Head of Sales

About the role

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.

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

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

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

Compensation Range

$350K - $450K