Chapter 2

Revenue: the eleven levers that move the top line

Price, product, retention, the sales engine, and the three fintech levers that turn a software company into the rail its customers' money runs on. The Invent levers live here, and so does the only evidence about revenue that is not a vendor's.

23 min read

Chapter 2 of 10Revenue23 min

Revenue levers are where the multiple is decided and where the marketing is loudest. Two rules sort them. First, the evidence for pricing is the strongest in this book because large vendors publish their own increases; the evidence for AI-driven pipeline is the weakest because the vendors measure their own activity. Second, the levers that create revenue the customer did not pay before (R2, R8, R9, R10) depend on rights and foundations established earlier (P2, P7, X3), and they are worth more than every internal-efficiency lever combined because they are the only ones a competitor cannot buy.

Each card's metrics block gives typical values at close and targets at years one and three for a company in the $5M to $100M range; the archetype pages in Part V put the specific numbers on specific companies.

R1 · Price and packaging

What it is. The multi-year program that follows the reset at close (P8): good-better-best tiers with AI capabilities in the upper tiers, removal of grandfathered discounts, value-based rather than seat-based anchors where the product's value is measurable, and a renewal uplift run cohort by cohort with a control group. A value-analysis agent computes, per account, the hours the platform saves, the transactions it processes and the events it handles, and produces the statement that anchors each renewal.

The line it moves. Revenue, flowing to EBITDA at roughly 90%.

Typical range and the evidence. Strong. Cumulative price realization of 6% to 10% on the retained base over three years is the range the case study and the public announcements support: Salesforce's 6% average list increase in August 2025 and Zylo's finding that SaaS spend rose nearly 8% in 2025 on a flat application count are the anchors.1 For pricing power in a regulated workflow, Workiva's second quarter of fiscal 2026 is the cleanest public proof: 97% gross retention, 111% net retention, revenue up 19%, and tiered pricing whose premium tiers carry a premium "north of 20%."2 Vista reports that Sonatype's customers migrated to scan-based pricing showed "a 40% ARR increase, 80% longer contracts, and no change in renewal or win rates," a portfolio company's result reported by its owner.3 The KeyBanc and Sapphire 2025 survey found "more than two-thirds (67%) of companies are already monetizing AI," favoring subscription over usage.4

Conditions. Usage instrumentation from P7; a pricing council that meets monthly; the first AI module (R2) ready before the first uplift cohort renews, so the increase attaches to visible value; the control cohort.

Kill criteria. Uplifted-cohort churn more than one point above control; or a single-renewal uplift above 10% without executive approval.

  • Price realization on renewals
    Revenue
    At close0%
    Year 1+3%
    Year 3+2% (cumulative +6 to +10%)
  • Share of base on new tiers
    Revenue
    At close0%
    Year 140%
    Year 390%
  • Churn in uplifted cohort vs control
    Retention
    At closen/a
    Year 1No worse
    Year 3No worse
  • Share of revenue with a value or usage anchor
    Valuation
    At close0%
    Year 15%
    Year 320%

Horizon and stage. Deploy. Day one hundred through year three.

How it translates. A: the largest lever, six points cumulative on a base priced in 2021. B: the premium tier is the one with the regulatory updates, and the uplift is the price of not falling behind. C: modest, and packaged with the payments attach. D: the riskiest, because the move from seats to hybrid is a price change the customer can see. E: the pricing decision is the services bundle.

R2 · The AI-paid product

What it is. A module the customer pays for, built on the data and workflow the platform already holds, priced at a share of the labor it replaces, and shipped inside twelve months of close. In a vertical it is the customer's own work made product: documentation, authorizations, appeals, reconciliations, filings, scheduling. In a horizontal it is the assistant, the agent or the credit pack layered on the seat.

The line it moves. Revenue (expansion ARR and attach), and the R&D mix, because the module is funded by the savings the Deploy levers produce.

Typical range and the evidence. Strong for the market, medium for any particular attach rate. Attach of 30% to 50% of the base at a module price of 15% to 30% of the core subscription is the range the case study uses and the public disclosures bracket. Atlassian's fourth quarter of fiscal 2026 shareholder letter reports Rovo adopters growing ARR "more than 2x faster than non-adopters," with the caveat that Atlassian publishes no matched cohort and larger customers adopt first.5 Figma reported that by the end of its second quarter of 2026 more than 80% of customers above $10,000 of ARR consumed AI credits weekly and that "approximately two-thirds" of renewing customers added full seats, which is the strongest public evidence that an AI product and seat expansion run together rather than substituting.6 Workday's agentic ARR was "approaching $500 million" in May 2026 with new agentic contract value up more than 200% year over year, on a base of more than 4,000 agent customers.7 In healthcare, the ambient documentation market prices from about $119 per clinician per month to $600, with the JAMA multisite study of 1,809 clinicians as the sober measure of value: 16.0 fewer minutes of documentation time per eight scheduled hours and 0.49 additional weekly visits.8 The rule the case study uses is to price at 25% to 35% of the labor value measured at design-partner customers.

