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Chief Of Staff

We invest in the holistic well-being of every team member through education reim💼 Full-time🗓 2026-07-27

Core

Strategic extension of the CEO driving alignment, AI transformations, new product lines, M&A, and enterprise sales support.

Role type

Chief of Staff (Executive)

Builds

Company-level AI transformations, new product lines, M&A initiatives, enterprise sales support

Domain

HR Tech / SaaS / AI

Deliverable

production ML models | product features | dashboards & analysis | client delivery | infrastructure

Required skills

Strategic planning, cross-functional leadership, project management, AI application, business acumen, data analysis, financial modeling, investor relations

Preferred skills

Startup founder experience

Technologies

AI tools

Responsibilities

Lead CEO's highest-priority initiatives end-to-end, pressure-test strategy with market research, serve as CEO proxy in meetings, lead functions during transitions, optimize processes and drive efficiency, build financial models and investor pitch decks

Seniority

Senior, hands-on IC

Rewrite
## About the Role Reporting to and as a strategic extension of the CEO, you will collaborate with Checkr's executive team to drive strategic alignment, set priorities, and help increase the speed and ambition of the business. You will lead a range of initiatives, from accelerating company-level AI transformations, to shaping new product lines, supporting M&A, and supporting enterprise sales. ## What You Bring ### Leadership and execution - A bias towards action, equally effective at setting direction and independently executing initiatives from start to finish - Proven experience leading cross-functional teams and bootstrapping initiatives from zero to one - Track record of planning and executing complex initiatives with world class project management - Track record of using AI to deliver impact - Earns trust quickly with customers, executives, board members, and investors - 10+ years of experience working at an executive level or equivalent track record - Startup founder experience strongly preferred ### Strategic thinking - Strong business experience and acumen. You love business as a science - Strong data analysis and problem-solving skills - Exceptional, concise written and verbal communication ## Responsibilities ### Lead strategic initiatives - Lead the CEO's highest-priority initiatives, end to end, from planning through execution - 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
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