Associate Chief of Staff, Executive Office

Boston, MA, US

Job Description / Skills Required

Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love.

We are looking for an Associate Chief of Staff, Executive Office who is eager to roll up their sleeves and help us execute our most critical company priorities. This role reports to our VP, Chief of Staff, and sits within our Executive Office, which reports to the CEO and supports the CEO, COO, and the rest of Toast’s Executive Leadership Team. The ideal candidate, regardless of background, is someone who is passionate about, and excels at:

  • Enabling those around them to be positive, effective, and successful
  • Constantly shifting between big picture brainstorming, thoughtful (and often hardcore) data analysis, building trusting relationships with a phenomenal executive team, scaling critical operating processes such as OKRs, and simply rolling up their sleeves to get tactical things done

This role will be responsible for helping run the operating system across all of Toast, ranging from monthly OKR accountability to quarterly business reviews to annual planning. They will also lean in heavily on our most critical priorities at any given time, tailoring the support to the needs of the challenge – sometimes lending a hand with investigative analysis, sometimes providing program management support, and other times identifying, staffing up, and motivating an internal tiger team to tackle the challenge.

About this roll* (Responsibilities) 

  • Work alongside the VP, Chief of Staff to manage the Toast-wide operating system (including its management cadence, metric reviews, decision-making frameworks, goal setting process, operating calendar, and communications)
  • Help plan, coordinate, and manage content for leadership, team meetings, and off-sites
  • Manage the flow of information across the Senior Leadership Team at Toast
  • Attend meetings and participate in projects with or on behalf of the Senior Leadership Team
  • Provide ad-hoc support on projects small to large; this could include market research, financial modeling, internal operating initiatives, and more

Do you have the right ingredients*? (Requirements)

  • 3-6 years of experience in consulting, investment banking, business intelligence, or fast-growth tech (restaurant experience is a bonus!)
  • Strike a healthy balance between deeply understanding the granular data and details of a challenge while being able to zoom out and communicate the top-down executive-level story
  • Able to embrace ambiguity, always taking the first pass at a challenge to provide structure and early momentum, while freely pivoting when the need arises
  • Process-focused and detail-oriented with strong project management skills
  • Excellent analytical and conceptual problem-solving skills
  • Proactive, hard-working, and resourceful in pushing progress forward and meeting accelerated timelines with minimal oversight

Our Spread of Total Rewards

  • Unlimited Vacation
  • Sabbatical opportunity after five years
  • Professional Development Reimbursement Program
  • Commitment to Employee Wellness through resources such as a quarterly Wellness Stipend
  • Various peer and company recognition programs 
  • 401(k) and matching
  • Medical, Dental, & Vision Coverage
  • Mental Health Benefits
  • Subsidized backup childcare

*Bread puns encouraged but not required




We are Toasters

Diversity, Equity, and Inclusion is Baked into our Recipe for Success.

At Toast our employees are our secret ingredient. When they are powered to succeed, Toast succeeds.

The restaurant industry is one of the most diverse industries. We embrace and are excited by this diversity, believing that only through authenticity, inclusivity, high standards of respect and trust, and leading with humility will we be able to achieve our goals.

Baking inclusive principles into our company and diversity into our design provides equitable opportunities for all and enhances our ability to be first in class in all aspects of our industry.

Bready* to make a change? Apply today!

Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact [email protected].

For roles based in the United States:  As part of our commitment to the health and safety of our employees and their families, all individuals entering our US workspaces are required to provide proof of full vaccination against COVID-19 unless they have an approved medical or religious accommodation.