The Honest Post-Mortem

Here's the clean, well-structured semantic HTML for the job posting (though this appears to be a case study rather than a job posting, I've reformatted it according to your rules):

Published 2026-04-15

About the Project

A post-mortem of olllo, a performance-review and accomplishment-tracking tool built solo across four months and shut down in March 2026.

People told me it was a real problem. Every conversation. Performance reviews that felt arbitrary. 1:1s that surfaced nothing. The 9pm panic of trying to reconstruct six months of work the night before a self-review was due. I built olllo to solve that. It works. People who tried it said it works. Even with the price gate removed, almost none of them showed up to use it consistently.

The Hypothesis

The bet was simple: If you can't remember your work, you can't advocate for it, and your career compounds slower than your effort deserves. The user bet was that low-friction daily capture, reinforced by weekly reflection and quarterly summaries, would compound into a case file that made reviews, 1:1s, and compensation conversations dramatically less stressful.

The business bet was that enough people felt this pain acutely enough to pay roughly $8/mo on an annual plan ($96/year before the beta discount) for a tool that replaced the ad-hoc notes app or Google Doc they were already mismanaging.

What Was Built

• Next.js 16 web app with onboarding, reflections, goals, and accomplishment tracking
• React Native mobile app with voice capture that transcribes audio and extracts structured STAR-format entries
• PWA for intermediate surfaces
• Multi-agent reflection flow using Claude Sonnet and Haiku across tiered calls
• Full infrastructure: rate limiting, feature flags, email authentication, consent management, referral loops, waitlist, free-forever grants

40+ numbered feature branches shipped, each gated through a speckit workflow requiring spec, clarifications, plan, tasks, and analysis pass.

User Feedback

The waitlist had 30 people. Fourteen filled out the survey, primarily senior individual contributors at enterprise companies (staff-level engineers and designers).

• Pain points: performance reviews, interviews, weekly planning, imposter syndrome about work tracking
• Desired features: clean record of wins, promotion-ready career story, weekly reflection prompts
• Top blockers: too much effort to capture things, didn't want another tool to maintain, unsure what to write, wouldn't remember to return
• Magic-wand answers: career path identification, habit development, energy organization

Key Metrics

• Waitlist signups: 30
• Survey completions: 14 (47%)
• Cohort A (free, n=10): 9 created → 5 onboarded → 3 active@1mo
• Cohort B (paid, n=20): 2 created → 0 onboarded → 0 active@1mo
• Paid conversions: 0

Lessons Learned

Signals I Explained Away

• Treated well-articulated pain as equivalent to willingness to show up
• Habit blockers (not pricing) were top concerns in survey
• Added features instead of confronting base rate of engagement

What I'd Do Differently

• Test the habit before building the tool (10-person cohort with weekly calls)
• Pre-sell before building (Stripe checkout with refund promise)
• Narrower ICP with urgent need (e.g., senior engineers prepping for promotion cycle)
• Focus on import over habit (pre-populate from Slack/email/calendar)
• Run willingness-to-pay experiment in month one
• Measure with people first (15-minute calls with first 20 users)

What I'd Keep the Same

• Problem framing around memory-and-recall
• Shipping solo with team-grade discipline (speckit workflow, constitution file)
• Tiered AI model strategy (Haiku for classification, Sonnet for reasoning)
• Decision to shut down when engagement was insufficient