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  • The brief
  • Start here
  • Idea portfolio
  • Effort vs impact
  • This week · 6
  • This quarter · 9
  • Big bets · 3
  • Wildcards · 3
  • How we can help
Generated Oct 23, 2026
  1. Programmable
  2. Playbooks
  3. Leland
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growth playbook · Oct 23, 2026

joinleland.com (opens in a new tab)

Leland growth playbook

Diagnosis

Leland is a venture-backed coaching marketplace ($19M raised, 36,000+ reviews at 4.99) that is hiring to scale paid acquisition across Google, Meta and LinkedIn, to turn its content library into social, and to build B2B and university sales.

The biggest blocker for paid is speed: the MBA category page takes real visitors 7 seconds with a 4.4-second server response, and the site fails Core Web Vitals. Search also misses easy wins: 1,277 expert answers titled only with coach names and no review markup on category pages.

This playbook fixes speed, titles and proof first, then builds the clip machine, livestream follow-up, coach amplification, joined-up B2B tracking and lean paid landing pages, with bets on outcomes data, alumni-led team deals and a coach matcher.

Growth Score

7/10

Biggest Opportunity

Leland already owns the content (livestreams, expert answers, reviews) and the supply (2,466 coaches); making it fast, findable and shareable multiplies every paid dollar.

Biggest Risk

Scaling paid onto slow pages and a broad catalogue raises acquisition cost, while focused rivals (Aced, Maven, boutique admissions firms) win specific categories.

01

Start here

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

  1. 1

    Make the MBA page load before scaling paid: real visitors wait 7 seconds and the server takes 4.4

    Measure server time for /mba from three regions and check whether it is cached.

    High impact First result in 1 month
  2. 2

    Title the 1,277 expert answers with the question people search, not the coach's name

    Change the title template on posts with three or more answers.

    High impact First result in 1 month
  3. 3

    Show the 36,000 reviews in search results with review markup on category pages

    Calculate the rating and count for the top 10 categories.

    High impact First result in 1 month

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.

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

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 · 6Big bets · 8Fill-ins · 5Reconsider · 2
Effort →

Showing 21 of 21 ideas

This week 6

Quick wins with a clear first action.

  • 01

    Leland is hiring a Performance Marketing Manager to scale Google, Meta and LinkedIn and test landing pages. The category pages are where paid clicks land, and the biggest one, /mba, is slow for real visitors: Largest Contentful Paint 7.0 s, Time to First Byte 4.4 s and INP 777 ms, against Google's limits of 2.5 s, 0.8 s and 200 ms. The whole site fails Core Web Vitals and is 43% slower than before. Every paid click starts with several seconds of a blank or frozen page.

    High impactMedium effort First result in 1 month Performance Marketing Manager

    First action

    Measure server time for /mba from three regions and check whether it is cached.

    How to measure it

    LCP at the 75th percentile on /mba

    Now
    –
    Target
    Under 2.5 s
    By
    60 days

    Steps

    1. 1

      Measure

      Server time and cache status for the top 10 categories.

      Software Engineer 1 day

    2. 2

      Cache

      Edge caching with short revalidation.

      Software Engineer 1 week

    3. 3

      First screen

      Render the first consultants on the server.

      Software Engineer 1 week

    4. 4

      Defer

      Chat and ad tags after interaction.

      Software Engineer 2 days

    5. 5

      Lighter variant

      Paid landing version per category.

      Performance Marketing Manager 2 weeks

    6. 6

      Test

      Conversion and cost per booking against the full page.

      Performance Marketing Manager 4 weeks

    7. 7

      Watch

      Chrome UX Report monthly.

      Software Engineer monthly

    First result
    1 month
    Cost
    Engineering time
    Owner
    Performance Marketing Manager

    Smallest test

    Turn on edge caching for /mba and compare a week of field data.

    Why it works

    Cache the category pages at the edge (they change a few times a day, not per visitor), render the first screen of consultants on the server and load the full list, filters and livestream module after it. Defer chat and ad tags until the visitor interacts. Then build a lighter paid landing variant per category and test it against the full page.

    Speed is a conversion lever and a cost lever: Google Ads rates landing-page experience, and every second of delay loses mobile visitors before they see a coach.

    Ready to use

    ChecklistCategory page speed list

    [ ] Server time under 0.8 s from US regions
    [ ] Category pages cached at the edge
    [ ] First 6 consultants rendered on the server
    [ ] Filters and livestreams load after first paint
    [ ] Chat and ad tags deferred
    [ ] Hero media sized for mobile
    [ ] Paid landing variant per top category
    [ ] Conversions verified in Google, Meta and LinkedIn

    Risks and how to handle them

    • Stale prices or availability

      Revalidate every few minutes and on coach updates.

    • Tracking breaks when tags are deferred

      Check conversions in each ad platform before and after.

    Evidence

    • Google PageSpeedMBA Admissions page (/mba), mobile, tested October 22, 2026: performance 29/100, lab LCP 10.0 s, Total Blocking Time 3,030 ms, 5.2 MB. Real visitors to this page: LCP 7.0 s, INP 777 ms, First Contentful Paint 6.0 s and Time to First Byte 4.4 s (Google's "good" limits are 2.5 s, 200 ms, 1.8 s and 0.8 s). The page lists admissions consultants from $85 to $399 an hour with ratings and free intro calls.Source
    • Google PageSpeedHomepage, mobile (October 22, 2026): performance 31/100; Largest Contentful Paint 11.5 s in the lab, where the largest element is the hero video; 9.2 MB and 227 requests, 5.2 MB of JavaScript of which about 3.2 MB is unused; 16 third-party services. Real visitors (Chrome UX Report): LCP 5.6 s and INP 530 ms, so the page fails Core Web Vitals; across the whole site LCP is 3.8 s at the 75th percentile and 43% slower than before.Source
    • HiringPerformance Marketing Manager (posted September 26, 2026): "own paid acquisition across Google, Meta, and LinkedIn" for the consumer business; "Run a steady stream of structured tests across audiences, offers, landing pages, and creative"; "build paid for B2B from close to the ground up, starting with the AI Builder Program for teams and companies and eventually extending to our university partners"; "Build reporting that ties spend to pipeline and closed revenue, not just form fills, signups or clicks."Source
    • Your websiteStructured data: coach profiles and the AI Builder Program page carry rating, review, offer and course markup; the homepage, the /mba category page and /reviews carry none.Source
  • 02

    Leland's community posts are expert answers to real questions ("If I have a low GPA, high GMAT - How should I stand out", 11 experts answered). But every page is titled only with the coach's name, sits at a random-ID URL and has no structured data, so search engines cannot tell what question it answers.

    High impactLow effort First result in 1 month Content & Creative Lead

    First action

    Change the title template on posts with three or more answers.

    How to measure it

    Organic clicks to posts

    Now
    –
    Target
    5x
    By
    90 days

    Steps

    1. 1

      Template

      Question as title and description.

      Software Engineer 1 day

    2. 2

      Readable URLs

      Slug from the question, with redirects.

      Software Engineer 2 days

    3. 3

      Structured data

      Q&A markup with all answers.

      Software Engineer 2 days

    4. 4

      Link

      From category pages and profiles.

