Job Post

Field Sales Trainer
401 Park Drive Suite 801
Boston, MA 02215

About Toast:

Toast is a rapidly growing start-up building the first all-in-one restaurant management software platform. Toast’s Android tablet based system helps restaurants to operate more efficiently and to connect with their customer base in new and innovative ways.  

We’re growing quickly and have a customer base comprised of cafes, restaurants, bars and nightclubs across the country. We work hard and care about our customers’ success. As a startup, we move fast and have a lot of opportunity for career growth, so if you’re passionate about your work and want to be in a fun and growing industry, join us!

Toast is looking for a Field Sales Trainer who wants to be part of a team that is transforming the way restaurants operate. You will be helping Toast to build and develop a field sales team in either the Eastern or Western US.  We are looking for candidates that have a track record of demonstrated success building strong customer facing and service oriented sales teams with experience in the restaurant and hospitality industry.

The field sales trainer coordinates and delivers the sales training and coaching to reps in a real-world setting to increase the productivity of un-ramped reps as quickly as possible to achieve the company’s sales goals.


  • Provides training support and reinforcement of tools that will enhance the performance of the sales Account Executive.
  • Responsible for reviewing and evaluating the progress of new AE’s during the first 180 days of employment and provide them with the relevant feedback that will help them in improving their individual performance.
  • Responsible for certification of competencies in various sales stages; pitch, approach, baseline demonstration, discovery, custom demonstration and proposal/closing.
  • Perform ride-alongs with the reps to observe and coach their performance.
  • The field trainer should model what “good looks like”.
  • Should be able to clearly and effectively communicate the expectations to the sales reps and guide them on how to add value to their overall work and performance.
  • Track training progress to sales results for all participants and communicate to local and HQ sales management.
  • Ensure that every AE applies the concepts taught in the classroom to their field work.
  • Support District Manager and RVP’s in driving key metrics to support sales goals.
  • Improve or develop training materials, in conjunction with the Sales Enablement team, as needed.
  • Attend meetings and other duties as assigned.
  • Smooth out the on-boarding process, increasing morale
  • Travel, as needed, to training locations.

Essential Skills:

  • To ensure success as a field trainer, one should have exceptional communication skills and should be able to teach and coach in a clear, concise manner.
  • Must have the ability to motivate the trainees to achieve high levels of performance.
  • Must be able to answer and solve questions of the trainee.
  • Must be empathetic towards the trainee's needs as well as respect his/her views.
  • Must be able to develop innovative ideas to meet the changing training needs.


  • 3+ years of sales experience with complex software and hardware solutions, professional services and/or prior experience in the POS industry
  • Demonstrated sales performance and quota achievement
  • Experience developing sales staff, helping to prospecting, qualify, and closing new business is desired but not required.
  • Experience working with software technologies providing customer demos.
  • Strong business acumen, goal oriented, with a proven track record of achieving targets and objectives. 
  • Driven – possesses a strong desire to be successful, self-starter and a true initiator 
  • POS and hospitality experience is desired but not required.
  • Ability to travel 50% - 75% of the time.


Category: Sales & Business Development

See What It's Like To Work Here

An all-in-one restaurant technology platform with powerful tools to cut costs, drive revenue, and engage customers.

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