This is a fully remote opportunity.
Gradient AI:
Gradient AI is revolutionizing Group Health and P&C insurance with AI-powered solutions that help insurers predict risk more accurately, improve profitability, and automate underwriting and claims. Our SaaS platform taps into one of the industry’s largest data lakes—tens of millions of policies and claims—to deliver deep, actionable insights. Trusted by leading carriers, MGAs, TPAs, and self-insured employers, Gradient AI has grown rapidly since our founding in 2018. Backed by $56M in Series C funding, we're scaling fast—and it's an exciting time to join the team.
About the Role:
We are looking for a driven, consultative Senior Sales Executive to join our team and sell our new predictive analytics solution for workers’ compensation claims management. This is a true hunter role. You will be joining at launch, building your pipeline from the ground up, and helping define what great looks like for this product in the market. If you have sold a new concept into the workers’ comp space and know what it takes to educate a buyer and close a deal, we want to talk with you.
How You Will Make an Impact:
- Build and own your pipeline through direct prospecting, industry relationships, and referrals across carriers, TPAs, brokers, MGAs, and self-insured employers
- Lead the full sales cycle from discovery through close, including demos, objection handling, proposals, and statements of work
- Serve as a credible voice in the market, connecting our software’s capabilities to real operational problems your buyers face every day
- Partner closely with product and customer success to provide market feedback and support strong client implementations
- Hit and exceed annual sales targets while helping shape our go-to-market approach in the early days of this product
What You Bring:
- 5+ years of SaaS or technology sales experience, with a meaningful portion spent selling into the workers compensation or P&C insurance market
- Direct experience selling to carriers, TPAs, brokers, MGAs and/or self-insured employers. You understand how these buyers think, how they buy, and what they care about
- Experience selling a new or emerging concept, not just an established product with a known category. You know how to build a case from scratch
- A track record of building your own book of business. You are a hunter who does not wait for leads to come to you
- Comfort with ambiguity. Strong communication and presentation skills, with the ability to demonstrate ROI and run a compelling demo
What We Offer:
- A fun, team-oriented startup culture.
- Generous stock options — we all get to own a piece of what we’re building.
- Unlimited vacation days.
- Flexible schedule that supports working from home.
- Full benefits package includes medical, dental, vision, 401k, paid parental leave, and more.
- Ample opportunities to learn and take on new responsibilities.
We are an equal opportunity employer.
On-Target Earnings (OTE): The anticipated on-target earnings (OTE) for this position is $275,000-$315,000 USD, inclusive of base salary with strong accelerators.
This role is also eligible for an equity grant and a comprehensive benefits package. In accordance with the Massachusetts Pay Transparency Law, we are providing a good-faith salary range for this position at the time of posting. The actual salary offered will depend on the level at which the candidate is hired, as well as their experience, skills, qualifications, and location. Compensation may grow over time through promotions and company-wide adjustments. If your salary expectations fall outside this range, we still encourage you to apply so we can have a conversation.
Skills Required
- 5+ years of SaaS or technology sales experience with meaningful portion selling into workers' compensation or P&C insurance market.
- Direct experience selling to carriers, TPAs, brokers, MGAs, and/or self-insured employers.
- Experience selling a new or emerging concept (ability to educate buyers and build a case from scratch).
- Proven track record of building your own book of business; hunter mentality and proactive prospecting.
- Ability to lead full sales cycle including demos, objection handling, proposals, statements of work, and closing.
- Strong communication and presentation skills with ability to demonstrate ROI and run compelling demos.
- Comfort with ambiguity and ability to partner with product and customer success to support implementations and provide market feedback.
Gradient AI Compensation & Benefits Highlights
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Healthcare Strength — Benefit descriptions highlight comprehensive medical, dental, and vision coverage, with mental health support via an Employee Assistance Program. Company‑paid life/AD&D and short‑ and long‑term disability further strengthen core protection.
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Leave & Time Off Breadth — Policies include unlimited vacation/PTO and 11 paid company holidays, with additional companywide recharge days and paid volunteer time noted. This breadth signals strong support for rest and flexibility.
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Parental & Family Support — Materials describe generous parental leave, including 12 weeks fully paid after a year of employment, alongside family medical leave. An onsite Mother’s Room further supports new parents.
Gradient AI Insights
What We Do
Gradient AI is revolutionizing Group Health and P&C insurance with AI-powered solutions that help insurers predict risk more accurately, improve profitability, and automate underwriting and claims. Our SaaS platform taps into one of the industry’s largest data lakes—tens of millions of policies and claims—to deliver deep, actionable insights. Trusted by leading carriers, MGAs, TPAs, and self-insured employers, Gradient AI has grown rapidly since our founding in 2018. Backed by $56M in Series C funding, we're scaling fast—and it's an exciting time to join the team.
Why Work With Us
Gradient is a fast-growing startup where you can make an impact, learn constantly, and grow quickly. We’re bringing AI and machine learning into the insurance space in new ways, and every team member plays a role in that innovation.
Gallery
Gradient AI Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
Working from the office is optional if you are local to our Boston office. For employees who do come in, it’s usually T/W/Th to focus on group collaboration.















