Chief of Staff, Product

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

• Competitive cash and equity compensation, and opportunity for advancement
• On-target Earnings OR Base Salary range (San Francisco, CA): $281,000—$330,000 USD