Why This Job is Featured on The SaaS Jobs
This Chief of Staff role sits at the center of a mature SaaS operator’s agenda, acting as an extension of the CEO across company-level priorities. The remit touches AI transformation, new product line exploration, and M&A support, which are common strategic levers for SaaS businesses refining their platform and expanding adjacent revenue streams. It is notable for its breadth across product, operations, and corporate strategy rather than being confined to a single function.
For a SaaS career, the value is in learning how leadership teams translate strategy into execution across multiple horizons. The work implies heavy exposure to cross-functional alignment, prioritization frameworks, and decision support through analysis, narratives, and financial modeling. Experience pressure-testing ideas with market and customer research also builds durable SaaS intuition around positioning and portfolio choices, skills that transfer into general management, product leadership, or operational strategy roles.
This role suits someone comfortable operating in ambiguity, producing crisp written artifacts, and moving between high-level context and hands-on delivery. It will fit professionals who enjoy orchestrating stakeholders, standing up initiatives from zero to one, and acting as a trusted proxy in executive settings. A track record with AI-enabled impact and executive-level collaboration will be especially relevant.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
Reporting to and as a strategic extension of the CEO, the Chief of Staff will be a force multiplier for Checkr’s leadership team. You will lead a range of initiatives, from accelerating company-level AI transformations, to shaping new product lines, and supporting M&A. As the right hand to the CEO, you will collaborate with Checkr’s executive team to drive strategic alignment, set priorities, and boost productivity across the business.
What you bring
Strategic thinking
- Strategic pattern-matching across ambiguous, evolving problems, often in low-information environments. Zooms out to see the system at the meta level, zooms in as needed to execute
- Strong data analysis and problem-solving skills
- Exceptional written communication. Can turn ambiguity into a clear one-pager
Leadership and execution
- Proven experience leading cross-functional teams and bootstrapping initiatives from zero to one
- Track record of planning and executing strategic initiatives with operational excellence
- Track record of using AI to deliver impact
- Earns trust quickly with executives, board members, and external stakeholders
- 10+ years of experience working at an executive level or equivalent track record
Bonus
- Entrepreneurial and product leadership background
- Consulting experience
Responsibilities
Lead strategic initiatives
- Lead the CEO's highest-priority initiatives, end to end, from planning through execution
- Stand up new functions, products, or business lines from zero to one
- Pressure-test strategy with customer, competitive, and market research
Extend the CEO
- Serve as a proxy for the CEO in internal and external meetings
- Collaborate tightly with other executive direct reports with a one team mentality
- Lead functions or initiatives during transitions or while key roles are being hired
- Take the pulse of the company and surface what the CEO needs to hear
- Collaborate with and coach other Checkr leaders
Drive operational excellence
- Optimize current processes and drive efficiency
- Improve communication and coordination across strategic initiatives
- Effectively communicate complex topics to junior and executive audiences alike
- Build presentations and financial models that frame critical decisions, including investor pitch decks and company narratives for external communications.
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
