Senior Director, U.S. Sales Enablement

Now, more than ever, the Toast team is committed to our customers. We’re taking steps to help restaurants navigate these unprecedented times with technology, resources, and community. Our focus is on building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. And because our technology is purpose-built for restaurants, by restaurant people, restaurants can trust that we’ll deliver on their needs for today while investing in experiences that will power their restaurant of the future.

About this roll*  (Responsibilities) 

Toast is looking for a Senior Director, US Sales Enablement to lead the strategy and execution of sales enablement across our New Business, Growth, Mid Market, Enterprise, and XDR teams. This critical role will oversee Toast’s Enablement team and play a pivotal part in empowering our sales organization to achieve its ambitious goals.

Reporting to the SVP of US Sales, the Senior Director will be responsible for designing and implementing enablement programs that align with Toast’s new Sandler sales methodology, driving measurable improvements in seller productivity and performance. This role will partner closely with GTM leadership to ensure cross-functional alignment and seamless execution of enablement initiatives.

What You’ll Do

• Develop and execute enablement strategies to drive adoption of Toast’s new Sandler sales methodology, ensuring consistent integration across diverse sales teams.
• Lead and inspire the Enablement team, fostering a high-performance culture through coaching, hiring, and operational excellence.
• Design and refine sales processes, methodologies, and messaging in partnership with GTM leaders to support scalable growth.
• Leverage data to inform decisions, track progress, and continuously optimize enablement programs for measurable impact.
• Collaborate cross-functionally with Product Marketing, Sales Leadership, HR, Sales Operations, and Finance to ensure alignment and seamless execution of sales enablement initiatives.
• Optimize sales tools and technologies like Salesforce, Chorus, and Salesloft to enhance seller productivity and streamline workflows.
• Continuously evaluate and improve performance by identifying gaps, designing targeted training, and driving consistent execution across the sales organization.

Do you have the right ingredients*? (Requirements)  

• 10+ years of experience in senior sales enablement or leadership roles within a SaaS or technology company.
• Proven expertise in sales methodologies such as Sandler, SPIN, Challenger, or MEDDPICC, with a demonstrated ability to drive adoption and success.
• Experience leading enablement initiatives for diverse sales organizations, including New Business, Growth, and SMB markets.
• Data-driven mindset with a track record of leveraging analytics to inform decisions and measure impact.
• Strong familiarity with sales tools and systems (e.g., Salesforce, Gong, HubSpot) to optimize seller productivity.
• Exceptional leadership skills with experience in building and managing high-performing teams through coaching and operational excellence.
• A collaborative approach with a proven ability to work cross-functionally with marketing, sales, operations, and HR teams.

Our Spread* of Total Rewards

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.

*Bread puns encouraged but not required

#DNI

The estimated Total Targeted Cash compensation range for this role is listed below. Total Targeted Cash for this role consists of a base salary, commission, plus the eligibility for equity and/or other benefits. This role qualifies for uncapped commissions. The starting salary will be determined based on skills, experience, and geographic location.

Total Targeted Cash$214,000—$342,000 USD

 

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