Tasks / Growth

Write a GTM plan

Can the model pick the customers who value the difference most, position against what they do today, and build a go-to-market that lasts beyond launch day?

Task type v1.1 · 2 tasksLast changed 6 Oct 2026 · ChangelogDifficulty

What AI gets right here, and what you’ll still have to catch

From 16 graded outputs by 8 models. 50% were usable with at most a quick edit.

Reliably right

Positioned against the real alternative100% pass
It names the real alternatives (accountant-run payroll with mistakes, owner spreadsheet with risk) and ties the message to confidence and accuracy that those alternatives lack.
GPT-6 Astra · ChatGPT · Payroll, for the people who fear it
Protects the self-serve engine100% pass
Uses the 70% free-to-paid stat and product-qualified deal data to argue against capping the free plan, and keeps self-serve open.
GPT-6 Astra · ChatGPT · Enterprise, without killing the engine
Does the capacity sums100% pass
Works out deals needed (69-80), qualified opportunities (134), and AE-years (8) with checkable arithmetic.
GPT-6 Astra · ChatGPT · Enterprise, without killing the engine

Where it slips

Avoids unsupported claims47% pass
Presents the incorrect 'five of six no decision' figure as established fact, which is an unsupported claim about the current situation.
Opus 5.5 · Claude · Enterprise, without killing the engine
Uses the supplied evidence correctly52% pass
The claim 'Five of our six losses on existing-user deals ended in no decision' is not supported by the data (4 no-decision, 2 Miro), so a statement about the current situation is invented.
Opus 5.5 · Claude · Enterprise, without killing the engine
Identifies material uncertainty73% pass
The plan does not name specific unknowns that could change the decision, nor does it say how they would be resolved or what would trigger a pivot.
Gemini 3.8 Flash · API · Payroll, for the people who fear it

How it’s graded

Each check is built on how world-class product and growth leaders do this work, as they’ve described it on Lenny’s Podcast, and names the leader it comes from.

Positioned against the real alternative
Does the plan name what the target customer does today without this product (including the status quo or doing nothing), and tie the message to the value that alternative lacks?
Passes when Names the real alternative and the differentiated value against it, and picks the segment that cares most about that value.
April DunfordLenny’s Podcast
Sells against a pain the buyer feels
Is the core message built on a pain or risk the target buyer already feels, with evidence from the material, rather than on generic upside like saving time?
Passes when Leads with the pain the evidence shows buyers care about, and uses that evidence to choose the message.
Jeanne DeWitt GrosserLenny’s Podcast
Diagnoses message or channel first
Does the plan work out whether the problem is the message (people reach it but don't convert) or the channels (the right people never see it), and spend accordingly?
Passes when Uses conversion and reach data to say which it is, and puts the effort there.
Emily KramerLenny’s Podcast
Plans beyond launch week
Does the plan say how demand keeps coming after launch, with the ongoing engine and what's measured over months, rather than treating launch day as the whole plan?
Passes when Gives the ongoing motion after launch and the measures that show whether it's working over time.
Arielle JacksonLenny’s Podcast

Plus our standard checks

Uses the supplied evidence correctly · Addresses the actual decision · Respects explicit constraints · Identifies material uncertainty · Avoids unsupported claims · Produces the required deliverable · and 3 written for each task, which you’ll see in the tasks below.

The tasks

Read the brief, then compare up to three outputs, each with the LLM judge’s verdict on every check. Highlights mark what a PM had to fix.

The brief

You're the VP Product at Flowboard. The board wants $5M of new enterprise ARR next year, and our CRO, Jordan Hale, has drafted the enterprise go-to-market below. The CEO has asked for your version before the board meeting: who we sell to, how the self-serve product and the sales team work together, what we say against the alternatives, the capacity it takes, and what you'd change in Jordan's plan and why. No more than 1,300 words. The files are attached.