      Software Engineer 2 days

    5. 5

      Quality bar

      Noindex posts with one short answer.

      Content & Creative Lead 1 day

    6. 6

      Report

      Clicks and signups from posts.

      Content & Creative Lead monthly

    First result
    1 month
    Cost
    Engineering time
    Owner
    Content & Creative Lead

    Smallest test

    Retitle 50 posts and compare clicks after a month.

    Why it works

    Change the title template to "<question> | <category> experts answer | Leland", use the question in the meta description and a readable URL, and add Q&A structured data with every expert answer. Link each answered question from the matching category page and coach profile.

    Questions are what applicants type into search and AI assistants; titled correctly, these pages become a long-tail SEO asset written by experts for free.

    Risks and how to handle them

    • Low-quality questions indexed

      Index only answered, edited questions.

    Evidence

    • Your websiteCommunity posts: the sitemap lists 1,277 /<coach>/post/<id> pages. Sampled posts (October 22, 2026) are expert answers to questions such as "If I have a low GPA, high GMAT - How should I stand out" ("11 experts have answered"), but each page's title is only the coach's name plus "| Leland", the URL is a random ID, and the page carries no structured data.Source
    • Your websiteStructured data: coach profiles and the AI Builder Program page carry rating, review, offer and course markup; the homepage, the /mba category page and /reviews carry none.Source
    • Your websiteContent library: 1,791 /library article pages (guides, top lists, how-tos by category), 2,466 coach profiles and 2,042 coaching packages in the sitemap.Source
  • 03

    Leland has 36,076 reviews at 4.99 average and 2,025 new ones last month. Coach profiles and the AI Builder Program page carry rating markup, but the homepage, category pages such as /mba and the reviews page carry none, so search results for "MBA admissions consultant" show no rating for Leland.

    High impactLow effort First result in 1 month Content & Creative Lead

    First action

    Calculate the rating and count for the top 10 categories.

    How to measure it

    Category page click-through

    Now
    –
    Target
    +15%
    By
    90 days

    Steps

    1. 1

      Calculate

      Rating and count per category.

      Software Engineer 1 day

    2. 2

      Markup

      Category and reviews pages.

      Software Engineer 2 days

    3. 3

      Visible rating

      Near the top of each page.

      Software Engineer 1 day

    4. 4

      Validate

      Rich Results Test.

      Software Engineer 1 hour

    5. 5

      Monitor

      Search Console enhancements.

      Content & Creative Lead weekly

    6. 6

      Use in ads

      Rating in ad copy and extensions.

      Performance Marketing Manager 1 week

    First result
    1 month
    Cost
    Engineering time
    Owner
    Content & Creative Lead

    Smallest test

    Mark up /mba and check it in the Rich Results Test.

    Why it works

    Add aggregate rating markup for each category from its own coaches' verified reviews, and an Organization rating on /reviews, following Google's rules for self-hosted reviews. Show the category rating near the top of each category page too.

    Ratings beside a result raise click-through, and the category's own rating is more persuasive than a sitewide one.

    Risks and how to handle them

    • Search engines ignore self-serving markup

      Show the rating visibly and use category-level reviews.

    Evidence

    • Your websiteHomepage (October 22, 2026): "Join millions of people reaching ambitious goals, building with AI, and leveling up their teams"; "36,076 reviews 4.99 avg 2,025 submitted last month"; four paths: Build with AI, Grow your career, Get into a top school, Leland for teams. The sitemap lists 225 category pages.Source
    • Your websiteStructured data: coach profiles and the AI Builder Program page carry rating, review, offer and course markup; the homepage, the /mba category page and /reviews carry none.Source
    • Your websiteReviews page: overall rating 4.99, with about 36k five-star, 214 four-star, 37 three-star, 22 two-star and 46 one-star reviews; review headlines name outcomes such as McKinsey interviews, a BCG offer, Columbia Business School admission and a Bain offer.Source
  • 04

    The Leland+ browse page lists "Write Exceptional MBA Essays (Duplicate)" next to other courses. Small slips like this on a paid catalogue make a premium product look unfinished.

    Medium impactLow effort First result in 1 week Content & Creative Lead

    First action

    Rename the duplicate course today.

    How to measure it

    Items failing the publish checklist

    Now
    –
    Target
    0
    By
    2 weeks

    Steps

    1. 1

      Fix

      The duplicate course.

      Content & Creative Lead 1 hour

    2. 2

      Audit

      All Leland+ items.

      Growth & Ops Intern: Courses & Events 2 days

    3. 3

      Merge

      Duplicated content.

      Content & Creative Lead 2 days

    4. 4

      Checklist

      Before anything goes public.

      Content & Creative Lead 1 day

    5. 5

      Thumbnails

      Missing or default images.

      Marketing Manager, Social Media & Creative 2 days

    6. 6

      Review

      Monthly catalogue check.

      Growth & Ops Intern: Courses & Events monthly

    First result
    1 week
    Cost
    $0
    Owner
    Content & Creative Lead

    Smallest test

    Fix the one title.

    Why it works

    Rename or merge the duplicate, then check every Leland+ title, description and thumbnail for drafts, duplicates and empty modules. Add a publish checklist so internal names never reach the public page.

    A tidy catalogue supports the subscription and the ads that will point to it.

    Risks and how to handle them

    • Breaking member bookmarks

      Redirect merged courses.

    Evidence

    • Your websiteLeland+ browse page: a course is listed publicly as "Write Exceptional MBA Essays (Duplicate)" next to "Break Into Private Equity: Recruiting & Application Basics" and "Select and Prepare Your MBA Recommenders".Source
  • 05

    The homepage says "Join millions of people", while every job post says Leland has "helped tens of thousands of people". Paid ads will reuse the homepage line, and ad platforms and careful buyers both expect claims that can be backed up.

    Medium impactLow effort First result in 1 week Performance Marketing Manager

    First action

    Pull registered users and paying customers to date.

    How to measure it

    Assets updated

    Now
    –
    Target
    100%
    By
    30 days

    Steps

    1. 1

      Pull numbers

      Users, attendees, customers.

      Strategy & Ops Intern 1 day

    2. 2

      Agree

      One figure and its definition.

      Performance Marketing Manager 1 day

    3. 3

      Update site

      Homepage and landing pages.

      Software Engineer 1 day

    4. 4

      Update ads

      All active creative.

      Performance Marketing Manager 1 day

    5. 5

      Update decks

      Sales and B2B materials.

      B2B Account Executive 1 day

    6. 6

      Review

      Quarterly refresh.

      Performance Marketing Manager quarterly

    First result
    1 week
    Cost
    $0
    Owner
    Performance Marketing Manager

    Smallest test

    Change the homepage line to the audited figure.

    Why it works

    Agree one figure and what it counts (registered users, livestream attendees, paying customers), use it on the homepage, ads, sales decks and job posts, and keep the review count beside it as proof.

    A specific, defensible number persuades more than a round one and avoids disapproved ads.

    Risks and how to handle them

    • Smaller number feels weaker

      Pair it with 36,000 reviews at 4.99.

