Job Openings
Enterprise Account Executive
About the job Enterprise Account Executive
Enterprise Account Executive
Location: Onsite — San Francisco, CA (5 days/week, required)
Travel: 1–2 conferences per month (avg. 3 days each)
Compensation:
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Base Salary: $125,000 – $175,000
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OTE: $250,000 – $350,000
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Equity: Included
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Visa Sponsorship: Case-by-case
The Opportunity
HireNow Staffing is partnering with a venture-backed, domain-specific AI company redefining how insurance organizations operate. This team is building technology that fundamentally changes underwriting, claims, and operational workflows—and they are entering a critical enterprise expansion phase.
We are seeking a seasoned Enterprise Account Executive who brings real insurance fluency, a stable track record, and the ability to close complex, six-figure deals in high-stakes environments. This role is not transactional and not remote—it is designed for sellers who want ownership, visibility, and influence while helping define enterprise go-to-market strategy from the inside.
Why This Role Stands Out
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True Enterprise Motion: Long sales cycles, multi-stakeholder deals, and land-and-expand growth.
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Insurance-Native AI: You'll sell into workflows that matter—underwriting, claims, and operations—not generic tooling.
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High Visibility: Early-stage environment where your wins directly shape product, pricing, and GTM direction.
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Onsite Culture: Daily collaboration with founders, product, and engineering in San Francisco.
Key Responsibilities
Candidates must demonstrate mastery across the following areas to be considered for interview:
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Own the entire enterprise sales cycle from qualified lead through discovery, demo, proposal, negotiation, and close
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Build deep understanding of insurance workflows and operational pain points to position AI-driven solutions credibly
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Navigate complex buying committees including underwriting, claims, operations, IT, and executive leadership
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Partner closely with SDRs and Marketing to convert inbound and outbound pipeline into closed revenue
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Maintain accurate pipeline management and forecasting using CRM tools (HubSpot preferred)
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Contribute directly to messaging, pricing, and positioning based on real customer conversations
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Identify and develop land-and-expand opportunities post-close, setting the foundation for long-term account growth
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Represent the company at industry conferences and events (1–2 per month)
What Success Looks Like
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Consistently land $100K+ ACV enterprise deals with clear expansion paths
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Exceed quota while maintaining 3–4x pipeline coverage
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Shorten sales cycles through disciplined deal management and strong stakeholder alignment
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Secure flagship insurance logos that accelerate brand credibility
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Provide actionable voice of customer insights that influence product and GTM strategy
Required Qualifications
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3+ years of full-cycle enterprise closing experience in a tech or SaaS environment
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Demonstrated experience selling to insurance companies or prior professional experience within the insurance industry
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Track record closing $100K+ ACV deals with exposure to land-and-expand motions
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Stable career history with clear progression (multiple sub-1-year stints without explanation will not be considered)
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Willingness and ability to work onsite in San Francisco, 5 days per week
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Willingness to travel regularly for conferences and industry events
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Bachelor's degree required
Preferred Qualifications (Strongly Emphasized)
Standout candidates will bring multiple of the following:
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Prior experience at an early-stage or high-growth startup
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Background selling AI, workflow automation, or data-driven platforms
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Insurtech experience or direct exposure selling into insurance-specific ICPs (e.g., Heads of Underwriting, Claims, or Ops)
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Proven history of consistent quota attainment and promotion
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Comfort operating in ambiguity and helping build enterprise sales processes from the ground up
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High EQ with the ability to sell complex, technical solutions to senior insurance leaders
Important Notes
This role is not a fit for candidates who:
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Have only sold SMB or mid-market deals
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Are unwilling to work onsite full-time in San Francisco
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Are unable to travel for conferences
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Have highly jumpy resumes without clear performance-based rationale