Director of Customer Success

The Wanderlust Group, Inc. Newport, Rhode Island, United States

About Dockwa

Dockwa is reshaping the $230+ billion marine industry. After 12 years of building trust with marina operators and boaters, we have achieved something rare: category-defining position in a fragmented industry ready for transformation.

The marina industry is experiencing a generational shift. Private equity consolidation is accelerating. Operators face pressure to run marinas like real businesses, not lifestyle assets. This creates the opportunity to become the default operating layer for an industry that has never had one.

About the role

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, 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.

Core responsibilities

• Net retention, expansion, churn, and renewal targets across 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.
• 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.

What we're looking for

• 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, 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
• You have shipped a 1:many program end to end and can name the metric it moved.
• Strong preference for vertical SaaS with embedded payments, a fragmented SMB operator base, and seasonality.
• Hands-on with CRM and marketing automation. Hub Spot experience is a plus.
• Plus: support or customer marketing background, experience under a growth-equity sponsor.

We will teach you the marina industry, our product, and our customers. We are not going to teach systems thinking or how to stay close to customers.