Senior Director, Sales Enablement

Summary

Join Toast as a Senior Director, US Sales Enablement and lead the strategy and execution of sales enablement across multiple sales teams. You will oversee the Enablement team, design and implement enablement programs aligned with the new Sandler sales methodology, and drive improvements in seller productivity. This role requires close collaboration with GTM leadership and cross-functional teams. You will leverage data to inform decisions and optimize enablement programs. The ideal candidate possesses extensive experience in sales enablement leadership within a SaaS or technology company and proven expertise in various sales methodologies. Toast offers a competitive compensation and benefits package.

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

• $178,000 — $285,000 USD (Pay Range)
• Cash compensation (overtime, bonus/commissions if eligible)
• Equity
• Benefits (details available at https://careers.toasttab.com/toast-benefits)