Head of Sales

Regal • New York, NY

8d • Hybrid

About The Position

Regal is seeking a Head of Sales to lead and scale our sales organization as we continue building one of the most successful Voice AI Agent platforms in the market. This leader will own sales strategy and execution across all segments, manage and grow a high-performing team, and help define how Regal wins in an increasingly competitive AI-driven landscape. This role is ideal for a sales leader who thrives in high-growth environments and can close complex deals. You’ll be hands-on, selling, shaping positioning, and refining our go-to-market approach while building a repeatable, scalable sales motion across the full customer lifecycle. As Regal’s Head of Sales, you’ll drive enterprise account mapping and strategy across all Voice AI customers to unlock larger deals, and as the organization scales, you’ll build, mentor, and lead a nascent yet hungry team of Account Executives.

Requirements

• 8+ years of sales experience, with a minimum of 2+ years leadership experience managing a sales function & team
• Proven success closing complex, high-value SaaS deals and building repeatable sales motions
• Strong executive-level selling skills, with the ability to navigate multiple stakeholders and long sales cycles
• Comfortable working cross-functionally with Marketing, Product, Customer Success, and Sales Operations
• Highly data-driven, with experience using metrics and forecasting to guide decision-making
• Passion for technology—especially AI—and the ability to clearly articulate value and ROI to customers
• Prior experience helping scale a high-growth startup, with a builder mindset and comfort operating in ambiguity

Nice To Haves

• If you think you’re missing relevant experience but you’re hungry and a fast learner (and can prove it), we want to hear from you!

Responsibilities

• Own and lead the end-to-end sales strategy and execution across all customer segments
• Manage and optimize the full sales process, from pipeline generation through close
• Partner closely with Marketing, Product, Engineering, and Customer Success to align go-to-market strategy and deliver exceptional customer outcomes
• Drive consistent, accurate sales forecasting and pipeline visibility
• Identify opportunities to accelerate revenue growth through improved positioning, pricing, packaging, and sales process improvements
• Hire, develop, and performance-manage a high-caliber team of Account Executives
• Establish scalable sales playbooks, metrics, and operating rhythms as the team grows
• Act as a voice of the customer, bringing market insights back to product and leadership teams

Benefits

• We’re building an in-person culture of entrepreneurs who want to win and build something meaningful.
• Hybrid roles are required in office T/W/TH and office optional M/F.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed