Director, Commercial Sales

About Checkr
Checkr is building the data platform to power safe and fair decisions. Established in 2014, Checkr’s innovative technology and robust data platform help customers assess risk and ensure safety and compliance to build trusted workplaces and communities. Checkr has over 100,000 customers including DoorDash, Coinbase, Lyft, Instacart, and Airtable.

We’re a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.

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.

What You’ll Do

• 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.

Key Functional Competencies

• New Logo Prospecting & Demand Generation
• Objection Handling & Value-Based Selling
• Business & Industry Acumen
• Value Discovery & ROI Positioning
• Account Team & Executive Alignment
• Forecasting & Pipeline Management
• Operational Excellence
• Strategic Communication & Influence

What You Bring

• 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%.

Required Skills

• Strategic sales planning and execution in a growth-stage environment