Senior Director, Sales Enablement

Summary

Join Toast as a Senior Director, US Sales Enablement and lead the strategy and execution of sales enablement across various sales teams. You will oversee the Enablement team, design and implement enablement programs aligned with Toast's new Sandler sales methodology, and drive improvements in seller productivity. This role requires close collaboration with GTM leadership and cross-functional teams. You will develop and execute enablement strategies, lead and inspire the Enablement team, design and refine sales processes, leverage data for decision-making, and optimize sales tools. The position demands extensive experience in sales enablement and leadership within a SaaS or technology company, proven expertise in sales methodologies, and strong leadership and collaborative skills. Toast offers competitive compensation and benefits.

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

Responsibilities

• 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

Benefits

• 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