Director of Customer Success

You will lead Dockwa's Customer Success function and a team of Marina Success Managers (MSMs). This is an operator's job. You will build the segmented operating model that does not exist yet, coach and grow the team that runs it, and stay close enough to customers to know whether any of it is working.

The role splits roughly three ways:

• 50% team leadership, account execution, and playbooks. Coach and develop the MSM team, hire into it, work Strategic and Mid-Market accounts alongside them, own renewal strategy and forecasting, and build segment-specific playbooks.
• 25% scaled programs and adoption at volume. Stand up segmentation, health and expansion scoring, and 1:many engagement that drives adoption and activation without requiring an MSM phone call. You will not build this alone. You will drive it across customer marketing, support, and product.
• 25% voice of the customer and cross-functional alignment. Synthesize feedback, usage, and win/loss data into product and GTM recommendations. Find the gaps between functions where customers fall through, and push them toward a plan.

A few things worth knowing before you apply.

• The team is in transition. You are inheriting a small team that has been managed reactively, and you will be hiring into it. If building your own bench is the part of the job you would want to delegate, this is not the right seat.
• You will not be handed a system. There is no formal tiering, no health scoring, and no 1:many program today. Standing those up is the first 90 days, and you will do it with the team you have rather than a CS ops function.
• Scale is the mandate, and customer time is still part of the job. We want your philosophy on how you stay close to customers as systems and automation take on more of the load. Co-managing enterprise relationships, saving deals, and getting on a plane to a marina in California are all part of this role.
• Our customers are seasonal. Marina renewals and usage concentrate around the boating season, and a great deal of our base staffs up with people who have never seen the product. An even quarterly cadence will get run over.
• We are acquiring. Dockwa is actively acquiring marine software companies. You will get integration reps. Prior M&A experience is not required.

• Net retention, expansion, churn, and renewal targets across SMB, Mid-Market, and Strategic segments.
• Productivity per MSM. Growing each rep’s book of business while the retention numbers improve.
• Activation. Getting marinas over the line from signed to genuinely transacting, which is the strongest driver of whether they stay.
• A differentiated operating model that does not exist today: pooled and reactive for SMB, proactive and assigned for Mid-Market, executive partnership for Strategic.
• Renewal forecasting, at-risk saves, and executive-level negotiation on complex accounts.
• Customer health scoring, Q  cadence, playbook library, and CS reporting to leadership.
• Escalations requiring account-level judgment: billing, pricing, contract disputes.
• Hiring, onboarding, and developing the MSM team as it turns over and grows.

• 7+ years in customer success or account management, with 4+ years leading CS teams and at least four direct reports.
• You have owned a retention or NRR number, not influenced one, and you can give us the baseline, the timeframe, and what you would do differently.
• You have personally implemented a segmentation or systemization change inside a team that did not have one, including the stakeholder alignment and the parts that did not go smoothly.
• You have shipped a 1:many program end to end and can name the metric it moved.
• You pull your own usage data. We do not have an analyst for you.
• Strong…