Conditions. The data rights from P2 and the governance from X3; two or three design-partner customers with a measurement protocol; a product manager who owns hours saved as the metric; a build-or-license decision per module (documentation and denials have third-party engines; scheduling and intake are built on the company's own data); an evaluation set, a bias review and a rollback plan per module.

Kill criteria. No module in general availability by month twelve; or attach below 10% of eligible customers six months after launch.

  • Paid AI modules in market
    Revenue
    At close0
    Year 11
    Year 33
  • Attach rate on eligible base
    Revenue
    At close0%
    Year 115%
    Year 345%
  • Expansion ARR from modules, % of ARR
    Revenue
    At close0%
    Year 13%
    Year 39 to 12%
  • Measured customer hours saved per week (median)
    Pricing power
    At close0
    Year 18
    Year 325
  • Share of R&D capacity on customer-facing AI
    R&D mix
    At close0%
    Year 135%
    Year 340%

Horizon and stage. Invent. Year one for the first module, years two and three for the rest.

How it translates. A: documentation, authorizations and appeals, sold to agencies that would otherwise hire. B: the regulatory determination itself, drafted by the product and signed by the customer. C: quoting, invoicing and dispatch assistance, packaged with payments. D: the assistant on the seat, priced as credits, where the risk is that credits cannibalize seats. E: configuration and reporting agents that customers used to buy as services hours.

R3 · Hybrid and usage pricing migration

What it is. Moving from seats to seat-plus-usage, credits or outcome pricing where seats are compressing, so that revenue tracks the value the product delivers rather than the number of people who log in.

The line it moves. Revenue and net retention; and the exit story, because buyers now underwrite seat exposure (P4).

Typical range and the evidence. Medium, and the direction is contested. Growth Unhinged's 2026 survey found hybrid pricing the most common model at 37%, AI credits at 29% adoption with a further 33% planning them, and per-seat retained by 29% of companies above $150M of ARR.9 The a16z argument buyers hear in diligence is that "if AI can handle a sizable proportion of customer support, companies will need far fewer human support agents, and therefore fewer Zendesk software seats."10 Against it, Figma's seat expansion above and HubSpot's second quarter of 2026 are the two public data points that matter: HubSpot introduced outcome-based pricing for several agents and lowered entry prices, and in the same quarter cut its net customer addition guidance to 5,000 to 6,000 a quarter on "weaker conversion rates and increased buyer hesitancy."11 The seat-compression story is real in support and sales-development roles and overstated as a general law, and a pricing migration is itself a demand shock.

Conditions. Usage instrumented at the action level (P7); a value metric the customer already tracks; a migration path that does not reprice the whole base in one renewal; a control cohort.

Kill criteria. Net retention in the migrated cohort below the unmigrated cohort after two quarters; or new-logo conversion falling more than 20% after the change.

  • Share of revenue with a usage or outcome component
    Revenue
    At close0%
    Year 15%
    Year 320 to 35%
  • Net retention, migrated vs unmigrated cohort
    Revenue
    At closen/a
    Year 1Equal or better
    Year 3Better
  • Seats in agent-compressible roles as % of ARR
    Exit story
    At closeMeasured
    Year 1Falling
    Year 3Below 25%

Horizon and stage. Reshape. Years one to two.

How it translates. A: a usage component on claims and visits, added to seats rather than replacing them. B: pricing per regulated product or filing, which the customer already counts. C: the transaction is the usage; this lever is R8. D: the central and riskiest lever, executed with the discipline HubSpot's quarter shows is needed. E: usage pricing is rare in enterprise; the migration is from services hours to subscription.

R4 · Expansion and cross-sell

What it is. Usage and health signals turned into expansion plays: new locations, new payers, headcount growth at the customer, feature usage that signals readiness for a higher tier, with the outreach drafted by agent and the account manager walking in with a business case. The customer success function becomes a revenue function measured on net retention.

The line it moves. Revenue (net retention).

