Bifurcated the org into R&D and GTM immediately — good framing that shows structural thinking
Identified two critical risks upfront: product-market fit maturity and brand reputation impact
Key insight: ‘People don’t like unsolicited advice’ — memorable one-liner, use it in the interview
Questioned whether recommendations are useful to the person seeing them (not just accurate) — sharp product thinking
Segmented SMB vs enterprise with different rollout strategies: broad opt-in for SMB, account-managed opt-in for enterprise
Worked backward from the 10-week board deadline to build a concrete timeline
Required CS/marketing materials before launch, not after
Added enterprise admin-level opt-in controls — shows thinking about customer’s internal rollout

Kill switch / feature flag. Initially missed. This is the single most important de-risking mechanism. Engineering flagged no way to turn off for a subset. Before anything ships, need a feature flag per account. Name this explicitly.
Role-based filtering is a prerequisite, not a nice-to-have. Without it, CFO-level insights go to procurement coordinators. Say: ‘This is 2–3 weeks of eng but it’s a launch blocker.’
Design not mentioned. Lindsie is in the room. One sentence: ‘Design would be embedded in the beta to observe how users interact with recommendations and validate contextual placement.’
Communication plan came late. Distinguish what each team needs and when: CS needs FAQs 2 weeks before beta. Marketing gets a phased story (beta announcement now, GA announcement later). Sales can’t pitch to enterprise prospects yet — managed timeline.

Weeks 1–2: Internal dogfooding + build feature flag/kill switch + CS/marketing prep
Weeks 3–5: SMB beta (defined segment, opt-in, tracking dismissal rates and sentiment)
Week 5: Go/no-go checkpoint — dismissal rates below 20%? Sentiment neutral or positive?
Weeks 6–8: If green, expand to broader SMB. Enterprise gets account-managed opt-in on separate track
Week 10: Board update with real data

Initial SMB beta is closed — Sales/Marketing prepare materials during this window
When broadly available for SMB, Marketing announces and runs campaigns
Enterprise requires different materials + engineering support for admin opt-in controls

Problem Solving Round Prep