Chief of Staff

Rupi Kaur is seeking a Chief of Staff to build and lead the operational infrastructure of her next creative chapter. As her work expands beyond publishing into performance, music, digital media, brand partnerships, and long-term IP development, she needs a strategic partner who can translate vision into structure and structure into execution.

This is a build role. The Chief of Staff will create the systems, write the processes, manage partners directly, and do the work before hiring others to support it. This is not a role where you oversee from a distance.

This is an executive leadership position within a founder-led cultural company. It is not a traditional operations role. The Chief of Staff reports directly to Rupi and serves as the connective tissue between her and the broader ecosystem of agents, partners, advisors, and contractors who work on her behalf.

This role exists so Rupi can remain in her highest creative and strategic capacity. The right person brings clarity, foresight, follow-through, and the judgment to know when to act and when to pause.

The Work

The Chief of Staff will own the operating rhythm of the company across the following areas. In every area, the expectation is that you are both the architect and the builder - designing the strategy and doing the work to make it real.

Operational Leadership

• Translate long-term creative vision into quarterly and annual operating plans - and build the tracking systems, documentation, and workflows to execute against them
• Oversee planning, coordination, and execution across verticals: publishing, touring, music, digital, partnerships, and long-term IP initiatives
• Build the project management infrastructure, operating cadences, and internal documentation from the ground up
• Track progress across workstreams and ensure follow-through - this means you are in the details: writing the recap, sending the follow-up, flagging the missed deadline, not waiting for someone else to do it
• Own the operating cadence: run syncs with external advisors, agents, and partners; maintain project timelines; surface decisions that need attention
• Draft and manage SOWs, briefs, timelines, and internal documents as needed. You are not handing this off - you are the person producing it.

Strategic Partnership + Decision Support

• Serve as a thought partner to Rupi, helping frame decisions, tradeoffs, and long-term strategy
• Identify strategic gaps, inefficiencies, and growth opportunities across the business
• Support launches, announcements, and major creative milestones with hands-on planning and coordination - from building the rollout timeline to writing the partner brief
• Act as the operational bridge between Rupi and her collaborators, partners, and advisors, ensuring nothing falls through the cracks

Managing the External Ecosystem

A significant part of this role is managing the network of external partners who work on Rupi's behalf: talent agents, publishers, publicists, brand partners, contractors, and representatives. These are people who are paid to deliver and who have other clients.

• Ensure external partners are performing, hold them accountable when they are not, and know when it is time to make a change. This requires someone who can lead with clear authority and warmth simultaneously - direct enough to get results, emotionally intelligent enough to preserve the relationships that matter.
• You will be the person on the phone chasing the contract, following up on the missed deliverable, and writing the recap email after the call. This is not a role where you delegate the follow-up.
• Manage and coordinate incoming contractors and consultants as the team scales
• Over time, build a small internal team beneath this role to support execution across verticals - but even as the team grows, you will remain hands-on

Why This Role

Rupi Kaur has sold over 12 million books across 43 languages and spent a decade building one of the most recognizable voices in contemporary culture. This is not a maintenance role. She is entering the second chapter of her career with new creative work, a live performance residency, a spoken word album, film and TV development, brand partnerships, and a full relaunch underway simultaneously.

The first Chief of Staff owns the architecture of that machine from day one. You will build the operating infrastructure, hire the team beneath you, and serve as the operational and strategic brain of a company with genuine cultural reach. You should be energized, not intimidated, by building at both levels - setting the vision for how things run and personally making sure they do.

Who You Are

• Systems-oriented but culturally sensitive. You build infrastructure that serves creative work, not the other way around.
• Equally comfortable framing a quarterly plan and building the tracker that runs it. You don't see execution as beneath you - you see it as where the real work lives.
• Strategically minded with strong creative instincts, sound judgment, and high emotional intelligence.
• Politically literate and values-driven. You understand the weight a public-facing cultural voice carries - particularly one that speaks to underrepresented communities - and you move accordingly and with care.
• Highly self-directed and self-motivated. You do not wait to be told what needs doing.
• You value integrity over speed.

Experience

• 5+ years in a Chief of Staff, Director of Operations, VP of Operations, or equivalent role within a founder-led or creator-led environment
• Background in entertainment, media, publishing, music, or cultural organizations strongly preferred. Experience working directly with or on behalf of a public-facing individual (artist, author, performer, founder, or cultural figure) is a significant advantage.
• Experience managing a public-facing brand that carries weight and consequence
• Comfort operating across creative and business contexts without defaulting to one
• Experience in political communications, advocacy, or movement spaces is a plus

Details

• Remote/hybrid with a preference for New York City but not limited to. Occasional travel required.
• Competitive salary commensurate with experience.