What the model was given6 items: About Flowboard, today.md, cro_enterprise_plan.md, enterprise_deals_last_12_months.csv, large_companies_using_flowboard.csv (companies over 1,000 employees with active self-serve or free teams), enterprise_win_loss_interviews.md

About FlowboardOnline whiteboards and diagramming for teams. Free plan, self-serve paid plans, and an enterprise plan sold by a small sales team.

today.md5 lines · Download

# Today

- Self-serve: 31,000 paying teams; free plan feeds 70% of new paying teams.
- Enterprise: 46 customers, average contract $64,000.
- Sales team: 3 account executives, closing about 10 enterprise deals a year each.

cro_enterprise_plan.md8 lines · Download

# Enterprise plan (CRO, draft for the board)

Target: $5M new enterprise ARR next year.
1. Cap the free plan at 3 users (today: unlimited users, 3 boards each), so teams have to talk to us.
2. Route every team over 10 seats to sales; remove self-serve checkout above 10 seats.
3. Hire 8 account executives and 6 SDRs; SDRs work outbound lists of Fortune 2000 companies.
4. Enterprise features: SSO, SCIM, audit logs, data residency.
…

enterprise_deals_last_12_months.csv65 rows · Download

deal,source,outcome,sales_cycle_days,acv_usd,lost_to
E-200,Outbound,won,201,32700,
E-201,Product-qualified (teams already using Flowboard),won,62,97000,
E-202,Product-qualified (teams already using Flowboard),won,61,108000,
E-203,Outbound,lost,192,,Miro (company standard)
E-204,Outbound,lost,204,,Miro (company standard)
E-205,Product-qualified (teams already using Flowboard),won,77,54200,
…

large_companies_using_flowboard.csv (companies over 1,000 employees with active self-serve or free teams)company,employees,teams_using_flowboard,active_users_30d,paying_seats,viewed_security_page_30d,asked_for_sso Aldergate Bank,15000,2,18,10,yes,yes Brightfield Bank,2400,6,54,36,yes,yes Corvel Logistics,15000,5,45,22,yes,yes Dunmore Holdings,4800,3,12,4,yes,yes Eastlake Health,1200,3,30,14,yes,yes Fennick Holdings,4800,8,48,30,yes,yes Galloway Retail,9000,9,36,20,yes,no Hartwell Group,1200,4,48,21,yes,no Iverson Retail,1200,3,18,9,yes,no Juniper Retail,1200,3,24,10,yes,no Kestrel Logistics,4800,1,12,6,yes,no Linton Group,1200,2,10,4,no,no Marlowe Group,2400,2,10,7,no,no Northcote Retail,9000,2,10,6,yes,no Oakhurst Group,9000,3,36,18,yes,no Pemberton Health,1200,1,6,2,yes,no Quayside Bank,4800,2,12,4,no,no Redfern Group,15000,3,18,10,no,no Stanway Health,9000,3,30,12,no,no Thornbury Bank,15000,3,24,12,no,no Upton Bank,9000,3,33,23,yes,no Varden Bank,2400,3,12,5,no,no Whitmore Bank,4800,2,8,5,no,no Yardley Logistics,15000,2,8,4,yes,no

enterprise_win_loss_interviews.md5 lines · Download

# Enterprise win/loss interviews (12 buyers, this year)

- Won (7): every win had teams already using Flowboard. "Our designers refused to give it up." "IT approved it because 300 people were already on it."
- Lost (5): four had standardised on Miro company-wide; switching meant migrating thousands of boards. One stayed on whiteboard photos and slides.
- What buyers said Flowboard does that Miro doesn't: real-time diagramming that stays tidy, and a free plan teams can start on without IT.

What a strong answer doesThe answer key the graders mark against

Builds enterprise sales on top of the self-serve engine instead of throttling it. The deals file shows product-qualified deals (teams already using Flowboard) won 19 of 25 at an average of about $72,600 and about 63 days, against outbound winning 4 of 25 at about $36,800 and about 190 days; product-qualified wins were about $1.38M of the $1.86M won. The free plan feeds 70% of new paying teams. So capping the free plan at three users and removing self-serve checkout above ten seats would choke the pipeline the enterprise business depends on, and the interviews say IT approved Flowboard because teams were already on it. Proposes product-led sales: AEs work the large-company list (multiple teams, SSO requests, security-page visits) with SSO and admin controls as the bridge, while keeping self-serve open. Positions against Miro and the status quo, not 'visual collaboration for the enterprise': where a company has standardised on Miro, don't lead with a migration; win where teams already use Flowboard, on tidy real-time diagramming and starting without IT. Reads outbound's poor results as a message problem as well as a channel one. Works out capacity: $5M at about $72,000 is about 70 deals, far more than three AEs close (about 30 a year), so it needs AE hiring focused on product-qualified accounts rather than SDR outbound lists. Plans the ongoing motion and the measures (product-qualified accounts, conversion, cycle time) beyond the first quarter.

