Job Context
The Director of AI sales owns the cross-sell engine across the Simpro Groupcustomer base. This leader builds, runs and scales a team of Solution Specialists who carry quota, run high-volume outbound and respond to inbound requests. They also partner with Account Managers to convert opportunities into closed revenue. This is a builder's seat. The Director sets the bar for intensity, deal execution and product fluency, and is personally accountable for the team's contribution to Group cross-sell revenue.
What You’ll Do
About the Role
Own Revenue Performance
- Carry and deliver the Solution Specialists team quota for cross-sell 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, including daily cadence, pipeline management, call and meeting expectations, and inspection processes.
- Establish measurable KPIs and performance standards across the team.
- Continuously optimize processes to improve conversion, productivity, and revenue outcomes.
Lead, Hire & Develop Talent
- Recruit, and develop high-performing Solution Specialists capable of managing volume, delivering compelling demos, and closing opportunities effectively.
- Make timely and decisive talent decisions to maintain a high-performance culture.
- Create a scalable onboarding and ramp program that accelerates time-to-productivity.
Coach to Close
- Conduct live call coaching, deal reviews, and pipeline inspections.
- Improve team performance in discovery, demo execution, objection handling, and closing strategies.
- Ensure every Specialist becomes measurably more effective within their first 30 days.
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.
Establish Product & Industry Expertise
- Ensure the team maintains deep knowledge across the full Simpro Group portfolio, including newly acquired products and solutions.
- Enable Specialists to clearly articulate integration value and cross-product business impact to customers.
Build & Scale Best Practices
- Develop and document scalable sales playbooks, including:
- Discovery and call structures
- Demo workflows
- Expansion strategies
- Integration narratives
- Objection handling frameworks
- Standardize and scale winning strategies across the organization.
Represent the Function
- Serve as the voice of the Solution Specialists organization within Revenue Leadership discussions.
- Bring data-driven insights, strategic recommendations, and solutions-oriented thinking to leadership conversations.
Qualifications
Required Experience
- Proven track record of leading teams that consistently exceed quota and deliver high-performance results.
- Experience leading high-velocity inbound, outbound, or expansion sales teams.
- Demonstrated success building sales motions, cadences, and operational frameworks from scratch.
- Strong experience hiring, ramping, and developing sales talent.
- Ability to lead through metrics, accountability, and operational discipline.
Technical & Leadership Skills
- Strong technical aptitude with the ability to independently run product demos and coach others effectively.
- Deep understanding of pipeline management, forecasting, activity metrics, and deal inspection processes.
- Experience partnering cross-functionally with Account Management, Marketing, Product, and Enablement teams.
- Excellent communication and leadership skills with a direct, decisive, and accountable management style.
Additional Requirements
- This is an in-office leadership role focused on building and scaling teams through in-person collaboration.
What We Can Offer You
- Novated leasing via salary packaging
- 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 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.
What You’ll Bring
What We Can Offer You
Responsible Time Off
Comprehensive medical, dental, vision package with 100% employer paid options
Additional 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 App
401k/Retirement Plan with 6% employer match
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!
Diverse training & internal networking opportunities across all of our product lines
Opportunities for career progression and development
Service recognition awards
Click here to find out more about working at Simpro Group!
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.
Skills Required
- Proven track record of leading teams that exceed quota
- Experience leading high-velocity sales teams
- Demonstrated success building sales motions and operational frameworks
- Strong experience hiring and developing sales talent
- Ability to lead through metrics and accountability
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.
-
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.
-
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.
-
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
Gallery
