Whippy is leading the way in AI-powered business communication, transforming how companies engage with customers using intelligent AI Agents. From customer support to marketing to sales, businesses rely on Whippy’s Voice AI and Chat AI to eliminate manual workflows—responding to inquiries, nurturing leads, screening job applicants, and automating high-value interactions at scale. By combining AI-driven messaging with omni-channel automation, Whippy replaces outdated tools with a single, powerful platform that helps businesses work smarter, faster, and more efficiently.

🚀 About the Role

The Head of Sales will play a critical role in scaling and optimizing our sales function, overseeing a team of 6 reps (SDRs & AEs) while carrying a small quota. This position is ideal for a highly analytical, data-driven leader who thrives in a fast-paced startup and understands how to leverage metrics, automation, and process refinement to drive results.

You’ll be responsible for coaching reps, analyzing performance data, refining sales strategies, and ensuring the team consistently meets and exceeds revenue goals. In addition to leadership, you'll also contribute directly by closing key deals and shaping the long-term sales strategy.

⚡ What You'll Do

• Drive sales efficiency through data & analytics – Track key metrics (conversion rates, pipeline velocity, lead quality) to refine strategies and improve performance.
• Coach and develop a high-performing team – Lead 1-on-1 coaching sessions, pipeline reviews, and performance check-ins to ensure reps hit quota.
• Define and optimize sales processes – Improve lead qualification, call scripts, objection handling, and forecasting models using a data-driven approach.
• Implement structured sales training – Build a repeatable training framework to onboard new hires and enhance existing reps’ skills.
• Support AEs in closing deals – Participate in sales calls, negotiations, and strategic client meetings to drive revenue.
• Leverage automation & technology – Optimize the team’s use of HubSpot, Apollo, and analytics tools to maximize efficiency.
• Align with marketing & product teams – Work cross-functionally to improve lead generation, messaging, and overall go-to-market strategy.

🎯 What We're Looking For

• 4+ years of SaaS sales leadership – Experience managing SDRs & AEs in a high-growth B2B startup.
• Strong analytical mindset – Ability to track, interpret, and act on performance data to optimize sales processes.
• Proven track record of success – Demonstrated ability to scale teams, exceed quotas, and improve sales efficiency.
• Hands-on leadership style – Comfortable balancing team coaching, process refinement, and closing deals.