Critical failures (cap the score at 40)

Endorses capping the free plan at three users or removing self-serve checkout above ten seats

Task

Staff-level · v1.0

The outputs

8 setups answered this brief.

GPT-6 AstraChatGPT100Usable with a quick edit Opus 5.5Claude91Usable with a quick edit Sonnet 5.5API84Needs more work GPT-6.1 SolAPI82Needs more work GPT-6 LunaAPI80Needs more work Haiku 5.5API80Needs more work Gemini 3.8 FlashAPI71Needs more work Gemini 3.5 Flash-LiteGemini57Needs more work

Sonnet 5.5API

Needs more than a quick edit11 of 13 checks passed

The output contains a factual error ('Six of the ten accounts above 10 seats have shown no IT interest' is wrong) and an unsupported effort claim, so a PM would need to re-check the data before using it.

Output

Enterprise GTM: VP Product recommendation

Bottom line: Jordan's plan sends our new hires at the channel that works worst and puts friction on the channel that works best. I'd back the enterprise features and some added sales capacity, but build the motion around the teams already using Flowboard. The board should see $5M as a stretch and about $3.4M as the likely case.

What last year's deals show

Last year we worked 65 deals, won 29, and booked about $1.86M of new ARR.

Source	Deals	Win rate	Avg won ACV	Avg won cycle	Share of new ARR
Product-qualified (teams already using us)	25	76%	$72.6K	63 days	74%
Inbound demo	15	40%	$55.1K	86 days	18%
Outbound	25	16%	$36.8K	190 days	8%

Outbound is two-thirds of the effort and 8% of the revenue. Of its 21 losses, 17 went to Miro as the company standard.

Across all sources, Miro took 26 of our 36 losses. "No decision" took 10, including 4 of the 6 product-qualified losses. The interviews agree: every win had teams already on Flowboard, and four of the five losses were Miro-standardised companies where switching meant migrating thousands of boards.

Who we sell to

Primary customer: a company with Flowboard already in several teams, where Miro is not yet the standard and IT is starting to engage.

The usage data lets us tier the 24 large companies already on Flowboard: - Tier A (6 accounts): asked for SSO. All six also viewed the security page. Aldergate, Brightfield, Corvel, Dunmore, Eastlake and Fennick together have 27 teams and 116 paying seats. Sales owns these now. - Tier B (10 accounts): viewed the security page but haven't asked for SSO. A product-led nudge and a light sales touch. - Tier C (8 accounts): no IT signal yet. Keep nurturing in-product.

Seat count is the wrong trigger. Aldergate (10 seats) and Dunmore (4 seats) asked for SSO and would be missed by a ">10 seats" rule. Six of the ten accounts above 10 seats have shown no IT interest.

Two gaps in this data: - The file covers only companies over 1,000 employees, so it understates our real product-qualified pool. - We don't record which incumbent tool a prospect uses. We should add that field now, because "Miro is the standard" predicts the loss.

How self-serve and sales work together

Self-serve generates demand and sales converts it.

Free plan stays open. It feeds 70% of new paying teams, and buyers cite "a free plan teams can start on without IT" as something Miro doesn't offer.
Checkout stays open at every size. Sales is triggered by signals: an SSO request, security page views, three or more teams in one domain, or a domain crossing an active-user threshold. A rep reaches out while the team keeps buying normally.
Sales sells the consolidation: security review, one contract, and an admin console, backed by the customer's own usage data ("300 people already use it"). That also answers the "no decision" losses, which need a champion kit and a usage-based business case.
Inbound demos are routed to the same team. A 40% win rate is worth keeping, but half the losses are to Miro standards, so qualify for the incumbent tool early.

What we say against the alternatives

Miro: don't contest "the enterprise whiteboard." Position as the best tool for real-time diagramming that stays tidy, and one that teams adopt without waiting for IT. Don't ask anyone to migrate. Win the team first and let usage make the case. Only 2 of 25 product-qualified deals went to Miro, versus 17 of 25 outbound deals.
Status quo (photos and slides): show the cost of the current process using their own team's usage.
Other tools: the data doesn't show us losing to any, so I'm making no claims about them.

Jordan's line, "The visual collaboration platform for the enterprise," is Miro's category claim, and it leaves out our actual advantages. I'd use something like: "Diagramming your teams already love, ready for IT to approve."

Capacity

Today each AE works about 22 opportunities a year (65 across 3 AEs) and closes about 10.

