Mid Level Chief Of Staff Jobs
Mid level chief of staff jobs go to professionals ready to own high-stakes projects end to end, align cross-functional teams, and drive executive decisions with limited day-to-day oversight. Openings run across Animal Care & Pet Services, Technology & Software, and Education, with a strong mix of remote and hybrid settings, and employers like Banfield Pet Hospital, Altruist, and NOOKS hiring at this level now.
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About Stepful
Stepful is a workforce platform redefining how America's largest health systems build, train, and retain their talent. Since our founding in 2021, Stepful’s trained over 32,000 practice-ready healthcare workers. Layering onto our successful direct-to-consumer training, Stepful partners with leading healthcare institutions to address the growing national shortage of healthcare workers. We’re improving access to quality healthcare for everyone, everywhere, and improving access to healthcare career ladders for those who need them most. Our students form the talent pipelines for major employers such as NY-Presbyterian, Mt. Sinai, HCA, Providence, CVS, and Walgreens. We have partnerships with half of the top 10 health systems in the US and are in process with many more. Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $55M Series C led by Oak HC/FT. We were named the #1 EdTech company in the U.S. by TIME for 2025.
Our Values
We credit much of our success to our exceptional team. We’re looking for mission-driven builders who thrive in fast-paced, ambiguous environments, and embody our four core values:
Care first: We do whatever it takes for our students to succeed.
Learn quickly: We test, learn with data, and iterate.
Build together: We win when we rely on each other.
Own it: We show up, take initiative, and show pride.
The opportunity
As Chief of Staff, you will act as a trusted advisor and the operating right hand to Stepful’s co-founders, owning cross-functional problems and helping the leadership team run the company with focus, speed, and clarity as we scale. You will own the systems that keep the organization aligned (our rhythm of business, planning cadences, and leadership communications) while driving high-priority special projects. Rather than a fixed set of tasks, you will handle complex, evolving challenges, so success requires self-direction and the ability to create value without constant oversight. This role reports directly to the CEO.
Act as a trusted partner to the co-founders and leadership team
- Maintain a bird’s-eye view of key initiatives and organizational health across Stepful; proactively surface risks, tradeoffs, and opportunities to leadership and drive teams to clear decisions
- Represent leadership’s thinking accurately and handle confidential information with sound judgment
- Set agendas and follow up on action items so leadership time is spent on the highest-priority items
Run the company’s operating system (“Rhythm of Business”)
- Translate leadership decisions and priorities into clear, actionable communication for the broader team (e.g., All Hands for both full-time and contractor teams)
- Facilitate quarterly and annual planning: Own and continuously improve Stepful’s core operating cadences (Monthly and Quarterly Business Reviews)
- Track company-wide KPIs and maintain the systems behind them, partnering with Finance to keep leadership’s source of truth accurate and up to date
Lead executive, board, and investor communications
- Draft Board materials and monthly investor updates, assembling the underlying data analysis
- Capture and communicate the state of the business clearly and concisely for both internal and external audiences
Drive cross-functional special projects end to end
- Own high-impact, cross-functional initiatives from problem definition through execution, working across teams like Learning & Operations, Growth, Product, Sales/Workforce Solutions, and more
- Dive into data and processes to find the insight that matters and turn it into action; build the analysis yourself where needed
- Support leadership on select external and partner relationships
- Set direction for company-wide events that celebrate wins and strengthen culture, partnering with the Employee Experience Manager to bring them to life (e.g., now-annual company-wide Stepfest offsite)
Examples of past special projects:
Building strategic partnerships to expand student career opportunities; opening a new revenue-driving growth channel; measuring and communicating Stepful's social impact to investors; and rolling out internal AI tooling to improve productivity.
What You’ll Bring
- 5+ years of experience, including in consulting, business operations, or a similar role at a high-growth startup.
- Highly analytical, with a structured approach to breaking down ambiguous problems; comfortable working directly with data
- Excellent written and verbal communication: clear, concise, and credible with senior and external audiences
- A strong collaborator who leads through influence and coordinates diverse stakeholders across levels and functions
- Sound judgment and discretion with confidential and sensitive information
- An owner’s mindset: you take initiative, drive work to outcomes, and hold a high bar for execution
- You thrive in a fast-paced, ambiguous environment and learn quickly through experimentation
- Passionate about Stepful’s mission: Empowering communities with accessible pathways to healthcare careers, regardless of background or circumstance.
About The Interview
- Step 1: Screening Call with Recruiter
- Step 2: Intro Call with Current Chief of Staff
- Step 3: Take-home assignment & presentation
- Step 4: Onsite interview at office in SoHo, NYC
Compensation
Base Salary: $140K - $160K
At Stepful, we're an equal opportunity employer and value diversity at our company. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.
Stepful is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic.
Compensation Range: $140K - $160K
About Stepful
Stepful is a workforce platform redefining how America's largest health systems build, train, and retain their talent. Since our founding in 2021, Stepful’s trained over 32,000 practice-ready healthcare workers. Layering onto our successful direct-to-consumer training, Stepful partners with leading healthcare institutions to address the growing national shortage of healthcare workers. We’re improving access to quality healthcare for everyone, everywhere, and improving access to healthcare career ladders for those who need them most. Our students form the talent pipelines for major employers such as NY-Presbyterian, Mt. Sinai, HCA, Providence, CVS, and Walgreens. We have partnerships with half of the top 10 health systems in the US and are in process with many more. Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $55M Series C led by Oak HC/FT. We were named the #1 EdTech company in the U.S. by TIME for 2025.
Our Values
We credit much of our success to our exceptional team. We’re looking for mission-driven builders who thrive in fast-paced, ambiguous environments, and embody our four core values:
Care first: We do whatever it takes for our students to succeed.
