals and installment payments. The CSM is measured on upgrades and feature adoption, including Direct Booking.
High impactMedium effort First result in 1 quarter Customer Success Manager
First action
Check which listing metrics are available per host to fill the report.
How to measure it
Host-plan customers upgraded
Now
–
Target
6% of the segment
By
1 quarter
Steps
Define the segment
Host plan, three or more properties, strong reviews.
Customer Success Manager 2 hours
Build the report
Views, booking rate and direct-booking potential per host.
Staff Product Manager 2 weeks
Write the campaign
Email and in-app with the report.
Customer Success Manager 1 day
Offer setup calls
The site goes live on the call.
Customer Success Manager ongoing
Track upgrades
By segment and source.
Customer Success Manager weekly
Share wins
Turn the best results into success stories.
Customer Success Manager monthly
First result
1 quarter
Cost
$0
Owner
Customer Success Manager
Smallest test
Send the report to 200 hosts and compare upgrades with a holdout.
Why it works
Risks and how to handle them
Evidence
Hospitable already publishes an industry report and a Q3 2026 Pulse report, with data from millions of listings. National reports get one news cycle; city-level numbers get local press, and property managers share data about their own market.
High impactMedium effort First result in 1 quarter Founder & CEO
First action
Check whether the Pulse data can be cut by city with enough volume.
How to measure it
Referring domains to city pages
Now
–
Target
150
By
2 quarters
Steps
Check data volume
Markets with enough listings to publish.
Staff Product Manager 1 week
Design the city template
Four charts and three takeaways.
Head of Design 1 week
Generate 50 pages
From the data, reviewed by a person.
Staff Product Manager 2 weeks
Write the national story
Headline findings for the quarter.
Founder & CEO 1 week
Pitch local press
Each city's page to its local reporters.
Founder & CEO 2 weeks
Add the badge
An embeddable "my market" card for managers.
Staff Product Manager 1 week
First result
1 quarter
Cost
About $5,000 a quarter in PR time
Owner
Founder & CEO
Smallest test
Publish five city pages and pitch each to two local reporters.
Why it works
Risks and how to handle them
Evidence
Hospitable already maintains guides to Airbnb regulations by state and city, and Align sells entity setup and liability cover. When a city changes its rules (permits, caps, taxes), hosts there need to act and need to know their exposure.
Medium impactMedium effort First result in 2 months Staff Product Manager
First action
List the 20 cities where most customers' properties are.
How to measure it
Hosts subscribed to rule alerts
Now
–
Target
5,000
By
1 quarter
Steps
Pick the cities
Top 20 by customer properties.
Staff Product Manager 1 day
Set up monitoring
Council agendas and news for each city.
Staff Product Manager 1 week
Build opt-in
Automatic by property address, one click to confirm.
Staff Product Manager 1 week
Write alert templates
What changed, what to do, by when.
Staff Product Manager 2 days
Add the Align step
Only where entity or cover is affected.
Sales Manager, Insurance Technology 1 day
Update the guides
Keep regulation pages current from the same work.
Staff Product Manager ongoing
First result
2 months
Cost
Monitoring time, about one day a week
Owner
Staff Product Manager
Smallest test
Send one manual alert to hosts in a city with a recent change and measure opens.
Why it works
Risks and how to handle them
Evidence
Mogul includes a Property Manager Marketplace, and Align also sells co-host and property manager liability insurance. A manager taking on new owners through the marketplace is taking on new liability at that moment.
High impactMedium effort First result in 1 quarter Sales Manager
First action
Count the managers in the marketplace and how many have Align policies.
How to measure it
Marketplace managers with Align liability
Now
–
Target
25%
By
2 quarters
Steps
Count the managers
Marketplace listings and current Align policies.
Sales Manager, Insurance Technology 2 hours
Design the badge
Simple, verified by Align.
Head of Design 3 days
Offer the review
Email and in-app to every marketplace manager.
Sales Manager, Insurance Technology 1 week
Run quotes
Producers quote liability for interested managers.
Account Executive, Insurance Tech ongoing
Show the badge to owners
On marketplace profiles and search.
Staff Product Manager 1 week
Measure
Policies sold and owner enquiries for badged managers.
Sales Manager, Insurance Technology monthly
First result
1 quarter
Cost
Design and product time
Owner
Sales Manager, Insurance Technology
Smallest test
Offer reviews to 50 marketplace managers and count quotes.
Why it works
Risks and how to handle them
Evidence
The insurance AE works leads from "Hospitable's real estate investor network". The moment an investor needs owner's insurance is the purchase of a property, which runs through a lender (often a DSCR lender) and an agent who specialises in rental investors, not through property software.
High impactMedium effort First result in 1 quarter Sales Manager
First action
List 20 STR-focused lenders and agent teams and the insurance requirements they set at closing.
How to measure it
Partner-sourced quotes
Now
–
Target
150 a quarter
By
2 quarters
Steps
Build the list
STR lenders and investor agent teams.
Sales Manager, Insurance Technology 1 week
Learn their requirements
What a policy needs to close a loan.
Account Executive, Insurance Tech 1 week
Build the partner link
A quote link that tags the partner.
Staff Product Manager 1 week
Write the offer
Quote before closing, Hospitable after.
Sales Manager, Insurance Technology 2 days
Sign first partners
Five partners in the first month.
Sales Manager, Insurance Technology 1 month
Report to partners
Quote status for their clients.
Account Executive, Insurance Tech ongoing
First result
1 quarter
Cost
Partner management time
Owner
Sales Manager, Insurance Technology
Smallest test
Ask three lenders to send their next five closings and count bound policies.
Build the monitor. A live page fed by the public registries and re-checked every day. Usually live within days.
Book a working session
Why it works
Risks and how to handle them
Evidence
Entity setup is one of Align's four components and the Sales Manager is asked to start with "getting their business entities set up right". Hosts search for this and rarely get a straight answer. The AE post also asks reps to run webinars.
Medium impactLow effort First result in 6 weeks Account Executive
First action
Book the first guest and set the date.
How to measure it
Entity checks booked per webinar
Now
–
Target
30
By
3 months
Steps
Book the guest
A tax or legal professional who works with STR owners.
Account Executive, Insurance Tech 1 week
Write the outline
Structures, lenders, insurers, mistakes.
Account Executive, Insurance Tech 2 days
Promote
Email, YouTube, community and Town Halls.
Account Executive, Insurance Tech 1 week
Run it
Live with questions.
Account Executive, Insurance Tech monthly
Publish the recording
YouTube with chapters.
Account Executive, Insurance Tech 1 day
Follow up
Entity and coverage checks for attendees.
Account Executive, Insurance Tech ongoing
First result
6 weeks
Cost
Guest fee if any
Owner
Account Executive, Insurance Tech
Smallest test
Run one session and count checks booked.
Why it works
Risks and how to handle them
Evidence

