Director, AI Sales

Director, AI Sales page is loaded## Director, AI Sales Apply locations:
Miami Office time type:
Full time posted on:
Posted Yesterday job requisition :
JR102117
** 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…