Job Context
Ready 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 Do
Own Revenue Performance
- Carry and deliver the AI Sales team quota for cross-selling 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 — daily cadence, pipeline management, call expectations, and inspection processes
- Establish measurable KPIs and performance standards across the team
- Continuously optimize processes to improve conversion, productivity, and revenue outcomes
- Develop and document scalable sales playbooks: discovery structures, demo workflows, expansion strategies, objection handling frameworks
Lead, Hire & Develop Talent
- Recruit and develop high-performing AI Sales Executives capable of managing volume, delivering compelling demos, and closing at speed
- Make timely and decisive talent decisions to maintain a high-performance culture
- Create a scalable onboarding and ramp program that accelerates time-to-productivity
- Conduct live call coaching, deal reviews, and pipeline inspections — improve team performance in discovery, demo execution, and closing
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
Represent the Function
- Serve as the voice of the AI Sales organization in Revenue Leadership discussions
- Bring data-driven insights, strategic recommendations, and solutions-oriented thinking to leadership conversations
What You’ll Bring
What You'll Bring
- 7+ years of B2B SaaS sales experience, including 3+ years in a sales management or leadership role
- Demonstrated track record of building and scaling high-performance sales teams
- Deep expertise in inside sales, cross-selling, and expansion revenue motions
- Exceptional coaching ability — you make every rep measurably better within their first 30 days
- Strong command of Salesforce, sales analytics, and pipeline management
- Experience in field service management, trades, or adjacent SaaS industries strongly preferred
- Executive presence — you represent this function at the leadership table with data and conviction
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
- 7+ years of B2B SaaS sales experience, including 3+ years in sales management or leadership
- Demonstrated track record of building and scaling high-performance sales teams
- Deep expertise in inside sales, cross-selling, and expansion revenue motions
- Proven ability to carry quota and drive consistent attainment against revenue targets
- Exceptional coaching ability with measurable rep improvement quickly
- Strong command of Salesforce, sales analytics, and pipeline management
- Executive presence and experience representing sales at leadership level
- Experience in field service management, trades, or adjacent SaaS industries
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