Learn quickly: We test, learn with data, and iterate.
Build together: We win when we rely on each other.
Own it: We show up, take initiative, and show pride.
The opportunity
As Chief of Staff, you will act as a trusted advisor and the operating right hand to Stepful’s co-founders, owning cross-functional problems and helping the leadership team run the company with focus, speed, and clarity as we scale. You will own the systems that keep the organization aligned (our rhythm of business, planning cadences, and leadership communications) while driving high-priority special projects. Rather than a fixed set of tasks, you will handle complex, evolving challenges, so success requires self-direction and the ability to create value without constant oversight. This role reports directly to the CEO.
Act as a trusted partner to the co-founders and leadership team
- Maintain a bird’s-eye view of key initiatives and organizational health across Stepful; proactively surface risks, tradeoffs, and opportunities to leadership and drive teams to clear decisions
- Represent leadership’s thinking accurately and handle confidential information with sound judgment
- Set agendas and follow up on action items so leadership time is spent on the highest-priority items
Run the company’s operating system (“Rhythm of Business”)
- Translate leadership decisions and priorities into clear, actionable communication for the broader team (e.g., All Hands for both full-time and contractor teams)
- Facilitate quarterly and annual planning: Own and continuously improve Stepful’s core operating cadences (Monthly and Quarterly Business Reviews)
- Track company-wide KPIs and maintain the systems behind them, partnering with Finance to keep leadership’s source of truth accurate and up to date
Lead executive, board, and investor communications
- Draft Board materials and monthly investor updates, assembling the underlying data analysis
- Capture and communicate the state of the business clearly and concisely for both internal and external audiences
Drive cross-functional special projects end to end
- Own high-impact, cross-functional initiatives from problem definition through execution, working across teams like Learning & Operations, Growth, Product, Sales/Workforce Solutions, and more
- Dive into data and processes to find the insight that matters and turn it into action; build the analysis yourself where needed
- Support leadership on select external and partner relationships
- Set direction for company-wide events that celebrate wins and strengthen culture, partnering with the Employee Experience Manager to bring them to life (e.g., now-annual company-wide Stepfest offsite)
Examples of past special projects:
Building strategic partnerships to expand student career opportunities; opening a new revenue-driving growth channel; measuring and communicating Stepful's social impact to investors; and rolling out internal AI tooling to improve productivity.
What You’ll Bring
- 5+ years of experience, including in consulting, business operations, or a similar role at a high-growth startup.
- Highly analytical, with a structured approach to breaking down ambiguous problems; comfortable working directly with data
- Excellent written and verbal communication: clear, concise, and credible with senior and external audiences
- A strong collaborator who leads through influence and coordinates diverse stakeholders across levels and functions
- Sound judgment and discretion with confidential and sensitive information
- An owner’s mindset: you take initiative, drive work to outcomes, and hold a high bar for execution
- You thrive in a fast-paced, ambiguous environment and learn quickly through experimentation
- Passionate about Stepful’s mission: Empowering communities with accessible pathways to healthcare careers, regardless of background or circumstance.
About The Interview
- Step 1: Screening Call with Recruiter
- Step 2: Intro Call with Current Chief of Staff
- Step 3: Take-home assignment & presentation
- Step 4: Onsite interview at office in SoHo, NYC
Compensation
Base Salary: $140K - $160K
At Stepful, we're an equal opportunity employer and value diversity at our company. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.
Stepful is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic.
Compensation Range: $140K - $160K
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Who's Hiring
Top Industries Hiring
- Animal Care & Pet Services
- Technology & Software
- Education
- Government & Public Sector
- Banking & Financial Services
Mid Level Chief Of Staff Jobs: Frequently Asked Questions
How do I get a mid level chief of staff job?
Position yourself around demonstrated ownership rather than task execution. Highlight instances where you coordinated cross-functional initiatives, translated strategy into operational plans, or resolved ambiguity without constant direction. Tailor your resume to show measurable outcomes, not just responsibilities. In interviews, speak to the problems you defined and solved, and show familiarity with how executives prioritize competing demands. A focused, evidence-backed application will stand out.
Which companies hire mid level chief of staffs?
Companies hiring mid level chief of staffs right now include Banfield Pet Hospital, Altruist, and NOOKS, based on current listings on Migrate Mate as of August 2026. At this level, hiring tends to come from growth-stage startups scaling their operations, mid-size companies formalizing executive support functions, and large enterprises building out dedicated chiefs of staff pipelines beneath senior leadership.
Are there remote mid level chief of staff jobs?
Yes, though availability varies by organization size and industry. About 13% of mid level chief of staff openings are remote or hybrid as of August 2026, reflecting the role's increasingly distributed nature across modern workplaces. Many employers offer hybrid arrangements that balance executive proximity with location flexibility, so it is worth filtering listings by work setting when you search.
How do I move up to a mid level chief of staff role?
Growth into a mid level chief of staff role typically comes from consistently taking ownership beyond your assigned scope. Focus on leading projects rather than contributing to them, building relationships across departments, and developing a reputation for clear communication under pressure. Seek out opportunities to support senior leaders directly, document the impact of your work in measurable terms, and deepen your understanding of how strategy translates into execution.
Which industries hire the most mid level chief of staffs?
Mid Level chief of staff roles concentrate in Animal Care & Pet Services, Technology & Software, and Education, based on current listings on Migrate Mate as of August 2026. These sectors tend to drive hiring at this level because they operate complex, fast-moving organizations where a dedicated operator close to leadership creates real efficiency gains and keeps strategic priorities on track.