Director, AI Sales
About The Position
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.
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
- Executive presence — you represent this function at the leadership table with data and conviction
Nice To Haves
- Experience in field service management, trades, or adjacent SaaS industries strongly preferred
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.
Benefits
- Responsible Time Off
- Comprehensive medical, dental, vision package with 100% employer paid options
- 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
- Diverse training & internal networking opportunities across all of our product lines
- Opportunities for career progression and development
- Service recognition awards
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
