Founding Engineer (Part-Time Contractor / Retainer)

About the Role

We’re a Chicago-based startup building a platform designed to help people feel less alone through safe, structured human connection. We’re moving from a marketing site into a production product with payments, scheduling, and video session workflows.

We’re hiring a Founding Engineer to own the build-out end-to-end with direct founder collaboration. This is not a maintenance role. You’ll ship weekly. If it’s a strong fit, scope and compensation can expand. Looking for a long-term tech founding partner.

What You’ll Build (v1)

• User accounts + authentication
• Stripe payments (Checkout + webhooks)
• Booking/scheduling + automated session links (Zoom or equivalent)
• Admin tools for operations (bookings, cancellations, refunds, guide status)
• Marketplace basics: contractor/guide portal to view sessions and accept/confirm assigned appointments
• Basic ticketing/member flows for group sessions

Requirements

Must have

• Shipped production web apps end-to-end
• Stripe integration experience (webhooks strongly preferred)
• Auth/account systems experience
• Comfortable deploying and running production (staging/prod, logs, monitoring)
• Clear communication and reliable delivery

Preferred

• React/Next.js
• Node.js or Python or Rails/Laravel
• Postgres (Supabase ok)
• Vercel/Render/AWS
• Calendly/Zoom and similar integrations

Working Style

• 40 hours/month to start
• Weekly check-in + async execution
• Short iterations with real deliverables
• Direct founder collaboration

To Apply:

Email us with the following:

• Resume / LinkedIn / Website
• 2–3 links to shipped production work (or brief descriptions if private)
• Availability (hours/week)
• One short answer (pick one):

Option A (payments):
Have you implemented Stripe Checkout + webhooks in production? Briefly describe which events you handled and how you ensured reliability (signature verification, idempotency, retries).

Option B (marketplace):
Have you built a two-sided product (customer + provider/contractor portal)? Briefly describe the core workflows you owned.

[email protected]

Job Types: Part-time, Contract

Pay: $1,200.00 per month

Expected hours: 10 per week

Work Location: Remote