Chief of Staff

Who you are

• 8+ years of client-facing experience working with Fortune 500 companies (e.g. consulting, banking, enterprise sales, etc.)
• Demonstrated experience managing high-performing teams with low ego and high EQ
• A self-starter who thrives in a fast-paced work environment; identifies opportunities for improvement and takes initiative to drive necessary change
• Outstanding organizational and analytical ability
• Exceptional executive presence, business acumen, and communication skills
• Experience managing cross-functional teams on multiple high-takes projects simultaneously, while maintaining a cool confidence
• Strong intellectual curiosity, judgment, and personal integrity
• An excellent sense of humor

What the job involves

• We are looking for a Chief of Staff to serve as a strategic partner to our Co-CEO and Co-Founder, Matt Kalmans
• You will play a pivotal role in refining, overseeing, and orchestrating the most critical initiatives to support and help drive forward the company’s most important priorities
• The Chief of Staff will work across a broad set of strategic functions, from business operations and finance to strategic planning and revenue enablement, to ensure that the business can scale to its fullest potential
• This position requires a blend of leadership, change management, analytical thinking, and operational acumen
• The Chief of Staff will “wear many hats” and requires thorough problem-solving across a variety of areas within the company
• This is a high-impact, high-visibility role based in New York, designed for a strategic thinker and doer, who can operate as an extension of the Co-CEO/Co-Founder, ensuring focus, clarity, and execution across multiple fast-moving workstreams
• Act as a trusted extension of the CEO, making informed decisions, resolving blockers, and maintaining momentum across multiple strategic initiatives
• Manage and refine an organizational-wide, operating model and cadence that ensures each function’s ability to deliver on their priorities and facilitates effective communication, cross-functional collaboration, and decision-making
• Develop models, memos, and other materials to help CEO scenario plan and make key operational decisions
• Help draft material including external and internal executive communications, all hands material, and rationalizing client facing material
• Oversee the Office of the CEO ensuring the team (Executive Assistants, Director of Strategy, Chief of Staff) are balancing internal and commercial priorities appropriately
• Support Matt in prioritizing his time and elevating his direct reports to operate expertly and independently
• Drive the company-wide goals and annual planning process

Benefits

• 35 days of Paid Time Off: 20 vacation days, 10 personal days, 5 sick days
• 14 company holidays
• Bereavement leave
• 16 weeks of fully paid parental leave inclusive of birth and adoption for primary and secondary caregivers
• Frequent company-wide and team social events such as games nights, cooking classes, summer boat cruises, paint & sip, karaoke, escape rooms, bowling, team dinners, baseball games, holiday parties, and plenty more
• Stocked fridge full of drinks and plenty of healthy (and less healthy) snacks
• Weekly happy hour and bagel breakfast
• Pre-tax commuter benefits
• $300 workstation budget to personalize your at-home or in-office space
• Hybrid in-office setup: we work from our offices in midtown Manhattan every Tuesday - Thursday and give the option to work from anywhere on Monday and Friday
• Applecart pays 75% contribution towards Medical, Dental and Vision
• 401(k) with 4% company match
• HSA and FSA
• OneMedical: On-demand primary care free to all employee whether you take our insurance or not
• Health Advocate: Personal healthcare concierge
• Teladoc: Network of virtual healthcare providers
• Talkspace: Online mental health therapy
• Headspace: Full access to the meditation app
• Kindbody: Fertility and gynecology services