Director, AI Sales

Simpro•Miami, FL

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
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