We believe conversations will become the #1 way to shop.

At Gorgias, we’re building the platform that makes this real: a unified AI agent that sells, supports, and re-engages customers across the entire journey. Conversational Commerce is the future of ecommerce, and we’re leading that shift.

Our mission is to turn every interaction between a brand and its customers into a relationship: personal, seamless, and intelligent. By combining deep product expertise with the latest in AI, we’re making shopping feel more natural, human, and connected than ever before.

To win, we focus relentlessly on:

Quality:

conversations that feel authentic and on-brand.

Experience:

effortless shopping from chat to checkout.

Re-engagement:

personal, 1-1 dialogue instead of noisy marketing.

The opportunity is massive. As AI reshapes how people buy, Gorgias is building the foundation for the next decade of ecommerce, where every brand has its own intelligent agent and every customer feels understood.

Join us to make Conversational Commerce real.

About the Team Technical Solutions is the technical arm of Gorgias for our biggest merchants. The team covers the full enterprise lifecycle with 2 groups of Solutions Engineers: pre-sales Solutions Engineers, who partner with Account Executives to win complex Enterprise and Named deals, and Forward Deployed Engineers, who embed with our highest-value merchants after signature to deploy, integrate and scale our AI Agent. The team is distributed across North America, Europe and Latin America, and works hand in hand with Sales, Implementation, Customer Success, Product, Engineering and Finance.

Our biggest merchants bring complex tech stacks, custom order systems, multi-store setups and high expectations.



This team closes the gap between what they need and what works in production.

About the Role As our

Head of Technical Solutions , you will own the technical side of Gorgias for enterprise merchants, from the first demo to production. You will lead both the pre-sales and post-sales Solutions Engineering teams, make sure what we sell is what we can deliver, and turn forward deployed engineering into a scalable, profitable professional services business. You will own the P&L; of professional services, including pricing and gross margin.

This is a player-coach role reporting to the COO. You will scope deals, build prototypes, review code and sit in customer Slack channels next to your team, especially in your first months. The perfect fit is an AI builder and a commercial operator in one person: someone who has already led a comparable transformation, turns constraints into an execution plan, and is as credible with an enterprise COO as with their engineers.

What You’ll Do Lead and build the team

Lead, hire and coach a distributed team of pre-sales Solutions Engineers and Forward Deployed Engineers. Set a high bar for technical quality, customer judgment and speed, and give direct, useful feedback.

Stay hands-on. Lead discovery on key deals, build proofs of concept, review architectures and code,



and jump into debugging when a deployment is at risk.

Build the operating cadence: OKRs, capacity planning, engagement reviews and dashboards that show the team’s impact on revenue, automation and retention.

Win enterprise deals (pre-sales)

Own the technical win on Enterprise and Named deals. Partner with Account Executives on discovery, technical qualification, tailored demos, proofs of concept and solution design.

Help close. Build mutual close plans with Sales, map technical stakeholders and success criteria, and handle technical objections, security reviews, integration reviews and RFP responses.

Drive enterprise win rate and deal velocity. Make Solutions Engineer coverage on every qualifying deal, pipeline hygiene and win and loss reviews standard practice.

Make sure what we sell is what we can deliver. Timelines are realistic, scope is written down before signature, and trials or proofs of concept that behave like production deployments get the same rigor.

Deploy and scale our AI Agent (post-sales)

Define and productize standard deployment offers: packaged Forward Deployed Engineering engagements with transparent scope, hours, deliverables and success measures, so most merchants can buy a standard package instead of a bespoke project.

Lead custom deployments for our most complex merchants: custom actions, integrations with order, warehouse and ERP systems, multi-store rollouts and bespoke builds, designed against real customer APIs.

Own the handoff from pre-sales to post-sales. Once a deal is scoped, one technical owner carries the action plan and delivery, with clear rules of engagement with Implementation Managers and CSMs so the customer never se

📌 Head of Technical Solutions (Winnipeg)
🏢 Gorgias
📍 Winnipeg