Tasks / Strategy

Develop product strategy

Can the model make a coherent choice grounded in the evidence, rather than list aspirations?

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. 38% were usable with at most a quick edit.

Reliably right

Produces the required deliverable100% pass
Complete strategy document in the requested form, length, and for the named reader; the board could act on it.
GPT-6 Astra · ChatGPT · Supply or demand for a stalled marketplace
Diagnosis before prescription100% pass
Diagnosis: students can't find the right tutor; actions (intake, recommendations, rematch, manual matching) directly address it.
GPT-6 Astra · ChatGPT · Supply or demand for a stalled marketplace
Tells the CEO plainly100% pass
It clearly states the enterprise-first plan is wrong for next year, backs it with numbers, and presents the alternative.
GPT-6 Astra · ChatGPT · Enterprise, says the CEO

Where it slips

Names an advantage that's hard to copy11% pass
Does not name a benefit and a barrier that a well-funded competitor couldn't copy; no moat is identified.
GPT-6 Astra · ChatGPT · Supply or demand for a stalled marketplace
Proposes tests that could fail42% pass
The SMB pilot lacks a numeric threshold for success; while the payback guardrail has a threshold and action, not every proposed test/gate meets the full requirement.
GPT-6 Astra · ChatGPT · Enterprise, says the CEO
Avoids unsupported claims44% pass
Presents 'root cause: we've let the loudest requests set the roadmap' and 'SMB remains our top-of-funnel' as facts without labelling them as hypotheses or citing evidence.
Haiku 5.5 · API · Enterprise, says the CEO

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.

Diagnosis before prescription
Does the strategy name the crux, the specific obstacle or opportunity the evidence points to, and do the proposed actions follow from that diagnosis?
Passes when States one crux grounded in the supplied evidence, and each major action visibly addresses it.
Bangaly KabaLenny’s Podcast
Names an advantage that's hard to copy
Does the strategy say what will make its position hard for an informed, well-funded competitor to copy (a benefit customers value plus a barrier to copying it), rather than relying on being first, on features, or on funding?
Passes when Names the benefit and the barrier, and why a capable competitor couldn't simply replicate it.
Hamilton HelmerLenny’s Podcast
Says what it gives up
Does the strategy name what the company will stop doing, or deliberately not do, in order to pursue it?
Passes when Names at least one real thing being dropped or declined, with the reason it loses out.
Gokul RajaramLenny’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 · Proposes tests that could fail · and 2 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 Cadence. Our CEO wants a strategy for next year the exec team can rally behind, and believes it's enterprise (the note is below). Write the strategy memo, in no more than 1,200 words: the diagnosis, the guiding policy (where we play and what we stop), the coherent actions for next year, and how we'll know it's working. Tell the CEO if you think they're wrong. The files are attached.

What the model was given6 items: About Cadence, ceo_note.md, unit_economics_by_segment.csv, enterprise_detail.md, mid_market_detail.md, smb_detail.md

About CadenceStaff scheduling and time tracking, sold to businesses with hourly workers.

ceo_note.md1 lines · Download

From the CEO: "I want a strategy for next year that the exec team can rally behind. I believe it's enterprise. Tell me if I'm wrong."

unit_economics_by_segment.csv3 rows · Download

segment,customers,avg_arr_usd,gross_margin_pct,support_cost_per_customer_year_usd,cac_usd,payback_months,net_revenue_retention_pct,logo_churn_year_pct
SMB self-serve,6200,1100,78,610,740,31,88,34
Mid-market,890,14500,81,1900,9800,9,118,7
Enterprise,34,96000,64,21000,118000,26,104,9

enterprise_detail.md4 lines · Download

# Enterprise detail

- Average sales cycle: 9 months. 5 of the last 8 deals needed custom features (built by the core team, about 14 engineer-weeks each).
- The CEO's plan: "Win enterprise. Hire 10 enterprise AEs and a solutions team, and build SSO, audit logs and custom workflows this year."

mid_market_detail.md5 lines · Download

# Mid-market detail

- Best-retaining segment. Expansion comes from adding locations and seats.
- Top requests: multi-location reporting, payroll integrations, shift templates.
- Win rate against our main competitor: 61%.

smb_detail.md4 lines · Download

# SMB self-serve detail

- 62% of support tickets come from SMB accounts. Free trial converts at 4%.
- Most SMB customers are on the $79/month plan with unlimited phone support.