Typical range and the evidence. Medium. Net retention from around 100% to 108 to 110% over three years is the case-study range. Vista reports ARR per customer success manager across seventeen selected portfolio companies rising "from $5.4 million in 2023 to $6.4 million in 2024 and $6.7 million in 2025," which supports the capacity assumption rather than the retention one.3 Gainsight's Aqua Security case reports churn predicted "with 95% accuracy" and a renewal forecast error falling "from 40% to under 5%."12 Workiva's 111% net retention and its 34% year-on-year growth in contracts above $300,000 is what the lever looks like at maturity in a regulated workflow.2

Conditions. The warehouse joining usage, support, billing and CRM at the account level; a purchased CS platform with the health model native or fed from the warehouse; success compensated on net retention; the packaging from R1, so expansion has something to sell.

Kill criteria. Expansion ARR below plan for two consecutive quarters with the signals in place, which means the packaging is wrong, not the signals.

  • Net revenue retention
    Revenue
    At close100 to 103%
    Year 1104%
    Year 3108 to 110%
  • Renewal forecast accuracy at 90 days
    Planning
    At close±25%
    Year 1±10%
    Year 3±5%
  • ARR per customer success manager
    Support and success
    At closeBaseline
    Year 1+5%
    Year 3+15 to 25%
  • Accounts with a quarterly review
    Retention
    At closeHalf
    Year 1All
    Year 3All

Horizon and stage. Reshape. Years one to two.

How it translates. A: new locations and payers at the agency. B: new regulations and product lines at the customer. C: new technicians and new service lines, and the payments attach itself. D: seat expansion into adjacent teams, and credits. E: new business units and add-on modules.

R5 · Retention

What it is. Early warning on churn from usage, support history, billing, conversation sentiment and champion changes, with intervention targeted at the accounts that respond to it rather than the ones most likely to leave; faster onboarding (G2); and product features the customer does not want to lose (R2).

The line it moves. Revenue (gross retention).

Typical range and the evidence. Strong for the targeting rule, medium for the delta. Gross retention improving two to three points over three years is the case-study range, and the evidence is that health models forecast churn well and that nobody has published a retention delta attributable to them. Ascarza's field experiments found that the highest-risk customers "are not necessarily the best targets" for retention spending and that targeting by sensitivity to the intervention is "significantly more effective than the standard practice of targeting customers with the highest risk of churning."13 SaaS Capital's 2026 benchmarks put median gross retention for bootstrapped companies between $3M and $20M of ARR at 91% and net retention at 103%.14 A health score tells you who is leaving; it does not tell you who can be kept, and the difference is the account manager's job.

Conditions. The same warehouse as R4; scores that show their drivers; outreach sent by people for the first year; an intervention budget that can be assigned by sensitivity rather than by risk.

Kill criteria. No measurable difference in retention between intervened and matched non-intervened accounts after four quarters, in which case the money moves to G2 and R2, where the retention effect is structural.

  • Gross revenue retention
    Revenue
    At close90 to 92%
    Year 1+1 point
    Year 3+2 to 3 points
  • Churned accounts with a reason recorded 90 days before
    Planning
    At closeFew
    Year 1Most
    Year 3All
  • Retention delta, intervened vs matched
    Revenue
    At closen/a
    Year 1Measured
    Year 3Positive

Horizon and stage. Reshape. Years one to three.

How it translates. A: the churn reasons are missed expectations at go-live and staff turnover at the agency; onboarding fixes the first. B: retention is structural (97% at Workiva) and the lever is small. C: retention follows payments attach, and Weave's 93% net retention with payments attached is the reminder that it does not follow automatically.15 D: self-serve churn is a funnel problem, not an account-management one. E: retention is set at implementation.

R6 · Win rate and cycle time

What it is. Call intelligence written back to the CRM, proposal and RFP drafts assembled from the knowledge base, security questionnaires answered from the compliance evidence library (O9), prospect-specific demo environments, and forecasting scored on engagement evidence rather than stage.

The line it moves. Revenue (new-logo ARR) and sales and marketing efficiency.

Typical range and the evidence. Medium; vendor results are plentiful and independent evidence is thin. Gong's analysis of 7.1 million opportunities found that teams that "deeply leverage AI generate 77% more revenue per representative," a correlation from the company that sells the AI.16 Conveyor's Intellistack case reports a 70% reduction in questionnaire turnaround and a two-to-threefold increase in capacity for a three-person security team.17 Forrester's study of Drata's platform, commissioned by the vendor, models sales time on security reviews falling by half, from 800 to 400 hours a year, and only a 0.2% operating-profit lift from it, which is the honest size of the revenue effect of compliance tooling.18 No independent study shows certification lifting win rates; the defensible claim is that it removes a gate and shortens one step of the cycle.

