Chief of Staff

About ApprentiScope

ApprentiScope is the leading workforce-management platform purpose-built for Registered Apprenticeship programs. Our customers range from Fortune 500 companies to State Governments. ApprentiScope’s robust platform replaces labor-intensive manual processes, enabling our customers to scale their programs, reduce their compliance burden, and generate measurable outcomes.

We are a seed-stage, fully remote company with a small, high-performing team. As the skilled trades become an ever-increasing national priority brought on by AI expansion and energy infrastructure modernization, ApprentiScope is positioned to define the category.

About the Role

We’re looking for a Chief of Staff to serve as a strategic partner to the CEO by sharing in the decision-making, carrying real authority, and helping unlock the next stage of the business. ​​This is a high-impact role at the center of a fast-moving company. You’ll operate across functions, drive critical initiatives forward, and directly shape the business's trajectory. The right person has done this before and thrives in environments where they are writing the playbook.

What You'll Do

1. Act as the CEO’s primary thought partner, sounding board, and force multiplier across all aspects of the business.
2. Own and drive cross-functional initiatives from scoping through execution, ensuring nothing falls through the cracks during periods of rapid growth.
3. Proactively identify strategic priorities, surface blind spots, and recommend high-impact actions before they become urgent.
4. Synthesize information from across the organization—customers, team, market, data—into clear recommendations for leadership.
5. Manage board prep, investor communications, and other high-stakes deliverables on behalf of the CEO.
6. Stand in for the CEO in meetings and decisions where appropriate, carrying full context and authority.
7. Build and refine internal processes, rituals, and operating cadences that help a small team punch above its weight.

What Success Looks Like

In the first 90 days, a successful Chief of Staff will:

1. Develop a deep understanding of the product, customers, market, and team dynamics—able to represent the CEO’s perspective in any conversation.
2. Own at least one major cross-functional initiative end-to-end, delivering a measurable outcome.
3. Establish a lightweight operating cadence (e.g., weekly leadership rhythm, board prep process) that noticeably improves clarity and execution.
4. Identify and begin closing the biggest operational or strategic gap holding the company back.

Over time, the measure of success is straightforward: the CEO has more capacity to focus on what only the CEO can do, and the business is growing faster and operating more smoothly because of your contributions.

What We're Looking For

1. Prior experience as Chief of Staff (or a comparable right-hand role to a CEO) at a startup. You’ve seen what early-stage chaos looks like, and you know how to bring structure without killing speed.
2. A bias toward action and strong execution instincts, especially in ambiguous, rapidly changing environments where perfect information is never available.
3. Exceptional judgment and the ability to anticipate what the company and CEO will need next—not just react to what’s in front of you.
4. Outstanding written and verbal communication skills. You can represent the CEO’s thinking to any audience—board members, customers, or team.
5. Comfort operating across strategy, operations, finance, people, and go-to-market. Generalist instincts with the ability to go deep where it matters.
6. High integrity, discretion, and the maturity to handle sensitive information and navigate complex dynamics.

Compensation

1. Base Salary: $100,000–$120,000
2. Equity: Meaningful early-stage stock options with a standard 4-year vest and 1-year cliff. As our first executive hire, this is a genuine opportunity to build significant equity in a company with strong momentum.