Location: Tampa, FL preferred (strong preference for South Florida, Miami / Fort Lauderdale, given proximity to major cruise line headquarters). Regular travel required, including at least one trip per year to Europe.
Employment Type: Full-time. Conference and client travel expected. Flexible for the right candidate with an established cruise industry book of business.
The Role
We're hiring a senior, dedicated new-business hunter to own outbound growth for OnDeck end to end. This is a high-trust, high-visibility role reporting directly to the President, with real ownership of the number.
What you'll own:
- New logo hunting across cruise and ferry operators, including outbound prospecting via LinkedIn, email, phone, and your own network
- Partner and channel development, including deepening relationships with existing partners like Otalio and identifying new ones
- Running deals from first contact through close, including legal and contracting support
- Owning and maintaining the OnDeck HubSpot pipeline
- Representing OnDeck at Seatrade Cruise Global (our anchor event), CLIA, and other industry conferences
- Learning the platform well enough to run lighter demos and discovery calls independently within the first few months
- Day-to-day management of our existing SDR, including 1:1s, activity coaching, and development planning (final performance decisions are shared with the President)
What this role does not own: account management or expansion revenue on existing customers. That stays with our Product Leader.
What We're Looking For
- 7-10+ years of enterprise B2B sales experience, with meaningful time in the cruise industry
- Strong preference for candidates who have sold technology or software into cruise lines specifically; adjacent maritime or hospitality tech is a plus
- An existing network inside cruise line commercial, IT, guest experience, or operations leadership
- A track record of self-sourced enterprise deals with long (9-18 month) sales cycles and six-to-seven-figure ARR
- Comfort representing a company on the floor at major industry conferences
- Experience coaching or managing a junior seller is a plus, not a requirement
Your First 90 Days
You'll spend your first 30 days learning the platform, the market, and the team. By 60 days, you'll have delivered a 12-month go-to-market plan and taken ownership of the pipeline. By 90 days, you'll be actively in-market: running outbound campaigns, meeting prospects, and building partner relationships, with a clear-eyed understanding that enterprise cruise sales cycles run long, so early quarters are about pipeline-building, not closed deals.
This is a rare kind of sales seat. You're not being handed a territory to maintain, you're being handed a market to build. New business for OnDeck has run on the President's nights and weekends up to this point, which means the pipeline, the relationships, and the ARR upside are wide open for the person who takes this on. You'll have real autonomy, a direct line to leadership, and uncapped upside as your book compounds year over year.
You'll also have a support system behind you that most standalone sales roles don't offer. We're part of Thompson Holdings Inc. (THI), a family of companies that includes Thompson Engineering, Thompson Consulting Services, and Watermark Architecture. THI is employee-owned, so the growth you help create doesn't just benefit outside shareholders, it benefits the people doing the work. That's backed by a 401k with ESOP match and excellent benefits overall, on top of a strong base, uncapped commission, and dedicated conference and travel budget.
If you want to build a market instead of maintaining one, backed by a stable, employee-owned parent company that's genuinely invested in your success, we'd love to talk.