Conditions. A clean CRM with defined stages; a conversation-intelligence tool; the compliance evidence library; an ideal customer profile refreshed from win-loss analysis; compensation that rewards representative productivity rather than headcount.

Kill criteria. Meetings held and pipeline created, not vendor-reported activity; if pipeline per representative has not risen 25% in two quarters the tooling is cut, not extended.

  • Pipeline per account executive per quarter
    Revenue
    At closeBaseline
    Year 1+60%
    Year 3+120%
  • Security questionnaire turnaround
    Sales cycle
    At close10 days
    Year 12 days
    Year 31 day
  • CRM completeness on open deals
    Forecast
    At close~55%
    Year 190%
    Year 395%
  • Share of new ARR closed without the founder
    Key-person risk
    At closeVaries
    Year 175%
    Year 3100%

Horizon and stage. Deploy. Year one.

How it translates. A: founder dependence is the real target. B: the security questionnaire is the sales cycle in regulated enterprise; O9 and R6 are one lever. C: velocity selling to small merchants, where the demo environment matters most. D: sales-assist on product-qualified leads. E: enterprise cycles where the RFP and the questionnaire consume weeks.

R7 · Demand generation after search

What it is. A content engine producing regulatory explainers, guides and product education weekly with expert review, structured for answer engines as much as for classic search; event follow-up inside 48 hours; per-account briefs for the target list; and outbound that is human-edited rather than fully generated. The metric is qualified inbound, never sessions.

The line it moves. Revenue and sales and marketing spend.

Typical range and the evidence. Strong for the headwind, weak for the fix. Ahrefs' February 2026 study of 300,000 keywords found that "the presence of AI Overviews now reduces the click-through rate for position 1 by ~58%," up from 34.5% a year earlier; SparkToro's clickstream analysis found US Google searches ending without a click 68.01% of the time in the first four months of 2026.19 On outbound, Hunter's 2026 report on 31 million emails puts the average sequence reply rate at 4.5%, and head-to-head tests found fully AI-written emails earning about 1.4% positive replies against 2% to 4% for human-written ones, with human-edited AI drafts doing best.20 Jasper's named results (WalkMe's 3,000 hours saved, Akbank's 40% time reduction) measure production, not pipeline.21 The 11x episode of March 2025, when TechCrunch found an AI sales vendor displaying customers it did not have, is the reason this card measures meetings held.22 No credible evidence exists for AI-driven cost-per-lead reduction in B2B; the target below is internal.

Conditions. Marketing automation connected to the CRM; a content operations workflow with subject-matter review; attribution that tracks first touch and influenced pipeline; per-domain volume caps on outbound.

Kill criteria. Inbound share of pipeline not rising after four quarters, in which case the spend moves to events and referrals, which is where it came from.

  • Qualified inbound leads per month
    Revenue
    At closeBaseline
    Year 12.5x
    Year 35x
  • Cost per qualified lead
    Marketing
    At closeBaseline
    Year 1−30%
    Year 3−40%
  • Inbound share of pipeline
    Revenue
    At close~10%
    Year 120%
    Year 333%
  • Content pieces per month, expert-reviewed
    Marketing
    At close2
    Year 112
    Year 320

Horizon and stage. Reshape. Years one to two.

How it translates. A: state-by-state regulatory content that support and sales agents also cite. B: the regulatory explainer is the product's shop window and its content is the moat. C: local and vertical content for a velocity funnel. D: the largest exposure to the search headwind, and the largest content engine. E: account-based briefs for a short target list.

R8 · Embedded payments

What it is. Becoming the rail the customer's money runs on: card and bank payments accepted inside the product, first through a referral or revenue-share arrangement with a processor, then, at volume, as a payment facilitator setting the merchant's rate and paying the processor cost-plus.

The line it moves. A fintech revenue line at roughly 35% to 45% gross margin, against 75% to 80% for subscription; gross profit per customer; and, when it is measured on the right denominator, the EV/revenue multiple, which mechanically compresses as payments mix rises.

