8+ years of B2B SaaS sales experience, including 3+ years in a leadership role
Proven success in building and scaling sales organizations to $XXM+ ARR
Ability to close complex enterprise deals while developing processes and teams
Experience creating GTM playbooks and revenue operations from the ground up
Data-driven approach to forecasting and pipeline management
Strong communication skills and executive presence
Low-ego, high-output mentality, comfortable with hands-on work and delegation
Responsibilities
Define and execute the revenue strategy and GTM playbook
Develop ideal customer profiles, segmentation, and pricing strategies
Build repeatable processes for pipeline creation and deal management
Own sales forecasting and metrics reporting for accountability
Serve as executive sponsor for key customer relationships
Recruit and develop a high-performing sales team
Collaborate cross-functionally with Product, Marketing, and Customer Success
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
Full Job Description
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
