Head of Sales

PenguinData is seeking a Head of Sales to lead the sales function and drive growth in the workforce management software market. The role involves transforming the sales function into a scalable, process-driven organization and building a repeatable revenue engine.

Requirements

• 5+ years of sales leadership experience in vertical SaaS, workforce management, field service, or similar B2B software environments
• Proven track record of scaling ARR from approximately $5M to $20M+
• Experience selling complex B2B software to operational and business buyers
• Strong understanding of pricing strategy, renewals, and expansion revenue models
• Experience using modern, AI-enabled sales and marketing tools to drive pipeline management, forecasting, and performance insights
• Comfort operating in founder-led and post-acquisition environments
• Hands-on mindset with the ability to lead demos, close deals, and build processes concurrently