Chief of Staff

Middesk•New York, NY

1d•Hybrid

About The Position

Middesk is hiring a Chief of Staff to work directly with its CEO as the company grows. The role advances the company’s most important priorities, strengthens its operating practices, and helps leadership focus on high-impact decisions and opportunities. It is highly cross-functional, with exposure to Product, Sales, Marketing, Operations, Finance, and People. The person in this role will move between strategy and hands-on execution, with responsibilities evolving as company priorities change. The Chief of Staff will lead cross-functional special projects, help run the company’s operating cadence and planning processes, and act as a trusted thought partner and representative for the CEO. The role also includes practical support that keeps the CEO effective, such as calendar management, weekly preparation, travel, and meeting follow-ups. The position is based in New York and requires working in the office at least three days per week.

Requirements

At least 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.
Ability to operate without a playbook, learn unfamiliar topics quickly, and find a practical path forward.
Clear written and verbal communication skills, including the ability to challenge ideas constructively and build credibility across functions and seniority levels without formal authority.
Strong judgment and discretion, including knowing when to act, seek input, or escalate.
Excellent organization and attention to detail while managing multiple projects and maintaining a high standard at pace.
A low-ego, high-ownership approach, prioritizing outcomes over credit and willingness to take on any task that advances the work.
Based in New York and able to work in the office at least three days a week.

Nice To Haves

Experience owning cross-functional initiatives in a fast-growing company.

Responsibilities

Own strategic initiatives that span teams, taking them from ambiguous problems to measurable outcomes.
Address the company’s highest-priority problems and opportunities where additional focus and momentum are needed.
Connect information and people across functions, identify opportunities and risks, and bring relevant stakeholders together to advance work.
Partner with the leadership team on quarterly planning, establishing clear priorities, owners, metrics, and accountability.
Run the company’s operating cadence, including leadership meetings, reviews, and performance tracking.
Prepare the quarterly board memo.
Track key decisions and commitments, flag risks early, and ensure work is completed.
Build lightweight processes and systems to help Middesk operate effectively as it scales.
Serve as a trusted thought partner to the CEO, offering an independent perspective, sound judgment, and constructive challenges to assumptions.
Represent the CEO in meetings and cross-functional discussions.
Manage details that support the CEO’s effectiveness, including calendar, weekly preparation, travel, and meeting follow-ups.