---
title: 'VP of Sales, Health Insurance Vertical at Gradient AI'
canonical: 'https://feeny.ai/job/vp-of-sales-health-insurance-vertical-gradient-ai-remote-md52bd0sp569'
type: 'job'
last_seen: '2026-09-19'
---

# VP of Sales, Health Insurance Vertical at Gradient AI

- **Company:** Gradient AI
- **Location:** Remote
- **Work type:** remote
- **Posted:** 2026-09-18
- **Last confirmed live:** 2026-09-19
- **Apply:** https://job-boards.greenhouse.io/gradientai/jobs/7999582003

## Job description

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 results-driven VP of Enterprise Sales to lead and grow a team of enterprise sales reps selling our AI-powered SaaS underwriting and analytics solutions to health insurance and benefits organizations. In this role, you’ll own your team's pipeline, forecasting, and quota attainment while instilling a consultative selling mindset across the group. The ideal candidate has led or coached sales teams before, brings credibility across the health insurance ecosystem, and has experience rolling out new sales methodologies that actually stick. They thrive coaching reps through complex, multi-stakeholder deals and are comfortable representing their team's results to leadership.

## How You Will Make an Impact

- Recruit, coach, and manage a team of enterprise sales reps, setting clear expectations around pipeline, forecasting, and consultative selling standards
- Own regional sales targets, ensuring the team hits, achieves, and exceeds monthly and annual quotas, with accurate forecasting and pipeline reporting in Salesforce
- Conduct regular 1:1s and pipeline reviews with each rep to identify coaching opportunities, remove blockers, and reinforce consultative selling as the standard, not a one-time initiative
- Lead by example on key deals, stepping into complex or strategic opportunities to model consultative selling and build credibility with major accounts
- Own hiring, onboarding, and ramp planning for new reps joining the team
- Identify underperformance early and create improvement plans, while recognizing and developing high performers on the team
- Partner with Marketing, Product, and Customer Success to relay field feedback and help shape regional demand generation and messaging
- Represent the team in leadership forecasting calls and QBRs, providing visibility into regional trends, risks, and opportunities

## Skills Needed to Succeed

- 10+ years of enterprise SaaS or technology sales experience, including experience leading, coaching, or mentoring a sales team
- Domain expertise in the health insurance space
- Proven experience hiring, onboarding, and developing sales talent, including identifying and addressing underperformance
- A strong consultative and strategic mindset with prior experience rolling out a new sales process or methodology across a team
- Ideally prior experience navigating complex buying committees, including Chief Actuaries, CMOs, VPs of Underwriting, and CFOs at health carriers and benefits organizations
- Outstanding verbal and written communication skills
- Ability to lead in a self-driven manner within a fast-paced, collaborative startup environment; comfort with ambiguity and a bias toward action

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.

OTE Range: The anticipated on-target earnings (OTE) for this position is $500k, inclusive of base salary with strong accelerators.

This role is also eligible for commission, 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.

## About Gradient AI

## Company Overview
- **One-liner**: Gradient AI provides proven artificial intelligence solutions that help insurance companies improve loss ratios and profitability by predicting underwriting and claims risks with greater accuracy and automating key processes.
- **Entity Type**: Private (Venture-Backed; latest venture round in July 2024; total funding $123.2M)
- **Headquarters**: Boston, Massachusetts, United States (1 Marina Park Drive, Suite 305, Boston, MA 02210)
- **Founded**: 2012 (spun out as an independent company in 2018)
- **Founders**: Not publicly disclosed

## Core Business
- **Primary industry/industries**: Insurance Technology (InsurTech), Artificial Intelligence, Machine Learning
- **Target customers**: Mid-market and large insurers across workers’ compensation, group health, and property & casualty markets; also serves TPAs, self-insured entities, brokers, captives, excess and surplus carriers, MGAs/MGUs, PEOs, reinsurers, and risk pools.
- **Mission or purpose statement**: To provide the fastest, most intelligent way to reduce risk and deliver quality decisions for the insurance industry, using AI and a vast dataset to power a better return on insurance risk.

