Chief of Staff

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.