Senior Director of AI Sales

About the Role

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 where 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.

Responsibilities

• 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
  • 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.
• Represent the Function
  • 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.

Requirements

• 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.

Skills

• Technical & Leadership Skills
  • 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.

Additional Requirements

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

Benefits

• Novated leasing via salary packaging
• Employee Assistance Program (24/7 confidential support on relationships, bereavement, finances)
• Generous Parental Leave Program
• Paid Volunteer Leave Days
• Public Holiday Exchange Scheme
• Talent Referral Program – get rewarded for referring a friend to join our team
• Casual dress and relaxed office environment
• Fun team camaraderie and events
• Opportunities for career progression and development
• Diverse training & internal networking opportunities across all of our product lines
• Service recognition awards
• Responsible Time Off
• Comprehensive medical, dental, vision package with 100% employer-paid options
• Additional benefits including:
  • Health Savings Account
  • Flexible Spending Account
  • Critical Illness Insurance
  • Hospital Insurance
  • Accident Insurance
  • Life Insurance and AD&D
  • Disability Insurance (available to purchase)
• Wellness Challenge App, Diabetes Prevention App, and Health Hub App
• 401k/Retirement Plan with 6% employer match

Core Values

• We Are One Team
• We Are Customer Centric
• We Are Growth Minded
• We Are Accountable
• We Celebrate Success