To reach $5M: - 60 product-qualified wins at 76% means about 79 opportunities, or $4.4M. - 12 inbound wins at 40% means 30 demos, or $0.66M. - That's about 109 opportunities, or roughly 5 AEs at today's load. - Product-qualified cycles are 63 days against 190 for outbound, so new AEs ramp faster on this mix. - Hire 3 AEs for 6 total. That gives a buffer, a faster ramp, and no outbound headcount.

Other hires (not part of Jordan's plan): - 2 reps who work product-qualified accounts, in place of 6 outbound SDRs. - 1 solutions engineer for security reviews. - 1 RevOps/growth analyst to build account-level usage scoring.

That's 7 sales-side heads against Jordan's 14, plus the engineering squad below.

The real risk is volume, not headcount. $5M needs product-qualified opportunities to roughly triple, from 25 to about 79. At double (50 opportunities), we land near $3.4M. The 24-company list can't deliver that alone, so RevOps needs to size the full pool, including sub-1,000-employee companies, before we commit to the board.

Engineering sequence: 1. SSO and SCIM first. Six accounts have already asked, and IT approval is the gate in our win stories. 2. Audit logs next. 3. Data residency only when a named deal requires it. Nothing in the loss data points to features. We lose to incumbency and indecision, so features are a gate, not a growth driver.

What I'd change in Jordan's plan

Jordan's item	My view
1. Cap free at 3 users	Reject. It throttles the source of 70% of new paying teams and 74% of enterprise ARR, and removes the "start without IT" advantage. If we need a lever, gate admin and security features, not users.
2. Remove checkout above 10 seats	Reject. Ten of the 24 large accounts are above 10 seats, and they are the ones converting. Keep checkout and trigger sales on IT signals.
3. 8 AEs + 6 SDRs on Fortune 2000 outbound	Replace. Outbound wins 16% of the time, at a $36.8K ACV and 190-day cycle, mostly against Miro standards. Hire 3 AEs and 2 product-qualified reps instead.
4. SSO, SCIM, audit logs, data residency	Keep, resequenced. SSO/SCIM first, audit logs second, residency on demand.
5. Messaging	Replace. It fights Miro on Miro's ground. Lead with team adoption and tidy diagrams, then IT readiness.

Why Jordan's plan lands short in-year (my estimate): an outbound AE produces about $368K a year (10 deals × $36.8K). New hires starting in Q1 won't see a first outbound close until around Q3, so 8 AEs yield well under $1M this year. Adding that to last year's $1.86M gives roughly $2.6M, before counting damage from the free cap and checkout changes to our best channel.

What I'd ask the board for

Commit to about $3.4M, with $5M as the stretch if product-qualified volume triples by mid-year.
Approve the smaller hiring plan and the SSO/SCIM squad.
Review progress quarterly on product-qualified opportunity count, win rate, and the share of losses to Miro.

I'd like to walk Jordan through this before the board meeting. We agree on the target and on the need for enterprise features. We disagree on where the next dollar of sales effort should go.

Claims the judge couldn’t find in the brief

Six of the ten accounts above 10 seats have shown no IT interest.
Outbound is two-thirds of the effort and 8% of the revenue.
We don't record which incumbent tool a prospect uses.
The file covers only companies over 1,000 employees, so it understates our real product-qualified pool.

Grades and run details

Decision model 96 · LLM judge 79

Decision model checks

passUses the supplied evidence correctly18%
passAddresses the actual decision98%
passRespects explicit constraints35%
passIdentifies material uncertainty96%
partialAvoids unsupported claims34%
passProduces the required deliverable82%
passFollows the deals data100%
passProtects the self-serve engine100%
passDoes the capacity sums96%
passPositioned against the real alternative99%
passSells against a pain the buyer feels77%
passDiagnoses message or channel first99%
passPlans beyond launch week100%

Run

Run: #1
API response time: 87 s
Submitted: 6 Oct 2026

Gemini 3.8 FlashAPI

Needs more than a quick edit10 of 13 checks passed

The output invents Miro's tagline and calls Miro the category leader without evidence, requiring fact-checking before use. Otherwise the plan is solid.

Output

MEMORANDUM

TO: Chief Executive Officer FROM: VP Product DATE: October 24, 2023 SUBJECT: Counter-Proposal to CRO Enterprise GTM Plan: Path to $5M New Enterprise ARR

Executive Summary

Reaching $5M in new enterprise ARR next year is achievable, but Jordan’s draft will choke the very engine that powers our business.