    Evidence

    • Your websiteHomepage (October 22, 2026): "Join millions of people reaching ambitious goals, building with AI, and leveling up their teams"; "36,076 reviews 4.99 avg 2,025 submitted last month"; four paths: Build with AI, Grow your career, Get into a top school, Leland for teams. The sitemap lists 225 category pages.Source
    • HiringCompany description in every post: "Leland is building the home for ambition in the age of AI. We connect people with the experts, programs, and communities they need to land the job, get into the school, or upskill"; "We help businesses become AI-native through training, hiring, and infrastructure. Since our founding in 2021, we've helped tens of thousands of people reach their most ambitious goals and raised $19M".Source
    • HiringPerformance Marketing Manager (posted September 26, 2026): "own paid acquisition across Google, Meta, and LinkedIn" for the consumer business; "Run a steady stream of structured tests across audiences, offers, landing pages, and creative"; "build paid for B2B from close to the ground up, starting with the AI Builder Program for teams and companies and eventually extending to our university partners"; "Build reporting that ties spend to pipeline and closed revenue, not just form fills, signups or clicks."Source
  • 06

    On mobile the homepage's largest element is the hero video, the page weighs 9.2 MB with 227 requests and 3.2 MB of unused JavaScript, and real visitors wait 5.6 s for the main content. Organic and brand traffic land here.

    High impactMedium effort First result in 1 month Software Engineer

    First action

    Replace the mobile hero with a poster and re-run PageSpeed.

    How to measure it

    Real-visitor homepage LCP

    Now
    –
    Target
    Under 2.5 s
    By
    60 days

    Steps

    1. 1

      Poster image

      Mobile hero.

      Software Engineer 1 day

    2. 2

      Lazy menu

      Load category links on open.

      Software Engineer 3 days

    3. 3

      Bundle audit

      Remove unused JavaScript.

      Software Engineer 1 week

    4. 4

      Tag review

      Remove duplicate or unused tags; name an owner for each.

      Performance Marketing Manager 2 days

    5. 5

      Re-test

      PageSpeed and field data.

      Software Engineer 1 day

    6. 6

      Budget

      Weight limit for new sections.

      Software Engineer ongoing

    First result
    1 month
    Cost
    Engineering time
    Owner
    Software Engineer

    Smallest test

    Ship the mobile poster this week.

    Why it works

    Show a compressed poster image on mobile and load the video only on larger screens or on tap, split the navigation menu (hundreds of category links) so it loads on open, and remove unused script bundles.

    The homepage is the brand's front door; halving its weight helps every channel.

    Risks and how to handle them

    • Video was driving engagement

      A/B test poster vs video on desktop.

    Evidence

    • Google PageSpeedHomepage, mobile (October 22, 2026): performance 31/100; Largest Contentful Paint 11.5 s in the lab, where the largest element is the hero video; 9.2 MB and 227 requests, 5.2 MB of JavaScript of which about 3.2 MB is unused; 16 third-party services. Real visitors (Chrome UX Report): LCP 5.6 s and INP 530 ms, so the page fails Core Web Vitals; across the whole site LCP is 3.8 s at the 75th percentile and 43% slower than before.Source
    • Your websiteHomepage (October 22, 2026): "Join millions of people reaching ambitious goals, building with AI, and leveling up their teams"; "36,076 reviews 4.99 avg 2,025 submitted last month"; four paths: Build with AI, Grow your career, Get into a top school, Leland for teams. The sitemap lists 225 category pages.Source

This quarter 9

The core plays for the next three months.

  • 07

    The social hire is told most of Leland's livestreams, webinars and courses "never make it onto social". There are 214 livestream pages and 29 live programs, each with hours of expert advice.

    High impactMedium effort First result in 1 quarter Marketing Manager

    First action

    Clip three moments from last week's best-attended livestream.

    How to measure it

    Signups attributed to social

    Now
    –
    Target
    +100%
    By
    2 quarters

    Steps

    1. 1

      Workflow

      Transcribe, find moments, cut.

      Marketing Manager, Social Media & Creative 2 weeks

    2. 2

      Guardrails

      Brand and tone templates.

      Content & Creative Lead 1 week

    3. 3

      Publish

      Daily on five platforms.

      Marketing Manager, Social Media & Creative daily

    4. 4

      Link

      Coach profile and next livestream.

      Marketing Manager, Social Media & Creative daily

    5. 5

      Report

      Weekly read on winners.

      Marketing Manager, Social Media & Creative weekly

    6. 6

      Hand to paid

      Top clips each week.

      Performance Marketing Manager weekly

    First result
    1 quarter
    Cost
    Tool subscriptions
    Owner
    Marketing Manager, Social Media & Creative

    Smallest test

    Publish ten clips in two weeks.

    Why it works

    Build the clipping workflow first: transcribe each recording, find the three strongest 30-60 second moments, caption and cut them for each platform, and link each clip to the coach's profile and the next free livestream. Publish daily and report weekly on what converts.

    Experts saying something specific and useful is the content that spreads in admissions and careers, and each clip advertises a bookable coach.

    Risks and how to handle them

    • Coaches object to clips

      Get consent in the livestream agreement.

    Evidence

    • HiringMarketing Manager, Social Media & Creative (posted September 26, 2026): "Leland has a massive library of content: hours of livestreams, webinars, coach sessions, and courses packed with expert advice ... Most of it never makes it onto social." The role clips it for LinkedIn, TikTok, Instagram, YouTube and X, builds an AI-powered clipping workflow, will "Help our coaches and team post more on LinkedIn" and "Pass winning organic content to performance marketing so it can be put behind paid".Source
    • Your websiteLivestreams and programs: 214 livestream pages and 29 live programs in the sitemap; the MBA page promotes upcoming free livestreams (one shows "97 registered") that people "can join for free".Source
    • Your websiteContent library: 1,791 /library article pages (guides, top lists, how-tos by category), 2,466 coach profiles and 2,042 coaching packages in the sitemap.Source
  • 08

    Free livestreams draw registrants (one MBA session shows 97 registered), and the Consumer AE handles thousands of customers from sign-up to purchase. Registrants have told Leland their goal and timeline by choosing the session.

    High impactLow effort First result in 1 quarter Consumer Account Executive

    First action

    Measure today's conversion from registrant to intro call.

    How to measure it

    Registrant-to-purchase rate

    Now
    –
    Target
    +50%
    By
    2 quarters

    Steps

    1. 1

      Baseline

      Registrant to intro call and purchase.

      Strategy & Ops Intern 1 week

    2. 2

      Routing

      By session category.

      Strategy & Ops Intern 1 week

    3. 3

      Next-day email

      Recording and two coaches.

      Consumer Account Executive 1 week

    4. 4

      Calls

      Engaged attendees.

      Consumer Account Executive ongoing

    5. 5

      Script

      By category.

      Consumer Account Executive 1 week

    6. 6

      Report

      Conversion by session.

      Strategy & Ops Intern monthly

    First result
    1 quarter
    Cost
    Staff time only
    Owner
    Consumer Account Executive

    Smallest test

    Follow up one week of registrants by hand.

    Why it works

    Route registrants by session category to the AE for that category; send a recording plus two matched coaches with free intro calls the next morning; call registrants who stayed to the end or asked questions.

    People who give an hour to a topic are the warmest leads Leland has, and a matched intro call is a small next step.

