Controller

A note from Kyle Sherman, Founder and CEO: We're not a lifestyle company, and we're not an early startup that could be gone in two years. We're profitable, everyone here owns equity, and we're going from tens of millions in revenue to hundreds of millions with as few people as possible. That means every person here directs AI agents the way a great Michelin-star chef runs a kitchen: high taste, high standards, and nothing leaves the pass that isn't right. It's hard, the fun kind of hard, and I'm looking for people who feel the same way.

A note from Will Zinsmeister, Chief of Staff: I own our budget, modeling, projections and board reporting, and I'm keeping them. What I need is the person who takes the day-to-day finance work off my plate and runs it well: billing, AP and AR, vendor payments, tax filings, the reconciliations that keep it all honest, and the month-end close. I'm not looking for a director or someone who wants to build a finance org. I want a doer who likes owning the details, leads our small but mighty accounting team, uses AI to get through the work faster, and tells me early when something looks off. If that's you, let's talk.

The Role

Flowhub has spent more than a decade building a retail platform for the big categories generic tools serve badly, and we run finance the way we run everything else: small, fast, and with every person directing the technology that does the heavy lifting. The company has been profitable since 2023. Our Chief of Staff owns the higher-level finance work: budget, modeling, projections, and board reporting. What the function needs now is a hands-on controller who owns the day-to-day and the close, and keeps it all clean.

As Controller, you'll run the work that keeps the business paid and paying: customer billing and the questions that come with it, accounts receivable and collections, vendor invoices and payments, and the filing calendar for sales and use tax and the rest. You'll keep the books reconciled and own the month-end close so the numbers the Chief of Staff reports on are right. This is execution work, done well and done fast, with AI and automation taking the repetitive parts so your time goes to judgment calls.

You'll also manage our two-person accounting team. You set their priorities, review what they produce, and help them grow, while keeping your own hands in the books.

You'll report to Will Zinsmeister, Chief of Staff, and work from our Coconut Grove HQ in Miami three days a week, with the rest of the week remote.

🚀 What You'll Own (Run It, Keep It Clean)

• Billing and AR. Customer invoices go out correctly and on time, billing issues are resolved directly with the customer, and collections don't slip.
• AP and vendor payments. Invoices in, approved, and paid when they should be, with a clean trail behind every payment.
• Tax filings and compliance. Sales and use tax and the rest of the filing calendar, filed properly and on time, without anyone having to ask.
• Reconciliations and the close. Accounts reconciled and the month-end close run on schedule, so the reporting that sits on top of it holds up.
• Lead the team. Set the week's priorities, check what comes in from each person, and coach both of them so the group gets sharper every month.
• Direct the work, don't just do it. Agents and automation handle the repeatable steps. You set the standard, check what comes back, and keep improving how the work gets done.

💚 You'll Probably Love This Role If:

• You're a player-coach. You do the work yourself and get it right, and you like making the two people beside you better at it.
• You have the accounting chops. AP, AR, billing, reconciliations, and the filing calendar are second nature.
• You direct AI, you don't just use it. You've changed how you work in the last six months because of it, and you want a role where handing the repeatable work to agents is the expectation, not the experiment.
• Hard problems give you energy. A billing error, a payment that didn't post, a filing due Friday: you find it, fix it, and make sure it doesn't happen twice.
• You want to be years ahead of your peers. Running the whole day-to-day of a finance function, with agents doing the repeatable work, is experience most accountants won't get until much later.
• You're low-ego and direct. You say what's broken, you own what's yours, and you flag problems early.

🚩 This Role Probably Isn't For You If:

• You want to run FP&A or the board deck. Budget, modeling, projections, and board reporting stay with the Chief of Staff. This role is the day-to-day engine underneath them.
• You're looking to build a finance department. You'll lead a team of two and stay in the work; there's no org to build, and that's by design.
• You want a steady nine-to-five. A filing deadline and a billing fire don't wait for Monday.
• Fully remote is non-negotiable for you. This role is hybrid, with regular days at our Coconut Grove HQ.
• You'd rather stay out of sight. On a team this size, there's nowhere to hide, and your work is visible every day.