Typical range and the evidence. Strong, because the public vertical platforms disclose it. Toast's third quarter of 2025 prepared remarks are the only public decomposition of a take rate: "Fintech net take rate was 61 basis points, and payments net take was 49 basis points," on a total take of 98 basis points across SaaS and fintech, with SaaS gross margin at 79%.23 Toast's full-year 2025 results put fintech revenue at $5,037M of $6,153M and fintech gross profit at $1.8B, a gross margin of roughly 36%.24 ServiceTitan's fiscal 2025 usage revenue was $173.8M of $771.9M (22.5%) on $68.5B of gross transaction volume, about 25 basis points, and two independent analyses of its S-1 found the take rate "roughly constant at 0.25% over time."25 The lower-middle-market datapoint is EverCommerce's 2025 10-K: "Payment-related transactions comprised approximately 20% of revenue in 2025," with $13.0B of annualized processed volume against "an aggregate annualized payment opportunity exceeding $100 billion," roughly 13% penetration, on 4.8% revenue growth.26 AppFolio's value-added services, dominated by payments, were 77% of third-quarter 2025 revenue, with units up 7% and revenue up 21%: two-thirds of the growth was monetization per unit.27

Two counterexamples belong on the card. Procore launched payments in 2023 into construction, a vertical of large invoices, lien waivers and bank rails, and its full-year 2025 results do not mention payments at all.28 Weave has payments attached, 72% gross margin and 93% net retention: attach trades margin for growth and does not fix retention.15 The a16z figure of 0.75% to 1% of volume for payment facilitators describes the gross spread billed to the merchant, not what a platform keeps; Toast's 49 basis points is the net.29 The build-your-own facilitator path costs low seven figures, takes twelve to twenty-four months across every source, and, per one processor's own account, breaks even above roughly $2B of annual volume with about 5 basis points a year lost to fraud and chargebacks; the registration fee is quoted at $5,000, $10,000 and $75,000 to $100,000 by three vendors, and no major provider publishes the referral-versus-facilitator revenue share at all, which is itself a diligence finding.30

Conditions. Customers who bill their own customers through the product (C is the archetype; A's agencies bill payers, not patients, so the lever is the agency's collections); merchant agreements and processor contracts read in P2; PCI scope decided in P7; a referral model first, with the facilitator decision deferred until volume justifies it; payments revenue reported on gross profit and net take in basis points, never on revenue.

Kill criteria. Attach below 10% of eligible volume eighteen months after launch; or net take below 30 basis points at scale, which means the processor has the margin.

  • Payments attach, % of eligible volume
    Fintech revenue
    At close0 to 13%
    Year 120%
    Year 335 to 50%
  • Net take rate on processed volume
    Fintech gross profit
    At closen/a
    Year 130 to 40 bps
    Year 340 to 50 bps
  • Fintech gross profit, % of total gross profit
    Gross profit
    At close0 to 10%
    Year 115%
    Year 325 to 30%
  • Fintech gross margin
    Gross margin
    At closen/a
    Year 130 to 35%
    Year 335 to 45%

Horizon and stage. Invent. Year one for the referral launch, years two and three for attach and the facilitator decision.

How it translates. A: agencies collect from payers, not consumers; the lever is private-pay collections only, small. B: no transaction to attach to. C: the lever that carries the bridge, from 12% attach on $6B of customer volume toward 40%. D: not applicable. E: enterprise customers run their own treasury; not applicable.

R9 · Adjacent fintech

What it is. Capital advances, embedded insurance, payroll and cards offered on top of the payments rail, underwritten on the transaction data the platform already sees.

The line it moves. Revenue, and balance-sheet risk if the platform holds any of it.

Typical range and the evidence. Medium. Toast Capital and other non-payments fintech "contributed $58 million in gross profit and 11 basis points in take rate" in one quarter.23 Shopify Capital originated $4.2B in 2025, up about 40%, while the share of deals considered current fell from 93.7% to 91.9%: attach growth is partly a credit-box story, and that is the balance-sheet risk buyers underwrite badly.31 Embedded insurance economics, from a vendor writing in a venture firm's knowledge project with one named platform partner, are "between 5-25% of the premium back to the partner platform," with a start-to-purchase rate above 3% in the first months and a goal of 10% over one to two years; insurance attaches at a tenth of the rate payments does.32 Housecall Pro's Stripe case reports fourfold growth in fintech engagement and 10,000 expense cards ordered across 40,000 customers, and the fact that the company has a chief fintech officer is itself the organizational signal.33 Embedded payroll attach rates are not published anywhere I could find.

Conditions. R8 at volume; a partner that carries the balance sheet; the data rights to underwrite on transaction history (P2); a regulatory review per product per state.

