Job Context
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 their 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.
What You’ll Do
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
What You’ll Bring
What You'll Bring
- 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
What We Can Offer You
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; and 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
to find out more about working at Simpro Group!
