Director, Mid Market Sales

United States of America

Job Description / Skills Required

Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love.

As the Director of MidMarket Sales, you will be building and coaching a team of Territory Account Executives that is transforming the way restaurants operate. You will be fanatical about coaching, developing and working closely with your sales team to help them understand a restaurant’s unique needs and develop a customized solution that helps their business thrive. 

About this roll* (Responsibilities) 

  • Carries the overall MidMarket sales quota 
  • Directly manages 5-6 Account Executives
  • Coaches & develops reps (through the established coaching plan documents)
  • Conducts efficient discovery meetings, live demos and crafting a solution that best meets the prospect’s needs
  • Support GVP/VP/SVP, Producing content and/or conducting portions of team calls, overseeing ongoing competitions, performing metric reviews, product training refresh/compliance, etc.
  • Spend time in the field helping Account Executives interest in Toast through ride-alongs, trade shows, and partnerships
  • Partner with teams across the business to ensure that expectations set during the sales process are met in delivery
  • Participate in the creation and execution of OKR related projects/initiatives
  • Leverage Salesforce to manage all sales activities


  • Coaching: Increase per ramped rep productivity
  • Communication: Improve understanding and adoption of critical initiatives, new offerings, as well as process and policy changes

Do you have the right ingredients*? (Requirements)

  • Combination of SaaS, Digital Marketing and Restaurant Industry Technology experience is required
  • 5-7+ years of relevant successful technology or professional services sales leadership experience at the C-level is required
  • Previous success in selling/leading sales efforts in environments with 6 to 12 month sales cycles
    • Proven sales skills in complex deal development, financial structuring, negotiations and closing with both new and existing clients
    • Previous experience managing the MEDDPICC, or similar, Sales methodology
  • Comfortable with process driven sales, reporting and tracking
  • Strong written and presentation based communication skills are required

Goal:  A leadership role with the primary goals of:

  • Developing your team to be high performing account executives
  • Identifying areas to improve processes, efficiencies throughout the Sales Cycle
  • Contributing to the advancement of all company initiatives, including DEI and all efforts to make Toast a word class Sales organization
  • Deliver the growth required to cement Toast as the vertical leader

Our Spread of Total Rewards

  • Unlimited Vacation
  • Sabbatical opportunity after five years
  • Professional Development Reimbursement Program
  • Commitment to Employee Wellness through resources such as a quarterly Wellness Stipend
  • Various peer and company recognition programs 
  • 401(k) and matching
  • Medical, Dental, & Vision Coverage
  • Mental Health Benefits
  • Subsidized backup childcare

*Bread puns encouraged but not required

We are Toasters

Diversity, Equity, and Inclusion is Baked into our Recipe for Success.

At Toast our employees are our secret ingredient. When they are powered to succeed, Toast succeeds.

The restaurant industry is one of the most diverse industries. We embrace and are excited by this diversity, believing that only through authenticity, inclusivity, high standards of respect and trust, and leading with humility will we be able to achieve our goals.

Baking inclusive principles into our company and diversity into our design provides equitable opportunities for all and enhances our ability to be first in class in all aspects of our industry.

Bready* to make a change? Apply today!

Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact [email protected].

For roles based in the United States:  As part of our commitment to the health and safety of our employees and their families, all individuals entering our US workspaces are required to provide proof of full vaccination against COVID-19 unless they have an approved medical or religious accommodation.