Director, AI Sales

Director, AI Sales
Build the Engine. Own the Number.

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 global 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, high-velocity sales, selling into a current customer base. 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 growing AI revenue across the existing customer base. You hire exceptional sellers, coach them to close, and build the systems that make winning repeatable.

What You'll Own
Own Revenue Performance
Carry and deliver the AI Sales team's quota for AI products cross-sold across the company's 23,000+ customer base.
Drive consistent attainment against weekly, monthly, quarterly, and annual revenue targets.

Build & Scale the Sales Motion
Define and implement the team's operating rhythm — daily cadence, pipeline management, call expectations, and inspection processes.
Manage and build upon established and 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.
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
7+ years of B2B SaaS sales experience, including 3+ years in a sales management or leadership role.
Hands-on approach; a coach player.
Ability to lead by example and the ability to sell.
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 CRM technology, sales analytics, and pipeline management.
Executive presence — you represent this function at the leadership table with data and conviction.

What We Can Offer You
Generous cash compensation plan and an uncapped ability to make substantial income.
Generous stock option plan to provide an opportunity for life changing money.
Comprehensive medical, dental, and vision insurance with 100% employer-paid options.
Health Savings Account (HSA), Flexible Spending Account (FSA), Critical Illness, Hospital & Accident Insurance.
Life Insurance, AD&D, and Disability Insurance.
401(k) / Retirement Plan with 6% employer match.
Talent Referral Program — get rewarded for referring great people.