We’re hiring a Mid-Market Account Executive to own net-new logo acquisition across mid-market accounts. This role is built for someone who thrives on outbound, builds their own pipeline, and takes pride in closing deals they sourced themselves. While we have an NYC sales office and prefer someone who can work in a hybrid model, we’re open to fully remote candidates for the right fit.

What You’ll Do

• Prospect every day and build your own pipeline (expect 40–50 calls a day plus email + LinkedIn).
• Book 5–7 solid demos a week by being consistent and following up well.
• Run deals end-to-end from first outreach to signed contract—across 1–6 month sales cycles.
• Lead real discovery calls that get to the truth early: urgency, decision-makers, budget, and timing.
• Give clear, no-fluff demos that show operators exactly how TripWorks helps them make more money.
• Keep deals moving, even when decisions take time or multiple people are involved.
• Manage your pipeline like a pro so you know where your number is coming from.
• Keep HubSpot up to date so nothing slips through the cracks.
• Hand off closed deals cleanly and work with onboarding to get customers winning fa

What You Bring

• 2–5 years of experience closing new business in a quota-carrying sales role
• A track record of creating your own pipeline through outbound (calls, emails, LinkedIn — you’re not afraid to start conversations)
• Comfort reaching out cold and turning curiosity into real opportunities
• Strong discovery instincts — you know how to ask the right questions and move deals forward with intention
• Experience selling into real-world, operationally complex businesses with multiple decision-makers
• Confidence managing your pipeline, deals, and forecasts in a CRM like HubSpot
• Ability to work hybrid from our NYC office is preferred, but not required
• Bonus points if you’ve sold SaaS, or worked in travel, hospitality, or marketplace-style tech
• Mamba Mentality - if you know you know

What Makes You a Great Fit

Grab a Shovel: You don’t wait for leads. You create momentum through consistent outbound and follow-through.

We Win Together: You collaborate closely with SDRs, marketing, and post-sale teams to win new logos and set customers up for success.

Push Further: You’re motivated by progress and results. You review your pipeline critically and look for ways to improve every week.

Think Like an Operator: You sell with empathy and realism, focused on solving real operational problems.

New Logo Mindset: You’re energized by opening doors, earning trust, and closing business where no relationship existed before.

Why Join TripWorks?

• Flexible work model: Work hybrid from our NYC sales office or fully remote, depending on location and fit.
• Top-Tier Health Benefits: We cover 100% of your medical premium and offer dental and vision plans.
• 401K Match: Full 3% employer match.
• Equity: All employees are owners in the business.
• Generous PTO: We encourage time away from work to recharge.
• Great People: Join a team of smart, kind, low-ego teammates who value impact.

Values-Driven Culture:

We take initiative, collaborate deeply, push beyond the status quo, and build with our customers in mind.

Ready to Apply?

If you’re excited about what we’re building and think you’d thrive at TripWorks, we’d love to hear from you. Apply now by emailing careers@tripworks.com with your resume and a brief note on why you’re interested.

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.

What You’ll Do

• 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 HubSpot.
• Represent TripWorks locally at meetings, industry events, and conferences.

What You Bring

• 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 HubSpot or similar CRM tools.

What Makes You a Great Fit

• Grab a Shovel: You have a true hunter mentality and a history of building pipeline through disciplined outbound and follow-through.
• We Win Together: You collaborate closely with sales leadership, leverage existing relationships responsibly, and focus on shared success.
• Push Further: You are metrics-driven, resilient, and consistently focused on improving your craft and results.
• Think Like an Operator: You understand how operators make decisions and can balance persistence with credibility in a relationship-driven market.

Location Requirement

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

Why Join TripWorks?

• Fully remote team.
• 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.

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Ready to Apply?

If you’re excited about what we’re building and think you’d thrive at TripWorks, we’d love to hear from you. Apply now by emailing careers@tripworks.com with your resume and a brief note on why you’re interested.