Kill criteria. Any product where the platform's own capital is at risk without a partner carrying it; or attach below 3% after twelve months.

  • Fintech products beyond payments
    Revenue
    At close0
    Year 11
    Year 32 to 3
  • Attach on eligible base
    Revenue
    At close0%
    Year 13%
    Year 38 to 10%
  • Non-payments fintech take, basis points of volume
    Fintech gross profit
    At close0
    Year 13
    Year 38 to 11
  • Credit exposure on the platform's own balance sheet
    Risk
    At close0
    Year 10
    Year 30

Horizon and stage. Invent. Years two to three.

How it translates. C only, in practice; a small insurance attach is conceivable in A (agency liability) and in D through partners, and neither carries a bridge.

R10 · Data products

What it is. Benchmarks, indices, regulatory content and analytics sold on the aggregate data the company already holds, inside the data rights P2 established and the governance X3 maintains.

The line it moves. Revenue.

Typical range and the evidence. Weak, and labelled so. The argument is from the pricing power of regulatory-workflow software: Workiva's premium tiers and 97% gross retention, and Veeva's fiscal 2026 non-GAAP operating margin of 44.9% at 16% growth in a single regulated vertical, which is what compliance as a product looks like at maturity.34 No independent attach or pricing data exists for data products sold by a lower-middle-market vertical platform, and the risk that runs the other way is real: regulatory content moats were built on the cost of reading and structuring primary sources, which is exactly the task models cheapen, so an incumbent's content moat should be re-underwritten rather than assumed. That is an argument, not a finding, and the card says so.

Conditions. Aggregation rights in customer contracts; de-identification that survives an expert review; a customer who has asked for the benchmark; a price that does not cannibalize the core.

Kill criteria. No paying customer within nine months of a pilot.

  • Customers whose contracts permit aggregation
    Feasibility
    At closeCounted in P2
    Year 1Rising
    Year 3Most
  • Data products in market
    Revenue
    At close0
    Year 1Pilot
    Year 31
  • Revenue from data products, % of ARR
    Revenue
    At close0%
    Year 10%
    Year 31 to 3%

Horizon and stage. Invent. Years two to three.

How it translates. B is the archetype: the regulatory content is the product and the benchmark across customers is the second product. A: payer-behavior benchmarks for agencies, if the rights exist. C, D, E: marginal.

R11 · Self-serve conversion

What it is. Onboarding agents, in-product guidance and product-qualified-lead scoring in a product-led funnel, so that the trial converts without a person and the sales team touches only the accounts that show buying signals.

The line it moves. Revenue (new-logo and expansion) and sales and marketing spend.

Typical range and the evidence. Medium, and the public evidence cuts both ways in the same quarter. HubSpot's customer agent "resolves 72% of support tickets without human escalation," more than 16,000 customers activated its data agent in a quarter, and more than 55% of its Pro-and-above customers use its agents; in the same call it cut net customer additions on weaker conversion rates after moving to credits and outcome pricing.11 Atlassian's Rovo adopters grow ARR twice as fast as non-adopters, on a self-selected base.5 The lever works on conversion and cost to serve; the pricing model it usually arrives with is what disturbs the funnel, and R3's kill criteria exist for that reason.

Conditions. Product usage instrumented at the action level; a defined product-qualified-lead threshold with a measured conversion history; sales-assist capacity that touches only qualified accounts; a stable pricing model during the measurement window.

Kill criteria. Trial-to-paid conversion below baseline after two quarters, or new-logo count falling more than 20% while cost per acquisition improves, which means the funnel narrowed rather than converted.

  • Trial-to-paid conversion
    Revenue
    At closeBaseline
    Year 1+15%
    Year 3+30%
  • Share of new ARR closed without a sales touch
    S&M
    At closeBaseline
    Year 1+10 points
    Year 3+20 points
  • Cost per new customer
    S&M
    At closeBaseline
    Year 1−20%
    Year 3−35%
  • Net customer additions per quarter
    Revenue
    At closeBaseline
    Year 1Not below baseline
    Year 3Growing

Horizon and stage. Reshape. Year one.

How it translates. D is the archetype and the whole card. C has a self-serve tail for the smallest merchants. A, B and E sell through people.

