Account Executive, Life & Annuity Insurance

We're hiring Overjet's first dedicated Account Executive for the life insurance market. This is a founding AE role. You will be the first AE hire for this team. You won't inherit a sales playbook; you'll build one, while closing deals at the same time. You'll work directly with our VP of Customer Success, Head of Product, and CEO to shape how we sell into life carriers, define our ideal customer profile, and turn early traction into a repeatable motion. The buyers are chief actuaries, heads of product, chief claim officers, and P&L owners at the nation’s largest carriers. They’re technical, they’re skeptical, and credibility comes from understanding their work and proving the platform’s value through a multi-stakeholder process, not from a pitch deck. This role is for someone who thrives in ambiguity, can navigate multi-stakeholder deals, and is energized by shaping a sales motion that’s still evolving.

Responsibilities

Own the full sales cycle end-to-end from prospecting, discovery, demo, negotiation, and close with no existing inbound motion to lean on; Validate and prioritize our existing 100-carrier target list into a working account plan in your first 30 days. Build and manage a pipeline of $1M+ across at least 10 prospects by the end of Q4, converting to signed pilots; Build the initial GTM playbook: ICP, buyer personas, messaging, objection handling, and discovery framework; Establish and own our customer expansion approach – drive adoption, retention, and growth within your accounts across adjacent teams and use cases; Navigate complex, multi-stakeholder buying committees: underwriting, actuarial, claims, customer service, compliance, and C-suite, and build credibility with technical and regulatory stakeholders, not just procurement; Partner with our insurance team to scope POCs, run high-signal demos, and translate customer feedback into product priorities; Collect customer and market feedback to inform the product roadmap, pricing, packaging, and go-to-market strategy; Help select and set up the early sales stack and reporting cadence for this business line, since none exists yet

Requirements

6+ years of enterprise SaaS sales experience selling specifically into the life insurance industry, with a proven, self-sourced book of business and existing relationships with life carrier stakeholders across claims, customer service, underwriting, actuarial, and distribution; Strong commercial instincts with a strong track record of closing complex, end-to-end enterprise deals with senior, multi-stakeholder buying groups; Working fluency in life insurance regulatory and compliance processes, data governance, and executive sign-off; Demonstrated ability to build a sales motion from scratch, including messaging, playbook, pipeline, without an established process to lean on; prior early-stage or startup sales experience strongly preferred; Comfort operating across long sales cycles (6–9 months is typical in this market) while still delivering against near-term pipeline goals; Intellectually curious, excited by AI, and ready to be a founding team member; Willing to go deep on your buyers' world (ratemaking, reserving, competitive analysis); Drawn to the risk, reward, ownership, and impact of an early-stage product and a new line of business.

Nice to have

Prior early-stage or startup sales experience

Benefits

Competitive Compensation and Equity; Hybrid workplace; 401k matching program; Medical, Dental and Vision coverage (99% employee premium covered, 75% dependent premium covered); Life and AD+D Insurance; 8 weeks Paid Parental Leave; Optional HSA with Employer contribution; Flexible Time Off and company paid holidays; Annual Learning and Development Stipend