Own a book of business and consistently 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 using best-in-class enterprise methodologies, with a thorough understanding of customer pain points
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 objection handling, stakeholder alignment, mullti-threading, and procurement navigation
Contribute 10–20% of pipeline through self-sourced efforts such as outbound prospecting, social selling, and event engagement
Represent Clasp externally at industry conferences and events, generating top-of-funnel opportunities and building trusted relationships
Maintain disciplined CRM hygiene, accurate forecasting, and clear next steps for all opportunities
Partner closely with SDRs and cross-functional teams to ensure seamless handoffs and improved conversion rates
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.

Enterprise Account Executive

Key skills