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.