GTM Architect at Workleap - AI & RevOps Career

Position: GTM Architect at Workleap - AI & RevOps Career Growth
GTM Architect at Workleap - AI & Rev Ops Career Growth in Wilmington

This is a genuinely rare role sitting at the intersection of AI engineering, revenue operations, and go-to-market strategy — a trifecta that is commanding increasing market premiums in 2024–2025. "GTM Architect" or "GTM Engineer" titles are emerging as some of the fastest-growing roles in B2B SaaS, and early movers building this skillset are well-positioned.

Compensation context: The base range of CAD $110k–$140k (OTE up to $155k) is competitive for a senior IC role at a Canadian tech company, though it trails comparable US-based roles by 20–30%. The LTIP is a meaningful differentiator for a ~20-year-old profitable company.

• Agentic AI workflow design using LLMs, MCP connectors, and tools like n8n — highly transferable and in short supply.
• Signal-based GTM strategy (product-led growth meets AI-driven outbound) — a rapidly maturing discipline.
• SQL-backed revenue analytics tied directly to business outcomes (renewals, NRR, LTV).
• Cross-functional stakeholder management without a PM — high autonomy, high visibility.

Green flags: No bureaucratic PM layer, clear ownership of business metrics, and a company with 15,000+ paying customers providing real production data to work with. The take-home case study hiring process signals they want proven builders, not credential collectors.

Watch for: "We move fast" and "ambiguity doesn't slow you down" language suggests a high-intensity environment. This suits senior ICs but may be challenging if you prefer structured roadmaps.

Company Description

Workleap is a Montreal-based tech company, founded in 2006. We're builders at heart — we make simple products that actually matter to the people who use them. We have two product lines:
Workleap Agent , our newest solution built to make every manager more effective, and Share Gate , the world's leading solution for Microsoft 365 migration and governance. More than 15,000 companies worldwide trust us to do exactly that. We're intentional about who joins us. If you're the kind of person who gets excited by a hard problem and wants to help shape what comes next, there's a place for you here.

Your

Role

Share Gate's customers generate rich signals (product usage, support interactions, renewal dates), but those signals aren't yet connected into an engine that protects and grows the revenue we already have. As our GTM Architect, Expansion & Retention, you'll design, build and ship AI agents and agentic workflows that turn those signals into saved renewals and cross-sell pipeline. This is an embedded engineering role within GTM, not back-office ops: you'll apply the signal-based, agent-first approach we already use for new customer acquisition to the customers we already have.

Your impact:

• Protect renewals by building AI agents that continuously monitor renewal health and flag at‑risk accounts to Account Managers early, with context, recommended next steps and enough lead time to act.
• Grow revenue from existing customers by designing and running an agentic cross‑sell motion: score fit for our second product line, research each account, personalize outreach, qualify interest and route genuine intent to the right salesperson with the full context needed to close.
• Define the signals your agents need and partner with Revenue Systems, which builds and owns the data flow between product usage and the CRM. Validate the data with SQL before you act on it.
• Replace manual workflows with AI agents and reusable pipeline modules (not one-off automations) that Account Management and Sales can run and own on their own.
• Tune both motions by owning reporting on pipeline generated, conversion, renewal outcomes and revenue impact, and by running controlled experiments without…