Director of Training and Development at Toast

| Chicago
!Sorry, this job was removed at 11:20 a.m. (CST) on Wednesday, July 24, 2019

StratEx is a ground-breaking tech company that offers a variety of HR and Payroll solutions to help empower restaurant/hospitality businesses by simplifying and streamlining their internal processes. The foundation on which we base our wide range of services is our proprietary HRIS software, eStratEx.

At StratEx, we are making a concerted effort to invest in our people. We are hiring a Director of Training and Development to help us build a best-in-class training department to help us not only cater to our clients, but also to ensure our people are becoming the best they can be, both personally and professionally.

Our Director of L&D will be someone who will partner with leadership and all departments to ascertain what knowledge, skills and abilities are required for each role at the organization. They will be responsible for designing and leading a multi-faceted training and development program to grow those competencies within our workforce; developing and launching a quality assurance program to ensure standardization and quality across all service teams; and partnering with a current resource to design a client-facing training strategy to provide a better client experience and decrease total volume of one-off trainings. This role will be expected to establish relevant KPIs and metrics for each role within the department. This role will also be responsible for managing internal training resources to ensure all system users are furthering their knowledge of our software, eventually rising to an expert level.   

The Director of L&D will quickly need to assess the current state of affairs, and then execute the necessary curriculum through varied approaches (such as utilizing our Litmos software but also in-person trainings). We also expect them to continuously optimize the program based on ongoing feedback and research, always striving for industry-leading results.


Job Responsibilities/Essential Functions include, but are not limited to:

  • Must be able to organize content in a meaningful way to teach employees crucial knowledge, skills and abilities required for job success

  • Work hand in hand with department leads to ensure each role’s learning objectives are met

  • Partner with a current resource to help design a client-facing training program, including managing “how-to” system training library

  • Build out a QA program to drive quality metrics across all service teams

  • Hire and manage new team members, including client-facing training resources and internal training and QA resources

  • Utilize varied learning theories and training approaches to avoid learner burnout and maximize adoption

  • Make best use of current L&D tools (e.g. Litmos and Articulate) to develop best-in-class training materials

  • Establish relevant KPIs and metrics to optimize all aspects of the L&D program

  • Create a material refresh process for updates based on manager and client feedback, system updates and industry changes/trends

  • Compile training materials not only on hard skills, but soft skills as well, including: managerial and leadership skills, client servicing skills, account management skills, brand value, etc.

  • Partner with marketing to further sales enablement efforts

  • Regular and predictable attendance in our Chicago office


Job Competencies include, but are not limited to:

  • Adaptability

  • Accountability

  • Organization

  • Leadership

  • Communication

  • Project Management

  • Influencing Skills

  • Innovation

  • Emotional Intelligence

  • Attention to Detail

  • Critical Thinking



  • Minimum of 5 years experience in learning, training and development of people (tech a plus!)

  • Bachelor’s Degree required

  • Experience leading end to end training initiatives, including a training team

  • Strong content development skills

  • Knowledge of Learning Management Systems (Litmos expertise a strong plus!)

  • Experience with Content Development tools (Articulate expertise a plus!)

  • Unparalleled Presentation Skills

  • General understanding of business principles

  • Proven project management, analytical and critical thinking skills

  • Strong initiative and the ability to work in a fast paced environment

  • Demonstrated collaboration and influencing skills

  • Exceptional Communication and interpersonal skills, ability to style-flex to different audiences

  • Comfortable with ambiguity; able to simplify the complex

  • Computer literacy required in all Microsoft and Google Products


Physical Requirements/Work Environment: 

  • Must be able to sit at a desk for extended periods of time while working

  • Must be able to proficiently operate a computer and desk phone as means of communication with colleagues and clients

  • Must be able to occasionally travel to on-site client meetings on a local and national scale

  • Must be able to clearly present HR material to groups of people either in person or via electronic means of communication


Equal Opportunity Statement:

Decisions and criteria governing the employment relationship with all employees at StratEx are made in a non-discriminatory manner, without regard to race, color, creed, religion, national origin, sex, marital status, pregnancy, disability, sexual orientation, gender expression, veteran status, age, FMLA status, or any other factor determined to be unlawful by federal, state or local statutes.

Read Full Job Description
Apply now

Technology we use

  • Engineering
  • Product
  • Sales & Marketing
    • .NETLanguages
    • C#Languages
    • JavascriptLanguages
    • ReactLibraries
    • ReduxLibraries
    • ASP.NETFrameworks
    • ExpressFrameworks
    • Node.jsFrameworks
    • MySQLDatabases
    • DynamoDBDatabases
    • 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
More Jobs at Toast30 open jobs
All Jobs
Data + Analytics
Dev + Engineer
Project Mgmt
Project Mgmt
Project Mgmt
Data + Analytics