Director of Customer Success in Newport, Rhode Island at The Wanderlust Group, Inc.

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 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.

What makes this job specific

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.

Core responsibilities

• 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, QBR 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, 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 preference for vertical SaaS with embedded payments, a fragmented SMB operator base, and seasonality.
• Hands-on with CRM and marketing automation. HubSpot experience is a real plus; you will be the CS lead on our Salesforce to HubSpot migration.
• 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.

How we work

We share this openly so you can evaluate whether Dockwa is the right environment for you. We believe in full transparency during the interview process—not to coach you on what to avoid, but to give you the complete picture.

We are a small team that is winning. Problems grow exponentially with each person, not linearly. We intentionally preserve a lean organization because we want people at the source of problems with clear ownership and autonomy.

We move fast. Context is something we try to give but it doesn't always land perfectly. It's always okay to ask why. Over time, the trust battery goes up.

Everything is solvable. But not everything should be solved. We hate context switching. We'd rather keep people deep in a problem than abandon cart—but we won't chase bad bets for the sake of it.

We have a remarkably good group of humans here. There are no rules or roads where we're going—which makes it damn fun to take the pen and shape the next few turns.

Why now

Retention, expansion, and activation are the growth levers at Dockwa right now. You get to do real CS work, support Strategic accounts, lead and build a team, own renewals, while building the leveraged programs that let a lean team punch above its weight. Your work shows up directly in the numbers.