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 Dirty Close your first 2-3 issues. Begin work on your first feature. Meet the product team and start diving into a major product area: payments, messaging, documents, scheduling, tools, infrastructure.

Days 14–30: Ship Your First Feature Close 5-10 issues a week. Ship your first feature. Begin work on your second feature and dive into your next major product area.

By Day 60: You're shipping a feature every two weeks and have deep context across at least three major product areas.

By Day 90: You're shipping a new feature every week. You own your product surfaces and are driving architectural decisions independently.

What We're Looking For

Must-haves:

• 6+ years of professional software engineering experience across the full stack
• Strong track record building and shipping B2B or B2B2C SaaS in Python or TypeScript
• Experience with payments systems, Stripe integrations, or fintech. You understand the stakes when real money is moving
• History of owning features end-to-end: you've scoped, built, shipped, and maintained production systems
• Mobile or Web development experience (iOS, Android, or React)
• You move fast, take initiative, and don't wait for permission to fix what's broken

Strong signals:

• You've scaled a product to tens of thousands of daily active users
• You've worked at an early-stage startup (seed to Series A) and thrived in the ambiguity
• You've built booking, scheduling, or marketplace systems
• You've designed and shipped AI-powered features (automation, fraud detection, recommendations)
• Technical leadership experience. You've mentored engineers, driven architectural decisions, or led a small team

About the degree thing: A CS or Engineering degree is great, but it's not what we're optimizing for. We care far more about what you've built, the pace at which you've shipped, and the impact you've had. If you've scaled a Python/React app to 100k+ users, led a complex Stripe integration, or built a product from zero to real revenue. That tells us more than any diploma.

Why PocketSuite

• Founder-led and product-obsessed. Chinwe (CEO) and Yang (CTO) are in the code and in the customer conversations. You'll have direct access to the people making strategic decisions.
• Real impact on real people. Our pros are hairstylists, trainers, therapists, and cleaners. When you ship a feature, you're directly helping someone put food on the table.
• Small team, big leverage. You won't spend months in planning meetings. You'll ship code that thousands of people use this week.
• The Rule of 5. We build simple, opinionated software. If it takes more than 5 seconds to figure out, we go back to the drawing board. That constraint makes the engineering genuinely interesting.

Details

• Location: Remote (US)
• Compensation: Competitive salary + equity
• Reports to: CTO

The interview process typically takes about 2-4 weeks depending on how easy it is to schedule interviews. I will be your main point of contact throughout the process and you can reach me anytime at yang@pocketsuite.io.

Day 1 30 minute phone interview and technical screen to assess high level fit
Day 2 two 60 minute technical interviews with a lead engineer and the CTO (may require writing code)
Day 3 two 30 minute interviews with a senior product manager and the CEO (these are non-technical interviews)

Decision: 3 reference checks with former colleagues, supervisors Discuss offer & benefits with a member of our HR team