Director Implementation, Employee Cloud

| Chicago
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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?

The Director of Customer Implementation will be responsible for the success of our new customer onboarding programs; and for scaling the function to successfully handle rapid growth. We believe an integrated point-of-sale and payroll solution that is reliable and easy to use will be a game-changer for the restaurant operators we serve, and this role will be directly responsible for increasing the number of customers we’re able to successfully set up on the platform each month. S/he will focus on the customer journey from completion of the sale through successfully running their first payroll and transitioning to our ongoing customer success teams. S/he will be responsible for hitting new customer implementation targets, customer satisfaction/loyalty, employee happiness, and the cost of implementation.

About this roll*: 

  • Drive a step-function increase in new customer go-lives by improving capacity and efficiency
  • Directly lead the implementation of new mid-market and enterprise customers; develop the playbook, lead the team, and ensure a seamless transition to ongoing support. 
  • Deliver a delightful, low effort experience for new customers getting started with Toast Payroll
  • People inspirer; unify the team around our mission of helping new customers launch on time, without errors, and with a positive first experience with Toast.
  • Process improvement leader; identify and prioritize systems/workflow enhancements that will make work easy for our team and customers
  • New customer experience designer; match customer needs with innovative approaches that are uniquely designed for the restaurant customers we serve.
  • Build a high performing team through effective org design, hiring, development, and recognition. 
  • Master of scale; build a strong team and smart processes that can handle 10x growth within a few years. Recognize areas of growth risk and act urgently to mitigate with scalable solutions.
  • Direct data synthesis and analytics (dashboards) to be sure we are data-driven in performance assessment and prioritizing actions.
  • Partner with GTM, Implementation, and other business areas to ensure smooth handoffs and a cohesive customer experience across products and journey stages.
  • Direct the enablement of the Implementation teams; ensure employees in all roles have the systems and training they need to be successful in their work.
  • Study voice-of-customer trends to analyze new customer feedback, intervene when needed, and be sure our team is acting on what we learn (product, people, systems)
  • Energizer and culture leader; this role will be key to modeling and building a culture of high performance, high morale, recognition/celebration, and fun.


Do you have the right ingredients*


  • Relentless heart for customers & strong ambition to create a uniquely rewarding experience for restaurant and small business operators
  • 10+ years in Customer Success with at least 2 years leading high-volume implementation functions
  • Experience at a high-growth tech company and/or providing payroll solutions to small biz’s at scale 
  • Record of building high performing teams with strong engagement, morale, and retention 
  • Obsessed with smart processes and optimizing for efficiency and customer delight. Experienced with process improvement to increase customer value in sustainable/lower cost ways.
  • Dynamic change leader; bring new ideas and engage the hearts & minds of the larger team with strong context and communication around change.
  • Ability to juggle multiple initiatives/projects with a relentless focus on driving the right outcomes for Toast and our customers.
  • Exceptional communicator; able to inform and inspire at all levels of the company with verbal, interpersonal, and writing skills.
  • Love for teamwork and commitment to building a paradigm-shifting customer experience together
  • Must be a techie; enthusiastic about using technology to solve problems for customers at scale.
  • Highly ethical leader; will earn and be worthy of our customers’ and employees’ trust
  • Ability to operate both strategically and tactically
  • Restaurant experience a significant plus



30-50% travel for non-Chicago based leader. Mostly to the service centers at the leader’s discretion, but will also include occasional trips to Boston or customer locations.

*Bread puns encouraged but not required

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Technology we use

  • Engineering
  • Product
  • Sales & Marketing
    • .NETLanguages
    • C#Languages
    • JavascriptLanguages
    • ReactLibraries
    • ReduxLibraries
    • ASP.NETFrameworks
    • ExpressFrameworks
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    • MySQLDatabases
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    • Google AnalyticsAnalytics
    • IllustratorDesign
    • PhotoshopDesign
    • SketchDesign
    • AsanaManagement
    • JIRAManagement
    • TrelloManagement
    • WordpressCMS
    • SalesforceCRM
    • Constant ContactEmail


We are located in the trendy, downtown area of Streeterville on Michigan Avenue. You can find us next to the Wrigley Building!

An Insider's view of Toast

What's something quirky about your company?

Our sticker obsession! We love collecting and trading them.


Manager of Snacks

What does your typical day look like?

6 cups of coffee, a Cliff bar, lunch at 2, and on my way home by 7!


Operations Specialist

How does the company support your career growth?

I meet with my manager every week to review my personal goals and discuss how I want to grow as a developer. We also get a yearly stipend that we can use to attend conferences and purchase books that expand our knowledge base.


Software Engineer

How has your career grown since starting at the company?

I've been extremely fortunate to have great mentors and managers who encouraged me to look at situations through different lenses. This has helped me identify opportunities to carve out new career paths. Four of the six roles I've held did not exist before I stepped into them.


L&D Specialist

What are Toast Perks + Benefits

Toast Benefits Overview

Like most tech companies, we offer commuter subsidization, full health coverage, endless snacks, and collaborative workspaces. But what makes us unique is our offerings beyond the standard spread of perks and benefits: unlimited PTO, 401(k) match, sabbatical after five years, $500 wellness stipend, fun company events, employee-led communities, peer-nominated Toasty Awards and most importantly, an environment where you can truly be yourself. If you want to get the inside scoop on what it's really like to work here, check out our instagram @lifeattoast and follow the hashtag #WeAreToasters.

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)
Acme employees can contribute up to $2700 annually to their FSA.
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Life insurance is equal to 1 times an employee's annual salary.
Wellness Programs
Onsite Gym
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
Eligible employees get a summer of paid sabbatical after their first 5 years of working at the company.
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Company Outings
Game Room
Our game room includes Ping Pong, Pool Table.
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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