🎯 Ideal Background (Not a Checklist)

• Hands-on ownership of AP, AR, billing, vendor payments, reconciliations, and the month-end close, in a role like senior accountant, accounting manager, or assistant controller.
• Time spent training, leading, or reviewing the work of others on a finance team.
• Experience at a software, payments, subscription, or multi-location retail business is a strong plus.
• Sales and use tax filings and registrations across states.
• Fluency with modern finance tooling (QuickBooks or NetSuite, Bill.com or Ramp, Stripe-style billing) and daily use of AI tools in the work.
• Bonus if you bring it. Subscription billing, a CPA or progress toward one, or time in cannabis or another tightly regulated industry.

🔑 The Hiring Process: Meet the Team

We respect your time. Each conversation should give you a clearer picture of whether this is the right move for you.

• Stage 1 (Recruiter Screen): A 30-minute conversation with Aaron Friedman, our talent acquisition partner, on your background, what you're looking for, and mutual fit.
• Stage 2 (People Team Connect): A 30-minute call with Denisse Flack, People Team leader at Flowhub.
• Stage 3 (Hiring Manager Connect): A 30-minute call with Will Zinsmeister, Chief of Staff and the hiring manager for this role, including a short working session on a realistic billing, AP, or filing scenario.
• Stage 4 (Leadership Connect, On-Site): An hour at our Coconut Grove HQ with Will and Royce Luque, VP of Sales.

Total time from first conversation to offer: roughly two to three weeks for a strong candidate.

🏁 The Deal

Here's what you're signing up for. Flowhub is a small team of high performers, and the work moves fast. In return, you own a function that matters, on a team small enough that your work gets seen. If that's the job you want, apply.

🌟 What's In It For You

• Compensation 💰: A competitive base salary calibrated to experience, plus equity in a profitable, well-funded company. This is a salaried role with no variable component.
• Full Benefits 🛡: Medical, dental, vision, life, disability insurance, and 401(k).
• Time Off 🌴: Unlimited PTO and paid holidays.
• Where You'll Work 📍: Hybrid, three days a week at our Coconut Grove HQ in Miami.
• Relocation 🚚: We'll help the right person relocate to South Florida.
• The Upside ⚡: A direct line to the Chief of Staff at a profitable company entering new retail categories, owning work the whole business depends on.

⭐ Our Values

• Mission-First. We're here to solve real problems for the operators we serve, not to chase what's trending.
• Maximum Urgency. Speed compounds. We act now, not later.
• Own It. No spectators. Everyone runs their part of the field.
• Championship Team. High bar, full trust, no carry-on talent.
• Efficient Execution. We scale process with technology, not headcount.
• Customer Obsessed. We earn our keep in our customers' stores. When something breaks at nine on a Saturday night, it's our problem, and we pick up.
• Positive Intent. We assume the best of each other and earn the right to disagree well.

🏪 About Flowhub

Flowhub exists so that the people who run stores can run them better. We build the retail platform for big categories that generic tools serve badly: point-of-sale, payments, e-commerce, inventory, compliance, loyalty, and analytics, with an agentic AI layer working alongside the operator. We proved it in cannabis, the hardest version of the job, where every new state was effectively a new country with its own regulator, rulebook, tax logic, and reporting. Liquor retail is launching now, and more categories follow.

Today more than a thousand retailers run on Flowhub, processing more than $4 billion in customer sales each year. The people behind those numbers are entrepreneurs: an owner who mortgaged a house to open a first location, a family running eleven locations across two states. Our software lets them ring up sales, stay compliant, run payroll, and hire their next employee. We have been profitable since 2023, we generate cash, and we are venture-backed, so this is not an early startup waiting on its next round.

We take on the biggest names in commerce software with a small team, and that is a choice. We run about a third the headcount of a company our size, and every person here directs AI agents to produce what three people used to. It is demanding; most people will not want to work this way, and that's fine. For the right person, it is the kind of experience you won't find anywhere else for years.

Founder and CEO Kyle Sherman built Flowhub from the inside out. As a Head of Compliance in the industry's earliest days, he ran headfirst into software that couldn't keep up with the rules and built the platform he needed. In 2014, he became the first to integrate with a state track-and-trace system, lobbying Colorado to open the API, which is now an industry standard. Kyle still sets the company's vision and strategy.

We're privately held and backed by top-tier investors, with a board that has scaled software companies to tens of millions of customers.

We hire people, not resumes, and we don't require a degree. If this role excites you and you think you'd be great at it, please apply.

Flowhub is an equal opportunity employer. We don't discriminate on the basis of race, color, religion, sex, national origin, age, disability, sexual orientation, gender identity, or any other protected characteristic. Need accommodations during the application or interview process? Reach out to us at hrteam@flowhub.com.