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.

• 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, 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.

• 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.

• 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.

• Develop and document scalable sales playbooks, including:
  • Discovery and call structures
  • Demo workflows
  • Expansion strategies
  • Integration narratives
  • 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.

• 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.

• Novated leasing via salary packaging
• Employee Assistance Program (24/7 confidential support on relationships, bereavement, finances)
• Generous Parental Leave Program
• Paid Volunteer…