Enterprise Account Executive

Clasp is a mission-driven, venture-backed startup transforming access to education and career pathways—starting with the healthcare workforce. By enabling employers to invest in future talent where it matters most—easing overwhelming student debt—our platform creates 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.

Fresh off our Series B, we’re 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.

Clasp is looking for a high-performing Account Executive to convert qualified demand into 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 guide prospects from first conversation through close using deep discovery, tailored solutioning, and data-backed storytelling. You’ll collaborate closely with SDRs, Marketing, Product, and Leadership to deliver a high-trust buying experience that reflects Clasp’s values. This role is critical to accelerating ARR growth, strengthening Clasp’s market presence, and ensuring customers see Clasp as a true strategic partner—not just a vendor.

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  Own a book of business and consistently meet or exceed quarterly ARR targets

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  Lead complex, consultative sales cycles from discovery through close, aligning Clasp’s solutions to customer business outcomes

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  Deliver well-structured and persuasive sales presentations using best-in-class enterprise methodologies, with a thorough understanding of customer pain points

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  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.

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  Build and manage strong middle-to-late funnel deal strategy, including objection handling, stakeholder alignment, mullti-threading, and procurement navigation

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  Contribute 10–20% of pipeline through self-sourced efforts such as outbound prospecting, social selling, and event engagement

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  Represent Clasp externally at industry conferences and events, generating top-of-funnel opportunities and building trusted relationships

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  Maintain disciplined CRM hygiene, accurate forecasting, and clear next steps for all opportunities

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  Partner closely with SDRs and cross-functional teams to ensure seamless handoffs and improved conversion rates

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  Bubble up feedback to Clasp’s Product team identifying enhancements frequently requested during sales processes that could be implemented to improve Clasp’s win rate and stickiness

• 4+ years of proven experience carrying a quota and consistently meeting or exceeding revenue targets in a B2B sales role

• Experience running consultative, value-based sales cycles—ideally in complex or enterprise environments

• Strong discovery, storytelling, and executive-level communication skills

• Ability to customize messaging, demos, and proposals based on stakeholder needs and business context

• Experience utilizing sales tools to inform more personalized sales conversations (e.g., zoom info, fathom, AI support)

• Comfort navigating multi-stakeholder deals, objections, and longer sales cycles

• Demonstrated ownership, discipline, and operational rigor, including forecasting accuracy and CRM hygiene

• Curiosity and learning agility, with interest in building domain expertise in regulated or complex industries (e.g., healthcare, student loans, HR/hiring)

• Familiarity with modern sales tools and CRM systems (e.g., Hubspot or equivalent)

• 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.

The base salary range for this position is competitive and will be commensurate with the candidate's experience, qualifications, and industry knowledge, ranging between $120,000 to $140,000 annually, with an on-target earnings between $280,000 to $300,000. In addition to the cash compensation package, we offer an attractive equity component as part of our compensation package, providing an opportunity for eligible employees to share in the success and growth of our company. We are committed to offering competitive compensation and benefits packages to attract and retain top talent.

If you are a highly driven individual with a passion for technology, and you thrive in a dynamic and fast-paced environment, we want to hear from you! Join us in revolutionizing the workforce solution industry and making a meaningful impact on businesses worldwide. Apply now to be a part of our growing team!

We are committed to creating a diverse and inclusive workplace where all employees feel valued, respected, and empowered to contribute their unique perspectives and talents. Clasp is an equal opportunity employer and prohibits discrimination and harassment of any kind. We embrace diversity and are dedicated to providing equal employment opportunities to all individuals regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.