Chief Product Officer Advisor
Ongoing Chief Product Officer advice: fit from retention curves, second-product timing, sunsets, product org shape, and board reporting.
Before & after
Same prompt, same agent — the only difference is the skill.
Product-market fit is critical for growth, and every company needs to think about how to achieve it. You should focus on understanding your customers' core problems, make sure your solution solves those problems better than alternatives, and validate that there's real demand. Many teams iterate on their product based on user feedback until they find something that resonates. It's also important to think about your positioning and how you'll communicate value to the market. Different metrics matter for different businesses, so you'll need to define what PMF looks like for you. Would you like to discuss specific frameworks or metrics?
CPO STRATEGY: PRODUCT-MARKET FIT ROADMAP QUARTER 1: PROBLEM VALIDATION • Interview 15 target accounts: CEO/operator, 3 use cases each • Document pain points: frequency, willingness to pay, current workarounds • Define ICE (Ideal Customer Profile): company size, revenue, industry vertical • Build proto: solve #1 ranked pain, 4-week user testing loop QUARTER 2: FIT SIGNALS • Launch with 5-8 pilot accounts (not random—hand-picked high-intent) • Track NPS + reason codes; target 50+ to claim category leadership • Measure: weekly usage (% active features), expansion (new use cases), retention (12-week cohort) • Portfolio: retire features <20% use; double down on #1 driver QUARTER 3: REPEATABILITY • Sales process: document what works; train AE on selection criteria • GTM: test inbound (content marketing) + outbound (ABM) channel split • Dashboard: track CAC payback vs LTV; require 24-month window minimum FIT DEFINITION FOR YOUR BIZ • Metric: 60%+ of active users return weekly • Churn: <5% monthly, caused only by churn out of industry • Upsell: 30% expand to multi-seat within 6 months
About this skill
Product leadership advice for a company past its first customers, grounded in your own retention and usage data. It tells you whether you really have fit, when a second product is premature, and how to shape the product org.
What it does
- Reads product-market fit from cohort retention shape by segment, not from signups or growth
- Applies second-product and portfolio rules: what is new (buyer, motion, tech) and what gets defunded
- Plans product sunsets with revenue at risk, contract notice, and migration steps
- Sketches product org structure and flags coordination-cost warning signs
- Outlines a stable product section for board meetings
What you get
A direct answer for quick questions, or one focused piece (fit assessment, sunset plan, org sketch, board outline). Heuristics are labeled as rules of thumb and missing data is marked for you to confirm.
Best for
Founders, heads of product, and new CPOs at seed to growth-stage companies deciding on fit, portfolio, and product org.
SKILL.md preview
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name: cpo-advisor
description: Ongoing Chief Product Officer advice for a scaling company - whether you really have product-market fit (read from retention curves, not signups), when to start a second product, how to split investment across core and new bets, when to sunset a product line, how to shape the product org as it grows, and how to report product to the board. Use when the user asks "do we have product-market fit?", "should we build a second product?", "how should I structure my product team?", "should we kill this product line?", "when do I hire a VP Product or CPO?", "how do I present product strategy to the board?", or just "I need a CPO's take on this".
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