What a strong answer doesThe answer key the graders mark against

Diagnoses from the unit economics: mid-market is the engine (payback 9 months, NRR 118%, churn 7%, wins 61% against the main competitor); SMB self-serve loses money once support and churn are counted (about $1,100 a year at 78% gross margin is about $860, minus $610 of support, leaves about $250 a year against $740 to acquire, with 34% leaving each year; payback 31 months, NRR 88%) and generates 62% of tickets; enterprise is slow and expensive (payback 26 months, 64% gross margin, 9-month cycles, 5 of 8 deals needing about 14 engineer-weeks of custom work). Tells the CEO the enterprise bet is wrong for next year: it would pull the core team into custom work and stretch payback. Policy: win mid-market, expanding on locations and seats; stop subsidising SMB support (change the plan or pricing, self-serve support, raise the entry price) rather than abandon it; serve enterprise only where it buys the product as is. Coherent actions: mid-market roadmap (multi-location reporting, payroll integrations, shift templates), SMB support and pricing changes, no custom enterprise work. Names what it gives up and how it'll know (mid-market NRR and payback, SMB support cost per customer).

Critical failures (cap the score at 40)

Recommends hiring the enterprise team and building custom workflows as next year's main strategy

Task

Staff-level · v1.0

The outputs

8 setups answered this brief.

GPT-6 AstraChatGPT87Usable with a quick edit Sonnet 5.5API87Usable with a quick edit GPT-6.1 SolAPI85Usable with a quick edit Haiku 5.5API81Usable with a quick edit GPT-6 LunaAPI75Needs more work Opus 5.5Claude71Needs more work Gemini 3.8 FlashAPI67Needs more work Gemini 3.5 Flash-LiteGemini56Needs more work

Gemini 3.5 Flash-LiteGemini

Needs more than a quick edit6 of 12 checks passed

The memo contains factual inaccuracies (incorrect SMB average price and net-negative margin claim) that a PM would need to correct before use; otherwise the reasoning is sound but the errors undermine trust in the evidence.

Output

MEMORANDUM

TO: CEO FROM: VP of Product DATE: October 24, 2023 SUBJECT: Product & Go-To-Market Strategy for Next Year

You asked for a strategy the executive team can rally behind, and stated your belief that our future lies in enterprise.

You are wrong. If we pivot our resources toward enterprise next year, we will stall our fastest-growing segment, burn cash on an unscalable product architecture, and distract the company from our true economic engine.

Here is our reality, our diagnosis, and the strategy we should actually pursue.

---

1. The Diagnosis: Where the Numbers Really Point

To evaluate your enterprise hypothesis, we have to look at the unit economics across our three segments (SMB, Mid-Market, Enterprise):

SMB Self-Serve (6,200 customers, $1,100 ARR): This segment is an anchor dragging us down. A 34% logo churn and 88% NRR means we are running to stay in place. Worse, 62% of our support tickets come from SMB accounts who pay an average of $79/month while demanding unlimited phone support. We are subsidizing their operations at a severe net-negative margin once support costs are factored in.
Enterprise (34 customers, $96,000 ARR): Enterprise looks glossy on the top line, but the mechanics are broken. Our payback period is 26 months, our gross margin has cratered to 64% (due to heavy support and custom engineering), and NRR is a mediocre 104%. As noted in the enterprise detail, 5 of our last 8 deals required custom features built by our core engineering team—averaging 14 engineer-weeks each. We are currently operating as a custom software consultancy for large accounts, not a scalable SaaS business.
Mid-Market (890 customers, $14,500 ARR): This is our crown jewel. Mid-market boasts an 81% gross margin, a lightning-fast 9-month payback period, a stellar 118% NRR, and a low 7% logo churn. We win 61% of deals against our main competitor here. Expansion happens organically as clients add locations and seats.

The Diagnosis: We are suffering from strategic schizophrenia. We are spending engineering cycles building bespoke features for 34 enterprise logos while burning support bandwidth on 6,200 low-end SMBs. Meanwhile, we are under-investing in the Mid-Market—the only segment where we have product-market fit, high retention, and clear competitive dominance.

---

2. The Guiding Policy

Where We Play: We will focus our go-to-market, product development, and company roadmap entirely on the Mid-Market (companies with roughly 100 to 1,000 hourly workers).

What We Stop: 1. We stop custom enterprise builds. We will not pull core engineers off the roadmap to build one-off workflows for enterprise deals. If a whale customer requires custom engineering, we walk away. 2. We stop optimizing for SMB acquisition. We will sunset active acquisition efforts for self-serve SMBs and strip away unscalable touchpoints (like unlimited phone support for $79/mo accounts) to stop the margin bleed. 3. We stop treating Enterprise as our primary growth vector. We will not hire 10 enterprise AEs or build a dedicated solutions team.

By pulling back from Enterprise and SMB, we concentrate all our capital on scaling what is already working brilliantly in the Mid-Market.

---

3. Coherent Actions for Next Year

To capture the mid-market opportunity, product and go-to-market will execute three synchronized moves:

#### Action 1: Productize for Mid-Market Expansion (Product & Engineering) Instead of building custom enterprise workflows (SSO, audit logs, and bespoke routing), our engineering team will build the top three requested features that drive multi-location expansion and stickiness in the Mid-Market: * Multi-location reporting: Giving regional managers roll-up visibility across disparate sites. * Robust payroll integrations: Deepening native syncs with major mid-market payroll providers to reduce administrative friction. * Advanced shift templates: Allowing complex scheduling rules to be deployed instantly across new locations.

