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 searching for a hands-on consultative Senior Sales Executive, Health to join our team and sell our SaaS underwriting and analytics solutions to the health insurance industry. This individual will understand the customer’s business objectives, the technical components of our solutions, and utilize a deliberate sales methodology in achieving sales objectives.
The successful candidate will demonstrate software sales expertise, desire to hunt and build your own pipeline, and have experience selling into the health insurance space. They will come with their own strategies, approaches, and have very strong self-motivation.
How you will make an impact:
- Build your own book of business from the ground up with a strong pipeline of prospective customers through direct prospecting, relationships, and referrals
- Lead all aspects of the consultative sales process including new business development, client research, objection handling, demoing, closing, and follow up
- Draft statements of work and pricing proposals
- Master our value proposition today and as the competitive landscape evolves
- Hit, achieve, and exceed monthly and annual sales targets
Skills needed to succeed:
- 7+ years of proven sales experience with at least a few years of hitting or exceeding quota
- Strong experience selling into the health insurance industry is a must
- Solid track record building your own book of business; someone who loves to hunt!
- Strong negotiation and presentation skills; experience running demos & ability to demonstrate ROI through the use of technology
- Prior experience selling into insurance leaders; outstanding verbal and written communication skills
- Ability to work in a self-driven manner within a fast-paced, collaborative environment
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 paternal 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 $300,000-$350,000 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
- 7+ years of proven sales experience with quota attainment
- Strong experience selling into the health insurance industry
- Proven ability to build your own book of business and prospect independently
- Software/SaaS sales expertise and consultative selling experience
- Strong negotiation and presentation skills; experience running demos and demonstrating ROI
- Experience drafting statements of work and pricing proposals
- Outstanding verbal and written communication skills
- Ability to work self-driven in a fast-paced, collaborative environment
What the Team is Saying
Gradient AI Compensation & Benefits Highlights
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Healthcare Strength — Healthcare is described as comprehensive—medical, dental, and vision coverage with life and disability insurance and an EAP, with day‑one eligibility via a PEO in some listings. Plan options, mental‑health benefits, and FSA support indicate broad coverage.
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Leave & Time Off Breadth — Time off includes “unlimited” PTO alongside 11 paid holidays and periodic company‑wide “recharge days.” These structured closures add predictable rest within a flexible time‑off model.
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Equity Value & Accessibility — Equity is granted to all new hires with a four‑year vesting schedule and opportunities for additional grants through merit and promotions. Performance bonuses and stated competitive salaries further strengthen total compensation.
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.
