Job Context
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
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
High-Velocity SaaS Closing: Proven track record as an Account Executive closing short-cycle, high-velocity SaaS deals ($5k–$10k ACV), typically navigating a 1-to-2 call close within a ~2-week sales cycle.
Account Expansion & Upsell Discipline: Strong experience positioning add-on tools into an established, warm customer base—specifically taking Delight (Simpro Group’s AI-powered marketing tool) directly to existing Simpro core accounts to drive incremental account value.
Full-Funnel Ownership & Outbound Discipline: Phone-first mentality with structured cadences to aggressively target, qualify, and build pipeline across our warm account portfolio.
End-to-End Deal Execution: Confident leading tailored product demos, driving commercial negotiations, and closing deals autonomously.
Value-Based Qualification & Urgency: Sharp qualification discipline to prioritize high-converting opportunities alongside a true closer's instinct—building urgency around buyer ROI rather than relying on discounts.
SMB Communication: Ability to translate AI and marketing tech concepts into simple, highly compelling business outcomes for busy, non-technical SMB owners.
Proven Performance: Consistent quota attainment with clear, quantifiable metrics you can speak to with confidence.
Nice to Have
Vertical SaaS / Field Service Experience: Prior experience selling within Vertical SaaS, trade/field service technology, or SMB marketing automation platforms.
What We Can Offer You
Employee Assistance Program (24/7 confidential support on relationships, bereavement, finances)
Generous Parental Leave Program
Paid Volunteer Leave Days
Public Holiday Exchange Scheme
Talent Referral Program – get rewarded for referring a friend to join our team!
Casual dress and relaxed office environment
Fun team camaraderie and events
Opportunities for career progression and development
Diverse training & internal networking opportunities across all of our product lines
Service recognition awards
Click here to find out more about working at Simpro Group!
Our Core Values
While experience in the above areas will be highly considered, it’s important to note they 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. Minority groups are encouraged to apply.
Visit simprogroup.com/au/company/careers to learn more about us and our values.
If you'd like to join a fun and progressive organisation, where there are opportunities to develop your career, please apply now with your CV/Resume.
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.
Skills Required
- Proven experience in a technical sales-support or sales engineering role
- Experience in Field Service Management or adjacent vertical software markets
- Strong understanding of SaaS products
- Excellent communication skills
- Proven ability to work cross-functionally
Simpro Software Group Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Simpro Software Group and has not been reviewed or approved by Simpro Software Group.
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Wellbeing & Lifestyle Benefits — Feedback suggests a four-day work week is a standout perk that supports work-life balance and can offset slightly lower market pay for some roles.
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Parental & Family Support — Feedback suggests parental leave is notably generous, including extended paid leave for primary and secondary caregivers along with return-to-work support.
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Inclusive Benefits Coverage — Feedback suggests benefits include unusually broad medical-travel support, including a dedicated travel-expense grant for medical procedures, which strengthens perceived inclusivity.
Simpro Software Group Insights
What We Do
Simpro is the total business management software for commercial trade service businesses. From job quoting and scheduling to inventory tracking, invoicing and everything in between, Simpro's smart technology solutions and expert long-term support help businesses build, repair and power their future with complete control over operations. Led by CEO Gary Specter and headquartered in Brisbane, Australia, Simpro supports more than 8,000 businesses and 200,000 users worldwide in the electrical, plumbing, HVAC, security and fire protection industries with 400+ employees in six global offices. In November 2021, Simpro acquired Clockshark, a US-based timesheeting and scheduling platform and AroFlo, an Australian-based job management software provider. Our company is seeing tremendous growth globally and especially in the US. As our team grows, so do our opportunities! Join us! We'd love to have you along for the ride!
Why Work With Us
We are ONE Team. No heroes. No egos. Just a diverse community of passionate people rolling up their sleeves and working hard to deliver exceptional technology, service and outcomes to each and every customer every day. Our values guide us: We are One Team We Innovate We Own It We Care We Have Fun We Understand
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