Head Of Sales (B2B SaaS - Insurance)

• We’re now looking for a Head of Sales to take full ownership of revenue execution, team performance, and scalable sales operations.

• Direct ownership of the sales function
• High-impact role with executive visibility
• Complex, meaningful product solving real industry problems
• Opportunity to build something scalable and lasting

This is a senior, hands-on leadership role with full accountability for revenue.

Depending on your background and strengths, this role can be:

• Player / Coach (closing strategic deals while leading the team), or
• Pure Sales Leader focused on team performance, process, and predictability

You will report directly to the CEO and own the entire sales function end-to-end.

Revenue & Execution

• Own pipeline creation, forecasting accuracy, and revenue delivery
• Set and hit quarterly and annual revenue targets
• Improve demo-to-close and win rates across segments (Retail, Mid-Market, Enterprise)
• Drive expansion and upsell within existing accounts

Team Leadership

• Hire, train, and manage SDRs and AEs
• Evaluate current team performance and level up execution
• Build a performance-driven culture with clear expectations and accountability
• Coach AEs on deal strategy, discovery, enterprise selling, and closing

Sales Strategy & Process

• Build and refine a repeatable outbound-led sales motion
• Strengthen inbound performance over time
• Improve CRM discipline, forecasting, and reporting
• Shorten sales cycles where possible while maintaining deal quality
• Align closely with Marketing, Product, and Customer Success

• Market: Insurance brokerages
• Deal sizes: Five to six figures in ARR
• Sales cycle: 3–12 months
• Motion: Primarily outbound, evolving to hybrid
• Segments: Retail, Mid-Market, Enterprise

• Predictable, well-qualified pipeline
• Consistent revenue delivery against targets
• Stronger AE performance and conversion rates
• Clear visibility into forecasts and deal health
• A sales team that runs with discipline, urgency, and confidence

Must-Haves (Non-Negotiable)

• Proven B2B SaaS sales leadership experience
• Experience scaling sales teams and processes
• Comfortable selling complex, high-value solutions
• Strong understanding of outbound sales and long sales cycles
• Data-driven, structured, and accountable leader

Ideal Background

• Experience selling into regulated or traditional industries (insurance, finance, etc.)
• Has built or rebuilt sales teams before
• Can balance strategy with execution
• Comfortable working directly with a CEO

• Base salary + performance-based bonus
• Structure may vary depending on whether the role is player/coach or purely leadership
• Long-term growth opportunity as the company scales