Jordan’s proposal relies on a legacy top-down playbook: restricting free/self-serve adoption and deploying cold outbound reps against Fortune 2000 accounts. The data from our last 12 months shows this approach is commercially unviable: * Cold outbound fails: Outbound win rates are 16%, sales cycles take 190 days, ACV is low ($36.8k), and 68% of losses go to Miro because they already hold the enterprise standard. * Product-Qualified Leads (PQLs) dominate: Enterprise deals originating from existing Flowboard usage boast a 76% win rate, a 64-day cycle, and an average ACV of $72.6k.

Flowboard does not win by out-shouting Miro in cold enterprise RFPs. We win via Product-Led Sales (PLS): landing virally with teams via our free and self-serve plans, and expanding into six-figure IT-sponsored enterprise contracts once organic adoption takes root.

---

What to Change in Jordan’s Plan & Why

Jordan's CRO Proposal	VP Product Recommendation	Why (Data-Backed Rationale)
:---	:---	:---
1. Cap free plan at 3 users (today: unlimited users, 3 boards).	Keep unlimited users / 3 boards. Introduce team-level sharing limits, but preserve viral intra-company collaboration.	Free plans feed 70% of self-serve paying teams. In enterprise win interviews, buyers explicitly cited that having "300 people already on it" forced IT approval. Capping users kills viral distribution and hands bottom-up adoption to competitors.
2. Remove self-serve above 10 seats; force teams to talk to sales.	Keep self-serve checkout up to 50 seats. Trigger automated sales outreach at 15+ seats or multi-team domain clusters.	31,000 paying teams rely on friction-free checkout. Shunting 11-seat teams to AEs bogs sales down in sub-$5k transactions instead of closing $70k+ enterprise contracts.
3. Hire 8 AEs and 6 cold SDRs targeting the Fortune 2000.	Hire 4 AEs and 2 Product BDRs (totaling 7 AEs, 2 BDRs). Point them exclusively at internal expansion and high-intent inbound.	Cold outbound yielded just 4 wins in 12 months. Reps running outbound into the Fortune 2000 run directly into entrenched Miro enterprise agreements. Product BDRs mining our existing base will generate 4x higher pipeline value.
4. Enterprise features: SSO, SCIM, audit logs, residency.	Agree, with precise sequencing: Prioritize SAML SSO, SCIM, and Domain Capture/Admin Console immediately.	6 large accounts (e.g., Aldergate Bank, Fennick Holdings) have already viewed security pages and requested SSO. Domain capture turns rogue usage into an immediate enterprise contract trigger.
5. Messaging: "The visual collaboration platform for the enterprise."	Messaging: "Precision diagramming and structured collaboration teams actually adopt."	"Visual collaboration platform" is Miro’s tagline. We cannot beat the category leader at their own positioning; we win on structured diagramming clarity and viral ease-of-use.

---

1. Who We Sell To (Target ICP)

We do not target cold accounts. Our Enterprise ICP consists of: * Target Accounts: Mid-market and Enterprise companies (1,000–15,000+ employees), heavily indexing on engineering, architecture, product, and design organizations. * Entry Footprint: Organizations with $\ge$2 active Flowboard teams or $\ge$20 active users across free/self-serve tiers. * Economic Buyers: VP of IT / CISO (concerned with governance, security, consolidation) paired with internal VP/Director Champions in Product/Engineering. * Immediate Target List: The 24 large enterprises already using Flowboard (e.g., Corvel Logistics, Brightfield Bank). Six of these companies already have multiple teams, paying seats, and active requests for SSO—representing an immediate pipeline of ~$450k ARR.

