Mid Market Account Executive

At TripWorks, we believe work should be meaningful, fast-paced, and a little bit adventurous. We're a 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 a Mid-Market Account Executive to win net-new operators doing $300K to $5M a year - real businesses with boats, aircraft, vehicles, and crews. Our deals run $25K-$100k. We run a deliberate, multi-call motion that pulls every decision-maker in through genuine excitement. What You'll Do Prospect daily from AI-enriched account lists that tell you who to call and why. Run a full discovery on 100% of your opportunities and spend your time learning the business like you might buy it. Prepare for every demo and prove it. Every demo has a prep requirement with a plan built from your discovery, tailored to the operator's story. Deliver demos that tell one operator's story back to them - their leaks, their season, their numbers. Run our confirmation framework after every demo, and use it to bring the other decision-makers into the process through your champion's excitement. Close on the operator's calendar and anchor every deal to a season and a go-live date that actually works for their business. Get in front of buyers when it matters: occasional travel to operators, industry events, and our NYC office. Keep HubSpot honest with stages that reflect reality, next steps on every deal, and clean handoffs to onboarding so your customers go live and stay. The is a full cycle Mid-Market Account Executive role. You’re confident in your ability to build your own pipeline and don’t rely on marketing to feed the engine. Consistency is paramount. What You Bring 2-5 years closing new business in a quota-carrying role - with deal cycles that took more than one call and more than one stakeholder. A discovery habit you can prove: you ask before you show, you take real notes, and your demos reflect what you heard. A preparation habit you're proud of. Outbound muscle: you build your own pipeline by phone and don't flinch at calling a business owner cold. Experience selling to owner-operators of real-world businesses like travel, hospitality, home services, fitness, or similar. You know how to talk to someone who answers their own phone. Comfort with numbers: revenue, processing rates, channel mix and you can do deal math out loud with a customer. Ability to work hybrid from our NYC sales office. Bonus points if you've sold SaaS with payments attached, or worked in the tours and activities world. What Makes You a Great Fit Grab a Shovel: You create your own momentum with consistent outbound, same-day follow-ups, no waiting for leads. We Win Together: You work your deals with our SDR, our field team, and onboarding and your customers become references because you set them up honestly. Push Further: You review your own calls, track your own numbers, and fix your own gaps before anyone asks. Think Like an Operator: You sell with empathy and realism. Prepared, Not Rushed: You believe deals are won in the work between the calls. Why Join TripWorks? A selling system, not a script: A defined motion - discovery, prepared demos, confirmations - built by sales leadership that still carries a bag. Flexible work model: Hybrid from our NYC sales office preferred; strong remote candidates considered. 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. #J-18808-Ljbffr