Sales Trainer at Toast

| Greater Boston Area
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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 focus of this position is to cultivate, develop and train a team of elite-performance Sales Associates. These teams are instrumental in managing our inbound leads and creating pipeline to fuel both our Inside Sale Representative and our Account Executive team. 

You will own enablement, training and delivery for our Sales Associate teams out of our Boston HQ. You will also collaborate closely with leadership across Sales Enablement, Sales Leadership, Marketing and Operations to execute a clear, global sales strategy to drive our growth. 

We are looking for a talented coach and trainer, with high social intelligence and the ability to motivate and develop a team of sales associates. You must be able to hold individuals accountable for hitting targets (past management experience is key) and be able to coach reps to a training plan to ultimately help facilitate deals that enter our system from the inbound marketing funnel. This role will work closely with marketing as the leads are entirely inbound, coaching reps to help win deals for the perspective AE/ISR through early stage qualification and discovery. 

The ability to provide feedback to reps and coach to a selling methodology to improve close rate is critical, as well as a high level of energy and excellent communication skills. You should be a team player with the ability to balance a competitive, fast-paced sales team with a respectful, healthy and fun work environment. 

About this roll*:

  • Deliver training and onboarding for a team of Toast SA’s build a culture of continued success and goal achievement through talent management, coaching, and training
  • Energize, motivate and manage and ramp large teams of junior sales associates, building a bench of future Toast Account Executives 
  • Develop plans, strategies and processes for acquiring business and achieving the sales goals
  • Partner with sales, marketing, operations, and enablement to build relevant content and educational programs for SA teams and managers 
  • Roll up your sleeves and deliver programs that will win more business! 

Do you have the right ingredients*

  • 2+ years of sales management experience, previous experience selling restaurant POS technology and/or restaurant management experience a plus
  • 2+years training/enablement experience 
  • Self-motivated with proven track record at achieving or exceeding goals and quota
  • Demonstrated experience with building and successfully scaling sales strategies and supporting processes
  • Proficiency with working with Salesforce data and the curiosity to find actionable insights
  • Strong ability to coach and mentor and motivate teams of salespeople through deals, as well as foster career development
  • Excellent presentation and communication skills written and verbal
  • Superb analytical and problem-solving skills

*Bread puns encouraged but not required

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Technology we use

  • Engineering
    • JavaLanguages
    • JavascriptLanguages
    • jQueryLibraries
    • ReactLibraries
    • AngularjsLibraries
    • ES6Libraries


Toast is headquartered in the heart of Fenway. Catch a Sox game, grab a bite, and stroll through one of the trendiest neighborhoods in Boston.
Toast values candidates with varied backgrounds — and these 3 employees prove it

An Insider's view of Toast

What’s the vibe like in the office?

Our office has both a relaxed but productive vibe. You'll see people with their heads down working, but you'll also see people hanging out and collaborating in open spaces. There's a good balance between work and play. When I'm not heads down coding, you'll find me playing guitar or hanging out in the Toast Pub.

Gabe Gonzalez

Associate Technical Sourcer, Previously: Software Engineer

How has your career grown since starting at the company?

I began as an Implementation Engineer, moved into instructional design, and now I am in my dream role as a Product Manager. This is afforded because Toast fosters a culture where experts in their domains are eager to give you a masterclass in what they do – you only need to ask and be willing to learn. This is the best perk when working at Toast.

Sean Park

Product Manager

What are some things you learned at the company?

Where should I start? For hard skills, I’ve learned more than I ever thought I would about Excel and Salesforce. I’ve also learned what it looks like when a company not only talks the talk, but walks the walk. We’ve been able to execute on what we’ve set out to do because we are willing to try new things, make mistakes, and learn from them.


Payments Relationship Manager

What are Toast Perks + Benefits

Toast Benefits Overview

Toast strives to provide competitive compensation and benefits programs that help to attract, retain and motivate the best and brightest people in our industry. Our total reward package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet our employees’ changing needs.

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)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
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
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Company Outings
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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