#### Action 2: Pivot Go-To-Market to Land-and-Expand (Sales & Marketing) We will reallocate budget from SMB acquisition and enterprise pipe-dreams directly into Mid-Market account executive and customer success headcount. * Our motion will focus on landing a mid-market business at a single location or division, then leveraging our stellar NRR (118%) to expand horizontally into new locations. * We will introduce tiered packaging that naturally captures revenue as mid-market clients add locations and seats.

#### Action 3: Streamline or Harvest the SMB Tier (Operations & Support) We cannot drop our existing 6,200 SMB customers overnight, but we must stop bleeding margin on them. * Transition self-serve SMB support away from expensive phone queues to a self-service knowledge base and AI-driven chat. * Raise prices on legacy low-tier plans to match the true cost-to-serve, accepting natural churn as a feature, not a bug, which frees up support capacity for our mid-market clients.

---

4. How We'll Know It's Working

If we execute this focus on the Mid-Market, we will see specific operational shifts within the next 12 months:

Mid-Market ARR Growth: Mid-market ARR growth rate accelerates by 35% year-over-year as we direct 80% of our sales and marketing capacity here.
Payback and Margins: Our blended gross margin climbs back toward 80%+ as high-margin mid-market revenue outpaces low-margin enterprise custom work and unprofitable SMB volume. Payback periods across the active customer base remain under 10 months.
NRR Expansion: Mid-market NRR increases from 118% to 122%+ driven by faster multi-location adoption of our new reporting and payroll features.
Engineering Velocity: Feature delivery velocity increases by 40% because engineering is no longer interrupted by 14-week custom enterprise implementations.

Summary

Pivoting to enterprise feels ambitious, but the data tells us it is a trap. We would be trading a high-margin, highly defensible leadership position in the Mid-Market to become a low-margin, high-friction consultancy for a handful of giants.

Let’s double down on where we win, where retention is highest, and where our unit economics sing. Let's own the Mid-Market next year.

Grades and run details

Decision model 71 · LLM judge 46

Decision model checks

partialUses the supplied evidence correctly3%
passAddresses the actual decision45%
passRespects explicit constraints54%
failIdentifies material uncertainty99%
failAvoids unsupported claims42%
passProduces the required deliverable76%
passReads the segment economics71%
passTells the CEO plainly100%
passDiagnosis before prescription100%
partialProposes tests that could fail49%
partialNames an advantage that's hard to copy59%
passSays what it gives up100%

Run

Run: #1
Time to output: 9 s
Submitted: 5 Oct 2026

GPT-6.1 SolAPI

Usable with a quick edit10 of 12 checks passed

The output is a well-reasoned, complete strategy memo with correct evidence; a product manager could use it with light edits to wording or emphasis without re-checking facts or logic.

Output

Cadence: Next-Year Strategy

To: CEO and executive team From: VP Product Decision: Make multi-location mid-market customers our growth engine—not enterprise.

1. Diagnosis: Our constraint is profitable, repeatable growth

I think the enterprise-first plan is wrong for next year. Enterprise may become attractive, but our current evidence does not justify hiring ten enterprise AEs, adding a solutions team, and committing the core product team to enterprise features simultaneously. That would scale a motion we have not yet made repeatable.

Our strongest business is already mid-market:

Segment	Current ARR¹	Gross margin	CAC payback	NRR	Annual logo churn
---	---:	---:	---:	---:	---:
SMB self-serve	$6.8M	78%	31 months	88%	34%
Mid-market	$12.9M	81%	9 months	118%	7%
Enterprise	$3.3M	64%	26 months	104%	9%

¹Customers multiplied by average ARR.

Mid-market contributes approximately 56% of current ARR, has the best retention and margins, and expands through additional locations and seats. Its 61% win rate against our main competitor suggests a competitive advantage worth reinforcing.

Enterprise has larger contracts, but not better economics. Sales take nine months; five of the last eight deals required custom features, consuming approximately 70 engineer-weeks. Those deals impose an opportunity cost beyond their acquisition expense: the core team cannot simultaneously build bespoke workflows and improve the product that drives our best-performing segment. Enterprise NRR of 104% provides little evidence that expansion will compensate for that burden.

SMB is also not an efficient growth engine today. Trial conversion is 4%, annual churn is 34%, and SMB generates 62% of support tickets. Unlimited phone support on a predominantly $79/month plan is a service promise poorly matched to customer value.

We should validate how support costs enter reported gross margin and payback before constructing a fully loaded profitability model. But the segment ranking is clear enough to act.

