Enterprise Account Executive

Hike Medical Hike Medical is reinventing musculoskeletal care, starting with feet. Our proprietary AI-vision platform turns a 30 second web-based (no sensors) foot scan into precision engineered, 3D-printed insoles that prevent pain before it starts. We're already protecting on-their-feet workforces at Fortune 50 leaders, major health systems, and middle America manufacturers. Fresh off a stealthy round with top tier VCs, we run a fast, no BS, execution-first culture out of Boston's Seaport as we sprint toward $100M ARR and standing with 10M Americans as they step into their shoes daily. First and only PDAC-approved 3D printed custom insole in the world 3 proprietary AI models that power the experience Two products: one for employers & health plans, one for clinics creating a virtuous cycle of clinician-labeled data Expanded care access to 100,000+ Americans to date What We're Looking For These are not hard-and-fast requirements we care more about crisp execution and ownership than checking every box. 610 years of B2B sales experience, with a strong track record closing enterprise or upper-mid-market deals Experience selling into employers, HR, benefits, healthcare, or adjacent enterprise buyers Healthcare, employer benefits, MSK, occupational health, or med-device experience Experience working with large enterprises and complex programs (e.g., Fortune 1000 employers, major health systems, large manufacturers) Deep understanding of the HR/benefits buyer and buying process Proven ability to manage a full sales cycle with multiple stakeholders and long timelines Track record of consistently hitting or exceeding quota Exceptionally strong relationship-building and communication skills, from operators to C-suite Extremely comfortable leading sales meetings, presentations, and executive discussions Highly organized with a strong system for pipeline management, forecasting, and follow-through Experience partnering closely with Customer Success, Operations, and Product On-site in Boston Nice-to-Haves Experience in venture-backed or high-growth early/growth-stage companies Familiarity working with benefits consultants or brokers (e.g., AON, Mercer, WTW, Gallagher, Lockton) Experience selling new or category-creating products into conservative or regulated markets Experience with HubSpot or similar CRM tools Primary Responsibilities Enterprise Sales Ownership: Own the full sales cycle for employer prospects, from initial outreach through contract execution, across multiple concurrent opportunities. Pipeline Generation & Management: Build and maintain a healthy pipeline through outbound efforts, inbound leads, partner channels, and broker relationships. Multi-Stakeholder Deal Leadership: Navigate complex buying committees across HR, Benefits, Finance, Legal, and Clinical stakeholders. Value-Driven Selling: Clearly articulate Hike's differentiated value proposition, outcomes, and ROI to senior decision-makers. Forecasting & Deal Discipline: Maintain accurate pipeline reporting and forecasts; proactively manage deal risks and next steps. Cross-Functional Collaboration: Partner closely with Customer Success to ensure smooth handoffs post-sale and strong launches. Market Feedback Loop: Share insights from prospects and closed-won/lost deals with Product, Operations, and Leadership to help shape roadmap and GTM strategy. What You'll Get Competitive cash compensation + equity Full medical, dental, and vision coverage $15K relocation bonus if needed Daily collaboration with the founding team and senior leadership Free custom insoles (of course)