Simpro Software
From Simpro Software's careers page
Status: listed on the employer's own careers page when we last checked (daily). Confirm on their site before applying.
As Director of AI Sales, you will own the cross-selling engine across the Simpro customer base.
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.
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.
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
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
Our Core Values
We Are One Team
We Are Customer Centric
We Are Growth Minded
We Are Accountable
We Celebrate Success
Simpro, AroFlo, BigChange & ClockShark are equal opportunity employers with a best-of-class onboarding program and supportive team environments. This means that we want everyone to feel welcome with us and to provide equal opportunities for everyone, regardless of age, disability, gender reassignment, marriage and civil partnership, pregnancy and maternity, race, religion or belief, sex or sexual orientation, or any other non-performance factor.
If you'd like to join a fun and progressive organization, where there are opportunities to develop your career, please apply now with your CV/resume.
Please note, no agencies will be accepted in the recruitment of this role.
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