Director of Sales

Cooper AI•San Francisco, CA

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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.