Job Context
Ready to lead a high-growth sales motion and earn at the highest level? As Senior Director, Sales Specialists, you will own the overarching product expertise and cross-selling engine across Simpro Group’s global customer base. This is a high-impact opportunity for an ambitious, high-energy sales leader looking to maximize their earning potential while building, scaling, and unifying an elite global Sales Specialist organization. You will directly lead, mentor, and empower frontline Sales Specialists running high-volume, high-velocity sales motions, as well as the sales specialist leaders who manage them. If you thrive in a true builder's seat and want your compensation to reflect your strategic impact, this is your role.The Mission
You'll set the bar for intensity, deal execution, and product fluency across the entire organization. You are personally accountable for the specialist organization's total revenue contribution in driving cross-sell, expansion, and product adoption into our 23,000+ customer base. You hire and elevate exceptional talent, coach leaders to build winning cultures, and architect the global systems that make high-volume product expansion repeatable.
What You’ll Do
Own Global Revenue Performance
Carry and deliver the global specialist revenue quota, driving cross-sell, expansion, and multi-product adoption across 23,000+ customers.
Drive consistent attainment against weekly, monthly, quarterly, and annual revenue targets across all specialist sub-teams.
Maintain rigorous pipeline visibility, taking full ownership of revenue forecasts, conversion analytics, and executive board reporting.
Build & Scale the Sales Motion
Define and implement the organization's operating rhythm—daily cadence, pipeline management, call inspection standards, and multi-tier operational processes.
Establish and build upon measurable KPIs and performance benchmarks across both individual specialists and leaders.
Continuously optimize sales workflows to improve conversion rates, rep productivity, and overall revenue outcomes globally.
Develop and document scalable sales playbooks: discovery structures, demo workflows, expansion strategies, and objection-handling frameworks.
Lead, Hire & Develop Talent
Lead a dual-layer team structure: directly manage and mentor Sales Specialists while hiring, coaching, and developing Sales Specialist Leaders.
Recruit and retain top-tier talent, building a high-intensity, revenue-driven culture across all tiers.
Make timely and decisive talent decisions to maintain a best-in-class performance standard across the organization.
Create scalable onboarding and ramp programs that accelerate time-to-productivity for new reps and new leaders alike.
Conduct executive deal inspections, 1-on-1 leader coaching, and live call reviews—improving overall team performance in discovery, demo execution, and closing speed.
Drive Cross-Functional Execution
Partner closely with Account Management and Sales leadership to maximize qualified opportunity conversion and seamless deal execution.
Collaborate with Marketing on targeted campaign plays, expansion initiatives, and product adoption pushes.
Provide Product and Engineering leadership with frontline customer insights and structured market feedback to shape future roadmap priorities.
Represent the Function
Serve as the primary voice of the Sales Specialist organization in revenue leadership discussions.
Bring data-driven insights, strategic recommendations, and solutions-oriented thinking to leadership conversations.
This job description is not an exhaustive list of duties and may be modified at the discretion of Simpro Group
What You’ll Bring
12+ years of B2B SaaS business development or sales experience, with 5+ years operating in a progressive management role, including experience managing leaders.
Proven track record of managing, coaching, and scaling teams running high-velocity inside sales, cross-selling, and expansion motions.
Hands-on, coach-player mindset—the ability to operate at a high strategic level while remaining close enough to the field to step in on strategic deals and coach live calls.
Demonstrated success in building high-performance sales organizations that consistently exceed multi-million-dollar revenue targets.
Exceptional leadership development skills—a proven ability to make both reps and frontline managers measurably better within their first 30 days.
Strong command of CRM technology, sales analytics, and pipeline management discipline (Salesforce or equivalent).
Executive presence—you represent this function at the leadership table with data, conviction, and strategic vision.
Background in field service, trades, or construction SaaS is strongly preferred.
Bachelor’s degree in Business, Commerce, Marketing, or a related field (or equivalent practical experience).
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 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
- Strong technical aptitude to independently run product demos and coach others
- Deep understanding of pipeline management, forecasting, activity metrics, and deal inspection processes
- Experience partnering cross-functionally with Account Management, Marketing, Product, and Enablement
- Excellent communication and decisive leadership style
- Must work in-office to build and scale teams through in-person collaboration
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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