---

2. The Product-Led Sales Engine: Product & Sales Alignment

Instead of sales acting as a barrier to product adoption, the product serves as the primary pipeline generation channel for sales.

``` [ Free Plan: Unlimited Users ] ──> [ Self-Serve Expansion (up to 50 seats) ] │ │ └───> [ Domain Consolidation Trigger ] <───┘ │ ▼ [ Enterprise Sales (SSO, Governance, Security) ] ```

1. Top of Funnel (Free): Maintain the unlimited-user tier to let individual squads adopt Flowboard without procurement hurdles. 2. Expansion Triggers (PQL Engine): Instrument automated alerts to the BDR/AE team when: * A single company domain crosses 20 active monthly users across workspaces. * A workspace admin visits `/security`, `/compliance`, or searches for "SSO". * Multiple corporate credit cards from the same domain are paying for disjointed self-serve accounts. 3. In-Product Enterprise Gates: * Domain Control & SSO: When IT attempts to enforce SSO, the domain is claimed, prompting an enterprise consolidation conversation. * Centralized Admin & Audit Logs: Free and self-serve plans lack cross-workspace audit logs, data retention policies, and SCIM provisioning.

---

3. Positioning Against Alternatives (Winning Against Miro)

In head-to-head enterprise RFPs against Miro, we lose (17 outbound losses last year were to Miro standards). Switching thousands of legacy boards is an impossible sell. We win by changing the battleground:

Dimension	Miro	Flowboard
:---	:---	:---
Core Value	Broad, freeform digital whiteboard. Can quickly become cluttered and unwieldy.	Structured, precision diagramming that stays organized in real time.
Target User	General business users, workshop facilitators, broad marketing.	Technical & Product teams: System architects, engineers, UX designers, technical PMs.
Enterprise Pitch	"Standardize everyone on a single massive whiteboard."	"Complement or replace messy whiteboards with structured architecture and technical execution workflows."
Pricing / Procurement	Expensive wall-to-wall licensing with heavy IT mandates.	Frictionless bottoms-up landing that consolidates high-value technical teams with zero onboarding friction.

Key Narrative: "Miro is where teams brainstorm; Flowboard is where technical teams design, architect, and build. Keep Miro for casual sticky-notes, or standardize on Flowboard for clean, mission-critical systems architecture."

---

4. Capacity Model & Math to $5M New Enterprise ARR

Jordan’s proposal to hire 8 AEs and 6 cold SDRs adds excessive headcount burn with terrible pipeline efficiency. By focusing on PQLs and high-intent inbound, our reps will achieve substantially higher conversion and velocity.

#### Operating Assumptions (Derived from Historical Data) * Average Enterprise ACV: $70,000 (historical PQL average is $72.6k; outbound was $36.8k). * Target ARR: $5,000,000 $\rightarrow$ Requires 72 closed enterprise deals. * Win Rate: 60% (blended between 76% historical PQL win rate and 40% inbound demo rate). * Deals Needed in Late-Stage Pipeline: $72 / 0.60 = \mathbf{120\text{ qualified opportunities}}$. * Sales Cycle: 65–75 days (allowing fast pipeline velocity and intra-year closes).

#### Staffing Requirements * Account Executives (AEs): * Experienced enterprise AE capacity on warm PQLs = 12 deals/year ($840k ARR quota). * 72 deals $\div$ 12 deals/rep = 6 fully productive AEs. * Plan: Retain our 3 current AEs; hire 4 new AEs (staggered: 2 in Q1, 2 in Q2 to account for ramp). Total = 7 AEs. * Business Development Reps (Product BDRs): * Hire 2 Product BDRs (not 6 cold outbound SDRs). * BDRs do not dial cold Fortune 2000 lists. They mine our 31,000 paying teams, identifying multi-license domains, mapping org charts, and securing meetings with IT directors and engineering leads. * Capacity: 2 BDRs generating 5 qualified enterprise pipeline meetings/month each = 120 qualified opportunities/year. * Total Headcount Investment: 6 new hires (4 AEs, 2 BDRs) vs. Jordan’s 14 new hires (8 AEs, 6 SDRs).

This delivers more than 50% savings in customer acquisition cost (CAC) while cutting execution risk.

---

5. Summary of Recommended Product & GTM Deliverables

1. Q1 Product Roadmap Enablers: * Ship SAML 2.0 SSO, SCIM user provisioning, and Centralized Domain Capture. * Build internal PLG scoring dashboard connecting Segment/Mixpanel product events to Salesforce/HubSpot (flagging $\ge$2 teams or SSO searches). 2. Q1 Pricing & Packaging: * Keep Free (unlimited users, 3 active boards). * Keep Self-Serve Pro/Team up to 50 seats. * Package SSO, SCIM, custom data retention, and audit logs exclusively in Enterprise. 3. Sales Enablement: * Arm sales with the "Architecture vs. Whiteboarding" competitive battlecards against Miro. * Launch warm outreach sequences immediately into the 24 identified large accounts already using Flowboard.