The central problem is resource allocation: we are tempted by large contracts while underinvesting in the customers where acquisition, retention, expansion, and product fit already reinforce one another.

2. Guiding policy: Win repeatable multi-location growth

Where we play: Businesses with hourly workers operating multiple locations, within our existing mid-market segment. We will refine that profile by industry, location count, and integration needs using our strongest retained and expanding cohorts—not assume every mid-market customer is equally attractive.

How we win: Make it easier to run scheduling, time tracking, and payroll handoffs consistently across locations. Land with a repeatable implementation, then grow as customers add locations and seats.

What we stop:

Do not execute the proposed enterprise hiring plan. No ten-AE expansion or dedicated solutions-team buildout next year.
Stop allowing individual prospects to commandeer the core roadmap. Custom workflows are not a strategic product category.
Stop optimizing SMB for signup volume while ignoring conversion, churn, and support burden.
Stop promising unlimited phone support to new low-price SMB customers. Change existing commitments carefully at renewal, with notice and clear alternatives.

We will retain and serve existing enterprise customers and accept selective new opportunities that fit the standard product. Enterprise remains an option to prove—not the company’s organizing strategy.

3. Coherent actions for next year

A. Build the multi-location operating backbone

Owners: Product and Engineering

Commit at least 70% of planned product capacity to the mid-market growth loop and its enabling reliability work.

Prioritize the three requests supported by current customer evidence:

Multi-location reporting: Give operators a consistent view across sites.
Payroll integrations: Reduce manual handoffs and implementation friction; prioritize providers used by our target customers.
Shift templates: Make repeatable scheduling easier across locations.

In Q1, confirm priority and scope through customer research, usage data, and lost-deal analysis. Ship in staged releases during Q2–Q3, then use Q4 to improve adoption and remove rollout friction. Success means customers using these capabilities—not merely features released.

SSO and audit logs enter the roadmap only where they unlock repeatable demand from our target segment or address necessary security obligations. We will not bundle them with speculative custom workflows.

B. Align selling and customer success around location expansion

Owners: Sales and Customer Success

Reallocate growth investment toward mid-market rather than enterprise headcount. Increase selling capacity in stages, conditional on cohort payback remaining healthy.

Create a standard qualification and implementation playbook. Establish an explicit location-expansion plan for suitable customers, including rollout milestones, adoption checkpoints, and commercial packaging that makes expansion straightforward.

Track why we win against our main competitor and turn that evidence into positioning, demonstrations, and onboarding. Product adoption, selling, and expansion should reinforce the same promise.

C. Repair SMB economics without abandoning customers

Owners: Growth and Support

For new customers, introduce clear support tiers, reserving phone support for appropriately priced plans. Improve onboarding and self-service around the largest ticket drivers. Test packaging and onboarding changes before broad rollout.

Do not increase SMB acquisition spending until conversion and cohort payback improve. Existing customers receive a transparent transition, not a surprise withdrawal of service.

D. Put enterprise behind an investment gate

Owners: CEO, Sales, Finance, and Product

Require executive approval for exceptions, with engineering effort and opportunity cost recorded before signing. Prefer standard-product deals; do not hide custom development inside revenue targets.

Reconsider a dedicated enterprise expansion only when successive cohorts demonstrate materially improved margins, payback approaching 12–15 months, and wins that do not depend on bespoke core-team work. A handful of large bookings is insufficient evidence.

4. How we will know it is working

Finance will establish consistent cohort definitions and quarterly reporting in Q1. Our proposed operating targets are:

Mid-market: NRR at least 120%; annual logo churn no worse than 7%; gross margin at least 80%; CAC payback no worse than 12 months as we scale.
Competitive position: Maintain at least a 60% win rate against our main competitor, using a consistent opportunity definition.
Product impact: Improve time to activate additional locations and adoption of reporting, integrations, and templates against Q1 baselines.
SMB repair: Lower tickets per customer and support cost per customer, improve trial conversion, and shorten new-cohort payback without worsening retention.
Execution discipline: Deliver the agreed mid-market capacity allocation and report every enterprise customization exception.

These are targets, not a revenue forecast. Finance should translate the strategy into a funded operating plan.

Bottom line: Next year should prove that Cadence can compound a repeatable advantage. Mid-market already shows that pattern. Enterprise currently does not.

Grades and run details

Decision model 83 · LLM judge 85

Decision model checks

passUses the supplied evidence correctly26%
passAddresses the actual decision100%
passRespects explicit constraints49%
passIdentifies material uncertainty48%
partialAvoids unsupported claims43%
passProduces the required deliverable72%
partialReads the segment economics36%
passTells the CEO plainly100%
passDiagnosis before prescription100%
partialProposes tests that could fail78%
partialNames an advantage that's hard to copy70%
passSays what it gives up100%

Run

Run: #1
API response time: 43 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.