Head of Sales

Company Overview

We've partnered with a leading technology company that is transforming the global insurance industry by combining AI automation with embedded fintech. This innovative organization is recognized for its outstanding finance automation platform, specifically designed for the insurance sector, and is driving significant digital transformation across the industry.

Role Overview

We are seeking a Head of Sales to lead the Sales team, focusing on acquiring new clients in SMB, Mid-Market, and Enterprise segments, and expanding current customer relationships. This pivotal role will enhance the Sales organization by managing a team of Account Executives (AEs), designing scalable systems, ensuring accurate forecasting, and personally handling key strategic accounts in a player-coach capacity.

Responsibilities

• Build and maintain a high-performance team culture with clear expectations, performance reviews, and quota accountability.
• Hire, onboard, and coach top-performing AEs, promoting sales discipline and consistent achievement of quotas.
• Develop and manage full-cycle sales playbooks tailored for different market segments (SMB/Mid-Market vs. Enterprise).
• Oversee forecasting and pipeline management, ensuring clean data hygiene and accurate commitments.
• Design the coverage model, including capacity planning, quotas, account assignments, and resource allocations.
• Personally drive and manage strategic accounts, exemplifying enterprise selling and engaging with CxOs.
• Document successful deal patterns and create scalable enablement assets (ROI tools, templates, FAQs).
• Collaborate with RevOps, Finance, and Customer Success on deal economics and expansion initiatives.
• Work with Marketing to refine message architecture and enhance competitive positioning.

Requirements

• 8+ years of experience in B2B technology sales.
• 2+ years of experience in leading sales teams.
• Proven track record in building and coaching high-performing, quota-carrying teams.
• Familiarity with Enterprise and SMB/Mid-Market sales processes.
• Strong skills in forecasting and pipeline management.
• Excellent communication skills and executive presence.
• Experience in insurance, financial services, or payments is a plus.
• High-growth startup experience is preferred.

Benefits

• Competitive base salary and meaningful equity in a fast-growing company.
• 100% health premiums for you and your dependents covered.
• 401k with employer matching options.
• Unlimited Paid Time Off (PTO).
• Monthly company-paid commuter benefit options.
• Parental and family leave.
• Lunch provided when in the office.
• Dog-friendly office environment!