Responsibilities
- Own the full sales cycle for employer prospects, from initial outreach through contract execution, across multiple concurrent opportunities.
- Build and maintain a healthy pipeline through outbound efforts, inbound leads, partner channels, and broker relationships.
- Navigate complex buying committees across HR, Benefits, Finance, Legal, and Clinical stakeholders.
- Clearly articulate Hike’s differentiated value proposition, outcomes, and ROI to senior decision-makers.
- Maintain accurate pipeline reporting and forecasts; proactively manage deal risks and next steps.
- Partner closely with Customer Success to ensure smooth handoffs post-sale and strong launches.
- Share insights from prospects and closed-won/lost deals with Product, Operations, and Leadership to help shape roadmap and GTM strategy.
Requirements
- 6–10 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 Have
- 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
Benefits
- 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…)
Work Arrangement
On-site — Boston
Additional Information
- Relocation bonus of $15K available if needed
- On-site requirement in Boston
