We are partnering with a high-growth, venture-backed company that is transforming how modern businesses manage risk and insurance through a technology-enabled, advisory-driven model.

Operating at the intersection of software, data, and professional services, the company replaces the traditional insurance brokerage with a modern, AI-enabled risk platform designed for high-growth companies operating in complex environments.

The company works with hundreds of category-defining organizations across consumer brands, hospitality, manufacturing, and emerging technology sectors. Leadership includes experienced founders and operators from top technology companies, and the business is backed by several well-known venture investors.

The company has achieved exceptional early growth and is entering its next stage of scale — making this a pivotal leadership hire within the go-to-market organization.

Sector: B2B Services / Technology-Enabled Professional Services

Stage: Series-A, VC-backed

Size: ~50 Employees

Role Focus: New logo acquisition, enterprise expansion, multi-stakeholder sales motions

The Role

This Head of Sales role will lead the next phase of growth for the company's revenue organization while continuing to personally participate in large, strategic sales opportunities.

This is a true player-coach leadership role. The individual will be responsible for both closing high-value enterprise opportunities and building the systems, culture, and talent required to scale the broader sales team.

The company sells into complex, trust-driven environments where executive stakeholders — including CFOs, CEOs, and senior operational leaders — are responsible for high-stakes financial and operational risk decisions. As a result, the sales motion is consultative, relationship-driven, and involves multi-stakeholder enterprise buying cycles.

This role will work closely with the founders and executive leadership team to refine go-to-market strategy, scale the sales organization, and build repeatable processes for continued growth.

This role is ideal for someone who wants:

• The opportunity to build a generational sales organization in a massive market
• Meaningful ownership over revenue outcomes
• A seat at the table shaping company strategy
• A balance of strategic leadership and hands-on selling

What We’re Looking For:

• 6–10+ years of experience in B2B enterprise sales
• Proven track record closing complex, high-value deals with mid-market or enterprise clients
• Experience leading teams while continuing to carry an individual quota (player-coach model)
• Strong executive presence and credibility with CFO- and CEO-level buyers
• Systems-oriented operator who can build repeatable sales processes
• Comfortable operating in high-growth, fast-moving environments

Experience in regulated or trust-driven industries such as insurance, fintech, compliance, cybersecurity, or professional services is a plus.

Why This Role Is Unique:

• Opportunity to build a revenue organization in a massive global market
• Exposure to highly sophisticated enterprise buyers
• Technology-enabled platform transforming a legacy industry
• Early leadership role with significant influence on company strategy

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