Sales Development Representative at The Wanderlust Group, Inc. – Newport, Rhode Island

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

As a Sales Development Representative (SDR) at Dockwa, you'll play a critical role in driving our growth by introducing marina operators to Dockwa for the first time. You'll own the top of our sales funnel—researching marinas, engaging prospects, and setting high-quality meetings that convert into paying customers.

This role reports to the Head of Sales and sits at the foundation of our go-to-market motion. You'll work closely with Account Executives, Marketing, and Customer Success to build pipeline that fuels our path to being the infrastructure of the marina industry.

This is a launchpad role. The best SDRs at Dockwa progress into Account Executive positions within 12-18 months. You'll receive hands-on coaching, clear performance metrics, and a defined career path into closing roles and sales leadership.

Core responsibilities

• Research and target marina operators that fit Dockwa's ideal customer profile
• Run persistent outbound outreach via phone, email, and LinkedIn
• Qualify inbound leads and convert interest into booked meetings
• Conduct discovery conversations to understand prospect needs, challenges, and goals
• Clearly articulate Dockwa's value proposition to marina operators
• Hand off context-rich, qualified opportunities to Account Executives
• Partner with AEs on target accounts and with Marketing on lead quality and messaging feedback
• Maintain accurate CRM records and activity tracking
• Share what's working in outreach and discovery to support team learning
• Build foundational sales skills and marina industry expertise with the goal of progressing into an AE role

What we're looking for

• 0-2 years of experience in sales, customer-facing, or business development roles (preferred but not required)
• Strong communication skills with genuine comfort picking up the phone and starting conversations with strangers
• Persistent and resilient: you don't take "no" personally and you find another angle
• Coachable and hungry to improve: you actively seek feedback and put it to work quickly
• Naturally curious: you ask good questions, dig into how things work, and want to understand the person on the other end of the call
• Quick on your feet: you can adapt mid-conversation when a prospect throws you something unexpected
• Ability to use CRM tools and modern sales technology (or eagerness to learn quickly)
• Genuine interest in boating, marinas, waterfront businesses, or marine technology
• Experience in marine, hospitality, or travel industries is a plus
• Bachelor's degree in Business, Economics, Psychology, or related field preferred but not required

Who thrives here

Dockwa is a lean, fast-moving team. People succeed here when they:

• Are high-agency: You don't wait for permission or perfect information. You identify problems, propose solutions, and drive outcomes.
• Get their hands dirty: You pick up the phone. You research accounts. You test new messaging. You don't just direct—you do.
• Think in first principles: You understand constraints and can reason from fundamentals rather than relying on playbooks.
• Embrace extreme ownership: When things go wrong (and they will), you own the outcome and fix it. No excuses.
• Balance speed with judgment: You know when to move fast and break things and when precision matters.
• Challenge ideas, then commit: You bring your perspective, debate vigorously, and then fully support the decision.

• On-target earnings (OTE) of $65,000–$85,000, including base salary and uncapped performance-based commission (exact compensation varies based on experience, location, and performance)
• Comprehensive medical, dental, and vision benefits for you and your family
• Flexible, remote-friendly work environment (Newport, RI headquarters)
• Clear, structured career path into Account Executive and sales leadership roles
• A team that values transparency, direct communication, and doing the work