Director Of AI Sales

What You’ll Do

The 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.

• 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.
• 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.
• Recruit, hire, 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.
• 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.
• Build and scale best practices: develop and document scalable sales playbooks, including discovery and call structures, demo workflows, expansion strategies, integration narratives, and objection handling frameworks.
• Standardize and scale winning strategies across the organization.
• Serve as the voice of the Solution Specialists organization within Revenue Leadership discussions.
• Bring data‑driven insights, strategic recommendations, and solutions‑oriented thinking to leadership conversations.
• Ensure the team maintains deep knowledge across the full Simpro Group portfolio, including newly acquired products and solutions.
• Enable Specialists to articulate integration value and cross‑product business impact to customers.

• Proven track record of leading teams that consistently exceed quota and deliver high‑performance results.
• Experience leading high‑velocity inbound, outbound, or expansion sales teams.
• Demonstrated success building sales motions, cadences, and operational frameworks from scratch.
• Strong experience hiring, ramping, and developing sales talent.
• Ability to lead through metrics, accountability, and operational discipline.
• Strong technical aptitude with the ability to independently run product demos and coach others effectively.
• Deep understanding of pipeline management, forecasting, activity metrics, and deal inspection processes.
• Experience partnering cross‑functionally with Account Management, Marketing, Product, and Enablement teams.
• Excellent communication and leadership skills with a direct, decisive, and accountable management style.

This is an in‑office leadership role focused on building and scaling teams through in‑person collaboration.