Job Summary

Our Client is hiring a Head of Enterprise Sales to lead and scale a high-performing team of Enterprise and Strategic Account Executives. This is a critical leadership role focused on winning complex, high-value customers while building the processes, coaching culture, and operational excellence needed to support the company's next phase of growth.

Reporting to the Chief Revenue Officer, you'll own enterprise new business performance, partner on strategic go-to-market initiatives, and help establish the company as the market leader within the enterprise segment.

About

Our Client is a fast-growing B2B SaaS company transforming how service-based businesses operate and grow. Their platform combines modern software with AI-powered capabilities to streamline operations, improve efficiency, and unlock new revenue opportunities for customers in complex, operationally intensive industries.

Following significant growth and recent funding, the company is expanding its enterprise go-to-market strategy and investing heavily in building a world-class sales organization. This is an opportunity to join at an exciting stage and help define how enterprise customers are acquired and scaled.

About the Role

This is a highly visible player-coach leadership position for someone who enjoys being close to the business.

The Head of Enterprise Sales will lead a team of Enterprise and Strategic Account Executives responsible for acquiring large, complex customers. You'll actively participate in executive-level sales cycles, coach sellers through sophisticated buying processes, and establish the operating cadence that enables predictable enterprise growth.

Success in this role requires equal parts leadership, execution, and strategic thinking. You'll partner closely with Marketing, Sales Development, Solutions Engineering, Customer Success, Product, and Revenue Operations to continuously improve enterprise pipeline generation, deal execution, and forecasting accuracy.

Responsibilities

• Own enterprise new business revenue across Enterprise 
• Lead, coach, and develop a high-performing team of Enterprise and Strategic Account Executives
• Act as a player-coach by participating in executive customer meetings and supporting complex sales opportunities
• Coach teams through multi-threaded, consultative enterprise sales cycles
• Drive strategic account planning and executive relationship development
• Lead deal strategy, pricing discussions, negotiations, and commercial execution on high-value opportunities
• Establish disciplined forecasting, pipeline inspection, and opportunity review processes
• Improve enterprise pipeline quality, conversion rates, and overall sales productivity
• Develop repeatable enterprise sales methodologies and best practices
• Partner with Marketing, SDRs, Customer Success, Product, and Revenue Operations to optimize the enterprise go-to-market motion
• Recruit, onboard, and develop top enterprise sales talent
• Use data and sales analytics to drive continuous improvement across the organization

Qualifications

• 8+ years of B2B SaaS sales experience with significant enterprise sales leadership experience
• Experience leading Enterprise and Strategic Account Executives in a high-growth SaaS environment
• Consistent track record of exceeding enterprise revenue targets
• Strong background selling complex software solutions into large organizations with multiple stakeholders
• Experience leading seven-figure or large six-figure ACV opportunities
• Demonstrated ability to coach executive-level selling, account strategy, and multi-threaded deal execution
• Strong forecasting discipline and operational rigor
• Experience building scalable enterprise sales processes during periods of rapid growth
• Excellent executive presence and communication skills
• Passion for coaching, developing talent, and building high-performing teams

Preferred Experience

• Enterprise SaaS with average contract values above $50K
• Experience selling into operational industries such as home services, construction, field services, manufacturing, logistics, or similar verticals
• Experience working alongside Product and Customer Success to support expansion opportunities
• Experience in AI-enabled or workflow automation software is a plus

Additional Information

• Reports to the Chief Revenue Officer
• Based in New York City
• Leads Enterprise and Strategic Account Executives
• High-impact leadership role with direct ownership of enterprise revenue growth
• Opportunity to help shape and scale the enterprise sales organization during a critical stage of company growth