Director of Sales

About the job

Our client is a B2B SaaS company. We are looking for a Director of Sales to build and lead our growing enterprise sales organization. You’ll lead a team of high-performing Enterprise Account Executives selling to insurers, MGAs, carriers, self-insureds, captives and claims organizations. You’ll be responsible for recruiting and developing the team, establishing a scalable sales motion, and creating the operating rhythm that turns individual seller success into predictable growth. This is a build-from-scratch opportunity: there's limited existing sales engine to inherit. You'll be excited to create the playbooks, structure, and culture that turn early wins into a repeatable growth engine. This is a hands-on leadership role for someone who knows how to coach enterprise sellers, navigate complex sales cycles, and build from scratch. You’ll work closely with our founders and senior leadership to shape our sales strategy, hiring plan, and approach to winning some of the most important customers in the insurance industry.

What You’ll Do

• Build and Lead the Sales Team: Recruit, onboard, coach, and retain a high-performing team of Enterprise Account Executives as we scale.
• Coach to Enterprise Excellence: Develop sellers through deal strategy, pipeline management, executive engagement, negotiation, and account planning.
• Join critical customer conversations and help reps navigate complex, multi-stakeholder deals.
• Own the Team’s Sales Performance: Establish clear expectations, inspect pipeline and forecast regularly, and create the operating cadence needed to consistently deliver against team ACV targets.
• Build the Sales Playbook: Turn what’s working into repeatable processes, from qualification and discovery through deal strategy, forecasting, negotiation, and close.
• Partner on Strategic Deals: Work alongside sellers on the most complex and consequential opportunities, helping shape strategy without owning an individual book of business.
• Build the Team for Scale: Partner with Talent and leadership to define the hiring profile, interview candidates, and build a sales organization that can scale with our growth.
• Partner Cross-Functionally: Bring customer and market insights to Product, Marketing, Claims, and Operations to improve our positioning, product, and overall go-to-market motion.
• Drive Executive-Level Customer Engagement: Build relationships with senior leaders across insurers, MGAs, carriers and claims organizations and help the team establish credibility with enterprise buyers.

What You'll Bring

• 3+ years of sales leadership experience with a track record of leading and developing enterprise sellers.
• 7-10+ years of enterprise sales experience, with experience personally navigating and closing complex, multi-stakeholder, multi-million-dollar deals.
• A strong track record of coaching enterprise sellers and improving team performance—not just individual sales performance.
• Experience building or refining sales processes, forecasting, pipeline management, and operating cadences in a growing organization.
• A builder’s mindset: you’re excited to create the systems, playbooks, and team around you rather than inherit a fully built sales organization.
• Strong executive presence and the ability to build trust with both internal stakeholders and senior enterprise customers.
• A high degree of ownership, curiosity, and comfort operating in a fast-moving, early-stage environment.

Nice to Have

• Experience selling B2B SaaS into insurance or financial services is a strong plus; deep industry expertise in insurance is not required.

Benefits

• Benefits Competitive Salary Equity - giving you direct stake in the future of an AI-native industry leader.
• Top-tier medical, dental, and vision insurance.
• 401k with company match.
• Flexible PTO and a work from home stipend.
• A fast-paced, high-talent density team that values transparency and shipping fast.

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