Best suited to mid-level product strategists with AI experience working in fast-paced B2B software environments.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Checkr via Greenhouse
About Checkr
Checkr is building the data platform to power safe and fair decisions. Over 140,000 companies and millions of people rely on Checkr for AI verification in the moments that matter most: getting a new job, a new place to live, a car ride, childcare, even a date. Customers include Uber, Pennymac, Airbnb, Doordash, Amazon, and Anthropic.
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.
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.
Pay Transparency Disclosure
We use geographic cost of labor as an input to develop ranges for our roles and as such, each location where we hire may have a different range. If this role is remote, we have listed the top to the bottom of the possible range, but we will specify the target range for an exact location when you are selected for a recruiting discussion. For more information on our compensation philosophy, see our website.
On-target Earnings OR Base Salary range (San Francisco, CA)$281,000—$330,000 USDWhat 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
At Checkr, we believe an in office work environment strengthens collaboration, drives innovation, and encourages connection. Our hub locations are Denver, CO; San Francisco, CA; Nashville, TN; and Santiago, Chile. Individuals are expected to work from the office 3+ days a week. In-office perks are provided, such as lunch five times a week, a commuter stipend, and an abundance of snacks and beverages. A relocation stipend may be available for those willing to relocate to a Checkr hub location.
Equal Employment Opportunities at Checkr
Checkr is committed to building the best product and company, which requires hiring talented and qualified individuals with a diverse set of perspectives and lived experiences. Checkr believes in hiring people of all backgrounds, including those whose histories are impacted by the justice system in accordance with local, state, and/or federal laws, including the San Francisco’s Fair Chance Ordinance.
Applicant Privacy Policy
If you are a California resident or are located in Alberta or British Columbia, our Applicant Privacy Policy applies to our collection and processing of your personal information when you apply for a role with us or otherwise participate in our recruitment process.
*Legitimate Checkr emails will always include our official domain name after the @ symbol (e.g., name@checkr.com or name@ext.checkr.com).
Source: Checkr careers (Greenhouse)