Head of Customer Success

A note from Kyle Sherman, CEO: I started Flowhub because the people running dispensaries deserve the same caliber of software that big retailers take for granted, and because I believed compliance technology could be the thing that finally took cannabis from the margins to the mainstream. We've spent close to a decade earning that trust with operators. The next chapter is about scaling how we show up for them after the sale, and the person Will is hiring will own that. I'll be involved at the points that matter. The rest of the time, I want this leader running the function the way they know how.

The Role

We're hiring a Head of Customer Success to own the outcome, not just the relationship. This is not a reactive support role. The leader in this seat is responsible for everything that happens after the deal closes (adoption, value realization, renewals, and expansion) and for the systems and team that make customers successful at scale.

You'll inherit a Customer Success function that's in motion but still underbuilt. The team is in place and the manager has been seated for over a year, but the systems most CS functions take for granted (account health scoring, QBR cadence, churn save framework, expansion motion, voice-of-customer feedback into Product) haven't been built yet. Our CSMs are all less than a year in. Our 1,000+ retailers need more from us than we're currently set up to deliver. The leader in this seat builds the post-sales operating system from here.

You'll also pick up management responsibility for our Product Support Manager. PS runs well today, so this is leadership oversight and connecting PS and CS as one customer experience, rather than day-to-day rebuilding. Onboarding sits under a separate function lead and remains separate, but you'll partner closely with that leader and with Royce Luque, our VP of Sales, to ensure the full customer journey holds together.

You'll report to Kyle Sherman, CEO, and work most closely with Will Zinsmeister (Chief of Staff) and Royce. This is a function-head seat with real autonomy. Exec involvement happens at the inflection points that matter, not the day-to-day. The rest of the time, this leader runs the function.

🚀 What You'll Own (Build, Coach, Scale)

• Retention and expansion outcomes. Own NRR, GRR, renewal execution, and expansion ARR as the metrics this role is measured against. Build the forecasting discipline and account-health visibility we don't have yet.

• The CS playbook. Account health scoring, QBR cadence for strategic accounts, churn save framework, expansion motion, and the voice-of-customer feedback loop into Product. None of this is structured today. You'll build it and make it stick.

• A junior team's development. Coach the current CS Manager into a stronger leader, develop the CSM team, and set the bar for what great customer partnership looks like at Flowhub. Hire ahead of growth as the company scales into new verticals.

• Management of Product Support. Our PS Manager will report to you. PS is well-run today, so this is leadership coverage rather than a rebuild. The win is connecting PS and CS so customers experience one Flowhub rather than two teams.

• Cross-functional rhythm. Set the operating cadence with Sales, Product, Onboarding, and Marketing. The handoffs are loose today. The new Head defines how they should work and runs them that way.

• Visibility with strategic accounts. Be present with our most important customers. Pick up the phone when it matters. Show the team what an executive-level customer partnership looks like.

💚 You'll Probably Love This Role If:

• You've built a CS function before. You've taken a team from reactive to proactive, built playbooks that get used, and have the retention numbers to show for it. This isn't your first time setting one up.

• You like building more than inheriting. No QBR template is waiting for you. No customer health dashboard exists yet. That's the opportunity, not the problem.

• You're a real coach. You've developed first-time managers into strong ones, and CSMs into senior CSMs. You know the difference between managing activity and developing people.

• You operate well without daily oversight. This role is built around real autonomy. You'll set the agenda, make calls without senior cover, and earn trust through what you ship. If that energizes you, this seat is built for you.

• You're SaaS to the core, and adaptable. Your CS instincts came from a real SaaS company. You're excited to bring that operating system into a vertical where the customer is a regulated retailer rather than another tech buyer.

• You're not allergic to cannabis. Our customers are dispensaries today. If that's a non-starter on a personal or moral level, this isn't the right home. If you can see it for what it is, a hard, real, growing business solving a meaningful operator problem, you'll be in good company here.

🚩 This Role Probably Isn't For You If:

• You haven't built CS systems before. We need someone who's already done the function-building work. We've talked to plenty of first-year directors who hadn't, and it hasn't been the right fit. Either two-plus years leading a CS team, or senior CSM scope on a larger team where you've owned meaningful pieces of the function. The title matters less than what you've built.

• You're coming out of cannabis. Our CSMs come from cannabis backgrounds intentionally, and that works at the IC level. For this leadership seat, we want someone whose CS muscle was built in a high-bar SaaS environment, joining cannabis fresh.

• You want a steady-state team to manage. We're not there yet. If your strength is keeping an established function humming, this isn't that.

• Remote-only is non-negotiable for you. Our Miami office is where this role sits. We can flex to one or two days remote, but you need to be in the office with the rest of the leadership team most of the week.