    Risks and how to handle them

    • Too pushy for free attendees

      Lead with the recording and resources.

    Evidence

    • Your websiteLivestreams and programs: 214 livestream pages and 29 live programs in the sitemap; the MBA page promotes upcoming free livestreams (one shows "97 registered") that people "can join for free".Source
    • HiringSales hires: a Consumer Account Executive (posted September 8, 2026) who will "manage the entire sales process from sign up to purchase for thousands of customers" across "30+ featured coaching categories"; a B2B Account Executive selling "Leland's AI Builder Program and other related offerings" to organisations; and a Strategy & Ops Intern (posted October 7, 2026) to own "lead sourcing, enrichment, scoring, and routing so the right leads reach the right rep or sequence" in HubSpot.Source
    • Google PageSpeedMBA Admissions page (/mba), mobile, tested October 22, 2026: performance 29/100, lab LCP 10.0 s, Total Blocking Time 3,030 ms, 5.2 MB. Real visitors to this page: LCP 7.0 s, INP 777 ms, First Contentful Paint 6.0 s and Time to First Byte 4.4 s (Google's "good" limits are 2.5 s, 200 ms, 1.8 s and 0.8 s). The page lists admissions consultants from $85 to $399 an hour with ratings and free intro calls.Source
  • 09

    The social hire is asked to help coaches post more on LinkedIn. Leland has 2,466 coach profiles, many with large followings in their fields, and each coach benefits when their profile gets bookings.

    High impactLow effort First result in 1 quarter Marketing Manager

    First action

    Send the kit to 50 top coaches.

    How to measure it

    Coach-link bookings

    Now
    –
    Target
    +30%
    By
    2 quarters

    Steps

    1. 1

      Kit design

      Posts, links, badge.

      Marketing Manager, Social Media & Creative 2 weeks

    2. 2

      Tracking

      Per-coach links.

      Software Engineer 1 week

    3. 3

      Pilot

      50 coaches.

      Expert community lead 1 month

    4. 4

      Results

      Bookings shown to coaches.

      Software Engineer 1 month

    5. 5

      Roll out

      All active coaches.

      Expert community lead 1 quarter

    6. 6

      Rank

      Monthly leaderboard.

      Marketing Manager, Social Media & Creative monthly

    First result
    1 quarter
    Cost
    Staff time only
    Owner
    Marketing Manager, Social Media & Creative

    Smallest test

    Pilot with 20 coaches.

    Why it works

    Give coaches a monthly kit: two ready posts from their own livestream clips or answers, a tracked profile link, and a "Top coach" badge. Show each coach the bookings their posts drove.

    Coaches' networks are full of exactly the people who buy coaching, and a tracked link shows them it pays.

    Risks and how to handle them

    • Coaches promote off-platform sales

      Keep bookings and rewards on Leland.

    Evidence

    • HiringMarketing Manager, Social Media & Creative (posted September 26, 2026): "Leland has a massive library of content: hours of livestreams, webinars, coach sessions, and courses packed with expert advice ... Most of it never makes it onto social." The role clips it for LinkedIn, TikTok, Instagram, YouTube and X, builds an AI-powered clipping workflow, will "Help our coaches and team post more on LinkedIn" and "Pass winning organic content to performance marketing so it can be put behind paid".Source
    • Your websiteContent library: 1,791 /library article pages (guides, top lists, how-tos by category), 2,466 coach profiles and 2,042 coaching packages in the sitemap.Source
    • HiringThe Ashby board lists 184 open "Coaches" postings (checked October 22, 2026), from MBA, consulting and AI careers to poker, pageant, dating and dental school, each recruiting experts for a category.Source
  • 10

    B2B paid starts with the AI Builder Program for teams, and reporting must tie spend to pipeline. But the business offer lives on leland.ai, universities on partner.joinleland.com and the AI Builder Program on joinleland.com, so a visitor moves between three sites and tracking breaks at each hop.

    High impactMedium effort First result in 1 quarter Performance Marketing Manager

    First action

    Click through each B2B path and note where tracking IDs drop.

    How to measure it

    Paid-sourced B2B pipeline

    Now
    –
    Target
    $500K
    By
    2 quarters

    Steps

    1. 1

      Map paths

      All B2B entry points.

      Performance Marketing Manager 1 week

    2. 2

      Cross-domain

      Analytics and ad tags.

      Software Engineer 1 week

    3. 3

      One form flow

      HubSpot across sites.

      Strategy & Ops Intern 2 weeks

    4. 4

      Landing pages

      One per B2B offer.

      Performance Marketing Manager 2 weeks

    5. 5

      Launch

      LinkedIn and Google tests.

      Performance Marketing Manager 1 month

    6. 6

      Report

      Spend to pipeline.

      Strategy & Ops Intern monthly

    First result
    1 quarter
    Cost
    Engineering and ad budget
    Owner
    Performance Marketing Manager

    Smallest test

    Fix cross-domain tracking first.

    Why it works

    Set up cross-domain tracking and one HubSpot form flow across the three sites, add a "for teams" page on joinleland.com that links to the program and the B2B offer, and send B2B ads to a single landing page per offer. Report spend to pipeline in one view.

    Without joined-up tracking, B2B paid will look worse than it is and get cut.

    Risks and how to handle them

    • Consumer visitors land on B2B pages

      Separate audiences and messages.

    Evidence

    • Your websiteBusiness offers sit on other domains: the footer's "For HR teams" and "Learn more" link to leland.ai ("Make Your Organization AI-Native | Leland": "upskill your people, deploy done-for-you AI systems, and hire AI-native talent"), and "For universities" links to partner.joinleland.com/universities.Source
    • HiringPerformance Marketing Manager (posted September 26, 2026): "own paid acquisition across Google, Meta, and LinkedIn" for the consumer business; "Run a steady stream of structured tests across audiences, offers, landing pages, and creative"; "build paid for B2B from close to the ground up, starting with the AI Builder Program for teams and companies and eventually extending to our university partners"; "Build reporting that ties spend to pipeline and closed revenue, not just form fills, signups or clicks."Source
    • HiringSales hires: a Consumer Account Executive (posted September 8, 2026) who will "manage the entire sales process from sign up to purchase for thousands of customers" across "30+ featured coaching categories"; a B2B Account Executive selling "Leland's AI Builder Program and other related offerings" to organisations; and a Strategy & Ops Intern (posted October 7, 2026) to own "lead sourcing, enrichment, scoring, and routing so the right leads reach the right rep or sequence" in HubSpot.Source
    • Your websiteAI Builder Program: "BOOTCAMP · 4 LIVE SESSIONS · ALL SESSIONS RECORDED", $1,499, 4.9 from 39 reviews; sessions on building a product without code, automating communication, analysing data and a demo day; a scholarship application and a "notify me" form for future cohorts.Source
  • 11

    Paid clicks for "MBA admissions consultant" land on a catalogue with dozens of consultants from $85 to $399 an hour, filters and livestreams. A visitor from an ad wants a short list they can act on.

    High impactMedium effort First result in 1 quarter Performance Marketing Manager

    First action

    Build one MBA page for the $100-199 band.

    How to measure it

    Paid cost per first booking

    Now
    –
    Target
    -25%
    By
    2 quarters

    Steps

    1. 1

      Pick categories

      Top five by spend.

