Chief of Staff
ApprentiScope
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About the role
Role Overview
As Chief of Staff, you will serve as a strategic partner to the CEO—sharing in decision-making, carrying real authority, and driving critical cross-functional initiatives. This is a high-impact role for someone who thrives in early-stage environments and can help write the playbook as the company grows.
Responsibilities
- Act as the CEO’s primary thought partner, sounding board, and force multiplier across all business areas.
- Own and drive cross-functional initiatives end-to-end (from scoping through execution), ensuring nothing falls through the cracks during rapid growth.
- Proactively identify strategic priorities, surface blind spots, and recommend high-impact actions before issues become urgent.
- Synthesize inputs across the organization (e.g., customers, team, market, data) into clear leadership recommendations.
- Manage board preparation, investor communications, and other high-stakes deliverables on behalf of the CEO.
- Stand in for the CEO in meetings/decisions where appropriate, with full context and authority.
- Build and refine internal processes, rituals, and operating cadences that help a small team execute effectively.
90-Day Success Criteria
- Develop deep understanding of product, customers, market, and team dynamics and represent the CEO’s perspective in any conversation.
- Own at least one major cross-functional initiative end-to-end with a measurable outcome.
- Establish a lightweight operating cadence (e.g., weekly leadership rhythm, board prep process) that improves clarity and execution.
- Identify and begin closing the biggest operational or strategic gap holding the company back.
Requirements
- Prior experience as Chief of Staff (or comparable right-hand role) at a startup.
- Comfort bringing structure without slowing down in early-stage environments.
- Strong execution instincts and bias toward action in ambiguous, rapidly changing settings.
- Exceptional judgment and ability to anticipate what the company/CEO will need next.
- Outstanding written and verbal communication; able to represent the CEO’s thinking to diverse audiences (board, customers, team).
- Ability to operate across strategy, operations, finance, people, and go-to-market.
- High integrity, discretion, and maturity to handle sensitive information.
Compensation
- Base salary: $100,000–$120,000
- Equity: Meaningful early-stage options (4-year vest, 1-year cliff)
Nice-to-haves
- Not explicitly stated (role emphasizes prior Chief of Staff/right-hand startup experience and strong generalist execution).
About ApprentiScope
ApprentiScope is a workforce-management platform built specifically for Registered Apprenticeship programs. It serves Fortune 500 companies and State Governments, helping them scale apprenticeship programs, reduce compliance burden, and achieve measurable outcomes. The company is seed-stage, fully remote, and focused on defining a growing national category in skilled trades.
Scraped 7/29/2026