Where-to-Play Product Strategy as the Prioritization Engine
Turn an integrated set of strategic choices into the filter that decides every roadmap trade-off.
- Difficulty
- Advanced
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 95%
Annie Pearl treats prioritization as a downstream consequence of strategy, not a separate exercise. A product strategy must explicitly answer winning aspiration, where to play (market → segment → persona), and how to win — and by naming where you play it simultaneously names where you don't. Once that is settled, feature debates collapse into a single question: does this serve the target persona? At Calendly this replaced endless case-by-case trade-off arguments with a standing answer.
Origin
Pearl explicitly credits the book Playing to Win by A.G. Lafley and Roger Martin for the underlying strategy cascade (winning aspiration / where to play / how to win). Her contribution is operationalizing it as the day-to-day prioritization filter for a product org, plus embedding it in Calendly's core value 'focus wisely' and in its document templates.
Core principles
- 01Strategy is an integrated set of choices about how you will win in a chosen marketplace — not a list of goals.
- 02Where you will NOT play is the load-bearing half of the choice.
- 03Most companies believe they have clarity on their target customer; ask an individual PM or designer and the clarity usually evaporates.
- 04Saying no feels scary, but it is what lets you build something amazing for the people who matter most instead of average for everyone.
- 05Serving the core ICP still incidentally serves adjacent users — you are choosing who you optimize for, not who you exclude.
How to run it
- 1
Write the winning aspiration
State the future position in one sentence. Calendly's: become the best place to schedule, prepare for, and follow up on your external meetings. It must be concrete enough to imply what is out of scope.
Pro tip Phrase it as a job the product wins, not a market-share number — it has to be usable by a PM in a feature argument.
- 2
Cascade where to play down to persona
Do not stop at 'market'. Name the market, then the segments of that market, then the personas within those segments. Calendly landed on externally-facing roles: sales teams, recruiting teams, customer success teams.
Watch out A horizontal product that grew virally will resist this hardest — everyone is technically a user, so no one is the user.
- 3
Name the explicit non-targets
Write down the personas you are knowingly deprioritizing. Calendly deprioritized solopreneurs, freelancers, and small businesses as design targets — which is why a heavily-requested Venmo integration stays unbuilt.
Pro tip Keep one canonical 'we will not build X because of Y' example on hand; it makes the strategy real to the org faster than the doc does.
Watch out Expect the leaving-money-on-the-table objection. It is a cultural shift, not a slide.
- 4
Push the choice into templates, not posters
Reinforce focus through the artifacts people actually fill in: opportunity-assessment docs, PRDs, and product-review templates that all ask who the target customer is, who the target user within that customer is, what their needs are, and how you will solve those needs better than any alternative on the market.
Pro tip Calendly is fully remote — the reinforcement mechanism has to live in documents and review rituals, not office walls.
- 5
Let teams prioritize themselves
With the strategy settled, hand prioritization back to teams. Feature A vs feature B is now resolved by which one delivers more value to the named persona, without escalation.
Watch out If executives keep re-opening the 'who do we serve' question, the strategy is not embedded and you have simply moved the argument.
In the wild
Small businesses and solopreneurs repeatedly ask for a Venmo integration (Calendly already has PayPal). Because the strategy names sales, recruiting, and customer success teams as the core ICPs, the request does not serve a target persona and is clearly deprioritized — not debated afresh each planning cycle.
→ A recurring, emotionally-loaded request is answered once by the strategy rather than re-litigated, and roadmap capacity stays on the target personas.
When Pearl joined, Calendly served freelancers, consultants, sales, recruiting, CS, and education — so PMs had no basis to choose between features. Honing the strategy on market → segment → persona was, in her words, one of the most impactful things done early in her tenure.
→ PMs gained rigor around the target market and persona, could prioritize without escalation, and delivered deeper value to the chosen users.
Common mistakes
Assuming you already have target-customer clarity
Leadership almost always believes the ICP is obvious. The test is asking an individual PM or designer — if their answer is fuzzy, the clarity exists only on the exec team's slide.
Treating strategy as a document rather than a decision filter
A strategy that does not visibly kill a popular feature request is not doing any work. If nothing is being said no to, the where-to-play choice has not actually been made.
Is it for you?
Best for
Product leaders at a horizontally-successful company (especially post-PLG) where PMs cannot resolve feature trade-offs because every user type is technically a user.
Not ideal for
Pre-PMF startups still searching for who the product is for — you need signal from real usage before you can credibly close doors.
From the transcript
“taken from a book called playing to win it talks about how strategy is really just an integrated set of choices that outline how you're…”
“there's always a bit of a hesitation to say no right and the idea is saying no is scary when in reality the ability to…”
“we have a template that sort of keeps reinforcing who's the Target customer who's the target user within that customer base what are their needs…”
From the episode
Behind the scenes of Calendly’s rapid growth
Annie Pearl (CPO)