Sources

  1. Salesforce, "Salesforce Pricing Update 2025," June 17, 2025, https://www.salesforce.com/news/stories/pricing-update-2025/ (V); Zylo, 2026 SaaS Management Index, January 29, 2026, https://zylo.com/news/2026-saas-management-index (I, vendor dataset)
  2. Workiva Q2 fiscal 2026 earnings call, August 4, 2026 (transcript via The Motley Fool, August 11, 2026). https://www.fool.com/earnings/call-transcripts/2026/08/11/workiva-wk-q2-2026-earnings-call-transcript/ (I, public company)
  3. Vista Equity Partners, AI Impact: Vista Portfolio 2026 Mid-Year Report, July 16, 2026, Vista-selected subsets (n=17 for ARR per CSM). https://www.vistaequitypartners.com/insights/ai-impact-vista-portfolio-2026-mid-year-report/ (V, portfolio)
  4. KeyBanc Capital Markets and Sapphire Ventures, private SaaS survey, November 13, 2025. https://www.prnewswire.com/news-releases/private-saas-company-survey-reveals-ai-driven-transformation-and-sustained-operational-excellence-302615030.html (I)
  5. Atlassian, Q4 FY26 shareholder letter, SEC filing, August 6, 2026. https://www.sec.gov/Archives/edgar/data/1650372/000165037226000031/teamq42026shareholderlet.htm (I, public company; no matched cohort)
  6. Figma Q2 2026 earnings call, August 12, 2026 (transcript via The Motley Fool); primary release at investor.figma.com. https://www.fool.com/earnings/call-transcripts/2026/08/12/figma-fig-q2-2026-earnings-call-transcript/ (I, public company)
  7. Workday Q1 fiscal 2027 earnings call, May 21, 2026. https://www.fool.com/earnings/call-transcripts/2026/05/21/workday-wday-q1-2027-earnings-call-transcript/ (I, public company)
  8. Rotenstein L. et al., "Changes in Clinician Time Expenditure and Visit Quantity With Adoption of AI-Powered Scribes," JAMA, April 1, 2026, https://jamanetwork.com/journals/jama/article-abstract/2847319 (I); pricing via Sacra (Abridge) and reseller listings for DAX Copilot, https://sacra.com/c/abridge/ (I, reported prices)
  9. Kyle Poyar, "The 2026 State of B2B Monetization," Growth Unhinged, May 13, 2026. https://www.growthunhinged.com/p/the-state-of-b2b-monetization-in-2026 (I)
  10. a16z, "AI is driving a shift towards outcome-based pricing," December 19, 2024. https://a16z.com/newsletter/december-2024-enterprise-newsletter-ai-is-driving-a-shift-towards-outcome-based-pricing/ (I, opinion)
  11. HubSpot Q2 2026 earnings call, August 12, 2026. https://www.fool.com/earnings/call-transcripts/2026/08/12/hubspot-hubs-q2-2026-earnings-call-transcript/ (I, public company)
  12. Gainsight, Aqua Security case study, undated. https://www.gainsight.com/customer/aqua-security-predicts-churn-with-95-accuracy-thanks-to-staircase-ai/ (V)
  13. Eva Ascarza, "Retention Futility: Targeting High-Risk Customers Might Be Ineffective," Journal of Marketing Research 55(1), 2018. https://papers.ssrn.com/sol3/papers.cfm?abstract_id=2759170 (I)
  14. SaaS Capital, "Benchmarking Metrics for Bootstrapped SaaS Companies," April 24, 2026. https://www.saas-capital.com/blog-posts/benchmarking-metrics-for-bootstrapped-saas-companies/ (I)
  15. Weave Q4 and full-year 2025 results, February 2026 (via Barchart): revenue $239.0M, gross margin 72.1%, net revenue retention 93%, payments not broken out. https://www.barchart.com/story/news/313943/weave-announces-fourth-quarter-and-full-year-2025-financial-results (I, public company)
  16. Gong Labs, "AI is now a trusted decision-maker in revenue teams," December 4, 2025, 7.1M opportunities. https://www.gong.io/press/new-gong-labs-research-finds-ai-is-now-a-trusted-decision-maker-in-revenue-teams (V, correlational)
  17. Conveyor, Intellistack customer story, undated. https://www.conveyor.com/customers/intellistack (V)
  18. Forrester Consulting, The Total Economic Impact of Drata, October 2025, commissioned by Drata. https://tei.forrester.com/go/Drata/automationplatform (V, sponsored)
  19. Ahrefs, "AI Overviews reduce clicks by 58% (update)," February 4, 2026, https://ahrefs.com/blog/ai-overviews-reduce-clicks-update/ (I); Search Engine Land on SparkToro/Similarweb, June 9, 2026, https://searchengineland.com/google-zero-click-searches-2026-study-479717 (I)
