Senior Director of AI Sales

Job Context The Seniors Director of AI sales owns the cross-sell engine across the Simpro Group customer base. This leader builds, runs and scales a team of Solution Specialists who carry quota, run high-volume outbound and respond to inbound requests. They also partner with Account Managers to convert opportunities into closed revenue. This is a builder's seat. The Director sets the bar for intensity, deal execution and product fluency, and is personally accountable for the team's contribution to Group cross-sell revenue. What You’ll Do About the Role Own Revenue Performance Carry and deliver the Solution Specialists team quota for cross-sell revenue across the Simpro Group portfolio. Drive consistent attainment against monthly, quarterly, and annual revenue targets. Maintain forecast accuracy and ensure a healthy, well-managed pipeline with no surprises. Build & Scale the Sales Motion Define and implement the team’s operating rhythm, including daily cadence, pipeline management, call and meeting expectations, and inspection processes. Establish measurable KPIs and performance standards across the team. Continuously optimize processes to improve conversion, productivity, and revenue outcomes. Lead, Hire & Develop Talent Recruit, and develop high-performing Solution Specialists capable of managing volume, delivering compelling demos, and closing opportunities effectively. Make timely and decisive talent decisions to maintain a high-performance culture. Create a scalable onboarding and ramp program that accelerates time-to-productivity. Coach to Close Conduct live call coaching, deal reviews, and pipeline inspections. Improve team performance in discovery, demo execution, objection handling, and closing strategies. Ensure every Specialist becomes measurably more effective within their first 30 days. Drive Cross-Functional Execution Partner closely with Account Management leadership to convert qualified opportunities into revenue. Collaborate with Marketing on campaign plays and expansion initiatives. Work with Enablement on onboarding and ongoing training programs. Provide Product teams with customer insights and market feedback that influence roadmap priorities. Establish Product & Industry Expertise Ensure the team maintains deep knowledge across the full Simpro Group portfolio, including newly acquired products and solutions. Enable Specialists to clearly articulate integration value and cross-product business impact to customers. Build & Scale Best Practices Discovery and call structures Demo workflows Expansion strategies Integration narratives #J-18808-Ljbffr Socket.dev