Vice President, Sales Enablement 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?

There is a close, symbiotic relationship between sales development and our overall GTM model. Our model is one that is rooted in data and optimization, therefore, having a keen understanding of the sales rep experience, culture, incentives, selling methodologies, teaching/learning styles, growth factors and leadership development all contribute to the frameworks and systems that we use to build, train, develop and measure our team. 

As the Vice President of Sales Enablement, you will act as the CEO of Toast’s Sales Enablement organization. You will drive global training, enablement and competency development programs for all sales functions across the GTM organization. Key elements include the strategic vision, definition, alignment, and execution of a high-quality and high-impact enablement portfolio. Said simply, you are equal parts strategist and operator, you value the insights that data can provide and are driven by building and developing world class teams.

About this roll*:


  • Own the overall learning journey and experience of every sales function across the sales organization. This includes the on-boarding and continuing education of BDRs, AEs, first line managers, sales leadership and sales enablement teams. 
  • Define the global sales enablement vision as well as the delivery and roll-out approaches of supporting solutions. 
  • Leverage business acumen, selling and leadership experience to improve and iterate on sales motions, processes, management techniques and learning paths to drive sales productivity and eNPS. 


  • World class team builder and talent developer 
  • Provide thought leadership and innovation in enablement and training to help strengthen and improve a continuous learning culture
  • Align with business and operations stakeholders across all levels of the organization to gain executive endorsement and commitment for defined initiatives

Operational Excellence

  • Leverage data and optimization techniques to deliver a world class ramping and continuing education experience for all sales functions while also supporting new product growth
  • Relentless focus on overall execution, content delivery and measurement
  • Measure and monitor the impact of the sales enablement organization
  • Work closely with cross-functional teams to build and execute new product deployment strategies. 

Do you have the right ingredients*?

  • 10+ years of software or SMB sales experience in a fast-paced environment including complex products and competitive environments within a structured, process oriented sales motion. 
  • Self-starter with an analytical and collaborative orientation; can think strategically and drive operational excellence
  • Prior experience selling into SMB a plus
  • Prior experience selling sophisticated software in a highly competitive environment where product, competitive and end user knowledge meet to provide a pathway to success. 
  • Demonstrated strong leadership and interpersonal skills and ability to build and motivate a large, high performing sales enablement team
  • Excellent planning skills combined with high reliability and say:do ratio. 
  • Excellent communication skills, including dealing with executives and senior management
  • MBA is a plus

*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

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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