Senior Director, Learning & People Development at Toast

| Greater Boston Area
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We’re not your traditional tech company. We recognize that talented people often come from outside the tech space. No matter what your background is, there’s a place for you at Toast. We’ve 86’d the conventional workplace for one where people can truly bring their full selves to work. Together, we empower restaurants of all sizes to build great teams, increase revenue, improve operations, and delight their guests. We pair our deep understanding of the restaurant industry with powerful cloud based software and restaurant-grade hardware to deliver an intuitive all-in-one platform. Join us on our mission to empower the restaurant community to delight guests, do what they love, and thrive. 

Bready to make a change?  

We’re looking for a Senior Director of Learning & People Development to build, promote, and manage the learning culture at Toast. S/he will be a leader with influence across the Toast organization to affect, implement, and overhaul learning development strategies and programs for all Toast employees. S/he will also work to enhance a culture of learning at Toast by leading and managing the instructional design, development, delivery and evaluation of onboarding events and programs, skill development frameworks for individuals and managers, learning methods and channel creation, and the implementation of a world-class training platform. Creativity, entrepreneurship, collaboration, and a get-stuff-done attitude are central to this person’s ethos. 

The role will report to the VP of People Success and will have the opportunity to support in the development and implementation of programs and processes that enhance the entire employee experience as a member of the People & Culture leadership team. We are eager to meet driven candidates who crave impact, thrive in ambiguity and want to experience a start-up in hyper-growth.

About this roll*

  • Be an ambassador for the Toast culture - helping to ensure a high bar for performance and a trusting, collaborative and fun environment (and have a blast doing so)
  • Create and implement new programs designed to help every Toaster realize their full potential, from onboarding to continued learning (and know that those programs are effective, and tweak if they’re not)
  • Align Toast on a central learning management system, know how to build upon it, and educate the company on the value of that platform (and know what to select and how to vet the right tools)
  • Build, socialize, and launch the learning and people development strategy at Toast (and know the value and place of the basics alongside that of the advanced stuff)
  • Develop relevant metrics to analyze and evaluate the effectiveness of programs and services offered through L&PD (and love working in the numbers)
  • Partner deeply with all functions including embedded Enablement teams to align and institute people journeys and operating models that clarify roles and responsibilities (and enjoy building those relationships)
  • Build and implement leadership development programs that inspire and support the growth of managers and leaders at all levels (and get your hands dirty while doing so) 

Do you have the right ingredients? 

  • Several years experience within and leading learning and people development functions
  • Experience building, re-building, and scaling teams at high-growth companies
  • Love of learning and developing individuals and teams to be high performing
  • Proven experience developing programs aimed at upskilling individuals and teams
  • Strong communications and change management skills
  • Desire to start from a place of “yes” with the courage to say “no” when appropriate
  • Ability to think creatively, build from left field, and seek unconventional approaches
  • Strong desire to focus on analytical insights and answers to tough problems
  • Desire to operate in a fast-paced, multinational organization
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Technology we use

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


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.
Toast values candidates with varied backgrounds — and these 3 employees prove it

An Insider's view of Toast

What’s the vibe like in the office?

Our office has both a relaxed but productive vibe. You'll see people with their heads down working, but you'll also see people hanging out and collaborating in open spaces. There's a good balance between work and play. When I'm not heads down coding, you'll find me playing guitar or hanging out in the Toast Pub.

Gabe Gonzalez

Associate Technical Sourcer, Previously: Software Engineer

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 are some things you learned at the company?

Where should I start? For hard skills, I’ve learned more than I ever thought I would about Excel and Salesforce. I’ve also learned what it looks like when a company not only talks the talk, but walks the walk. We’ve been able to execute on what we’ve set out to do because we are willing to try new things, make mistakes, and learn from them.


Payments Relationship Manager

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 stand up
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
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Team workouts
Retirement & Stock Options Benefits
401(K) Matching
Company Equity
Performance Bonus
Child Care & Parental Leave 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
Stocked Kitchen
Happy Hours
Recreational Clubs
Fitness Subsidies
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
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