VP CS Enablement & Customer Education 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?

This role will be responsible for implementing enablement programs across the Toast Customer Success teams with a goal of driving higher productivity and consistency across the organization. This will include leading the teams focused on Customer Success employee onboarding and on-going training for individual contributors and managers at all levels, as well as partnering with Toast’s Leadership and Development teams - who focus on general employee onboarding - to ensure proper comprehensive onboarding. The person in this role will help define the CS Enablement vision, and lead and manage a team that will execute on that vision. This is a high impact, high visibility role that will have direct impact on Toast’s largest team – Customer Success.

About this roll*: 

  • Develop and implement an enablement strategy: With senior leaders across Customer Success, develop a vision for a comprehensive enablement approach, along with the concrete objectives and key results that will be needed to achieve that vision over time. Manage a team to these OKRs.
  • Build the CS Enablement Team: Hire a team capable of executing on our vision to complement the current team. You will directly manage and coach a team that will train and enable our multi-functional organization. This team will grow and evolve over time.
  • Create appropriate process and infrastructure: Coordinate with the Toast L&D team as well as enablement functions in other departments to select or create the appropriate tools, process and other infrastructure needed to implement and scale enablement programs. Examples may include survey tools, CMS and LMS.
  • Dive in as needed: As CS Enablement is expanding to beyond the first 90 days of a CS Toaster’s experience, there may be the need to do hands-on work. This may range from developing and delivering specific trainings to helping manage logistics.
  • Special Projects: Ad-hoc project work as needed, as we grow our CS Enablement program. Collaborate with other specialists as well as CS leadership in order to identify areas that can benefit from targeted improvements.

Do you have the right ingredients*

  • 5+ years in an L&D or enablement function, including familiarity with instructional design, learning management systems, ROI measurement
  • 3+ years of managing individual contributors
  • 3+ years in an Enablement role servicing geographically-distributed teams of at least 100 employees
  • A track record of successfully managing and delivering complex cross-functional projects
  • Able to establish and maintain effective working relationships with internal and external stakeholders
  • Enjoy interacting with new people, whether new hires or existing employees, across the company, in an open and inclusive way
  • Naturally intellectually curious, looking to learn and grow
  • Excited with helping shape a growing team at Toast

*Bread puns encouraged but not required

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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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