Account Executive - Life & Annuity Insurance

Overjet Is Bringing Its Technology to Life Insurance

Overjet is the global-leader in dental AI — thousands of dental providers and insurers already run on our platform, including many of the life carriers we're now targeting for this expansion. We built our category-defining position on a technology advantage that we are now bringing into life insurance.

This isn't a slide-deck idea — it's a real product, with established customer relationships, and a green light to build. And it means the person who takes this role gets something rare: the chance to operate within an early-stage startup team, with a proven platform, real traction, and the backing of a company that's already growing very fast as the leading player in an adjacent industry.

The Mission and the Hard Part

Overjet built its category-defining position in dental AI on a real technology advantage, and we're now moving that advantage into life insurance, where several of the carriers we're targeting are already our customers on the dental side. There is no Account Executive for this business today. If this seat sits empty, our 100-carrier target list stays a spreadsheet instead of a pipeline, and a proven platform with real traction never turns into a repeatable motion. You're the first dedicated Account Executive for life insurance, working directly with our Customer Success team, Head of Product, and CEO to define who we sell to, how we sell to them, and what a signed deal actually looks like in this market.

There's no playbook and no inbound to lean on: you're prospecting, discovering, demoing, negotiating, and closing against chief actuaries, heads of product, chief claims officers, and P&L owners who are technical, skeptical, and unimpressed by a slide deck. Deal cycles run six to nine months, and you'll be judged on pipeline built and deals closed while you're still building the muscle that makes both possible. If building a sales motion from a validated target list, rather than working one that's already humming, sounds like the fun part of the job rather than the scary part, keep reading.

What You'll Own

• You will own the full sales cycle for life insurance, from first prospect conversation through signed pilot, which means there's no handoff of a warm lead to make this easier: you're finding, diagnosing, pitching, negotiating, and closing every deal yourself.

• You will own our life insurance pipeline math, which means validating and prioritizing the 100-carrier target list into a real account plan in your first 30 days, and building a $1M+ pipeline across at least 10 prospects by the end of Q4.

• You will own the GTM playbook for this business line, which means writing the ICP, buyer personas, messaging, and objection handling from scratch, not adapting one that already exists elsewhere at Overjet.

• You will own credibility with technical, regulatory buyers, which means going deep enough on ratemaking, reserving, and competitive dynamics that underwriting, actuarial, claims, and compliance stakeholders treat you as someone who understands their world, not a vendor working a checklist.

• You will own customer expansion once a deal closes, which means driving adoption, retention, and growth within your accounts across adjacent teams and use cases, not just moving on to the next logo.

• You will own the early sales stack and reporting cadence for this business line, which means picking the tools and the rhythm, since none exists yet.

What Makes the Right Candidate Keep Reading

You need real, self-sourced experience selling enterprise SaaS specifically into life insurance, with existing relationships across claims, underwriting, actuarial, and distribution, because this role has no warm network to borrow. Beyond the résumé line, this is a job for someone with genuine tolerance for ambiguity and the intensity to build a sales motion while also being measured against a number this quarter, someone who gets curious about a buyer's regulatory and data governance world instead of treating it as friction. Prior early-stage or startup sales experience matters here, since you'll be building the process at the same time you're running it. If you need a mature buying process and an established playbook to sell well, this market and this role will frustrate you.

• Education: Bachelor's degree preferred, not required

• Skills: Full-cycle enterprise sales, closing skills with multi-stakeholder buying committees, working fluency in life insurance regulatory and compliance processes

• Experience: 6+ years of enterprise SaaS sales experience selling specifically into the life insurance industry

Why Overjet? 

• Competitive Compensation and Equity

• Hybrid workplace that provides flexibility, vibrant in-person workspaces, and the ability to build strong connections across all of Overjet - regardless of location

• 401k plans with a 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

Our Hybrid Workplace

We have a unique hybrid workplace at Overjet — which combines the teamwork of meeting in person, with the flexibility of working from anywhere.

Many of our positions are based in San Mateo, New York City, Boston, and Salt Lake City. The Jetters who live in these “geo-hubs” come to the office on Tuesdays and Wednesdays, while having the option to work from home the rest of the week.

Our People Team is happy to answer any questions about what hybrid work means for your specific role!

Overjet's Values

• Excellence: Aim Higher

• Velocity: Quickly Deliver Results

• Ownership: Go the Extra Mile

• Win-win: Care Deeply

Company Recognition

• Included on Best Places to Work by BuiltIn lists in 2026: #3 overall in the US, #1 in NYC, #1 in San Francisco, and #2 in Boston

• #4 on FastCompanys's Most Innovative Companies list in Healthcare for 2026

• Named one of the TIME Best Inventions of 2024

• Recognized in Newsweek’s Most Loved Workplaces in America 2024

• Won the Dental Health category at the Digital Health Awards 2024 and 2024 Best Places to Work by Built In

• Recognized as one of the Top Startups of 2023 by LinkedIn

• Included on the definitive 2022 Forbes AI 50

EEOC

Overjet is an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We believe diversity enriches our team so we hire people with a wide range of identities, backgrounds, and experiences. Even if you don't meet 100% of the qualifications for this job, we strongly encourage you to apply! 

If you are a Colorado resident: Please contact us by emailing [email protected] to receive compensation and benefits information for this role. Please include the job title in the subject line of the email.