Life at Toast Blog

Better Together: How Mentorship Sets the Sales Team Up for Success


Jordan F.

Onboarding Sales Enablement Manager


When I started as an account executive in 2018 and became a mentee, it helped me learn the day to day of the position, systems, and daily tools. Shadowing meetings and understanding the best way to organize were at the top of my list. Then when I became a mentor, I was able to help others ramp faster based on my learning curve and help them understand what to expect while holding an open space to troubleshoot and grow. Now as an onboarding sales enablement manager, I get to help take our mentee/mentor relationships to the next level to ensure we’re doing all we can to best support our sales team members grow their skills and thrive at Toast. 

The Sales Mentor Program is a four month program for account executives that starts in their third week at Toast, after they have participated in Family Meal (our company wide onboarding experience) and Sales Bootcamp. Bootcamp is a two week sales training program provided by our Onboarding Sales Enablement team which is followed by support from the coaching team for the remainder of the ramping period. Prior to Bootcamp, district managers will match their new reps with a tenured, successful rep on their team or region to provide support. The mentor will drive the outcomes by building on strength, expertise, sharing career stories and key lessons learned while being a role model and asking for feedback. During our monthly “Mentoring the Mentor” sessions, we review the weekly one-on-one requirements, give additional resources and guidelines, hear from current and past mentors, and give updates on ramping reps’ goals. Mentors and mentees regularly continue their relationship past the four month period. 


We continue to refine how we enhance the experience from this program but some of the key benefits we’ve found after launching this program are:

  • Reducing the feeling of isolation in a remote environment
  • Assisting in setting and achieving goals
  • Formalizing connections that allow for social learning throughout the org

Another major benefit is that there is a financial bonus incentive for the new hire and the mentor. The bonus is tied to the mentee’s performance during this ramping period of this program. This ties right in to our #OneTeam value at Toast.

Hear more about the value of this program from a few of our Sales team members:

“Being a mentee helped not only build up my knowledge of the system and processes, but also my confidence in representing the system. My mentor's tenure with the company was such an amazing benefit. Any situation I ran into she has worked through before and is able to offer guidance.”

Margaret H.

Territory Account Executive 

“My mentor helped me navigate obstacles while working remotely. This was integral in my success. My mentor also taught me how adhering to a process and finding success come with time and consistency.”

Zoravar G.

Territory Account Executive

“Being a mentor has helped get a different point of view of the sales process. It has also helped me learn how to approach my coaching conversations differently based on personalities or goals.”

Juan M.

Team Lead - Field Sales

“Being a mentor has broadened my perspective that my communication and influence creates ripple effects across time and more individuals than just my mentee. I learned more about myself and what it really means to coach someone to reach their aspirations.”

Michelle C. 

Regional Vice President

“As a mentor, I can always be there to lend a hand or be a shoulder for the newer reps going through exactly what I went through in the beginning. I truly believe I am able to help them become more successful by handing down the tricks of the trade that I have learned throughout my time here.”

Stacee G.

Senior Account Executive


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