Lead Generalist Engineer

Who We Are

PocketSuite started with a simple observation. Our CEO Chinwe experienced yet another late arrival with her cleaner then wait 60 to 90 days to send an invoice. She was ready to pay on the spot, but the cleaner was juggling multiple calendars and an out-of-state accounting business partner just to run their business. Chinwe teamed up with Yang, her co-founder and engineer #5 at NetSuite, who had helped build business management systems for Fortune 500s because he wanted to do the same thing for the solo hairstylist, the mobile dog groomer, the independent therapist.

That was 2015 (YC W16). Today, PocketSuite is the all-in-one platform thousands of service professionals and SMBs use to get booked, get paid, and communicate with their clients. We call it the Rule of 5: if our pros can't figure out a feature in 5 seconds, we haven't done our job. That constraint shapes every line of code we ship.

What makes us different from the dozen other "booking and payments" tools? We go vertical. We don't build a generic calendar and call it a day. We build the specific workflows a dog trainer needs to manage multi-session packages, or the exact invoicing flow a mobile hairstylist needs when they're finishing up at a client's kitchen table. That verticalization strategy a mile wide, an inch deep on the features that actually matter is why our pros stay.

We're a small, founder-led team. Chinwe and Yang still check in code, review PRs and talk to customers every day. You won't be a cog here.

The Role

We're looking for a Lead Engineer who can own entire product surfaces end-to-end from database schema to deploy. Your initial role is as a senior individual contributor reporting directly to the CTO, with a clear path to technical leadership as the team grows.

This is not a "maintain the monolith" role. You'll be shipping net-new features across payments (Stripe integration, fraud scoring, Stripe Capital), real-time messaging, scheduling, and AI-powered workflow automation all within a mobile-first codebase serving iOS, Android, and React web clients backed by a Python API layer. As the 6th engineer on the team, you are going to be a foundational engineer on the team delivering 10x the impact across 10x the surface footprint you would at most other companies.

What You'll Actually Work On

Payments & fintech: Extend our payments integration, build out lending flows, and improve our automated fraud scoring and merchant underwriting system. You'll deal with real money, real edge cases, and real compliance constraints.

Messaging & notifications: Architect and ship improvements to our real-time messaging system that tens of thousands of pros rely on daily to communicate with their clients and team members.

Scheduling & booking: Build the features that let a solo operator or SMB manage online bookings, automated team staffing, resource and facility management, automated dynamic pricing and discounting based on booking history and availability, and recurring appointments synced to all of your Google calendars.

AI & automation: Design industry tailored onboarding experiences, customizable data models, workflow automations, seamlessly deployed agents, smart marketing campaigns, and API integrations that help pros grow their business without adding headcount.

Infrastructure: Own scaling, performance optimization, test automation, and deployment pipelines across a platform processing millions of transactions and serving tens of thousands of concurrent users across multiple platforms. We ship fast you'll make sure we ship safely.

The Stack

Python · React · iOS · Android · Postgres · SQLite · Ubuntu · Docker

Your First 90 Days

Days 1–7: Get Oriented Align on company vision and 2026 priorities. Meet the engineering team. Set up your dev environment. Learn the product by exploring the code and actually using it book a session, send an invoice, message a client. Start getting to know our customers and why they chose us.

Days 7–14: Get Your Hands Dir