Big bets 3

Larger plays that can change the trajectory.

Free-plan hosts can already earn trip insurance commissions (US only), and Professional includes a direct booking website. Guests often skip protection on OTAs, and Hospitable's own report says long stays booked far ahead carry the highest cancellation risk.
High impactHigh effort First result in 2 quarters Staff Product Manager
First action
Check state rules on pre-selected trip insurance and the carrier's requirements.
How to measure it
Direct bookings with trip insurance
Now
–
Target
25%
By
2 quarters
Steps
Check the rules
State regulations and carrier terms for default options.
Sales Manager, Insurance Technology 1 month
Design checkout
Clear price, easy opt-out, plain wording.
Head of Design 2 weeks
Build it
Checkout option and OTA post-booking message.
Staff Product Manager 1 month
Show host earnings
A monthly earnings card.
Staff Product Manager 2 weeks
Pilot
A group of direct-booking hosts.
Staff Product Manager 1 month
Roll out
All eligible hosts with an opt-out for the host.
Staff Product Manager 1 month
First result
2 quarters
Cost
Product time and compliance review
Owner
Staff Product Manager
Smallest test
Test a prominent unselected option with 100 direct-booking hosts first.
Why it works
Risks and how to handle them
Evidence
The Sales Manager is told to target "the broader market" beyond the 25,000 customers. Most US short-term rental owners do not use Hospitable, but all of them need owner's insurance, and Align already shops one application across carriers.
High impactHigh effort First result in 2 quarters Sales Manager
First action
Design the minimum quote flow that carriers accept without an account.
How to measure it
Policies bound for non-Hospitable owners
Now
–
Target
1,000
By
2 quarters
Steps
Design the flow
Address, property, channels, coverage.
Staff Product Manager 1 month
Carrier review
Confirm the flow meets carrier needs.
Sales Manager, Insurance Technology 1 month
Build it
Standalone pages on the Align site.
Staff Product Manager 2 months
Write state pages
One per top-20 state.
Account Executive, Insurance Tech 1 month
Staff producers
Scale the team for open-market volume.
Sales Manager, Insurance Technology ongoing
Offer Hospitable
Free connection after a policy binds.
Customer Success Manager ongoing
Who to approach
Proper Insurance
Specialist short-term rental insurer.
Steadily
Landlord and STR insurance online.
First result
2 quarters
Cost
Product build plus producer headcount
Owner
Sales Manager, Insurance Technology
Smallest test
Run a landing page with a callback form in two states and count requests.
Why it works
Risks and how to handle them
Evidence
The Pulse report asks "who ends up paying when something goes wrong", and the Align page says relying on the OTA claims process means delays. Hospitable holds the reservation, the messages and often the smart lock data, which is the evidence a claim needs.
High impactHigh effort First result in 2 quarters Staff Product Manager
First action
Measure today's average time from claim to decision.
How to measure it
Average days to claim decision
Now
–
Target
under 5
By
2 quarters
Steps
Measure today
Current time from claim to decision.
Sales Manager, Insurance Technology 1 week
Map the evidence
Which product data a claim needs.
Staff Product Manager 2 weeks
Build the claim pack
Automatic evidence bundle from the reservation.
Staff Product Manager 2 months
Agree terms with carriers
The guarantee window and process.
Sales Manager, Insurance Technology 1 month
Launch the promise
In product, on the Align page and in sales.
Sales Manager, Insurance Technology 2 weeks
Publish results
Average decision time every quarter.
Sales Manager, Insurance Technology quarterly
First result
2 quarters
Cost