Claims the judge couldn’t find in the brief

Miro is the category leader.
'Visual collaboration platform' is Miro's tagline.

Grades and run details

Decision model 77 · LLM judge 71

Decision model checks

failUses the supplied evidence correctly51%
passAddresses the actual decision84%
partialRespects explicit constraints26%
failIdentifies material uncertainty75%
partialAvoids unsupported claims43%
passProduces the required deliverable77%
passFollows the deals data94%
passProtects the self-serve engine100%
passDoes the capacity sums94%
passPositioned against the real alternative73%
passSells against a pain the buyer feels56%
passDiagnoses message or channel first80%
passPlans beyond launch week90%

Run

Run: #1
API response time: 47 s
Submitted: 6 Oct 2026

Check by check

Where the outputs differ comes first. Open a check to read the judge’s reasons. “Mixed” means the two graders disagreed.

Where they differ 2

Uses the supplied evidence correctlyMixedWrong

Sonnet 5.5 · API

Several claims about the current situation are unsupported or incorrect: 'Six of the ten accounts above 10 seats have shown no IT interest' is false (only 2), 'Outbound is two-thirds of the effort' has no basis, and 'We don't record which incumbent tool a prospect uses' is not in the supplied context.

Gemini 3.8 Flash · API

Claims that Miro is the category leader and that 'visual collaboration platform' is Miro's tagline are not in the supplied context.

Identifies material uncertaintyRightWrong

Sonnet 5.5 · API

Names the key unknown (size of the full product-qualified pool), bounds the risk ($3.4M likely vs $5M stretch), and says RevOps must size the pool before committing.

Gemini 3.8 Flash · API

The output does not name unknowns that could change the decision or how they would be resolved.

All got wrong 1

Avoids unsupported claimsWrongWrong

Sonnet 5.5 · API

Presents 'Outbound is two-thirds of the effort' and 'Six of the ten accounts above 10 seats have shown no IT interest' as facts when the first is unsupported and the second is incorrect.

Gemini 3.8 Flash · API

It presents 'Miro is the category leader' and 'Miro's tagline' as facts without evidence, and 'cold outbound fails' as an unqualified conclusion.

All got right 10

Addresses the actual decisionRightRight

Sonnet 5.5 · API

Commits early to a clear recommendation (reject free cap and checkout removal, build on product-qualified, target $3.4M with $5M stretch) and states what would change it (product-qualified volume tripling).

Gemini 3.8 Flash · API

The memo commits to a clear counter-proposal with specific changes, ICP, and capacity plan.

Respects explicit constraintsRightRight

Sonnet 5.5 · API

The output is a memo within ~1,200 words, addresses all requested topics, and does not endorse capping the free plan or removing self-serve checkout.

Gemini 3.8 Flash · API

The output is a memo to the CEO under 1,300 words, respecting the form and length.

Produces the required deliverableRightRight

Sonnet 5.5 · API

Delivers a complete, actionable memo to the CEO/board within the word limit, covering all requested elements.

Gemini 3.8 Flash · API

The memo covers all requested elements: who to sell to, self-serve/sales alignment, positioning, capacity, and changes to Jordan's plan.

Follows the deals dataRightRight

Sonnet 5.5 · API

Computes win rate, deal size, and cycle time by source and builds the motion around product-qualified accounts.

Gemini 3.8 Flash · API

It computes win rate, deal size, and cycle by source and builds the motion on product-qualified accounts.

Protects the self-serve engineRightRight

Sonnet 5.5 · API

Uses the 70% free-plan conversion and product-qualified deal data to argue against capping the free plan and removing checkout, and keeps self-serve open.

Gemini 3.8 Flash · API

It uses the 70% free-to-paid stat and PQL data to argue against capping, and keeps self-serve open up to 50 seats.

Does the capacity sumsRightRight

Sonnet 5.5 · API

Works out deals needed (60 product-qualified, 12 inbound), total opportunities (109), and AEs required (5, hire 3 to reach 6), with checkable arithmetic.

Gemini 3.8 Flash · API

It calculates 72 deals at $70k ACV, 120 opportunities at 60% win rate, and 6 AEs, with checkable sums.

Positioned against the real alternativeRightRight

Sonnet 5.5 · API

