Gradient AI is hiring a

Senior Sales Executive, Workers' Compensation


Gradient AI:    

Gradient AI is a fast-growing startup, bringing state-of-the-art Artificial Intelligence (AI) and Machine Learning (ML) solutions to the trillion-dollar insurance industry.  Founded in 2018, we have recently raised $20M from top Insurtech investors to continue fueling our growth.  Our software-as-a-service platform provides bias-free, data-driven insights, enabling insurance companies to profitably run their business and expand their offerings to underserved people and markets.   

About the Role:

We are searching for a Senior Sales Executive to sell our solutions-based claims and underwriting solutions to the workers' compensation industry. This person 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 have a deep network selling into the workers' comp space, demonstrate enterprise software sales expertise, desire to hunt and build your own pipeline, strong technical skills, and drive.

Key Responsibilities:

  • Develop your own book of business 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, pricing, closing, and follow up
  • Craft compelling 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


  • 7+ years of enterprise software/solution selling experience
  • Extensive experience selling into the workers comp insurance space
  • Solid track record building your own book of business from the ground up; someone who loves to hunt!
  • Strong negotiation, presentation, and closing skills
  • Prior experience selling to Directors and up to C-Suite Executives; senior presence
  • 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 including medical, dental, vision, 401k, and more.  
  • Ample opportunities to learn and take on new responsibilities.  

Travel is expected for this role.

Chosen as a top place to work and best paying company by BuiltInBoston!

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