Director, AI Sales

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 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. Welcome to Simpro! Together with AroFlo, BigChange and ClockShark we are one team made up of many nationalities. We are customer-centric, always putting our customers and teammates first. We take accountability, owning both our innovations and our mistakes. We're growth-minded, constantly learning and evolving. And most of all, we celebrate our successes together! Simpro Group provides best-in-class SaaS field service management solutions to trade and field service businesses worldwide. The group comprises four industry-leading companies, Simpro, AroFlo, BigChange and ClockShark, with offices across North America, Australia, New Zealand and the UK. Simpro, AroFlo & BigChange provide comprehensive field service management software for growth-minded trade and field service businesses, while ClockShark specializes in time-tracking and scheduling software solutions. Together, these companies seek to drive businesses forward with solutions that empower teams to work smarter, provide foundations for business scaling, and offer data-driven insights to fuel decision-making. Simpro Group serves over 22,000 businesses and over 400,000 users worldwide and has a global workforce of more than 600 employees. Ready to transform your business? Explore our products at simprogroup.com, aroflo.com, bigchange.com and clockshark.com. Simpro Group has been made aware of fraudulent recruitment activity where individuals are impersonating our company and hiring managers to deceive job applicants. These scammers are using a fraudulent website and email domain (simprogroupcareers.com) and may contact you with illegitimate job offers. Their goal is typically to steal your personal information for identity theft or to trick you into paying for fake application fees, background checks, or equipment. If you have been contacted by someone you suspect is not a legitimate Simpro Group recruiter, or if you have any doubts about a job posting, please do not respond. Do not provide any personal information or payment. We take this matter very seriously and have reported this fraudulent activity to the relevant global authorities. We are committed to ensuring a safe and transparent recruitment process for all candidates.