Motion Recruitment | Jobspring | Workbridge

Insurance Tech Sales

Chicago, Illinois

Hybrid

Direct Hire

$125k - $175k

We’re hiring a Founding Sales / Business Development Executive to help build and scale the go-to-market motion at a fast-growing AI startup transforming the insurance industry. This is a first-AE / early sales hire with real ownership: defining the sales playbook, shaping customer engagement strategy, and closing complex six-figure enterprise deals.

You’ll work closely with the Head of Sales and founding team, selling to brokerages, carriers, MGAs, TPAs, claims organizations, and insurance-adjacent legal teams. This role is ideal for either A senior P&C insurance professional (broker, producer, underwriter, account manager, claims leader) moving into high-growth tech, or A proven enterprise SaaS seller eager to specialize in insurance and AI-driven workflows.


Required Skills & Experience
  • 10+ years of experience in either P&C insurance (broker, producer, underwriter, account manager, claims), or Enterprise B2B SaaS sales with $100K+ ACV deals
  • Consistent quota attainment (top 20% performer preferred)
  • Strong hunter mindset with comfort generating pipeline from scratch
  • Experience selling to VP/C-level buyers in complex sales cycles
  • Strong business and financial acumen; able to articulate ROI clearly
  • Executive presence, credibility, and excellent communication skills
  • Entrepreneurial mindset with comfort operating in ambiguity
Desired Skills & Experience
  • Deep understanding of insurance workflows and pain points
  • Early-stage startup experience (Seed–Series B)
  • Familiarity with AI / ML concepts and AI-powered sales tools
  • Existing relationships within the insurance ecosystem

The Offer
  • Equity eligible
You will receive the following benefits:
  • Medical, Dental, and Vision Insurance
  • Vacation Time
  • Stock Options


Applicants must be currently authorized to work in the US on a full-time basis now and in the future.

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