We power successful restaurants.
Boston, MA

Senior Director, Executive PMO

| Greater Boston Area
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Now, more than ever, the Toast team is committed to our customers. We’re taking steps to help restaurants navigate these unprecedented times with technology, resources, and community. Our focus is on building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. And because our technology is purpose-built for restaurants, by restaurant people, restaurants can trust that we’ll deliver on their needs for today while investing in experiences that will power their restaurant of the future. 

The Senior Director of Executive PMO will be responsible for building out the Executive PMO function to support our rapid growth. You will partner with executive sponsors and senior leadership to define, build and operationalize our cross-functional project management process. In addition, you will help set Toast standards for organizational excellence and will be responsible for ensuring that cross-functional projects are planned, managed, and governed in a consistent, transparent, and disciplined manner.  This position is best suited for a self-starter who thrives on designing operating models and providing structure. The ideal candidate should have: the ability to flex between the strategic and the tactical, outstanding verbal and written communication skills, and a high level of energy and flexibility to get things done and thrive in a fast-paced, team-oriented environment.

About this roll* (Responsibilities) 

  • Develop the Exec PMO’s  project intake, management, and operating model that will coordinate cross-functional projects.
  • Refine intake strategy and prioritization framework to ensure we are solving the right problems, in the right order that will drive the highest value and impact to business.
  • Work with project managers across the organization to develop consistency and standardize processes across the broader project management organization.
  • Ensure projects are completed on time, within budget and scope, and consistent with established standards.
  • Use strong business acumen to manage risk and escalate impediments through a defined process for faster decision making.
  • Provide analysis, status reports, and metrics to executive sponsors and senior management on a regular cadence.
  • Lead the continuous improvement of PMO methodologies, standards, tools, and policies
  • Serve as a liaison between project teams and other functional areas of the organization..
  • Mentor, motivate and lead members of the project team. Ensure project team members take action and accountability for their assigned projects and workload.
  • Design the Exec PMO organization for scale.

Do you have the right ingredients*? (Requirements)

  • Experience developing and running a PMO organization for a minimum of 5 years with a proven history of delivering on-time/budget, large-scale, complex cross-functional initiatives.
  • 10+ years of experience in cross-functional, program management environments and or/consulting.
  • A good understanding of project methodology and how to apply it to real world situations.
  • Proven capacity for identifying risks and managing trade-offs in a highly complex environment.
  • Excellent communication and presentation skills to effectively interact and influence at various levels of the organization.
  • Strong experience in consultative problem-solving. Exemplary skills in bringing structure to complex and ambiguous situations.
  • Extraordinary influencer who is great at connecting the dots at the organization, strategy, program, and project levels.
  • Results-oriented with a demonstrated sense of urgency to drive multiple projects to successful completion.
  • Proven strength in positions of leadership. Able to mobilize, inspire, and lead internal/external teams without direct authority.
  • A demonstrable track record of fostering a successful team atmosphere.

*Bread puns encouraged but not required


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.

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Where we are

Toast is headquartered in the heart of Fenway. Catch a Sox game, grab a bite, and stroll through one of the trendiest neighborhoods in Boston.

Technology we use

  • Engineering
    • JavaLanguages
    • JavascriptLanguages
    • KotlinLanguages
    • jQueryLibraries
    • ReactLibraries
    • AngularjsLibraries
    • ES6Libraries

What are Toast Perks + Benefits

Toast Benefits Overview

Toast strives to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total reward package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet our employees’ changing needs.

Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
Daily sync
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Open office floor plan
Dedicated Diversity/Inclusion Staff
Unconscious bias training
Someone's primary function is managing the company’s diversity and inclusion initiatives
Diversity Employee Resource Groups
We have 14 employee resource groups, known as Toast Communities, dedicated to empowering employees.
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Pet Insurance
Wellness Programs
Team workouts
Mental Health Benefits
Retirement & Stock Options Benefits
401(K) Matching
Company Equity
Performance Bonus
Child Care & Parental Leave Benefits
Child Care Benefits
Generous Parental Leave
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Company sponsored family events
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Volunteer Time
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Company Outings
Game Room
Stocked Kitchen
Happy Hours
Recreational Clubs
Fitness Subsidies
Home Office Stipend for Remote Employees
Professional Development Benefits
Job Training & Conferences
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
Mentorship program
Time allotted for learning
Online course subscriptions available
Customized development tracks

An Insider's view of Toast

How would you describe the company’s work-life balance?

Toast is a pretty special place to work. I really enjoy the collaborative and supportive work culture. Toast goes out of its way to take care of employees through additional days off to flexible hours to peer groups and training.


Senior Engineering Manager

How do you collaborate with other teams in the company?

Being a part of the R&D team, I collaborate closely with cross-functional partners like Product, Design, Quality and Documentation to ensure alignment across the team and ultimately execution. Since joining Toast, I have been stretched both technically and non-technically, grown my career and become a stronger engineer and a more effective leader.


Manager, Software Engineering

How has your career grown since starting at the company?

I began as an Implementation Engineer, moved into instructional design, and now I am in my dream role as a Product Manager. This is afforded because Toast fosters a culture where experts in their domains are eager to give you a masterclass in what they do – you only need to ask and be willing to learn. This is the best perk when working at Toast.

Sean Park

Product Manager

What unique initiatives do you have that encourage innovation?

I love our bi-annual company-wide Hackathons! The mission is to provide all Toasters with the opportunity to innovate on Toast’s products, processes, & culture while fostering new connections between teams and people. I absolutely love seeing Toasters come together; the energy, enthusiasm, & passion for making Toast better is incredibly inspiring!


Senior Director of Product Management

How does the company support your career growth?

When Toast hires you, they immediately invest in you and give you every bit of support to ensure you are not only successful but in the best position for growth. Aside from the great support resources, Toast has a team of some of the smartest people in tech that I've been able to learn from.


Senior District Sales Manager
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