4+ years in management consulting, business operations, strategy, or chief of staff roles
Proven experience managing cross-functional initiatives from ambiguity to measurable results
Ability to operate independently and learn quickly in fast-paced environments
Strong written and verbal communication skills, capable of constructive challenge
Demonstrated judgment and discretion in decision-making
Exceptional organizational skills with attention to detail across multiple projects
Low-ego, high-ownership mindset focused on outcomes over credit
Must be based in New York and work in-office at least three days a week
Responsibilities
Drive high-impact special projects from concept to measurable outcomes
Address the company's highest-priority challenges and opportunities
Facilitate cross-functional collaboration to identify opportunities and risks
Partner with leadership on quarterly planning and accountability
Manage the company's operating cadence, including meetings and performance tracking
Prepare the quarterly board memo and track key decisions
Establish lightweight processes to enhance operational efficiency as the company scales
Benefits
Opportunity to work closely with the CEO and leadership team
Exposure to all areas of the company, enhancing cross-functional skills
Dynamic role with evolving responsibilities as company priorities shift
Chance to drive significant impact through strategic initiatives
Collaborative work environment focused on high-impact outcomes
Full Job Description
The Role
As Middesk grows, the number of important decisions across the company keeps climbing. As Chief of Staff, you'll work directly with our CEO to advance the company's most important priorities, strengthen how we operate, and keep leadership focused on the highest-impact decisions and opportunities.
This is a highly cross-functional role with exposure to every part of the company, from Product and Sales to Marketing, Operations, Finance, and People. You'll move between big-picture strategy and hands-on execution, and the scope will evolve as the company's priorities change.
We need someone who can get up to speed on anything quickly, turn ambiguous problems into clear plans, and see the work through to results.
What You'll Do:
Drive high-impact special projects
Own strategic initiatives that cut across teams, taking them from ambiguous problems to measurable outcomes.
Step into the company's highest-priority problems and opportunities wherever extra focus and momentum are needed.
Connect the dots across functions, surface opportunities and risks, and bring the right people together to move work forward.
Run the company operating system
Partner with the leadership team on quarterly planning, with clear priorities, owners, metrics, and accountability.
Run the company's operating cadence, including leadership meetings, reviews, and performance tracking.
Own preparation of the quarterly board memo.
Track key decisions and commitments, flag risks early, and make sure work gets done.
Build lightweight processes and systems that help Middesk operate well as it scales.
Be a force multiplier for the CEO
Serve as a trusted thought partner, bringing independent perspective, sound judgment, and a willingness to challenge assumptions.
Represent the CEO in meetings and cross-functional discussions.
Own the details that keep the CEO effective, including calendar, weekly preparation, travel, and meeting follow-ups.
What We're Looking For:
4+ years of experience in management consulting, business operations, strategy, or a chief of staff role supporting senior executives.
A track record of owning cross-functional initiatives from ambiguous problem to measurable result, ideally in a fast-growing company.
Comfort operating without a playbook, and the ability to learn unfamiliar topics quickly and find a practical path forward.
Clear written and verbal communication, with the ability to challenge ideas constructively and build credibility across functions and levels of seniority without formal authority.
Strong judgment and discretion, including knowing when to act, when to seek input, and when to escalate.
Excellent organization and attention to detail across many projects at once, holding a high standard even when moving fast.
A low-ego, high-ownership approach. You care about the outcome more than the credit, and no task is too small if it moves the work forward.
Based in New York and in the office at least three days a week.
About Middesk
Middesk is a San Francisco-based company that provides a platform for businesses to verify the legitimacy of other businesses. The company was founded in 2018 by Kyle Mack and Kurt Ruppel. Middesk's platform uses machine learning algorithms to analyze public data and provide insights into a company's legitimacy, such as its legal structure, ownership, and financial health. The company's customers include banks, insurance companies, and other businesses that need to verify the legitimacy of their partners and vendors.
