Account Executive (Mid Market)

Account Executive (Mid-Market)



At TripWorks, we believe work should be meaningful, fast-paced, and a little bit adventurous. We're a growing 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 energized by blank territory, motivated by creating something from nothing, and driven to win new business, you'll fit right in.

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 many 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 1–3 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 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?

• Top-Tier Health Benefits: We cover 100% of employee medical premium and offer dental and vision plans.
• 401K Match: Full 3% employer match.
• Equity: All employees are owners in the business.
• 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.