Product build and carrier negotiation
Owner
Staff Product Manager
Smallest test
Build the evidence pack by hand for the next 20 claims and measure the time saved.
Why it works
Risks and how to handle them
Evidence

Wildcards 3

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

The Host plan already includes "Running the business through agents with MCP", and the Pulse report says hosts are ready to hand AI more decisions than software allows. Hosts and the developers who serve them look for agent tools in MCP registries and AI client directories.
Medium impactLow effort First result in 1 month Staff Product Manager
First action
Check whether any rival property software is listed in MCP directories.
How to measure it
Trials attributed to MCP listings
Now
–
Target
200
By
90 days
Steps
Audit directories
Which STR tools are listed.
Staff Product Manager 2 hours
Write the listing
Capabilities, permissions and examples.
Staff Product Manager 1 day
Submit listings
Registry and AI client directories.
Staff Product Manager 1 day
Make the video
A real inbox handled by an agent with approvals.
Staff Product Manager 2 days
Tag signups
UTM per listing.
Staff Product Manager 1 hour
Collect feedback
From the first agent users.
Staff Product Manager ongoing
First result
1 month
Cost
$0
Owner
Staff Product Manager
Smallest test
List in one directory and count installs.
Why it works
Risks and how to handle them
Evidence
Hospitable pays affiliates $200 for every host they refer, including free-plan signups, and creators and coaches in the short-term rental world already send hosts to it. The insurance team needs warm leads, and these affiliates talk to hosts about running the business properly.
Medium impactLow effort First result in 1 month Sales Manager
First action
Check state rules on referral rewards for insurance and set the reward.
How to measure it
Affiliate-sourced policy reviews
Now
–
Target
100 a month
By
90 days
Steps
Check the rules
Permitted flat referral rewards by state.
Sales Manager, Insurance Technology 2 weeks
Set the reward
A flat amount per completed review.
Sales Manager, Insurance Technology 1 hour
Build the link
An affiliate-tagged review link.
Staff Product Manager 2 days
Write talking points
What a review is and is not.
Account Executive, Insurance Tech 1 day
Tell the top affiliates
Personal note to the 50 biggest.
Sales Manager, Insurance Technology 1 week
Track
Reviews, quotes and policies by affiliate.
Sales Manager, Insurance Technology monthly
First result
1 month
Cost
Flat rewards per review
Owner
Sales Manager, Insurance Technology
Smallest test
Offer it to ten affiliates for one month and count reviews.
Why it works
Risks and how to handle them
Evidence
Insurance has a trust problem: hosts expect claims to be slow and contested. The best proof that Align is different is a host whose claim was paid quickly, and that moment is rarely used.
Medium impactLow effort First result in 1 month Account Executive
First action
List the last ten quickly paid claims.
How to measure it
Claim stories published
Now
–
Target
10
By
90 days
Steps
List recent claims
Paid within target time.
Account Executive, Insurance Tech 2 hours
Write the ask
A short, grateful note.
Account Executive, Insurance Tech 1 hour
Send after payout
Automatic after each fast payout.
Staff Product Manager 2 days
Draft stories
For hosts who agree.
Account Executive, Insurance Tech ongoing
Add to the Align page
A "claims paid" section.
Sales Manager, Insurance Technology 1 day
Use in sales
Stories in insurance sequences.
Account Executive, Insurance Tech ongoing
First result
1 month
Cost
$0
Owner
Account Executive, Insurance Tech
Smallest test
Ask five recent claimants and see how many agree.
Why it works
Risks and how to handle them
Evidence

