Regional Vice President, Retail Field Sales - Pacific Coast

Toast•Los Angeles, CA

18h•Remote

About The Position

Toast Retail is a new and significant investment by Toast, launched in January 2025, aiming to revolutionize the retail industry with an all-in-one operating system for retailers. The initial focus is on acquiring key customers in the CPG space. Toast for Retail helps businesses streamline operations, optimize inventory, enhance customer experience, and drive growth. The Regional Vice President will lead a field sales team, overseeing District Sales Managers and Territory Account Executives across California, the Southwest, and Hawaii. This role involves driving performance against sales, employee engagement, and customer satisfaction goals. Key responsibilities include hiring, onboarding, coaching, and developing the team. The leader will need a deep understanding of omni-channel journeys and a data-first approach to demand generation and pipeline management to meet aggressive retail growth targets.

Requirements

5+ years of B2B technology sales leadership experience.
At least 3 years directly leading managers of quota-carrying sales teams.
Proven ability to operate effectively at both strategic and hands-on execution levels.
Clear perspective on sales methodologies and their application in dynamic environments.
Commitment to frontline enablement, with attention to detail and a passion for team success.
Experience in building and scaling sales in emerging markets or with new product categories.
Strong collaborator with a track record of fostering a results-driven, inclusive, and team-oriented culture.
Proficiency in sales funnel management and applying data to drive operational excellence.

Nice To Haves

Background in the retail or point-of-sale (POS) industry is a plus.

Responsibilities

Develop and lead a comprehensive Retail Marketing strategy to drive acquisition, engagement, and revenue across retail customers.
Ensure all retail marketing strategies align with revenue goals, owning full-funnel performance from lead generation to conversion and retention in partnership with Sales, Product, and Finance.
Build the operating model, analytics capabilities, measurement frameworks, and data infrastructure to optimize funnel performance and forecast demand and outcomes.
Champion best practices in multi-channel marketing (digital advertising, organic content, email, field/partner programs, local campaigns) to reach and convert retail business owners.
Partner as a core member of the Retail Leadership Team to architect unified go-to-market programs, collaborating across Product & Engineering, Sales & Customer Success to embed marketing strategies throughout the merchant lifecycle.
Partner with the core Marketing organization to leverage global scale in brand identity, joint funnels, and shared data infrastructure, collaborating on performance marketing best practices for vertical efficiency and full-funnel optimization.