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 - 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 trainer, 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, convert new leads, manage their operations, 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're an operating system that includes the specific workflows a dog trainer needs to manage multi-session packages, or the exact invoicing flow an esthetician needs when they're finishing up at the spa. That verticalization strategy - a mile wide, an inch deep on the features that actually matter - is why our service businesses stay.

We're a small, founder-led team. Chinwe and Yang still check in code, review PRDs, 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 small business or multi-location service franchise manage online bookings, automated team staffing, resource and facility management, automated dynamic pricing and discounting based on client profile, booking history, and availability, as well as 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, workflows, 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:

• 7+ 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 payment 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 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 estheticians, pet boarders, dog trainers, therapists, and cleaners. When you ship a feature, you're directly helping someone put food on the table, pay their rent or mortgage, and keep their team employed.
• 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
• Benefits: Medical, dental, and eye insurance / 401K / unlimited vacation
• Reports to: CTO

About the interview

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 and supervisors. Discuss the offer & benefits with a member of our HR team.

About PocketSuite

Hi! We're PocketSuite!

PocketSuite is a YC-backed mobile platform for service businesses, ranging from dog trainers, pet resorts, fitness trainers, photographers, and home cleaners to estheticians, hairstylists, therapists, and life coaches.

Businesses use PocketSuite to get booked, paid, and message their clients. We make the work of running your own business simple for small businesses and multi-location service franchises. PocketSuite empowers the U.S. market of 20 million service professionals, generating $800 billion in sales, with a mobile cloud solution for running their businesses. Thousands of businesses run on PocketSuite. Over 500,000 clients book and pay their Pros on PocketSuite today, and we're growing fast.

PocketSuite lets any small business owner run their business entirely over text. We also have a desktop solution for businesses. On average, our customers are paid by their clients in under 24 hours, grow income by 30% within a few months of joining PocketSuite, and spend fewer hours per day on scheduling and payment collection after switching to PocketSuite. From calendar sync to appointment confirmation to contract e-signatures to text message auto-reminders, PocketSuite is both easy to use and eliminates meaningless work so small and midsize service businesses can do more of what they love - serve their clients. If you can send text messages, you can use PocketSuite.

Our Values ⚖️

1. Engineers and product-obsessed - we loathe over-engineering, we cringe anytime a customer reports a bug, and we release new versions every 2 weeks.
2. We love our customers - solving their problems and helping them grow and succeed in a rapidly changing world. Oh yeah, we also love their 5-star reviews.
3. We love disrupting the status quo - we believe everyone globally in the industries we're going after will be using a mobile app as their primary business tool by 2021.
4. We understand that it is critical to measure what matters. So we don't take victory laps nor do we pause to take a break unless the scoreboard reflects that we are #winning as it relates to our customer delight and growth goals.
5. We don't just think of this as a job. In our spare time, this is what we do and who we are. Our obsession with small and midsized service businesses, fintech, smart growth, and cool apps is a 24/7 thing.
6. We believe only three things matter as we build out our business: building a great product, delivering awesome customer service, and a killer instinct for activating and engaging new users.