Vice President, Retail Sales

1 month ago
Full-time
Executive
Sales and Business Development
Toast

Toast

Toast is an all-in-one platform for restaurants, offering tableside ordering, online ordering, and labor management to empower businesses in the food service industry.

Hotels, Restaurants & Leisure
1K-5K
Founded 2012

Description

  • Develop and execute the Retail division’s overarching sales strategy aligned to Toast’s corporate vision and financial targets.
  • Own strategy and performance of the XDR (sales development) function to generate a robust top-of-funnel pipeline and ensure seamless handoffs to field sales.
  • Optimize outbound and prospecting strategies and set XDR goals to maximize pipeline quality.
  • Drive rapid organizational scaling through hiring plans, partnership with talent teams, and identification of talent gaps during hyper-growth.
  • Optimize sales processes, methodologies, and tools (e.g., Salesforce, Chorus) to improve team efficiency and tactical execution.
  • Lead and directly manage Area VPs and Regional VPs to ensure consistent execution, coaching, and performance across regions.
  • Partner cross-functionally with R&D, Product Marketing, Sales Enablement, Onboarding, HR, Sales Operations, and Finance to align resources and go-to-market plans.
  • Leverage data and analytics to track performance, design targeted programs, and measure impact on business outcomes.
  • Oversee talent identification and succession planning to build a pipeline of future sales leaders and maintain high employee engagement (eNPS).

Requirements

  • 10+ years of B2B technology sales leadership experience with a proven track record managing managers of managers (AVPs/RVPs) in high-growth environments.
  • Significant experience building and scaling sales organizations in emerging markets or for new product categories.
  • Deep understanding of the retail or point-of-sale (POS) industry is highly preferred.
  • Proven ability to lead both high-level strategic planning and frontline sales execution.
  • Experience overseeing sales development/XDR functions and optimizing outbound prospecting and lead handoffs.
  • Expert proficiency in sales funnel management and using data to inform complex business decisions.
  • Track record of hiring and scaling teams rapidly during hyper-growth.
  • Exceptional communication, interpersonal, and inspirational leadership skills to build a results-driven, inclusive culture.
  • MBA preferred but not required.

Benefits

  • Total Targeted Cash range of $377,000–$603,000 USD (includes base, commission, benefits, and equity if eligible).
  • Role qualifies for uncapped commissions.
  • Competitive compensation and benefits programs with a total rewards philosophy focused on flexibility and employee wellbeing.
  • Hybrid work model with remote-friendly (#LI-REMOTE) arrangements and regional flexibility.
  • Access to AI tools and learning opportunities across disciplines to accelerate work and professional growth.
  • Commitment to inclusive hiring, reasonable accommodations for candidates with disabilities, and a diverse workplace culture.

Interested in this position?

Apply directly on the company website

Apply Now

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