Chief of Staff, Product

About the team/role

In this highly strategic role, you will partner with executives and senior leaders both across the business and within the Product org. As Chief of Staff reporting directly to the CPO, you will have an immediate impact on our CPO’s productivity from day one, streamlining strategic initiatives and aligning objectives across teams. You will act as our CPO’s right hand.

You will play a central role in transforming how we build products—accelerating product development processes and embracing AI to move faster and smarter. If you have a deep understanding of product functions and are exceptionally strong in business strategy, planning, program management, team alignment, and are an excellent communicator, please apply — we can’t wait to meet you.

What you’ll do

• Act as a proxy to the CPO in terms of driving organizational efficiency and productivity across the Product org
• Drive the transformation of product development processes to be faster and more efficient, with a strong emphasis on embracing AI
• Partner directly with executives across Checkr on major initiatives where Product is a key lever, including new product lines, M&A, and board prep.
• Bootstrap new initiatives, fill gaps on the leadership team, conduct customer and competitive research, and coach teammates 
• Assist in goal setting, aligning, executing, and reporting on expected outcomes within the Product org. Leverage data and analytics to provide insights and recommendations on product strategy and team performance.
• Understand the pulse and climate of the Product org and its employees
• Drive decisions on product strategy, resource allocation, and cross-functional tradeoffs. Author strategy docs as the byproduct of those decisions.

What you bring

• High EQ, grit, humility, curiosity, AI track record, entrepreneurial mindset, and product leadership.
• 7+ years of relevant experience in a fast-paced, high-growth environment, including product strategy, product operations, program management, business operations, or management consulting.
• Deep understanding of product functions with strong technical fluency.
• Phenomenal communication and relationship-building skills — knowing how to quickly build high-trust relationships and influence others through a variety of approaches.
• Strategic pattern-matching across ambiguous problems. Zooms out to see the system, zooms in when the work demands it.
• A tenacity for getting things done with strong project management skills and the ability to set and keep deadlines at a fast pace without losing accuracy.
• Experience in planning and leading complex, strategic, cross-functional initiatives.
• Proven ability to transform processes and drive operational improvements, with a particular interest in leveraging AI to accelerate product development.
• Experience in B2B software or platform businesses preferred.
• Product strategy background a plus.
• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes.

What you’ll get

• 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