Head of Sales

Who We Are Cooper AI is building AI for commercial insurance, taking the manual, time‑consuming work off professionals' plates so they can focus on what actually matters: serving clients and growing their business. Cooper works directly inside the tools teams already use, turning these workflows into fast, automated experiences that save hours every week and unlock meaningful efficiency gains. 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 Head 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 We set our salary ranges using compensation data from companies similar to our stage and size. For this role, the estimated OTE range for this position is $350,000 - $450,000 + accelerators. The actual base salary will vary depending on multiple factors unique to each candidate, including location, job-related knowledge, transferable skills, and our assessment of your level during the interview process. Cooper offers equity for all full‑time employees, which is not included in the range listed above and will have an impact on your overall compensation. Cooper offers a wide range of best‑in‑class, comprehensive benefits including 100% employer paid healthcare plans, an up to 4% 401k match program, paid time off, parental leave, wellness reimbursement, work‑from‑home stipend and more. Cooper is committed to building a diverse and inclusive workforce. If you’re interested in this role, but do not meet 100% of the qualifications listed above, we encourage you to apply. We'd like to consider you for this position and roles that may be a fit in the future. Cooper is an Equal Opportunity Employer and considers applicants for employment without regard to race, color, religion, sex, orientation, national origin, age, disability, genetics or any other basis forbidden under federal, state, or local law. Cooper considers all qualified applicants in accordance with the San Francisco Fair Chance Ordinance. #J-18808-Ljbffr