Senior AI Sales Executive

Job Many businesses in our customers' world run on tight profit margins — around 5% on average. We've built the AI back-office solution to change that. We're not asking you to squeeze more money from customers — we're asking you to help them become more profitable than they've ever been. That's the job. That's the mission.

The Mission As a Senior AI Sales Executive, you are the highest-level individual contributor in our AI sales organization. You operate on the most complex, highest-value deals in our existing customer base — leading from the front, setting the standard for deal execution, and mentoring the next generation of AI Sales Executives.

You own the full AI sales motion: warm pipeline from Account Managers, self-generated outbound into strategic accounts, complex multi-stakeholder deals, and strategic expansion opportunities that require a seller who can operate at the executive level.

What You’ll Do

• Job Description Lead the Most Strategic Deals Own the most complex, highest-value AI expansion opportunities in the customer base
• Navigate multi-stakeholder buying processes — owner, CFO, operations lead — with confidence and credibility
• Run executive-level business case conversations that tie AI capabilities directly to margin improvement and operational ROI Carry and exceed a senior quota — you set the ceiling on what's possible for this team
• Set the Standard for AI Selling Be the product authority across the entire Simpro Group AI portfolio — go deeper than anyone else on integration, configuration, and business impact
• Model best-in-class demo execution, discovery discipline, and objection handling for the broader AI Sales team
• Partner with leadership to develop and refine the playbook — your instincts shape how the whole team sells Mentor AI Sales Executives — sharing deal strategy, coaching live conversations, and accelerating their development Generate & Convert at the Highest Level Self-source a robust pipeline through strategic outbound into high-value, non-managed accounts
• Converting at a higher rate on more complex deals — your experience means you close what others can't
• Bring the voice of the customer to product, marketing, and leadership — your frontline insight shapes strategy
• Stay ahead of the AI landscape, the competition, and customer trends so you can out-position anyone in the room
• This job description is not an exhaustive list of duties and may be modified at the discretion of Simpro Group.

What You’ll Bring

• 5+ years of B2B SaaS sales experience — quota attainment history that proves you belong at this level A successful track record of closing complex deals at volume and revenue impact that speaks for itself. Demonstrated ability to close complex, multi-stakeholder deals at speed and volume
• Executive presence — credible and compelling with business owners, CFOs, and operations leaders
• Deep technical fluency — you go beyond the demo script into integration logic, workflow configuration, and business architecture A history of mentoring and elevating the performance of peers and junior sellers
• Experience in field service, trades, or construction SaaS is strongly preferred
• Mastery of Salesforce or equivalent CRM; strong pipeline discipline Our Core Values While experience in the above areas will be highly considered, it’s important to note it will be secondary to the person with the right determination, attitude and compatibility. Our culture and core values are very important to us: 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. We embrace and support culture diversity and Equal Employment Opportunity. Aboriginals, Torres Strait Islanders and minority groups are encouraged to apply. . Visit simprogroup.com/au/company/careers to learn more about us and our values. We would like to take this opportunity to thank all candidates for their application. *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.