# Enterprise Sales Director - Health

**Company:** [Gradient AI](https://hotfix.jobs/companies/gradient-ai)
**Location:** Remote
**Role:** Account Executive
**Experience:** 10+ years
**Skills:** SaaS Sales, Enterprise Sales, Negotiation, Presentation Skills, CRM, Roi Modeling, Technical Demos, Forecasting
**Posted:** 2026-05-29

> The Enterprise Sales Director - Health will lead enterprise sales efforts for AI-powered SaaS underwriting and analytics solutions within the health insurance ecosystem. This role involves owning the full sales cycle, strategic prospecting, and exceeding sales targets.

## Job Description

## How you will make an impact:

* Own and grow a pipeline of enterprise opportunities across the group health ecosystem through strategic prospecting, existing relationships, and referral networks
* Lead the full consultative sales cycle from discovery and needs assessment through solution design, ROI modeling, contract negotiation, and close—engaging underwriting, actuarial, and C-suite stakeholders throughout
* Craft compelling statements of work, pricing proposals, and executive-level business cases that clearly articulate Gradient AI’s value to health plan and benefits decision-makers
* Develop deep domain expertise in AI-powered underwriting and stop loss analytics, and clearly communicate how our solutions drive loss ratio improvement, operational efficiency, and portfolio growth for health insurance clients
* Hit, achieve, and exceed monthly and annual sales targets; provide accurate forecasting and pipeline reporting in CRM

## Skills needed to succeed:

* Bachelor’s degree required; 10+ years of enterprise SaaS or technology sales experience, with at least 5 years selling into the health insurance space
* Demonstrated ability to build and close a book of business from scratch; a hunter mentality with proven quota attainment at or above 100%
* Strong negotiation and presentation skills; experience running technical demos and building ROI models tailored to health insurance and benefits stakeholders
* 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 work 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.

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