Solutions Lead, International Upmarket

Toast • Boston, MA

6d • Hybrid

About The Position

Toast is hiring a Solutions Lead to own the technical side of International upmarket deals involving restaurant groups with 16 to 500 locations across the UK & Ireland, Canada, and Australia. The role leads technical engagement for International deals over 15 locations, from discovery and tailored demonstrations through labs, procurement, handoff, and go-live. The Solutions Lead partners with sales to connect technical fit to business outcomes and builds trusted relationships with customer executives, IT leaders, operations leaders, and systems owners.

The role architects solutions that fit customers’ existing technology stacks and the capabilities and payments rules available in each market. It leads security, IT, and compliance reviews, including vendor questionnaires, PCI scoping, and technical RFP responses. It also documents customer needs for product and engineering, presents the roadmap accurately, designs and documents workarounds where appropriate, and ensures onboarding and implementation teams understand what was promised and configured.

As the International upmarket solutions function grows, the Solutions Lead will establish engagement practices, reusable assets, and collaboration with the International SMB Solutions team; help define, hire, and develop the team; and identify repetitive work to streamline. The role also feeds product gaps, lost-deal reasons, and market differences back to product and sales leadership. The position operates in a build-mode environment where territory definitions, processes, and tools are still taking shape, and requires travel across the UK & Ireland, Canada, and Australia (30%+).

Toast describes its work model as hybrid. The company provides AI tools across disciplines and describes a total rewards package that includes compensation and benefits, with further benefits information available on its careers site.

Requirements

• At least 7 years in solutions architecture, solutions engineering, or technical consulting.
• At least 4 years supporting mid-market or enterprise deals with 6–12+ month sales cycles and buying committees.
• A strong track record of tailored demonstrations for multi-stakeholder buying committees and complex labs or pilots that lead to signed decisions.
• Ability to build and maintain demo environments, data, lab configurations, and resets, adapting them for different markets.
• Experience in hospitality, retail, or payments technology serving multi-location operators.
• Experience taking complex deals through lab or pilot to go-live, including the ability to explain what went wrong and what was changed.
• Fluency with REST APIs, webhooks, authentication, and data flows; ability to read API documentation, sketch an architecture, and test assumptions. Coding is not required.
• Knowledge of PCI DSS scope and privacy regimes such as UK GDPR, PIPEDA, and the Australian Privacy Act, and comfort owning security reviews.
• Ability to provide a sanitized requirements document, solution design, or BRD as an interview example.
• Executive presence with C-suite and IT leaders, including the ability to communicate a negative decision while maintaining the relationship.
• International experience across more than one market or regulatory regime.
• Willingness to travel across the UK & Ireland, Canada, and Australia (30%+).
• Comfort working in build mode, with evolving territory definitions, processes, and tools, and willingness to contribute opinions on them.
• Ability to run a demonstration during the interview and walk through an end-to-end lab.

Nice To Haves

• Hands-on experience with enterprise POS or hospitality platforms in the relevant markets.
• Experience integrating ERP, HR, or workforce management systems.
• MEDDPICC experience.

Responsibilities

• Run tailored demonstrations based on discovery, customer workflows, menus, systems, market, and the needs of different buying-group stakeholders.
• Define success criteria with customers before labs; build and maintain lab environments, track issues, drive escalations and root-cause analysis, and close labs with a decision and agreed next step.
• Own technical outcomes through go-live, remaining involved through procurement and handoff and ensuring delivery matches what was sold.
• Architect solutions that fit multi-location customers’ existing technology stacks and the products and payment rules available in each market.
• Lead security, IT, and compliance reviews, including vendor security questionnaires, PCI scoping conversations, and technical sections of RFPs.
• Write actionable business requirements documentation for product and engineering, including customer problems, customer language, workarounds, segment-level impact, and options with tradeoffs.
• Present the product roadmap credibly to executive and IT audiences without overpromising.
• Partner with sales to build business cases and translate technical fit into outcomes such as labor, speed of service, and revenue.
• Design and document workarounds for complex product gaps, and assess when a workaround would create unacceptable debt by go-live.
• Build trusted relationships with customer IT leads, operations leaders, and systems owners.
• Provide onboarding and implementation teams with a clear record of promises, configurations, and rationale for a clean handoff.
• Establish the engagement model for when and how account executives involve Solutions, qualify technical fit early, and disqualify unsuitable deals quickly.
• Build reusable assets, including market-specific demo environments, reference architectures, an RFP library, and BRD standards.
• Coordinate with the International SMB Solutions team on clear lanes, shared tools, and cross-coverage.
• Help define, hire, and develop the International upmarket solutions team as the business scales.
• Identify repetitive work, such as RFP responses, security questionnaires, discovery notes, and demo resets, and systematically reduce it.
• Report product gaps, lost-deal reasons, and market differences to product and sales leadership.
• Travel across the UK & Ireland, Canada, and Australia, with travel of 30% or more.

Benefits

• Toast describes a total rewards package that includes benefits and is intended to support a healthy lifestyle and flexibility; specific benefits are not listed in the posting, and the company directs candidates to its benefits website for details.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed