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Director, Commercial Sales

United States, Denver Employment contract · Job Posted October 18, 2025
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Job Description

The Director of Commercial Sales will be responsible for driving sustained revenue growth and customer expansion within Checkr’s Commercial segment (500–5,000 employee size). This leader will oversee a team of high-performing Senior Managers & Commercial Account Executives who focus on both new customer acquisition and expansion within existing accounts. Reporting to the VP of Sales, this leader will play a critical role in scaling Checkr’s go-to-market strategy for the Commercial segment — accelerating growth through strong execution, data-driven decision making, and cross-functional collaboration. The Director will foster a culture of performance, accountability, and continuous improvement centered on customer value and partnership.

Job Responsibility

  • Develop and execute the strategy to accelerate Commercial revenue growth through new logo acquisition
  • lead and empower 3 Commercial Sales Managers and a growing organization of 26+ Commercial Account Executives to achieve quota goals, accelerate career development, and foster a culture of high performance and engagement
  • partner cross-functionally with Marketing, Product, and Revenue Operations to align pipeline generation, product positioning, and sales enablement
  • establish scalable sales processes, forecasting rigor, and performance metrics to ensure predictable, repeatable success
  • drive operational excellence and continuously improve systems, tools, and workflows to maximize sales productivity and efficiency
  • build trusted relationships with customers, helping them understand the value of Checkr’s platform and how it supports their business goals
  • collaborate with internal stakeholders to represent the voice of the customer and inform product roadmap decisions
  • partner with Enablement to deliver world-class onboarding, training, and ongoing development programs for the Commercial sales team
  • contribute to broader Sales leadership discussions on strategy, planning, and talent development across the Revenue organization
  • lead with empathy and accountability while modeling Checkr’s values of Grit, Ownership, Transparency, Humility, and Connection to build an inclusive, growth-oriented culture

Requirements

  • 7+ years of progressive sales leadership experience, including 3+ years in second-line leadership roles overseeing Commercial or Mid-Market teams and driving growth in a SaaS or consumption-based revenue model
  • experience building and sustaining a culture of outbound demand generation focused on proactive prospecting, strong pipeline creation, and cross-functional collaboration with Marketing
  • proven record of leading teams to exceed revenue targets and build repeatable, scalable sales processes
  • deep understanding of full-cycle sales — from lead generation through multi-stakeholder negotiations and expansion
  • strong business acumen with experience managing complex, multi-solution sales motions
  • excellent cross-functional collaboration skills with Marketing, Product, Customer Success, and Finance
  • demonstrated ability to lead through change, navigate ambiguity, and motivate teams in a fast-paced environment
  • passion for developing talent and fostering inclusive, high-performing teams
  • exceptional communication and executive presence, with the ability to influence at all levels
  • enthusiastic willingness to travel up to 25%
  • strategic sales planning and execution in a growth-stage environment
  • driving proactive outbound demand generation
  • skilled in forecasting, pipeline management, and data-driven decision making
  • proven ability to manage competing priorities and maintain focus under pressure
  • exceptional written and verbal communication
  • self-starter with strong ownership and results orientation

What we offer

  • A fast-paced and collaborative environment
  • learning and development allowance
  • competitive cash and equity compensation and opportunity for advancement
  • 100% medical, dental, and vision coverage
  • up to $25K reimbursement for fertility, adoption, and parental planning services
  • flexible PTO policy
  • monthly wellness stipend, home office stipend
  • in-office perks such as lunch four times a week, a commuter stipend, and an abundance of snacks and beverages

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