Director of Sales
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The posting
Who We Are
Cooper is an AI coworker for the insurance industry. Getting a business insured involves mountains of paperwork: filling out repetitive forms, re-typing the same information into one insurance company's website after another, and comparing offers by hand. Cooper does that busywork automatically, right inside the tools people already use, so brokers and their teams can focus on advising clients instead of pushing paper. We're a small team with deep insurance roots, teaching AI to do real, trusted work in a massive, overlooked industry.
Backed by Lightspeed, General Catalyst, and Valor, Cooper AI is building from the ground up to modernize a $1T+ global insurance industry.
About the Role
As Director of Sales, you will own and build Cooper AI's entire revenue engine. This is a rare opportunity to step in at the ground floor when product-market fit has emerged, early customers are seeing real results, and we're ready to scale. You'll partner directly with the founders to build the GTM playbook, close strategic deals, and hire the team that will take us from early traction to $XXM+ ARR. This is a builder role for someone who thrives in ambiguity, loves being close to the customer, and has the instincts to turn an early-stage product into a category-defining go-to-market motion.
What You'll Do
- Define and execute Cooper AI's revenue strategy, sales motion, forecasting, and GTM playbook
- Develop ICP definitions, segmentation, qualification frameworks, and pricing strategy
- Build and optimize repeatable processes for pipeline creation, deal management, and customer expansion
- Own and report on sales forecasting, dashboards, and metrics - bringing rigor and accountability to the revenue function
- Serve as executive sponsor for key customers and prospects, building relationships at the C-suite level
- Recruit, hire, and develop a world-class sales organization across AEs, SDRs, Sales Engineers, and CSMs as we scale
- Be a true cross-functional partner, working closely with Product and Engineering to translate customer feedback into roadmap influence, Marketing to align on messaging, pipeline generation, and campaigns, and Customer Success to drive smooth onboarding, retention, and expansion revenue.
What You'll Bring
- 8+ years of B2B SaaS sales experience, with at least 3 years in a leadership role
- Proven track record of building and scaling sales organizations from early traction to $XXM+ ARR
- Demonstrated ability to personally close complex, multi-stakeholder enterprise deals while simultaneously building process and team
- Deep experience developing GTM playbooks, sales processes, and revenue operations from scratch
- A data-driven, AI-first approach to forecasting and pipeline management, with strong analytical instincts
- Exceptional communication and executive presence - comfortable in the boardroom and on the whiteboard
- Low-ego, high-output - you're as comfortable rolling up your sleeves as you are delegating
Preferred Qualifications
- Experience selling into the insurance industry - carriers, MGAs, brokerages, or related financial services verticals
- Background in AI, workflow automation, or vertical SaaS for highly regulated industries
- Prior experience at a high-growth startup (Seed–Series C), ideally as a first or second sales leadership hire
- Experience working alongside technical founders and influencing product roadmap based on customer insights
Benefits
- Competitive salary & equity
- Medical, dental & vision insurance
- Monthly wellness stipend
- 401k with company match
- Unlimited PTO
- Company sponsored lunch 5x per week
- Off sites, happy hours, and team building events
Taken from Cooper's own posting, last seen live on 14 Nov 2026.
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The application
Your details, CV and LinkedIn, then 3 questions.
- 1.What are your preferred pronouns?Short answer · optional
- 2.Do you require any authorization to work in the US?Yes or no
- 3.Are you willing and able to work 4 days a week in our New York City office?Yes or no
From Cooper's apply page, checked 12 Nov 2026.
About Cooper
An AI coworker that turns insurance submissions into filled ACORD forms, carrier portal entries, compared quotes and proposals, sold to retail agencies, wholesale brokers, MGAs, insurers and claims TPAs.
Pay schedule: Commission and equity on every sales seat, with the pay stated as OTE for the commercial and mid-market AEs and the SDRs; benefits include medical, dental and vision insurance, a 401(k) with company match, unlimited or flexible PTO, a monthly wellness stipend for AEs and company-paid lunch five days a week.
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