Why This Job is Featured on The SaaS Jobs
This Chief of Staff role sits at a classic SaaS leverage point: the office of the CEO, where strategic priorities translate into operating reality. The remit spans AI transformation, new product lines, and M&A support, signaling a company dealing with portfolio and platform decisions rather than a single-workstream focus. For SaaS professionals, that mix is notable because it touches the mechanisms that most often reshape growth trajectories: product strategy, operational alignment, and inorganic expansion.
Over time, the role builds a toolkit that travels well across SaaS environments. It emphasizes turning ambiguous inputs into crisp narratives, using analysis to frame decisions, and driving cross-functional execution without direct authority. Exposure to company-level prioritization and executive communication also develops a practical understanding of how SaaS businesses allocate resources across product, go-to-market, and internal systems, including applied AI in day-to-day operations.
This position fits someone who prefers breadth over ownership of one function and who is comfortable switching between strategy and delivery. It is well-suited to operators with experience partnering with senior leaders, translating complex topics into decision-ready artifacts, and building momentum across multiple stakeholders. It will appeal to candidates who want proximity to inflection-point work and are motivated by high-trust, high-judgment execution.
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
