Enterprise Account Executive

Clasp is transforming access to education and career pathways, starting with the healthcare workforce. We enable employers to invest in future talent where it matters most while easing overwhelming student debt. We’re creating lasting bonds between employers and employees. We believe that when employers have a stake in the cost of education, we can create a more sustainable, equitable, and skilled workforce.

As a mission-driven, venture-backed startup, we’re fresh off our Series B, entering our next phase of growth. Clasp is a Forbes Fintech 50 company, a SHRM portfolio company, and has been named by Business Insider as one of the “Top 14 Healthcare Startups to Watch in 2026” and one of the “43 Startups to Bet Your Career On in 2025.”

We’re not just building a fintech product; we’re driving economic mobility. If you’re excited to build, grow, and make a real impact, join us.

What We Need

Clasp is looking for a high-performing Account Executive to hunt and close long-term, high-value customer partnerships. This is a consultative, enterprise sales role for someone who thrives in complex buying environments, owns a deal end-to-end, and brings curiosity, discipline, and strategic thinking to every deal.

As an AE at Clasp, you will own the sales lifecycle from networking and outreach to generate qualified deals, to guiding the prospect through their buyer’s journey. You’ll lead the process every step of the way, from first conversation through close using deep discovery, tailored solutioning, and data-backed storytelling. You’ll collaborate closely with Leadership, Marketing, Product, and Partner Success to deliver a high-trust buying experience that reflects Clasp’s values. This role is critical to accelerating ARR growth, creating a new category in the marketplace, and upholding Clasp as a partner, not a vendor.

What You’ll Do

• Own an assigned territory to consistently generate your pipeline through networking, event attendance, and outbound prospecting
• Close deals to meet or exceed quarterly ARR targets
• Lead complex, consultative sales cycles from discovery through close, aligning Clasp’s solutions to customer business outcomes
• Deliver well-structured and persuasive sales presentations that frame the value of a Clasp partnership within the prospect’s priorities and problems
• Develop and design custom programs for customers based on a deep understanding of their business requirements; provide thorough, data-driven ROI analysis to make the business case
• Build and manage strong middle-to-late funnel deal strategy, including regular touchpoints, stakeholder alignment, multi-threading, and purchase process mapping
• Represent Clasp externally at industry conferences and events, generating top-of-funnel opportunities, and building trusted relationships
• Maintain disciplined CRM hygiene and accurate forecasting for all owned companies, contacts, and deals
• Work cross-functionally with Marketing and Partner Success teams to ensure seamless handoffs and improved conversion rates
• Provide feedback to Clasp’s Product team identifying enhancements frequently requested during sales processes that will improve Clasp’s win and retention rate

What You’ll Need

• 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 Clasp’s offering
• Demonstrated ownership, discipline, and operational rigor, including forecasting accuracy and CRM hygiene

What Will Set You Apart

• Showing your sales skills during the interview process with your preparation, questions, follow-ups, and creativity
• 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

What We Give In Return

• Competitive cash and equity compensation
• Health benefits (health, dental, & vision)
• 401k match
• Commuter benefits
• Flexible PTO policy
• Opportunities to grow and perform in a fast-paced environment alongside a stellar team