Director, AI Sales

Job ContextReady 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 DoOwn Revenue Performance Carry and deliver the AI Sales team quota for cross-selling revenue across the Simpro Group portfolioDrive consistent attainment against monthly, quarterly, and annual revenue targetsMaintain forecast accuracy and ensure a healthy, well-managed pipeline with no surprisesBuild & Scale the Sales MotionDefine and implement the team's operating rhythm — daily cadence, pipeline management, call expectations, and inspection processesEstablish measurable KPIs and performance standards across the teamContinuously optimize processes to improve conversion, productivity, and revenue outcomesDevelop and document scalable sales playbooks: discovery structures, demo workflows, expansion strategies, objection handling frameworksLead, Hire & Develop TalentRecruit and develop high-performing AI Sales Executives capable of managing volume, delivering compelling demos, and closing at speedMake timely and decisive talent decisions to maintain a high-performance cultureCreate a scalable onboarding and ramp program that accelerates time-to-productivityConduct live call coaching, deal reviews, and pipeline inspections — improve team performance in discovery, demo execution, and closingDrive Cross-Functional ExecutionPartner closely with Account Management leadership to convert qualified opportunities into revenueCollaborate with Marketing on campaign plays and expansion initiativesWork with Enablement on onboarding and ongoing training programsProvide Product teams with customer insights and market feedback that influence roadmap prioritiesRepresent the FunctionServe as the voice of the AI Sales organization in Revenue Leadership discussionsBring data-driven insights, strategic recommendations, and solutions-oriented thinking to leadership conversationsWhat You'll Bring7+ years of B2B SaaS sales experience, including 3+ years in a sales management or leadership roleDemonstrated track record of building and scaling high-performance sales teamsDeep expertise in inside sales, cross-selling, and expansion revenue motionsExceptional coaching ability — you make every rep measurably better within their first 30 daysStrong command of Salesforce, sales analytics, and pipeline managementExperience in field service management, trades, or adjacent SaaS industries strongly preferredExecutive presence — you represent this function at the leadership table with data and convictionWhat We Can Offer YouResponsible Time OffComprehensive medical, dental, vision package with 100% employer paid optionsAdditional 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 App401k/Retirement Plan with 6% employer matchGenerous Parental Leave ProgramPaid Volunteer Leave DaysPublic Holiday Exchange SchemeTalent Referral Program – get rewarded for referring a friend to join our team!Diverse training & internal networking opportunities across all of our product linesOpportunities for career progression and developmentService recognition awardsOur Core ValuesWe Are One TeamWe Are Customer CentricWe Are Growth MindedWe Are AccountableWe Celebrate SuccessSimpro, 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.Please note, no agencies will be accepted in the recruitment of this role.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.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!Ready to transform your business? Explore our products at simprogroup.com, aroflo.com, bigchange.com and clockshark.com.