Mobile / Product Leadership / 0-to-Scale
Gather
A dating app for practicing Catholics. Fractional CTO & Head of Product.
Client
Gather
Role
Fractional CTO, Head of Product
Timeline
2022 – 2024
The problem
Dating apps have a values problem. The dominant platforms optimize for engagement — swiping, matching, messaging — without any mechanism for filtering by the things that actually predict long-term compatibility for serious relationship seekers. For practicing Catholics, this meant wading through thousands of profiles to find someone who shares the same fundamental worldview.
Gather's hypothesis was that a values-first matching experience, built specifically for practicing Catholics, could unlock a highly underserved market. The founding team had product vision and faith; they needed someone who could translate that into engineering decisions, team structure, and a product that could actually scale.
The leadership challenges:
The engineering team was talented but needed structure — no clear sprint cadence, no roadmap process, no on-call rotation
The product had feature sprawl: too many things half-built, not enough things shipped
The matching algorithm was effectively random; there was no quality signal being captured
CAC was high because the onboarding funnel had a 60%+ drop-off before profile completion
The approach
The first 30 days were diagnostic. I spent time with the full team — engineering, design, growth — and with real users. The goal was to understand what was actually happening versus what the team believed was happening.
Ship the foundation, cut the sprawl.
We froze the roadmap for six weeks and shipped only bug fixes and retention-critical improvements. The goal was stability first — a product that worked reliably was worth more than a product with ten new features that mostly worked. That period also let the team build confidence in the process before introducing process changes.
Rebuild the onboarding funnel.
The 60%+ onboarding drop-off was a product problem, not a marketing problem. We redesigned the profile completion flow around progressive disclosure: ask less upfront, earn the right to ask more as engagement increases. The redesigned funnel dropped the drop-off rate by 38% within two sprints.
Values-based matching signals.
We introduced a lightweight values questionnaire — not a quiz, but a series of prompted choices that surfaced compatibility signals without feeling clinical. These signals fed into the matching algorithm, shifting it from proximity-and-age toward values-alignment + engagement patterns.
The first job of a fractional CTO isn't to build. It's to diagnose what's actually broken versus what feels broken.
The work
Product & Engineering Leadership
Established sprint cadence, roadmap process, and engineering rituals (retros, postmortems, on-call rotation)
Rebuilt the product brief template and introduced a lightweight PRD process that reduced scope churn
Hired and onboarded two senior engineers; restructured team into product squads vs. platform squad
Led technical interviews and established the engineering hiring bar
Weekly executive-level product and engineering updates to board and investors
Product Improvements
Redesigned onboarding funnel: progressive disclosure, contextual prompts, reduced required fields
Introduced values-based compatibility signals into the matching algorithm
Built in-app events feature for local Catholic community gatherings — reduced reliance on matching as the only path to connection
Redesigned notification strategy: fewer, smarter, opt-in by category
Shipped dark mode (finally)
The outcome
Onboarding completion rate improved from ~40% to ~78% within the first quarter. 7-day retention improved by 22%. The engineering team shipped consistently for the first time, with a meaningful reduction in production incidents.
The in-app events feature became the highest-engagement surface in the product within two months of launch — users were converting matches to real meetings at a meaningfully higher rate when events were involved.
Retention is a product problem, not a marketing problem. Fix the funnel before you scale spend.
Tech stack
React Native
Node.js
PostgreSQL
AWS
Redis
Expo
TypeScript
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