      Performance Marketing Manager 1 week

    2. 2

      Template

      Three coaches, reviews, intro call.

      Software Engineer 2 weeks

    3. 3

      Bands

      Budget versions.

      Performance Marketing Manager 1 week

    4. 4

      Ads

      Matching copy per band.

      Performance Marketing Manager 1 week

    5. 5

      Test

      Against full pages.

      Performance Marketing Manager 1 month

    6. 6

      Scale

      Winners to more categories.

      Performance Marketing Manager monthly

    First result
    1 quarter
    Cost
    Engineering time
    Owner
    Performance Marketing Manager

    Smallest test

    Test one page for a month.

    Why it works

    Build lean landing pages per top category and budget band: three top-rated coaches, their results and prices, free intro calls, reviews and a "help me choose" option to an AE. Test against the full category page.

    Fewer, better choices convert better for first-time buyers, and budget bands match the ad's promise.

    Risks and how to handle them

    • Coaches left out feel slighted

      Rotate by rating and availability.

    Builds on

    Evidence

    • Google PageSpeedMBA Admissions page (/mba), mobile, tested October 22, 2026: performance 29/100, lab LCP 10.0 s, Total Blocking Time 3,030 ms, 5.2 MB. Real visitors to this page: LCP 7.0 s, INP 777 ms, First Contentful Paint 6.0 s and Time to First Byte 4.4 s (Google's "good" limits are 2.5 s, 200 ms, 1.8 s and 0.8 s). The page lists admissions consultants from $85 to $399 an hour with ratings and free intro calls.Source
    • HiringPerformance Marketing Manager (posted September 26, 2026): "own paid acquisition across Google, Meta, and LinkedIn" for the consumer business; "Run a steady stream of structured tests across audiences, offers, landing pages, and creative"; "build paid for B2B from close to the ground up, starting with the AI Builder Program for teams and companies and eventually extending to our university partners"; "Build reporting that ties spend to pipeline and closed revenue, not just form fills, signups or clicks."Source
    • Your websiteReviews page: overall rating 4.99, with about 36k five-star, 214 four-star, 37 three-star, 22 two-star and 46 one-star reviews; review headlines name outcomes such as McKinsey interviews, a BCG offer, Columbia Business School admission and a Bain offer.Source
  • 12

    The new Strategy & Ops intern will own lead scoring and routing so the right leads reach the right rep, and the Consumer AE covers 30+ categories. Sign-ups differ hugely: a deferred MBA applicant months out versus an MBA applicant with a deadline in weeks.

    High impactLow effort First result in 1 quarter Strategy & Ops Intern

    First action

    Add the timeline question to sign-up.

    How to measure it

    Hot leads contacted within an hour

    Now
    –
    Target
    90%
    By
    1 quarter

    Steps

    1. 1

      Questions

      Goal and timeline at sign-up.

      Software Engineer 1 week

    2. 2

      Score

      Category, timeline, engagement.

      Strategy & Ops Intern 2 weeks

    3. 3

      Route

      Hot leads to AEs.

      Strategy & Ops Intern 1 week

    4. 4

      Sequences

      Automated for the rest.

      Strategy & Ops Intern 2 weeks

    5. 5

      Review

      Conversion by score band.

      Strategy & Ops Intern monthly

    6. 6

      Tune

      Weights each month.

      Consumer Account Executive monthly

    First result
    1 quarter
    Cost
    Staff time only
    Owner
    Strategy & Ops Intern

    Smallest test

    Score one week of sign-ups by hand.

    Why it works

    Ask two questions at sign-up (goal and timeline), score leads by category value, timeline and engagement (livestreams, coach views), route high scores to AEs within an hour and the rest to automated sequences.

    Fast, relevant follow-up to the few hottest leads lifts revenue without more traffic.

    Risks and how to handle them

    • Extra sign-up friction

      Make questions optional and one tap.

    Evidence

    • HiringSales hires: a Consumer Account Executive (posted September 8, 2026) who will "manage the entire sales process from sign up to purchase for thousands of customers" across "30+ featured coaching categories"; a B2B Account Executive selling "Leland's AI Builder Program and other related offerings" to organisations; and a Strategy & Ops Intern (posted October 7, 2026) to own "lead sourcing, enrichment, scoring, and routing so the right leads reach the right rep or sequence" in HubSpot.Source
    • Your websiteLivestreams and programs: 214 livestream pages and 29 live programs in the sitemap; the MBA page promotes upcoming free livestreams (one shows "97 registered") that people "can join for free".Source
    • Google PageSpeedMBA Admissions page (/mba), mobile, tested October 22, 2026: performance 29/100, lab LCP 10.0 s, Total Blocking Time 3,030 ms, 5.2 MB. Real visitors to this page: LCP 7.0 s, INP 777 ms, First Contentful Paint 6.0 s and Time to First Byte 4.4 s (Google's "good" limits are 2.5 s, 200 ms, 1.8 s and 0.8 s). The page lists admissions consultants from $85 to $399 an hour with ratings and free intro calls.Source
  • 13

    Paid marketing will "eventually" support Leland's university partners, and universities are a sales-led B2B line. Career centres need expert sessions for students and alumni; Leland already runs free livestreams on exactly those topics.

    Medium impactMedium effort First result in 2 quarters B2B Account Executive

    First action

    Offer the series to five current university partners.

    How to measure it

    New university partners

    Now
    –
    Target
    10
    By
    2 quarters

    Steps

    1. 1

      Package

      Series, branding, reports.

      B2B Account Executive 2 weeks

    2. 2

      Pilot

      Five universities.

      B2B Account Executive 1 month

    3. 3

      Run

      Monthly sessions.

      Growth & Ops Intern: Courses & Events monthly

    4. 4

      Report

      Attendance and follow-up.

      Strategy & Ops Intern monthly

    5. 5

      Convert

      Paid partnerships.

      B2B Account Executive 1 quarter

    6. 6

      Paid support

      Ads to target universities.

      Performance Marketing Manager 1 quarter

    First result
    2 quarters
    Cost
    Staff time only
    Owner
    B2B Account Executive

    Smallest test

    Run one co-branded session.

    Why it works

    Offer partner universities a co-branded monthly livestream series (consulting, banking, AI careers) with attendance reports, and use it as the opening offer for paid partnerships.

    A free, useful pilot opens doors that a cold pitch does not, and attendance data proves value.

    Risks and how to handle them

    • Free series never converts

      Set conversion terms upfront.

    Evidence

    • Your websiteBusiness offers sit on other domains: the footer's "For HR teams" and "Learn more" link to leland.ai ("Make Your Organization AI-Native | Leland": "upskill your people, deploy done-for-you AI systems, and hire AI-native talent"), and "For universities" links to partner.joinleland.com/universities.Source
    • Your websiteLivestreams and programs: 214 livestream pages and 29 live programs in the sitemap; the MBA page promotes upcoming free livestreams (one shows "97 registered") that people "can join for free".Source
    • HiringPerformance Marketing Manager (posted September 26, 2026): "own paid acquisition across Google, Meta, and LinkedIn" for the consumer business; "Run a steady stream of structured tests across audiences, offers, landing pages, and creative"; "build paid for B2B from close to the ground up, starting with the AI Builder Program for teams and companies and eventually extending to our university partners"; "Build reporting that ties spend to pipeline and closed revenue, not just form fills, signups or clicks."Source
  • 14

    The social role is asked to pass winning organic posts to performance marketing. Clips that already earn saves and shares are pre-tested ad creative.

