Enterprise Account Executive
$350kMotivity Resources
Enterprise Account Executive AI × Insurance | High-Value Deals | Build the Enterprise Motion Hybrid | San Francisco OR NYC | $350K+ OTE (uncapped commission) The client is hiring an Enterprise Account Executive to help scale a fast-growing AI company operating in one of the most complex and opportunity-rich industries: insurance. This role is critical to expanding market presence, landing flagship enterprise logos, and shaping how AI is sold into a traditionally conservative vertical. You'll own meaningful deals, influence GTM strategy, and help professionalize the enterprise sales motion as the company scales. If you're a strong closer who thrives in ambiguity and wants real ownership, not just quota, this is the role. AI in a High-Stakes Industry You'll sell AI-native solutions into the insurance ecosystem-complex workflows, risk-sensitive buyers, and real transformation potential. Real Revenue Ownership This is a full-cycle role with meaningful ARR responsibility, expansion upside, and a direct line between your execution and company growth. Build While You Sell You won't inherit a static playbook. You'll help refine messaging, pricing, and positioning based on what the market is actually telling you. Flagship Logos, Not Volume Selling Success here means landing and expanding strategic enterprise accounts-not chasing SMB deal counts. What You'll Do Own the Full Sales Cycle
- Manage deals from qualified lead through discovery, demo, proposal, negotiation, and close
- Partner with SDRs and marketing to develop and convert high-quality pipeline
- Quickly learn prospect workflows and pain points
- Position solutions with credibility to insurance buyers and operators
- Maintain a clean, accurate pipeline and forecasts in CRM
- Deliver reliable quarterly forecasts and deal progression
- Actively contribute to messaging, positioning, and pricing evolution
- Provide structured feedback based on live deal learnings
- Consistently meet or exceed new-logo ARR targets
- Close enterprise customers within the target insurance segment
- Maintain 3-4× pipeline coverage with a mix of self-sourced and SDR-sourced opportunities
- Demonstrate consistent stage progression without stalled deals
- Shorten average sales cycle
- Improve stage-to-stage conversion rates
- Forecast within ±20% accuracy
- Ensure clean handoffs to CSM/AM with expansion opportunities identified early
- Support strong year-one renewals and account growth
- Produce quarterly "voice of customer" insights
- Surface objections, competitor signals, and product requests
- Influence roadmap and GTM strategy with 2-3 adopted insights per quarter
- 3+ years of full-cycle closing experience as an Enterprise AE at a tech startup
- History of consistent promotions and increased responsibility
- Experience closing $100K+ ACV deals
- Proven ability to manage $1M+ quotas with expansion potential
- Background selling into the insurance vertical or prior insurance experience
- Undergraduate degree
- Strong proficiency with CRM and sales automation tools (e.g., HubSpot, Apollo)
- Comfortable with ambiguity and building sales processes
- Strong communicator with high IQ and EQ
- Consultative, credible, and outcome-oriented
- Frequently changing roles (we're looking for 2-3+ years of tenure per role )
- Uncomfortable owning complex deals end-to-end
- Looking for a highly structured, fully built enterprise sales org
- AI + insurance is early, complex, and wide open
- Real ownership of enterprise deals and GTM evolution
- Opportunity to help define how this category is sold
- Clear path to growth as the enterprise motion scales
Vacancy posted 2 days ago
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