## Products & Services
- **Underwriting Solutions**: AI-powered underwriting platform that uses a rich dataset (tens of millions of policies and claims plus economic, health, geographic, and demographic data) to improve quote turnaround time and give a more complete picture of risk. Customer result: over 300% decrease in quote turnaround time and an increase in Direct Written Premium per Employee.
- **Claims Management Solutions**: Machine learning-based claims management that predicts claims risk early, reduces combined loss ratio and expense ratio, and lowers claim expenses through intelligent automation. Customer result: 10–15% decrease in combined loss ratio and expense ratio.
- **Full-Cycle SaaS Platform**: End-to-end platform addressing both underwriting and claims, leveraging the same unified AI and data engine. All solutions are delivered as Software-as-a-Service.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (Private company).
- **Key Metric**: Total funding of $123.2M across 5 rounds (per LinkedIn); latest venture round of $3M in July 2024. Annual revenue not publicly disclosed (LinkedIn estimates $5.7M).
- **Notable Investors/Partners**: MassMutual Ventures, Sandbox Insurtech Ventures, BSC Capital, American Family Ventures, Forté Ventures, Stone Point Capital. Also SOC 2 compliant and HITRUST certified.
- **Growth Signals**: Headcount of 105 employees (+11.5% YoY); over $300 million in savings realized by customers (independently verified); named Built In’s Best Places to Work for 5 consecutive years.

## Competitive Advantages
- **Massive proprietary dataset**: Combines tens of millions of insurance policies and claims with hundreds of external data points (economic, health, geographic, demographic) that competitors with smaller datasets cannot match.
- **Proven results**: Independently verified multi-year studies showing significant improvements in loss ratios, quote turnaround, and claim expenses.
- **Full-cycle platform**: Covers both underwriting and claims management, allowing seamless integration and consistent risk insights across the insurance lifecycle.
- **Deep industry roots**: Originally incubated within one of the world’s largest actuarial consulting firms, giving the team deep domain expertise.

## Strategic Focus
- Continue expanding into mid-market and large enterprise insurance segments across workers’ comp, group health, and P&C.
- Leverage growing dataset and AI models to further reduce claim costs and improve underwriting accuracy.
- Scale sales and partner channels (current open roles include Enterprise Sales Director and Senior Sales Executive).
- Maintain strong compliance and security posture (SOC 2, HITRUST) to win in regulated markets.

## Why Work Here
- **Culture & Values**: Gradient emphasizes “We Before Me,” innovation (“Create Waves, Innovate”), and integrity (“Do the Right Thing”). They foster a collaborative, inclusive environment where employees can be their authentic selves.
- **Work Flexibility**: Accommodates flexible schedules and work-from-home; described as having “a life outside the office.” Current job postings list several roles as remote.
- **Compensation & Perks**: Competitive salaries, bonus plans, comprehensive health benefits (medical, dental, vision), employee assistance plan, equity participation, generous PTO plus 11 paid holidays, and MacBooks for every new hire.
- **Growth Opportunities**: A fast-paced, growth-stage startup that emphasizes learning and development; employees gain exposure to AI, ML, and InsurTech—a cutting-edge, disruptive industry.
- **Recognition**: Voted Built In’s Best Places to Work 5 years in a row.

## Sources
1. [gradientai.com](https://www.gradientai.com/)
2. [gradientai.com - About](https://www.gradientai.com/about)
3. [gradientai.com - Careers](https://www.gradientai.com/careers)
4. [linkedin.com - Gradient AI](https://www.linkedin.com/company/gradientai)
5. [Greenhouse - Gradient AI Jobs](https://job-boards.greenhouse.io/gradientai)

## Other roles at Gradient AI

- [Principal Data Scientist](https://feeny.ai/job/principal-data-scientist-gradient-ai-remote-0xbrj8knmcj5)
- [Staff Data Scientist](https://feeny.ai/job/staff-data-scientist-gradient-ai-remote-q3y0xp5872xp)
- [Senior Data Scientist](https://feeny.ai/job/senior-data-scientist-gradient-ai-remote-01q8zzd8n0m0)
- [Senior Sales Executive - P&C](https://feeny.ai/job/senior-sales-executive-p-c-gradient-ai-remote-ta62x0pw7ttf)