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Salary: USD 120,000 - 140,000 / annual
Clasp is a venture-backed fintech startup transforming access to education and career pathways, particularly within the healthcare workforce. The company enables employers to invest in future talent while helping employees manage student debt, creating sustainable bonds between employers and employees. Clasp is a Forbes Fintech 50 company and has been recognized by Business Insider as a top healthcare startup to watch.
As an Enterprise Account Executive, you will own the full sales lifecycle for high-value, long-term customer partnerships in a consultative, complex enterprise environment. You will generate qualified pipeline through networking, outreach, and event attendance within an assigned territory. Your responsibilities include leading discovery conversations, designing custom programs tailored to customer business requirements, delivering data-driven ROI analyses, and closing deals to meet quarterly ARR targets.
You will manage complex, multi-stakeholder sales cycles from initial contact through close, using deep discovery and strategic storytelling. You'll develop middle-to-late funnel deal strategy with regular touchpoints, stakeholder alignment, and purchase process mapping. You'll represent Clasp at industry conferences and events to generate top-of-funnel opportunities and build trusted relationships. Cross-functional collaboration with Marketing, Product, and Partner Success teams is essential to ensure seamless handoffs and improved conversion rates. You'll maintain disciplined CRM hygiene, accurate forecasting, and provide product feedback based on sales insights.
The role is remote-eligible but requires up to 30% travel within the US.
REQUIREMENTS:
- 2+ years of proven experience carrying a quota and consistently meeting or exceeding revenue targets in a B2B sales role
- 2+ years of experience working at a Series B or earlier B2B startup
- Experience running consultative, value-based sales cycles in complex or enterprise environments
- Strong coachability and critical thinking skills to continuously improve
- Demonstrated curiosity and learning agility in becoming an industry expert in regulated or complex industries
- Ability to customize messaging, demos, and proposals based on stakeholder needs and business context
- Comfort navigating multi-stakeholder deals, objections, and longer sales cycles
- Comfort with embracing evolving processes, resources, and proof points given the early nature of the offering
- Demonstrated ownership, discipline, and operational rigor, including forecasting accuracy and CRM hygiene
PREFERRED QUALIFICATIONS:
- Experience selling in the Healthcare space
- Experience selling to HR and Talent Acquisition departments
- Familiarity with modern sales tools including HubSpot, Google Drive, ZoomInfo, Fathom
