Chief of Staff - Office of the CEO

The Opportunity

We’re looking for a strategic, highly organized, and resourceful Chief of Staff to join the team at Postman. Reporting to the Head of Operations, you’ll serve as a close partner to both the Head of Operations and the CEO, ensuring the CEO is supported, focused, and operating at maximum effectiveness.

In this role, you’ll help drive alignment, streamline execution, and keep communication flowing to the CEO and across the leadership team.You’ll be at the center of how decisions get made and how company-wide priorities move forward.

This is a high-impact, high-trust position that’s ideal for someone who thrives in a fast-moving environment and wants to shape strategy from the inside. It’s also a launchpad: Chiefs of Staff often go on to lead business functions, start new initiatives, or step into senior leadership roles. You’ll get unmatched visibility into how the company runs, and the opportunity to help shape Postman’s direction. This is an exciting opportunity for anyone who wants to: 

What You’ll Do

• CEO Enablement & Prioritization - Ensure the CEO is focused on what matters most. Lead efforts across the Office of the CEO to optimize time, information flow, and decision-making, all while reducing friction, sharpening priorities, and maximizing impact across the business.
• Executive Team Alignment - Partner with the Head of Operations to keep the executive team aligned and effective. Reinforce priorities, ensure follow-through on key decisions, and help resolve cross-functional tensions before they escalate.
• Strategic Project Leadership - Lead or drive forward special projects that sit between functions or lack a clear home. These may include strategic initiatives, organizational pilots, or early-stage ideas the CEO wants to incubate before handing off.
• Leadership Team Cadence - Support the company’s operating rhythm (OKRs, business reviews, offsites, and board meetings) by ensuring the CEO and the leadership team are prepped, key messages are clear, and the right follow-through happens post-meeting.
• Cross-Functional Momentum - Serve as a connective layer across teams, surfacing blockers, clarifying ownership, and helping ensure strategic initiatives aren’t slowed by ambiguity or misalignment.

About You

• Strategic and business-minded: You have 6+ years of experience in roles focused on strategy, consulting, or operations, especially in high-growth or fast-paced tech startups.
• A skilled cross-functional operator: You’ve successfully managed complex projects, worked directly with executive stakeholders, and know how to drive alignment across teams with competing priorities.
• A sharp thinker and problem-solver: You bring strong analytical and strategic thinking skills, with the ability to quickly break down problems and identify actionable paths forward.
• An exceptional communicator: You write and speak with clarity, precision, and influence, tailoring your message to different audiences and situations.
• Meticulous and reliable: You have high attention to detail, strong organizational instincts, and a track record of follow-through.
• Calm under pressure: You’re comfortable with ambiguity, stay steady in fast-changing situations, and bring order and clarity to chaos.
• Bonus: An MBA or equivalent business training is preferred, but not required.