Deputy Chief of Staff

About Us:

Rent the Runway (RTR)  is transforming the way we get dressed by pioneering the world’s first Closet in the Cloud. Founded in 2009, RTR has disrupted the $2.4 trillion fashion industry by inspiring women with a more joyful, sustainable and financially-savvy way to feel their best every day. As the ultimate destination for circular fashion, the brand now offers infinite points of access to its shared closet via a fully customizable subscription to fashion, one-time rental or ownership. RTR offers designer apparel and accessories from hundreds of brand partners and has built in-house proprietary technology and a one-of-a-kind reverse logistics operation. Under CEO and Co-Founder Jennifer Hyman’s leadership, RTR has been named to CNBC’s “Disruptor 50” five times in ten years, and has been placed on Fast Company’s Most Innovative Companies list multiple times, while Hyman herself has been named to the “TIME 100” most influential people in the world and as one of People magazine’s “Women Changing the World.”

 

About the Job:

This is a unique, high-velocity entry point into Rent the Runway for an ambitious recent graduate. As the Deputy Chief of Staff, you will serve as the operational backbone of the Office of the CEO.

While this role is heavily grounded in executive administration (expect 70% of your time to be logistics, scheduling, and "gatekeeping"), it is inteded as a rotational apprenticeship. You will also have a front-row seat to high-level decision-making and provide hands-on support to the Chief of Staff on strategic initiatives. After ~12-24 months of mastering executive operations, successful candidates can expect to transition into a functional business role within the company (e.g., Marketing, Strategy, Operations).

Responsibilities

Executive Operations (70%)

• Strategic Time Management: You will own and optimize the CEO’s time and schedule. You will ensure she has the necessary prep time, travel buffers, and information before every interaction. You will filter incoming requests and be the first point of contact for executives and third-parties to meet with the CEO. 
• Logistics & Travel: Manage end-to-end travel logistics (flights, hotels, ground transport) with zero error rate, ensuring the CEO remains productive and stress-free while mobile.
• Board of Directors Support: Manage Board and Committee scheduling and calendars, including planning meetings and events, and provide reasonable support for the Company’s Executive Chairman.
• Brand & Thought Leadership: Proactively research and vet high-impact speaking engagements and PR opportunities for the CEO/Rent the Runway and own Press communications.

Chief of Staff Support & Strategic Projects (30%)

• Strategic Research: Partner with the Chief of Staff to research industry trends, competitor activities, and new market opportunities, summarizing findings into digestible briefs for the executive team.
• Meeting Prep & Follow-Up: Draft agendas, create briefing materials, and sit in on select leadership meetings to capture action items and ensure follow-through.
• Special Projects: Support the Chief of Staff on cross-functional initiatives (e.g., OKR planning, internal communications, or culture-building events), often acting as a liaison between the Office of the CEO and other departments.
• Presentation Design: Assist in building and refining decks for internal all-hands, board presentations, or external speaking engagements.
• Office Leadership & Culture: Serve as the "glue" of the office by spearheading internal connectivity and morale; you will own the logistics and execution for critical functions, including weekly All-Hands meetings, executive offsites, and holiday parties

Why This Role?

• Mentorship: You will report directly to the Chief of Staff, receiving daily mentorship on how to navigate a high-growth tech company.
• Exposure: You will see how a CEO operates up close—learning how decisions are made, how meetings are run, and how strategy is formed.
• Growth: This is not a career destination; it is a launchpad. We want you to grow out of this role and into a leader within RTR.

 

About You:

• Undergraduate degree required.
• Experience: 0–1 years (internships in fast-paced environments count)
• Passion: A demonstrated interest in Fashion, Technology, or the Circular Economy is a plus
• Incredibly Organized: You are likely the friend who plans the group trip. You love checklists, hate lateness, and get satisfaction from bringing order to chaos. You are always one step ahead
• Communication: Impeccable written and verbal communication and presentation abilities. You must be able to interact with individuals at all levels, including senior executives and board members, handling sensitive situations with poise and discretion
• Mindset: A natural multitasker with a nimble business mind. You are focused on developing creative solutions and can juggle multiple competing tasks and demands without losing attention to detail
• Tech-Savvy: You are a native user of G-Suite (Docs, Sheets, Slides) and can learn new tools quickly

Benefits:

At Rent the Runway, we’re committed to the wellbeing of our employees, and aim to create a workplace that fosters both personal and professional growth. Our inclusive benefits include, but are not limited to:

• Paid Time Off including vacation, paid bereavement, and family sick leave - every employee needs time to take care of themselves and their family.
• Universal Paid Parental Leave for both parents + flexible return to work program  - because we know your newest family member(s) deserve your undivided attention.
• Paid Sabbatical after 5 years of continuous service - Unplug, recharge, and have some fun!
• Exclusive employee subscription and rental discounts -  to ensure you experience the magic of renting the runway (and give us valued feedback!).
• Comprehensive health, vision, dental, FSA and dependent care from day 1 of employment - Your health comes first and we’ve got you covered.
• 401k match - an investment in your future.
• Company wide events and outings - our team spirit is no joke - we know how to have fun!
• Office centric work - our corporate employees and technical leaders have the option to work remotely on Fridays, in accordance with Company policies.

Rent the Runway is an equal opportunity employer. In accordance with applicable law, we prohibit discrimination against any applicant or employee based on any legally-recognized basis, including, but not limited to: race, color, religion, sex (including pregnancy, lactation, childbirth or related medical conditions), sexual orientation, gender identity, age (40 and over), national origin or ancestry, citizenship status, physical or mental disability, genetic information (including testing and characteristics), veteran status, uniformed service member status or any other status protected by federal, state or local law.

The anticipated base salary for this position is $65,000 to $80,000. The actual base salary offered will depend on a variety of factors, including without limitation, the qualifications of the individual applicant for the position, years of relevant experience, level of education attained, certifications or other professional licenses held.