Portfolio Jobs

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

Toast International is building its upmarket business across the UK & Ireland, Canada, and Australia, focused on restaurant groups with 16 to 500 locations. We're hiring a solutions leader to own the technical side of every International deal over 15 locations. Your demos and labs are where our deals are won or lost. You'll start as a player-coach, carrying deals yourself, and you'll build the International upmarket solutions team as the business grows.

About this role:

• • Run demos that win the room. Build every demo from discovery. Show a 40-site group their own menu, their own workflows and the systems they already run, in their market's version of the product. Tailor it to each person in the buying group, from the head of ops to the IT lead to finance. Leave each of them with a reason to champion Toast.
  • Run labs that end in a decision. Agree success criteria with the customer before the lab starts. Build and maintain the lab environment, track every issue, drive escalations and root cause analysis, and close the lab with a clear yes or no. No lab ends without an agreed next step.
  • Own the technical outcome through go-live. The deal isn't won until the customer is live and it matches what we sold. Stay involved through procurement and handoff.
  • Architect the solution. Design how Toast fits into a multi-location group's existing stack:
  • ERP, payroll and HR (e.g. Workday)
  • Inventory, loyalty, gift card processors and kiosks
  • Delivery and custom integrations
  • Network and hardware
  • Multi-entity and franchise structures, and data migration

  All of it within what's actually available, and what payments rules allow, in each market.

  • Lead security, IT and compliance reviews. Own vendor security questionnaires, PCI scoping conversations and the technical sections of RFPs.
  • Speak product's language. Write BRDs that product and engineering can act on: the problem, the customer's own words, workarounds tried, what's at stake across the segment (not just one account), and options with tradeoffs. Turn one customer's ask into a case for the platform.
  • Present the roadmap with credibility. Walk executive and IT audiences through what exists, what's coming and what isn't, without overpromising. Keep their trust when the answer is "not yet."
  • Sell outcomes, not features. Partner with sales to build the business case. Translate technical fit into the outcomes the economic buyer cares about, such as labor, speed of service and revenue. When a buyer is weighing a feature gap, help them see it against the full value of the platform, and make sure their IT team feels heard along the way.
  • Engineer workarounds, and know when to hold the line. Design and document solutions to complex gaps, and judge when a workaround creates debt we'll pay for at go-live.
  • Build real relationships outside the sales thread. Become the trusted counterpart to the customer's IT lead, head of operations and systems owners, relationships that hold up on their own merit.
  • Hand off cleanly. Give onboarding and implementation a clear record of what was promised, what was configured and why, so delivery matches the sale.
  • Build the function. Set the engagement model for when and how AEs bring you in, qualify technical fit early and disqualify fast, and build reusable assets: demo environments for each market, reference architectures, an RFP library and BRD standards.
  • Partner across Solutions. Work closely with the International SMB Solutions team on clear lanes, shared tools and cross-coverage.
  • Grow the team. Help define, hire and develop the International upmarket solutions team as the business scales.
  • Own your own leverage. Continuously find the repetitive parts of the role (RFP answers, security questionnaires, discovery notes, demo resets) and systematically get them off your plate.
  • Close the loop on what's broken. Feed product gaps, lost-deal reasons and market differences back to product and sales leadership, so the next deal is easier than the last.

Do you have the right ingredients:

• An elite demo and lab track record. You've run tailored demos for multi-stakeholder buying committees and taken complex labs or pilots to a signed decision. In the interview, you'll run a demo for us and walk us through a lab you ran end to end.
• You build and maintain your own environments. Demo data, lab configurations and resets are your job, done fast and adapted for each market.
• 7+ years in solutions architecture, solutions engineering or technical consulting, with at least 4 supporting mid-market or enterprise deals with 6 to 12+ month cycles and buying committees.
• Experience in hospitality, retail or payments technology serving multi-location operators.
• You've taken complex deals through lab or pilot to go-live. You can walk us through one end to end, including what went wrong and what you changed.
• Integration fluency: REST APIs, webhooks, authentication and data flows. You can read API docs and sketch an architecture on a whiteboard. Coding isn't required, but you can test your own assumptions.
• Security and compliance fluency: PCI DSS scope, and privacy regimes such as UK GDPR, PIPEDA and the Australian Privacy Act. You're comfortable owning a security review.
• Writing that product teams act on. Bring a sanitized requirements doc, solution design or BRD to the interview.
• Executive presence with C-suite and IT leaders, including delivering "no" and keeping the relationship.
• You've mentored or led SEs, or built a presales process from scratch, and you want to build a team.
• International experience across more than one market or regulatory regime. Willing to travel across the UK & Ireland, Canada and Australia (30%+).
• Comfort working in build mode, where territory definition, process and tooling are actively being shaped and you're expected to have an opinion on them.

Special Sauce (non-essential skills, nice to have):

• Hands-on experience with enterprise POS or hospitality platforms in these markets
• ERP, HR or workforce management integration experience
• MEDDPICC

What success looks like in year one

• Every 16+ location deal gets a tailored demo, and every lab has agreed success criteria and ends in a decision.
• Deals we win go live on the timeline we agreed. No stalls, no churn, no post-sale surprises.
• AEs know exactly when and how to bring you in, and technical fit is settled early in the cycle, not in week ten.
• Product changes a decision because of a BRD you wrote.
• A clear plan for the next upmarket solutions hire.

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy
We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.