Senior Director, Sales Specialist

About this role

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

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