Positions against Miro (don't contest the enterprise whiteboard; win the team first) and the status quo (photos and slides), and picks the segment where Miro is not the standard.

Gemini 3.8 Flash · API

It names Miro and the status quo (whiteboard photos) as alternatives, and positions on structured diagramming for technical teams.

Sells against a pain the buyer feelsRightRight

Sonnet 5.5 · API

Leads with the pain of IT approval friction and the risk of losing a tool teams already love, backed by interview evidence that IT approved because people were already using it.

Gemini 3.8 Flash · API

The message leads with the pain of messy whiteboards and lack of adoption, supported by win/loss interviews.

Diagnoses message or channel firstRightRight

Sonnet 5.5 · API

Diagnoses that outbound has poor conversion (16% win rate) and long cycles, and shifts effort to the product-qualified channel while also changing the message against Miro.

Gemini 3.8 Flash · API

It diagnoses cold outbound as a channel problem and Miro's positioning as a message problem, shifting spend to PLS.

Plans beyond launch weekRightRight

Sonnet 5.5 · API

Describes the ongoing motion (product-led nudges, sales outreach on signals, RevOps scoring) and measures (opportunity count, win rate, share of losses to Miro) beyond launch.

Gemini 3.8 Flash · API

It describes ongoing PLS triggers, BDR mining, and a Q1 roadmap with scoring dashboard, not just launch.

Results

Every setup we’ve tested on this task type, across all its tasks and repeats, graded on the current checklist. Calibrated.

#	Model · Harness	Decision model	LLM judge	Runs	Critical failures
1	GPT-6 AstrawithChatGPT	100.0	100.0	2	None
2	Opus 5.5withClaude	96.0	85.2	2	None
3	GPT-6 LunawithAPI	94.2	89.3	2	None
4	GPT-6.1 SolwithAPI	93.8	78.0	2	None
5	Sonnet 5.5withAPI	98.1	77.7	2	None
6	Haiku 5.5withAPI	94.2	77.7	2	None
7	Gemini 3.8 FlashwithAPI	73.9	81.9	2	None
8	Gemini 3.5 Flash-LitewithGemini	74.2	63.5	2	None

What you get for the cost

No setup scores within 5 points of the leader at half its cost or less here, so the leader is also the best value.

Nobody beats these on both score and cost

Task score and relative cost by setup
Setup	Task score	Relative cost (cheapest = 1)
GPT-6 Luna · API	90	1.0×
Haiku 5.5 · API	82	3.3×
Gemini 3.5 Flash-Lite · Gemini	68	3.5×
Gemini 3.8 Flash · API	77	11×
GPT-6.1 Sol · API	84	16×
Sonnet 5.5 · API	84	46×
Opus 5.5 · Claude	91	75×
GPT-6 Astra · ChatGPT	100	81×

Cost is each output’s tokens at the model’s list price, shown relative to the cheapest setup. Runs done in an app have no usage meter, so theirs are estimated from the same setup’s measured runs. How we compare cost

The PM job

Taking a product or add-on to market with marketing and sales.

Why it matters

Launch plans fail by trying to reach everyone, by selling upside nobody feels, and by treating launch day as the whole plan.

What good looks like

One primary segment: those who value the difference most
Positions against what customers do today
Sells against a pain the buyer feels, with evidence
Diagnoses whether the problem is the message or the channel
Plans beyond launch week

Deliberately not measured

Creative copywriting quality

Capability tested

Go-to-market judgement

The failure we’re looking for

Every channel, every segment, and nothing after launch day

Grading

Decision model and LLM judge, calibrated against a blind PM review

What AI gets right here, and what you’ll still have to catch

Reliably right

Where it slips

How it’s graded

Positioned against the real alternative

Sells against a pain the buyer feels

Diagnoses message or channel first

Plans beyond launch week

Plus our standard checks

The tasks

The outputs

Output

Enterprise GTM: VP Product recommendation

What last year's deals show

Who we sell to

How self-serve and sales work together

What we say against the alternatives

Capacity

What I'd change in Jordan's plan

What I'd ask the board for

Claims the judge couldn’t find in the brief

Grades and run details

Decision model checks

Run

Output

Executive Summary

What to Change in Jordan’s Plan & Why

1. Who We Sell To (Target ICP)

2. The Product-Led Sales Engine: Product & Sales Alignment

3. Positioning Against Alternatives (Winning Against Miro)

4. Capacity Model & Math to $5M New Enterprise ARR

5. Summary of Recommended Product & GTM Deliverables

Claims the judge couldn’t find in the brief

Grades and run details

Decision model checks

Run

Check by check

Where they differ 2

All got wrong 1

All got right 10

Results

What you get for the cost

About the task

The PM job

Why it matters

What good looks like

Deliberately not measured