- Experience
- Any
- Salary
- USD 100,000 – USD 120,000 / year
- Openings
- 1
- Posted
- 3 weeks ago
- Work mode
- Work from home
- Eligibility
- Candidates with prior Chief of Staff experience or comparable startup leadership support experience who are comfortable operating in a fully remote, fast-moving seed-stage environment.
- Resume
- Required to apply
Job description
About ApprentiScope
ApprentiScope is a workforce-management platform designed specifically for Registered Apprenticeship programs. Its customers include large enterprises as well as state-level government organizations. The platform is built to replace time-consuming manual workflows, helping customers expand apprenticeship programs, reduce compliance work, and track meaningful results.
The company is seed-stage, fully remote, and run by a compact, high-performing team. It is already profitable and still in growth mode, reflecting strong demand for the product. With skilled trades gaining national importance due to AI-driven expansion and modernization of energy infrastructure, ApprentiScope is well positioned to help shape this category.
About the Role
ApprentiScope is hiring a Chief of Staff to act as a strategic partner to the CEO. This person will share in decision-making, take ownership of important work, and help move the company into its next phase. The role sits at the center of a fast-moving business and requires someone who can work across functions, lead key initiatives, and influence company direction. The ideal candidate has done this type of work before and is comfortable building structure in environments where the process is still being defined.
Responsibilities
- Serve as the CEO’s main strategic partner, sounding board, and multiplier across the business.
- Lead cross-functional projects from early scoping through delivery, making sure important work stays on track during rapid growth.
- Spot strategic priorities ahead of time, identify blind spots, and recommend high-value actions before issues become urgent.
- Pull together insights from customers, internal teams, market signals, and data into clear guidance for leadership.
- Handle board preparation, investor updates, and other high-stakes communications on the CEO’s behalf.
- Represent the CEO in meetings and decisions when appropriate, with the full context and authority to do so.
- Create and improve internal systems, routines, and operating rhythms that help a small team perform well beyond its size.
What Success Looks Like
In the first 90 days, success means quickly building a strong understanding of the product, customers, market, and team so you can speak for the CEO with confidence. You should also take ownership of at least one major cross-functional initiative from start to finish and deliver a clear measurable result. In addition, you’ll be expected to set up a simple operating cadence such as weekly leadership meetings or a board-prep workflow that improves execution and clarity. Another early win would be identifying the biggest operational or strategic constraint and beginning to close it.
Longer term, the role is successful when the CEO gains more time to focus on only the work the CEO can do, while the company grows faster and runs more smoothly because of your contribution.
Requirements
- Previous experience in a Chief of Staff role, or a similar right-hand position supporting a startup CEO. You understand early-stage chaos and know how to impose structure without slowing momentum.
- A strong action orientation and solid execution skills, especially in uncertain and fast-changing environments where decisions often need to be made without perfect information.
- Excellent judgment and the ability to think ahead about what the company and CEO will need next, not only what is immediately visible.
- Strong written and verbal communication skills, with the ability to communicate the CEO’s perspective effectively to board members, customers, and internal teams.
- Comfort working across strategy, operations, finance, people, and go-to-market functions, with broad generalist instincts and the ability to go deep where needed.
- High integrity, strong discretion, and the maturity to handle sensitive information and complex interpersonal situations.
Compensation
The base salary for this position is $100,000 to $120,000. The role also includes meaningful early-stage equity in the form of stock options, with a standard 4-year vesting schedule and a 1-year cliff. As the company’s first executive hire, this is a real opportunity to earn substantial ownership in a business that already has strong momentum.