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.

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 'll inherit a Customer Success function that's in motion but still under built.

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, Q  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.

• 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, Q  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 e 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’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 Q  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.…