Strategic Account Executive

At Trip Works, we believe work should be meaningful, fast‑paced, and a little bit adventurous. We're a fully remote team powering the experiences industry, helping tour and activity operators grow their businesses with tools that actually work.

We're not big on fluff or hierarchy. We value progress over perfection, action over ego, and results over buzzwords. Our team is small, scrappy, and serious about helping our customers win.

If you're the kind of person who sees a problem and grabs a shovel, who thrives on feedback, and who's always looking for ways to level up, you'll fit right in.

We're hiring an Account Executive based in Hawaii to own net‑new revenue across the region. This is a full‑cycle, quota‑carrying role focused on closing mid‑market and enterprise deals in a relationship‑driven market.

You will work directly with our VP of Sales
, who has lived and sold in Hawaii and brings a deep understanding of the local market, a strong operator network, and existing referral partnerships already in motion. This role is not starting from zero. Meaningful groundwork has already been done, and you'll be expected to build on that foundation, expand active relationships, and convert momentum into closed revenue.

This role is ideal for a seller who understands how to operate in Hawaii, combining disciplined outbound with relationship‑led selling, credibility, and follow‑through.

• Own the full sales cycle for net‑new logos across Hawaii, from outbound prospecting through close
• Self‑source pipeline while effectively leveraging existing relationships, referral partners, and traditional outbound efforts
• Close deals across mid‑market and enterprise segments
• Build and execute account plans for top Hawaii‑based operators
• Break into competitive, relationship‑led accounts and win against entrenched incumbents
• Lead strong discovery conversations and business‑case‑driven demos
• Navigate complex buying processes with multiple stakeholders and executive buyers
• Partner closely with the VP of Sales on deal strategy, forecasting, and regional growth
• Maintain a disciplined, accurate pipeline in Hub Spot
• Represent Trip Works locally at meetings, industry events, and conferences

• 3 to 7 years of mid‑market and or enterprise SaaS sales experience
• Proven success closing net‑new business in a full‑cycle role
• History of sourcing 70 percent or more of pipeline through outbound efforts
• Experience selling in competitive environments with entrenched incumbents
• Ability to run a repeatable prospecting cadence and articulate it clearly
• Experience with Hub Spot or similar CRM tools

You have a true hunter mentality and a history of building pipeline through disciplined outbound and follow‑through.

You collaborate closely with sales leadership, leverage existing relationships responsibly, and focus on shared success.

You are metrics‑driven, resilient, and consistently focused on improving your craft and results.

You understand how operators make decisions and can balance persistence with credibility in a relationship‑driven market.

• Must live in Hawaii and be actively engaged in the local business community

• Competitive base salary with uncapped commission tied to net‑new revenue
• Full medical, dental, and vision coverage
• 401(k) with company match
• High‑ownership role with direct access to sales leadership
• Equity for all employees
• Generous PTO
• Smart, low‑ego teammates who value impact