    High impactLow effort First result in 1 quarter Performance Marketing Manager

    First action

    Pick last week's three best clips.

    How to measure it

    Clip-ad cost per booking

    Now
    –
    Target
    -20% vs other creative
    By
    1 quarter

    Steps

    1. 1

      Rank

      Completion and saves.

      Marketing Manager, Social Media & Creative weekly

    2. 2

      Adapt

      Ad cuts and captions.

      Marketing Manager, Social Media & Creative weekly

    3. 3

      Launch

      Meta, YouTube, LinkedIn.

      Performance Marketing Manager weekly

    4. 4

      Measure

      Cost per booking.

      Performance Marketing Manager weekly

    5. 5

      Share back

      What converts.

      Performance Marketing Manager weekly

    6. 6

      Retire

      Fatigued ads.

      Performance Marketing Manager weekly

    First result
    1 quarter
    Cost
    Existing ad budget
    Owner
    Performance Marketing Manager

    Smallest test

    Run three clips as ads.

    Why it works

    Each week, take the three best clips by completion and saves, run them as ads in their category with a link to the lean landing page, and feed results back to the social team.

    Organic testing lowers creative risk and keeps the ad accounts supplied with fresh, credible content.

    Risks and how to handle them

    • Coach consent for ads

      Add paid use to the coach agreement.

    Builds on

    Evidence

    • HiringMarketing Manager, Social Media & Creative (posted September 26, 2026): "Leland has a massive library of content: hours of livestreams, webinars, coach sessions, and courses packed with expert advice ... Most of it never makes it onto social." The role clips it for LinkedIn, TikTok, Instagram, YouTube and X, builds an AI-powered clipping workflow, will "Help our coaches and team post more on LinkedIn" and "Pass winning organic content to performance marketing so it can be put behind paid".Source
    • HiringPerformance Marketing Manager (posted September 26, 2026): "own paid acquisition across Google, Meta, and LinkedIn" for the consumer business; "Run a steady stream of structured tests across audiences, offers, landing pages, and creative"; "build paid for B2B from close to the ground up, starting with the AI Builder Program for teams and companies and eventually extending to our university partners"; "Build reporting that ties spend to pipeline and closed revenue, not just form fills, signups or clicks."Source
  • 15

    Leland has 1,791 library articles plus thousands of expert answers. Readers of a guide on "private equity vs venture capital" are prospects for those coaches, but the guide is a dead end if it does not lead to a coach or livestream.

    Medium impactMedium effort First result in 1 quarter Content & Creative Lead

    First action

    Find the 50 articles with the most traffic and check their links to coaches.

    How to measure it

    Library-to-booking rate

    Now
    –
    Target
    +50%
    By
    2 quarters

    Steps

    1. 1

      Audit

      Top 50 articles.

      Content & Creative Lead 1 week

    2. 2

      Module

      Coaches and livestream.

      Software Engineer 2 weeks

    3. 3

      Match

      Category tagging.

      Content & Creative Lead 2 weeks

    4. 4

      Merge

      Overlapping articles.

      Content & Creative Lead 1 month

    5. 5

      Track

      Article to booking.

      Strategy & Ops Intern monthly

    6. 6

      Expand

      All articles.

      Content & Creative Lead 1 quarter

    First result
    1 quarter
    Cost
    Engineering time
    Owner
    Content & Creative Lead

    Smallest test

    Add the module to ten articles.

    Why it works

    Add a module to every article with two matched coaches, the next free livestream in that category and related expert answers; merge overlapping articles; track article-to-booking conversion.

    Content that leads to a next step pays for itself; content that does not only collects traffic.

    Risks and how to handle them

    • Feels salesy

      Keep the module below the article content.

    Evidence

    • Your websiteContent library: 1,791 /library article pages (guides, top lists, how-tos by category), 2,466 coach profiles and 2,042 coaching packages in the sitemap.Source
    • Your websiteCommunity posts: the sitemap lists 1,277 /<coach>/post/<id> pages. Sampled posts (October 22, 2026) are expert answers to questions such as "If I have a low GPA, high GMAT - How should I stand out" ("11 experts have answered"), but each page's title is only the coach's name plus "| Leland", the URL is a random ID, and the page carries no structured data.Source
    • Your websiteLivestreams and programs: 214 livestream pages and 29 live programs in the sitemap; the MBA page promotes upcoming free livestreams (one shows "97 registered") that people "can join for free".Source

Big bets 3

Larger plays that can change the trajectory.

  • 16

    Leland's reviews name outcomes (McKinsey interviews, a BCG offer, Columbia admission, a Bain offer). Aggregated, they show which schools and firms Leland clients reach, which no single consultant can show.

    High impactMedium effort First result in 3 quarters Content & Creative Lead

    First action

    Add an optional outcome tag to the review form.

    How to measure it

    Tagged outcomes

    Now
    –
    Target
    5,000
    By
    1 year

    Steps

    1. 1

      Outcome tag

      Review form field.

      Software Engineer 2 weeks

    2. 2

      Backfill

      Tag existing reviews.

      Strategy & Ops Intern 1 month

    3. 3

      Analyse

      By category.

      Strategy & Ops Intern 1 month

    4. 4

      Privacy review

      Anonymise.

      Legal counsel 2 weeks

    5. 5

      Publish

      Report and category stats.

      Content & Creative Lead 1 month

    6. 6

      Use

      Ads and sales.

      Performance Marketing Manager ongoing

    First result
    3 quarters
    Cost
    Staff time only
    Owner
    Content & Creative Lead

    Smallest test

    Publish outcome stats for one category.

    Why it works

    Ask reviewers to tag their outcome, then publish a yearly report by category (schools admitted, firms joined, time to offer) with anonymised data, and use the figures in ads, category pages and sales.

    Outcome proof is the decisive buying factor in admissions and career coaching, and a report earns press and links.

    Risks and how to handle them

    • Overclaiming

      Report only tagged, verified outcomes.

    Evidence

    • Your websiteReviews page: overall rating 4.99, with about 36k five-star, 214 four-star, 37 three-star, 22 two-star and 46 one-star reviews; review headlines name outcomes such as McKinsey interviews, a BCG offer, Columbia Business School admission and a Bain offer.Source
    • Your websiteHomepage (October 22, 2026): "Join millions of people reaching ambitious goals, building with AI, and leveling up their teams"; "36,076 reviews 4.99 avg 2,025 submitted last month"; four paths: Build with AI, Grow your career, Get into a top school, Leland for teams. The sitemap lists 225 category pages.Source
    • Google PageSpeedMBA Admissions page (/mba), mobile, tested October 22, 2026: performance 29/100, lab LCP 10.0 s, Total Blocking Time 3,030 ms, 5.2 MB. Real visitors to this page: LCP 7.0 s, INP 777 ms, First Contentful Paint 6.0 s and Time to First Byte 4.4 s (Google's "good" limits are 2.5 s, 200 ms, 1.8 s and 0.8 s). The page lists admissions consultants from $85 to $399 an hour with ratings and free intro calls.Source
  • 17

    The AI Builder Program costs $1,499, is rated 4.9 from 39 reviews and is now being sold to teams. Individual alumni who built something at work are the best internal champions for a team purchase.