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

Agency

3 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.

Monitors1A live page fed by the public registries and re-checked every day.

Tools for the rest

Talk

Fill the events in this plan

These ideas are events. Talk gets registrants for them and tells you who's coming and what their company does before the day.

Plan an event

Other companies we have researched, each read from what they are hiring for.

See every playbook and website review

30/60/90 roadmap

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

Days 1 to 306 ideas
Policy reviews, annual conversions, rating prompts, trust fixes, conference meetings and Town Halls for prospects.
Programmable can ship 1 of these in days.
Days 31 to 607 ideas
In-product insurance triggers, the mid-market list, the migration service, the upgrade campaign, the entity webinar, MCP listings and affiliate reviews.
Days 61 to 908 ideas
City reports, rule alerts, marketplace liability, lender partners and claim stories; decide the big bets.

Hospitable growth playbook

Diagnosis

A free 24-hour policy review for the 25,000 customers: upload your declarations page, get your gaps back

An annual-plan campaign for monthly customers after their third paid month

Ask for an App Store rating right after a host gets a five-star guest review

This week 6

How to run it: A free 24-hour policy review for the 25,000 customers: upload your declarations page, get your gaps back

Steps

Why it works

Why it works

Ready to use

Risks and how to handle them

Risks and how to handle them

Evidence

Evidence

How to run it: An annual-plan campaign for monthly customers after their third paid month

Steps

Why it works

Why it works

Risks and how to handle them

Risks and how to handle them

Evidence

Evidence

How to run it: Ask for an App Store rating right after a host gets a five-star guest review

Steps

Why it works

Why it works

Risks and how to handle them

Risks and how to handle them

Evidence

Evidence

How to run it: Fix what a careful buyer sees first: a 2024 meta description and an F for security headers

Steps

Why it works

Why it works

Risks and how to handle them

Risks and how to handle them

Evidence

Evidence

How to run it: Pre-book meetings with property managers for the next two industry conferences

Steps

Why it works

Why it works

Risks and how to handle them

Risks and how to handle them

Evidence

Evidence

How to run it: Turn the public bi-weekly Town Halls into a sales signal and an invitation

Steps

Why it works

Why it works

Risks and how to handle them

Risks and how to handle them

Evidence

Evidence

This quarter 9

How to run it: Offer insurance at the two moments hosts need it: a new property connected and a guest damage alert

Steps

Why it works

Why it works

Risks and how to handle them

Risks and how to handle them

Evidence

Evidence

How to run it: A mid-market list of property managers with 20 to 200 listings, built from public listing data

Steps

Why it works

Why it works

Risks and how to handle them

Risks and how to handle them

Evidence

Evidence

How to run it: A done-for-you switch from Guesty, Hostaway or OwnerRez, finished in a day

Steps

Who to approach

Why it works

Why it works

Risks and how to handle them

Risks and how to handle them

Evidence