• You prefer a heavy approval culture. This role is built for someone who can run without it. If you're used to taking every call up the chain before acting, the autonomy here will feel uncomfortable.

🎯 Ideal Background (Not a Checklist):

• 6+ years in Customer Success, Account Management, or a related post-sales role, with a track record of owning retention and growth.

• Demonstrable CS function-building experience. Either 2+ years directly leading a CS team, or senior IC scope on a larger CS team where you've owned meaningful pieces of the function-building work (playbooks, account health systems, QBR cadence, churn save framework, expansion motion). The title matters less than what you've actually built.

• You've built CS at a SaaS company through a high-growth stage, ideally Series B through D. You've lived the version of this story we're in now.

• Vertical SaaS comfort (restaurant tech, home services, healthcare practice management, legal tech, multi-location SMB SaaS, or similar). Regulated and compliance-heavy environments translate especially well.

• Strong analytical instincts. You set the metrics, read the data, and act on it. You don't outsource that.

• Familiarity with CS platforms and modern CRM (Salesforce, Gainsight, ChurnZero, Catalyst, or similar).

• A tenure pattern that suggests you finish what you start. Two-plus years at each of your most recent roles tells us a lot.

🔑 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 (Initial Screen): A 30-minute call with Denisse Flack, People Team leader at Flowhub.

• Stage 3 (Leadership Conversation): A 45-minute deep dive with Will Zinsmeister, Chief of Staff, and Royce Luque, VP of Sales.

• Stage 4 (Leadership Panel): A 60-minute panel with Will, Royce, Denisse, and our CS Manager on your CS function-building approach, leadership style, and how you'd come in.

• Stage 5 (CEO Final): A conversation with Kyle Sherman, CEO, on the company, the role, and the bigger picture.

Total time from first conversation to offer: roughly 2 to 3 weeks for a strong candidate.

🌟 What's In It For You

• Compensation 💰: Up to $225K OTE in year one, with flex for the right candidate, plus meaningful equity in a profitable, well-funded company.

• Full Benefits 🛡️: Medical, dental, vision, life, disability insurance, and 401(k).

• Time Off 🌴: Unlimited PTO and paid holidays.

• The Workspace 📍: Our Miami office, where leadership is in-person most of the week. We work in a hybrid model when it makes sense and on-site because the work is better when we're together.

• The Real Win ⚡: A chance to build the post-sales function for a company that's already won the hardest version of regulated retail, with the runway to expand into the next several. The foundation is here. The team is hungry. The playbook is yours to write.

⭐ 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.

• Dispensary Obsessed. The retailer is the boss. Their problem is our problem.

• Positive Intent. We assume the best of each other and earn the right to disagree well.

🌿 About Flowhub

Flowhub builds the technology that runs regulated retail. We exist to solve the hardest operational and compliance problems in American commerce, the ones that decide whether a business in a tightly regulated market clears its first audit or its hundredth. Cannabis is where we started, and where we became the fastest-growing regulated retail technology company in the country.

Flowhub powers compliance, point-of-sale (POS), payments, e-commerce, inventory management, loyalty, and analytics for thousands of cannabis retailers nationwide. We process more than $4 billion in our customers' sales each year, achieved profitability in 2023 (a milestone almost no one else in this category has reached), and help high-volume dispensaries automate operations, grow revenue, and deliver a better customer experience.

Founder and CEO Kyle Sherman built Flowhub from the inside out. As a Head of Compliance at early cannabis companies, he ran headfirst into the inefficiencies of existing platforms and set out to create software that would accelerate workflows, increase accuracy, and simplify compliance. He desperately needed it, and found others did too. Flowhub was born. Back in 2014, before most of the industry existed, he became the first to integrate with the state's Metrc tracking system, lobbying Colorado to open the API that's now an industry standard. Kyle still sets the company's vision and strategy.

Flowhub is privately held and backed since the start by serious capital and serious people. Our investors include PayPal, Headline, Poseidon, Shawn "Jay-Z" Carter, Evolv Ventures (the Kraft Heinz Company's venture arm), and the founders of Venmo. Our board includes Blake Irving, who, as CEO, took GoDaddy from a few thousand customers to more than 20 million. We're a founding member of the US Cannabis Roundtable (USCR), the lobbying and advocacy group working to normalize and professionalize the market at the federal level.

This is an inflection point. POS-native e-commerce launched in 2025, marketing came with it, and our 2026 brand evolution positions Flowhub as the regulated retail technology company it has always been, with a roadmap into adjacent verticals where age-gated, compliance-heavy operators need a platform they can actually run on.

We hire people, not resumes. 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 [email protected].