    High impactHigh effort First result in 3 quarters B2B Account Executive

    First action

    List alumni companies from past cohorts.

    How to measure it

    Alumni-sourced team deals

    Now
    –
    Target
    15
    By
    3 quarters

    Steps

    1. 1

      List companies

      Past cohort employers.

      Strategy & Ops Intern 1 week

    2. 2

      Business case

      One-pager template.

      B2B Account Executive 2 weeks

    3. 3

      Demo day invite

      Managers welcome.

      Growth & Ops Intern: Courses & Events per cohort

    4. 4

      Team price

      Seats and terms.

      B2B Account Executive 2 weeks

    5. 5

      Route

      Alumni leads to B2B AE.

      Strategy & Ops Intern 1 week

    6. 6

      Track

      Pipeline from alumni.

      Strategy & Ops Intern monthly

    First result
    3 quarters
    Cost
    Staff time only
    Owner
    B2B Account Executive

    Smallest test

    Invite one cohort's managers to demo day.

    Why it works

    At the demo day, invite alumni to bring their manager; give each a one-page business case and a team price; route alumni companies to the B2B AE; track team deals sourced from alumni.

    Bottom-up champions shorten B2B sales cycles and cost nothing to acquire.

    Risks and how to handle them

    • Alumni do not want to sell

      Make the business case ready to forward.

    Evidence

    • Your websiteAI Builder Program: "BOOTCAMP · 4 LIVE SESSIONS · ALL SESSIONS RECORDED", $1,499, 4.9 from 39 reviews; sessions on building a product without code, automating communication, analysing data and a demo day; a scholarship application and a "notify me" form for future cohorts.Source
    • HiringSales hires: a Consumer Account Executive (posted September 8, 2026) who will "manage the entire sales process from sign up to purchase for thousands of customers" across "30+ featured coaching categories"; a B2B Account Executive selling "Leland's AI Builder Program and other related offerings" to organisations; and a Strategy & Ops Intern (posted October 7, 2026) to own "lead sourcing, enrichment, scoring, and routing so the right leads reach the right rep or sequence" in HubSpot.Source
    • HiringPerformance Marketing Manager (posted September 26, 2026): "own paid acquisition across Google, Meta, and LinkedIn" for the consumer business; "Run a steady stream of structured tests across audiences, offers, landing pages, and creative"; "build paid for B2B from close to the ground up, starting with the AI Builder Program for teams and companies and eventually extending to our university partners"; "Build reporting that ties spend to pipeline and closed revenue, not just form fills, signups or clicks."Source
  • 18

    Visitors face 2,466 coaches, 2,042 packages and 225 categories, and the Consumer AE helps each find "the right expert(s) and offering(s)". A matcher can do that first step for everyone.

    High impactHigh effort First result in 3 quarters Software Engineer

    First action

    Prototype the questions with AEs' most common discovery questions.

    How to measure it

    Match-to-booking rate

    Now
    –
    Target
    15%
    By
    3 quarters

    Steps

    1. 1

      Questions

      From AE discovery calls.

      Consumer Account Executive 2 weeks

    2. 2

      Rules first

      Simple matching logic.

      Software Engineer 1 month

    3. 3

      Launch

      On top categories.

      Software Engineer 1 month

    4. 4

      Learn

      From bookings.

      Software Engineer 1 quarter

    5. 5

      AE handoff

      For complex cases.

      Strategy & Ops Intern 2 weeks

    6. 6

      Measure

      Conversion vs browsing.

      Strategy & Ops Intern monthly

    First result
    3 quarters
    Cost
    Engineering time
    Owner
    Software Engineer

    Smallest test

    Run the questions as a form for MBA visitors.

    Why it works

    Ask four questions (goal, deadline, budget, background), recommend three coaches and a package with reasons, and offer an AE call for complex cases. Learn from bookings to improve the matches.

    Guided choice raises conversion in large marketplaces and frees AEs for high-value buyers.

    Risks and how to handle them

    • Poor matches hurt trust

      Show reasons and let users browse.

    Evidence

    • HiringSales hires: a Consumer Account Executive (posted September 8, 2026) who will "manage the entire sales process from sign up to purchase for thousands of customers" across "30+ featured coaching categories"; a B2B Account Executive selling "Leland's AI Builder Program and other related offerings" to organisations; and a Strategy & Ops Intern (posted October 7, 2026) to own "lead sourcing, enrichment, scoring, and routing so the right leads reach the right rep or sequence" in HubSpot.Source
    • Your websiteContent library: 1,791 /library article pages (guides, top lists, how-tos by category), 2,466 coach profiles and 2,042 coaching packages in the sitemap.Source
    • Google PageSpeedMBA Admissions page (/mba), mobile, tested October 22, 2026: performance 29/100, lab LCP 10.0 s, Total Blocking Time 3,030 ms, 5.2 MB. Real visitors to this page: LCP 7.0 s, INP 777 ms, First Contentful Paint 6.0 s and Time to First Byte 4.4 s (Google's "good" limits are 2.5 s, 200 ms, 1.8 s and 0.8 s). The page lists admissions consultants from $85 to $399 an hour with ratings and free intro calls.Source

Wildcards 3

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

  • 19

    Leland's job board lists 184 open coach postings, from AI careers to poker and pageants. Where demand outstrips coach supply, buyers leave; where supply is high and demand low, coaches churn.

    Medium impactLow effort First result in 1 quarter Expert community lead

    First action

    Rank categories by sign-ups per available coach.

    How to measure it

    Categories in balance

    Now
    –
    Target
    80%
    By
    2 quarters

    Steps

    1. 1

      Data

      Demand and coach hours by category.

      Strategy & Ops Intern 2 weeks

    2. 2

      Rank

      Imbalance score.

      Strategy & Ops Intern 1 week

    3. 3

      Recruit

      Under-supplied categories.

      Expert community lead ongoing

    4. 4

      Market

      Over-supplied categories.

      Performance Marketing Manager ongoing

    5. 5

      Close

      Postings with no demand.

      Expert community lead 1 month

    6. 6

      Review

      Monthly.

      Strategy & Ops Intern monthly

    First result
    1 quarter
    Cost
    Staff time only
    Owner
    Expert community lead

    Smallest test

    Rank the top 30 categories.

    Why it works

    Compare searches and sign-ups by category with available coach hours each month; prioritise recruiting where demand is high, and point paid and social at categories with spare coach capacity.

    Balancing supply and demand is the core growth lever of any marketplace.

    Risks and how to handle them

    • Niche categories never balance

      Treat them as experiments with a review date.

