Who you are

- 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

- 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, including standing up sales enablement and sales operations functions

- Demonstrated ability to close complex, strategic deals directly with customers

- Experience managing a distributed sales team across different languages, currencies, and buyer behaviors

- Experience designing onboarding and ramp programs that get new reps productive quickly

- Comfort operating in ambiguity across markets at different stages of maturity, from established to nascent

- Experience with SMB customers is preferred

- Restaurant, hospitality, or vertical SaaS experience preferred

- Willingness to travel across regions

- Based in Canada or the UK

- Sales-first: energized by being in the field with customers,



not removed from it

- Builder mentality: comfortable creating process and infrastructure from scratch, not just inheriting it

- Adaptable across markets: doesn't force a single playbook onto every region

- Solid operator: detail-oriented on pipeline, forecasting, and deal mechanics

- Collaborative cross-functional partner

- Humble and authentic

- Entrepreneurial spirit

What the job involves

- Reports to: COO, International

- 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 new reps and hit number without depending on any one person's local knowledge

- 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

- 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

- 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

- 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

Benefits

- Peer and company recognition programs

- Unlimited Vacation
- Sabbatical opportunity after five years

- Professional Development Reimbursement Program

- Commitment to Employee Wellness through resources such as a quarterly Wellness Stipend

- Various peer and company recognition programs

- 401(k) and matching

- Medical, Dental, & Vision Coverage

- Mental Health Benefits

- Subsidized backup childcare

📌 Vice President of International Sales (Canada)
🏢 Toast
📍 Canada