  20. Hunter, The State of Cold Email 2026, 31M emails; Saleshandy, "AI vs human cold emails," June 20, 2026. https://hunter.io/the-state-of-cold-email ; https://www.saleshandy.com/blog/ai-vs-human-cold-emails/ (I, vendor datasets)
  21. Jasper, WalkMe and Akbank case studies, undated. https://www.jasper.ai/case-studies/walkme ; https://www.jasper.ai/case-studies/akbank (V)
  22. TechCrunch, "a16z- and Benchmark-backed 11x has been claiming customers it doesn't have," March 24, 2025. https://techcrunch.com/2025/03/24/a16z-and-benchmark-backed-11x-has-been-claiming-customers-it-doesnt-have (I)
  23. Toast, "Third Quarter 2025 Earnings Call, Prepared Remarks," November 2025. https://s28.q4cdn.com/141746709/files/doc_financials/2025/q3/Q3-25-Prepared-Remarks.pdf (I, public company)
  24. Toast, "Toast Announces Fourth Quarter and Full Year 2025 Financial Results," Business Wire, February 12, 2026. Gross margin derived from fintech revenue and fintech gross profit as reported. https://www.businesswire.com/news/home/20260212058106/en/Toast-Announces-Fourth-Quarter-and-Full-Year-2025-Financial-Results (I, public company)
  25. ServiceTitan, fiscal 2025 results, March 13, 2025, https://investors.servicetitan.com/news-releases/news-release-details/servicetitan-announces-fiscal-fourth-quarter-and-full-year (I); Wing Venture Capital, "ServiceTitan's IPO: A Deep Dive," December 2024, https://www.wing.vc/content/servicetitans-ipo-a-deep-dive ; Tanay Jaipuria, "ServiceTitan S-1 Breakdown," December 5, 2024 (I, analyses of the S-1)
  26. EverCommerce, Form 10-K for fiscal 2025 (via StockTitan filing summary; verify verbatim against EDGAR before quotation). https://www.stocktitan.net/sec-filings/EVCM/10-k-ever-commerce-inc-files-annual-report-40fc74a758a9.html (I, public company)
  27. AppFolio, third quarter 2025 results. https://ir.appfolioinc.com/news-releases/news-release-details/appfolio-inc-announces-third-quarter-2025-financial-results (I, public company)
  28. Procore, fourth quarter and full year 2025 results, February 2026; no mention of Procore Pay. https://www.procore.com/press/procore-announces-fourth-quarter-and-full-year-2025-financial-results (I, public company)
  29. a16z, "Fintech Scales Vertical SaaS," updated September 9, 2024. https://a16z.com/fintech-scales-vertical-saas/ (I, opinion)
  30. Stripe Connect pricing, accessed September 10, 2026, https://stripe.com/connect/pricing (V, published pricing); Stax, "What are the costs of being your own payments facilitator?", updated February 7, 2025, https://staxpayments.com/blog/what-are-the-costs-of-being-your-own-payments-facilitator/ (V); Tilled, "The day-to-day of operating as a payment facilitator," October 19, 2021, cited for mechanism only, https://www.tilled.com/blog/the-day-to-day-of-operating-as-a-payment-facilitator (V, dated); Payroc, "ISV Payment Models Compared," April 24, 2026, no figures, https://blog.payroc.com/isv-payment-models-compared-referral-vs-gateway-vs-iso-vs-payfac (V)
  31. deBanked, "Shopify Capital Finishes 2025 With $4.2B in MCAs and Business Loans," February 18, 2026. https://debanked.com/2026/02/shopify-capital-finishes-2025-with-4-2b-in-mcas-and-business-loans/ (I, trade press)
  32. Cole Riccardi (Authentic), "How to Succeed In Scaling Your Embedded Insurance Product," Tidemark Vertical SaaS Knowledge Project, chapter 110. https://www.tidemarkcap.com/vskp-chapter/how-to-succeed-in-scaling-your-embedded-insurance-product (V, one named platform)
  33. Stripe, "Housecall Pro grows into a complete fintech platform using Stripe," undated. https://stripe.com/customers/housecall-pro (V)
  34. Workiva, as 2; Veeva, fiscal 2026 results, March 4, 2026. https://www.prnewswire.com/news-releases/veeva-announces-fourth-quarter-and-fiscal-year-2026-results-302704492.html (I, public company)

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