    Evidence

    • HiringThe Ashby board lists 184 open "Coaches" postings (checked October 22, 2026), from MBA, consulting and AI careers to poker, pageant, dating and dental school, each recruiting experts for a category.Source
    • Your websiteHomepage (October 22, 2026): "Join millions of people reaching ambitious goals, building with AI, and leveling up their teams"; "36,076 reviews 4.99 avg 2,025 submitted last month"; four paths: Build with AI, Grow your career, Get into a top school, Leland for teams. The sitemap lists 225 category pages.Source
    • HiringPerformance Marketing Manager (posted September 26, 2026): "own paid acquisition across Google, Meta, and LinkedIn" for the consumer business; "Run a steady stream of structured tests across audiences, offers, landing pages, and creative"; "build paid for B2B from close to the ground up, starting with the AI Builder Program for teams and companies and eventually extending to our university partners"; "Build reporting that ties spend to pipeline and closed revenue, not just form fills, signups or clicks."Source
  • 20

    Leland sells career coaching and AI upskilling to individuals while also selling training to companies. Many employees have learning budgets but do not know how to ask.

    Medium impactLow effort First result in 1 month Consumer Account Executive

    First action

    Write the request letter template.

    How to measure it

    Employer-paid purchases

    Now
    –
    Target
    10% of career sales
    By
    2 quarters

    Steps

    1. 1

      Letter

      Template.

      Content & Creative Lead 1 week

    2. 2

      Invoice

      Company billing option.

      Software Engineer 2 weeks

    3. 3

      Pages

      Career and AI pages.

      Software Engineer 1 week

    4. 4

      Sales script

      Mention on calls.

      Consumer Account Executive 1 day

    5. 5

      Track

      Reimbursed purchases.

      Strategy & Ops Intern monthly

    6. 6

      Feed B2B

      Repeat employers to B2B AE.

      B2B Account Executive monthly

    First result
    1 month
    Cost
    Staff time only
    Owner
    Consumer Account Executive

    Smallest test

    Add the letter to the AI Builder Program page.

    Why it works

    Add a one-page request letter, an invoice option and a receipt that meets typical learning-budget rules to career and AI pages; track purchases that use it.

    Removing the price barrier for employed buyers lifts conversion on high-ticket packages.

    Risks and how to handle them

    • Low uptake

      Promote in the checkout step.

    Evidence

    • HiringCompany description in every post: "Leland is building the home for ambition in the age of AI. We connect people with the experts, programs, and communities they need to land the job, get into the school, or upskill"; "We help businesses become AI-native through training, hiring, and infrastructure. Since our founding in 2021, we've helped tens of thousands of people reach their most ambitious goals and raised $19M".Source
    • HiringSales hires: a Consumer Account Executive (posted September 8, 2026) who will "manage the entire sales process from sign up to purchase for thousands of customers" across "30+ featured coaching categories"; a B2B Account Executive selling "Leland's AI Builder Program and other related offerings" to organisations; and a Strategy & Ops Intern (posted October 7, 2026) to own "lead sourcing, enrichment, scoring, and routing so the right leads reach the right rep or sequence" in HubSpot.Source
    • Your websiteAI Builder Program: "BOOTCAMP · 4 LIVE SESSIONS · ALL SESSIONS RECORDED", $1,499, 4.9 from 39 reviews; sessions on building a product without code, automating communication, analysing data and a demo day; a scholarship application and a "notify me" form for future cohorts.Source
  • 21

    Leland collects about 2,025 reviews a month at a 4.99 average, many naming concrete outcomes. They are mostly read on profiles; few are used in social or ads.

    Medium impactLow effort First result in 1 month Marketing Manager

    First action

    Ask five recent reviewers for a short video.

    How to measure it

    Testimonials per month

    Now
    –
    Target
    20
    By
    1 quarter

    Steps

    1. 1

      Select

      Top outcome reviews.

      Marketing Manager, Social Media & Creative weekly

    2. 2

      Permission

      Request and release.

      Marketing Manager, Social Media & Creative weekly

    3. 3

      Produce

      Cards and clips.

      Marketing Manager, Social Media & Creative weekly

    4. 4

      Publish

      Social channels.

      Marketing Manager, Social Media & Creative weekly

    5. 5

      Paid

      Best ones as ads.

      Performance Marketing Manager weekly

    6. 6

      Landing pages

      Category testimonials.

      Software Engineer 1 month

    First result
    1 month
    Cost
    Staff time only
    Owner
    Marketing Manager, Social Media & Creative

    Smallest test

    Publish five testimonial cards.

    Why it works

    Each week, pick the five strongest outcome reviews, ask the reviewer for permission and a 20-second video, and publish them as cards and clips; use them on lean landing pages and ads.

    Peer outcomes persuade more than brand claims, and the supply is constant.

    Risks and how to handle them

    • Reviewers decline

      Use text cards with first name and outcome.

    Evidence

    • Your websiteHomepage (October 22, 2026): "Join millions of people reaching ambitious goals, building with AI, and leveling up their teams"; "36,076 reviews 4.99 avg 2,025 submitted last month"; four paths: Build with AI, Grow your career, Get into a top school, Leland for teams. The sitemap lists 225 category pages.Source
    • Your websiteReviews page: overall rating 4.99, with about 36k five-star, 214 four-star, 37 three-star, 22 two-star and 46 one-star reviews; review headlines name outcomes such as McKinsey interviews, a BCG offer, Columbia Business School admission and a Bain offer.Source
    • HiringMarketing Manager, Social Media & Creative (posted September 26, 2026): "Leland has a massive library of content: hours of livestreams, webinars, coach sessions, and courses packed with expert advice ... Most of it never makes it onto social." The role clips it for LinkedIn, TikTok, Instagram, YouTube and X, builds an AI-powered clipping workflow, will "Help our coaches and team post more on LinkedIn" and "Pass winning organic content to performance marketing so it can be put behind paid".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.

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)
Website review of joinleland.com More example playbooks and reviews

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See every playbook and website review

Independent research. Programmable wrote this playbook from public sources, as they stood on October 23, 2026, and cites them throughout. Leland did not commission, review or endorse it, and Programmable is not affiliated with Leland. 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 Leland runs its business.

Something wrong, or do you represent Leland? 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

    Category page speed, question titles for expert answers, review markup, catalogue clean-up, one reach figure and a lighter homepage; start the employer-pay kit and testimonials.

  2. Days 31 to 6010 ideas

    Clip machine, livestream follow-up, coach LinkedIn kit, cross-domain B2B tracking, lean paid pages, lead routing, university series, clips to paid and library links; the demand map.

  3. Days 61 to 903 ideas

    Commit to the outcomes report, alumni-led team deals and the coach matcher.

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 coaches with insider experience. The most cited problem: choosing among many coaches.

  • Free intro calls and livestreams before paying
  • High hourly prices
  • In their words: “M7”

Market

Competitive landscape

4 competitors compared: Aced (formerly Exponent), Maven, ADPList and Boutique admissions firms (e.g. Stacy Blackman).

  • Gap to exploit: Published outcome data across coaches
  • Aced (formerly Exponent): Narrower than admissions and careers
  • Maven: Less 1-on-1 coaching

Hiring signals

Leland is building a marketing engine on top of a large marketplace.

  • Performance Marketing Manager: Scale paid; test landing pages; build B2B paid. Ideas 1, 10, 11.
  • Marketing Manager, Social Media & Creative: Library never reaches social. Ideas 7, 9, 14.
  • Consumer Account Executive: Sign-up to purchase for thousands of customers. Ideas 8, 18.

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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