Director, AI Sales

About the Role

Ready to lead a high-growth sales motion and earn at the highest level? As Director of AI Sales, you will own the cross-selling engine across the Simpro customer base. This is a high-impact, fast-paced opportunity for an ambitious, high-energy sales leader looking to maximize earning potential while building and scaling an elite sales team. You will lead quota-carrying AI Sales Executives running high-volume outbound strategies to turn warm pipeline into closed revenue. If you thrive in a true builder's seat and want your compensation to reflect your impact, this is your role.

The mission: You'll set the bar for intensity, deal execution, and product fluency across the team. You are personally accountable for the team's contribution to Group cross-selling revenue. You hire exceptional sellers, coach them to close, and build the systems that make winning repeatable.

Responsibilities

• Own Revenue Performance
  • Carry and deliver the AI Sales team quota for cross-selling 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 — daily cadence, pipeline management, call expectations, and inspection processes
  • Establish measurable KPIs and performance standards across the team
  • Continuously optimize processes to improve conversion, productivity, and revenue outcomes
  • Develop and document scalable sales playbooks: discovery structures, demo workflows, expansion strategies, objection handling frameworks
• Lead, Hire & Develop Talent
  • Recruit and develop high-performing AI Sales Executives capable of managing volume, delivering compelling demos, and closing at speed
  • 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, and closing
• 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
• Represent the Function
  • Serve as the voice of the AI Sales organization in Revenue Leadership discussions
  • Bring data-driven insights, strategic recommendations, and solutions-oriented thinking to leadership conversations

Requirements

• 7+ years of B2B SaaS sales experience, including 3+ years in a sales management or leadership role
• Demonstrated track record of building and scaling high-performance sales teams
• Deep expertise in inside sales, cross-selling, and expansion revenue motions
• Exceptional coaching ability — you make every rep measurably better within their first 30 days
• Strong command of Salesforce, sales analytics, and pipeline management
• Experience in field service management, trades, or adjacent SaaS industries strongly preferred
• Executive presence — you represent this function at the leadership table with data and conviction

Benefits

• 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
• 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
• Diverse training & internal networking opportunities across all of our product lines
• Opportunities for career progression and development
• Service recognition awards

Core Values

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