Terrain — Company Context | PM Agent Kit Workbook

// 01 · why this exists

Context changes everything.

Real PM agent work improves significantly when the agent has durable product, customer, business, and team context. Skills like prd-draft, sprint-plan, business-case, and status-update all read context files that tell the agent what your product does, who your users are, what your team looks like, and how your org makes decisions. Without that context, output is generic. With it, output is specific and directly applicable.

Terrain gives every day a consistent practice environment. You don't need to expose your real company's data to see the kit working at full capacity. All 20 days reference the same product, metrics, and problems — so you can see how the skills chain together across a real product context.

// 02 · what terrain is

Terrain is a fictional two-sided marketplace where independent outdoor guides list bookable experiences — surf lessons, alpine climbs, foraging walks, sea kayaking tours, fly fishing instruction — and adventurers discover and book them. Unlike Airbnb Experiences or Viator, Terrain is built exclusively for the outdoor and adventure category, with curation and verification standards tuned for that context.

Business model: Guides pay an 18% take rate on each booking. Adventurers pay a 3% platform fee at checkout. Terrain also offers Guide Pro — a $29/month subscription that includes an analytics dashboard, priority search placement, and bulk availability management.

// 03 · business snapshot

Founded2021

StageSeries B · $28M raised

HQDenver, CO

Headcount~85

GMV (annualized)$18M

Take-rate rev.~$3.2M (18% of GMV)

Avg booking value$185

Active guides2,400 (38 US states)

Monthly actives47,000 adventurers

Guide Pro subs340 (~14% of active guides)

// 04 · the users

personas/marco.md

Marco — the guide

Age 34, freelance surf instructor, San Diego CA. On Terrain for 18 months; runs 3–5 sessions per week. Primary income source.

Core goals: Consistent, predictable income; ability to raise prices as reputation grows; repeat customers.

Pain points: Juggling availability across multiple platforms manually; no-show adventurers when cancellation windows are loose; getting buried in search results as guide supply grows; payouts arrive T+3 so cash flow is tight; no visibility into listing views vs. bookings.

personas/jamie.md

Jamie — the adventurer

Age 29, product designer, Seattle WA. Books 4–6 guided outdoor experiences per year; comfortable spending $150–$300 for a half-day experience.

Core goals: Authentic, local experiences that feel curated; confidence in the guide's credibility before booking.

Pain points: Hard to assess whether a guide matches their skill level; booking takes 1–2 days waiting for guide confirmation; cancellation anxiety around unclear policies; no way to see what experiences friends have done.

// 05 · primary recurring stakeholders

You are the Adventurer Experience PM — you own the demand side of the marketplace: how adventurers discover, evaluate, book, and return to Terrain. Other names appear in the prompts, but the five people below recur most often. Know them before Day 1.

Name	Role	What they care about
Dana Park	VP of Product	OKR progress, GMV growth, guide retention, booking conversion. Signs off on anything touching H1 goals, cross-squad resources, or public commitments. You write for her constantly.
Jordan Lee	PM, Guide Experience	Guide onboarding, listing creation, availability, payouts, Guide Pro. Closest cross-squad peer — any feature touching the listing object or guide-side Instant Book requires coordination. Day 1 opens with a Slack from Jordan.
Chris Okafor	EM, your squad	Technical approach, story point estimates, on-call rotation. Coordinate on sprint capacity, Android sequencing, and design availability before committing stories.
Priya Anand	Head of Marketing	Launch timing, App Store positioning, external messaging. Give two weeks' heads-up before any GA launch. Appears in Android GA, retro synthesis, and launch checklist days.
Marcus Webb	Legal	Regulatory exposure, cancellation policy, guide liability. Required loop-in for any feature that changes cancellation terms, surfaces guide credentials, or introduces new data collection.

// 06 · key metrics

Metric	Value
Guide listing activation rate	62%
Detail-to-booking rate	8.2%
Overall booking conversion	2.8%
Guide 12-month retention	71%
Adventurer repeat rate	38%
Cancellation rate	14%
Guide Pro attach rate	14%

// 07 · current priorities

Improve guide activation from 62% to 75% without lowering quality standards
Expand Instant Book safely — beta is live with 15% of guides; 22% of eligible guides have opted in; detail-to-booking conversion is about 32% higher on Instant Book listings
Ship Android GA in 6 weeks — payment edge cases and push notification reliability are the open blockers
Improve adventurer repeat behavior from 38% to 45%
Reduce avoidable cancellations from 14% toward the 7–9% industry benchmark

// 08 · four active product problems

problem.01→guide-activation

Guide activation drop-off

38% of guides who register never publish an experience. Root cause hypotheses: listing setup friction, pricing uncertainty, no signal about time-to-first-booking.

problem.02→cancellation-rate

High cancellation rate

14% vs. 7–9% industry benchmark. Split approximately 60% adventurer-initiated, 40% guide-initiated.

problem.03→repeat-rate

Low adventurer repeat rate

38% complete 2+ bookings in 12 months. No structured re-engagement loop exists; all repeat behavior is organic.

problem.04→instant-book-adoption

Instant Book guide adoption

Only 22% of beta-eligible guides have opted in despite about 32% higher detail-to-booking conversion on Instant Book listings. Guides cite calendar conflicts and no-show risk.

// 09 · shipped & in-flight

Shipped: Core marketplace, Guide Pro, iOS app, Instant Book beta.

In-flight: Instant Book rollout, Android GA, expanded Guide Pro analytics dashboard.

Under consideration: Group booking, seasonal/multi-day experiences, Trust & Safety improvements, social layer.

// 10 · how to use this context

You don't need to memorize Terrain. The relevant details — metrics, personas, stakeholder names, product rules — are embedded in each day's advanced prompt. The goal is to notice how richer context changes agent output, then apply the same pattern to your own company later.

When you're ready to use the PM Agent Kit with your real product, replace the Terrain files with your own company context and the skills adapt automatically.