VP, International Sales

Reports to: COO, International

About the Role
Toast is building an all-in-one cloud-based restaurant management platform. As we expand beyond the US, our international regions - Canada, EMEA, APAC, and LATAM - represent both a proven playbook to execute against and a set of markets that require a sales organization built from the ground up rather than copied wholesale from the US motion.

This role owns Sales, Sales Enablement, Sales Operations, and Onboarding across every region outside the US. This person needs to be able to sit across the table from a customer, work a complex deal to close, and get into the details of pricing and contracting - while also building the scalable infrastructure (enablement, operations, onboarding) that lets each region ramp current reps and hit number without depending on any one person's local knowledge.

What We Are Solving For

A senior sales leader who stays in the field - meets with customers directly, works and closes strategic and complex deals personally, and gets into the details of pricing, contracting, and competitive positioning rather than managing purely through others.

Someone who can build a globally distributed, scalable, repeatable sales motion with meaningfully different buyer behavior, competitive dynamics, currencies, and channel structures - not a leader who tries to force the US playbook onto every region unchanged.

A builder who has a playbook for standing up and driving high performing Sales Enablement, Sales Operations, and Onboarding as accelerators (not afterthoughts to direct sales), so new markets and new hires ramp quickly and consistently

Someone comfortable prioritizing ruthlessly across a wide portfolio - four regions, multiple languages, and markets at very different stages of maturity, from established (Canada, UK) to nascent

Responsibilities
Sales Leadership & Execution

Own the international sales number across Canada, EMEA, APAC, and LATAM, in close partnership with the COO, International





Personally engage with customers and prospects on strategic and complex deals - get in the room, negotiate, and close

Build and manage pipeline and forecasting cadence across all four regions; report accurately and consistently to the COO, International and ELT

Identify and resolve deal blockers directly, including pricing, competitive threats, and contract terms

Sales Enablement & Operations

Build scalable sales enablement infrastructure - training, playbooks, competitive intelligence, and tooling - tailored to each market's buyer and competitive landscape

Own sales operations across regions: territory design, quota setting, compensation plan design (in partnership with Finance and People), CRM hygiene, and reporting

Design and implement onboarding programs for new sales hires across all regions, with clear ramp-time and productivity benchmarks

Organization & Talent

Build and scale a sales organization across Canada, EMEA, APAC, and LATAM - hiring, structuring, and developing in-market sales leaders

Balance centralized best practices with the market-specific flexibility each region needs (language, buyer behavior, competitive dynamics, channel structure)

Travel regularly to each region to build relationships with team members, customers, and partners, represent Toast Internationally.

Cross-Functional Partnership

Partner closely with the COO, International on market entry sequencing and go-to-market model selection (direct/resale/channel) by market

Partner with Product on roadmap needs specific to international sales motions and with Marketing on regional demand generation

Partner with Finance on forecasting, pricing, and deal economics across currencies and markets

Requirements

Location: must live in Canada or the United Kingdom

Proven experience as a senior sales leader who has personally carried and exceeded a quota - not solely a leader of other quota-carriers

Experience building and scaling a sales organization across multiple international markets,

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📌 VP, International Sales (Manitoba)
🏢 WinsAbove
📍 Manitoba