Head of Sales

We are entering our next phase of growth, and we’re hiring a Head of Sales to lead and scale our commercial engine. This role owns everything related to revenue: strategy, execution, people, and process. You will be responsible for turning ambition into predictable results.

Why Us

• Full mandate to design and run the sales organization
• High-visibility leadership position with direct access to the executive team
• A sophisticated product that addresses real, deeply rooted challenges in the insurance industry
• The chance to build a durable, scalable revenue operation from the ground up

The Opportunity

This is a senior leadership role with end-to-end responsibility for sales performance and revenue outcomes.

Depending on your experience and strengths, the role can be shaped as:

• Player–Coach: personally leading and closing strategic deals while developing the team, or
• Sales Leader: fully focused on team effectiveness, process maturity, and forecasting reliability

You will report directly to the CEO and act as the ultimate owner of the sales function across all segments.

Key Responsibilities

Revenue Ownership

• Take responsibility for pipeline generation, forecast accuracy, and revenue delivery
• Define and consistently achieve quarterly and annual growth targets
• Increase conversion rates from demo to close across Retail, Mid-Market, and Enterprise customers
• Identify and execute expansion, upsell, and cross-sell opportunities within existing accounts

Team Development & Leadership

• Recruit, onboard, and develop high-performing SDRs and Account Executives
• Assess current team capabilities and raise execution standards across the board
• Establish a results-driven culture built on clarity, accountability, and continuous improvement
• Provide hands-on coaching on discovery, deal strategy, enterprise sales motions, and closing

Sales Strategy & Operations

• Design and evolve a repeatable, outbound-focused sales motion
• Gradually strengthen inbound contribution as the engine matures
• Enforce strong CRM usage, pipeline hygiene, and reporting discipline
• Optimize sales cycle length without compromising deal quality or customer fit
• Partner closely with Marketing, Product, and Customer Success to ensure alignment

Sales Context

• Industry: Insurance brokerages
• Deal size: Mid to high five-figure, extending into six-figure ARR
• Sales cycle: Typically 3 to 12 months
• Go-to-market motion: Predominantly outbound, moving toward a hybrid model
• Customer segments: Retail, Mid-Market, Enterprise

What Success Looks Like (6–12 Months)

• A healthy, well-qualified, and predictable pipeline
• Reliable revenue performance against defined targets
• Noticeable improvement in AE productivity and close rates
• Clear, trustworthy forecasting and visibility into deal status
• A sales organization operating with focus, urgency, and confidence

Ideal Candidate Profile

Required Experience

• Demonstrated success leading sales in a B2B SaaS environment
• Hands-on experience scaling sales teams and formalizing processes
• Track record of selling complex, high-value solutions
• Deep familiarity with outbound-led sales and extended buying cycles
• Strong analytical mindset with a structured, metrics-driven approach

Strong Plus If You Have

• Experience selling into regulated or traditional industries such as insurance or financial services
• Previously built or turned around sales organizations
• Ability to move seamlessly between strategic thinking and execution
• Comfort operating as a close partner to a CEO and executive team

Compensation & Growth

• Competitive base salary with performance-based incentives
• Final structure depends on whether the role includes direct deal ownership
• Significant long-term growth opportunity as we scale

If you’re a Head of Sales with a proven ability to build, lead, and scale revenue organizations, we’d love to hear from you. Apply now.

Only candidates selected for further consideration will be contacted.