GTM Engineering - ShareGate

Pingboard; Canada; Hybrid; CAD 110,000 - 140,000; Full time

Benefits offered by this job

LTIP program

RRSP + health insurance + telemedicine

Annual wellness budget

Flexible vacation policy

Job summary

Workleap is seeking a GTM Architect, Expansion & Retention to design, build, and ship AI agents that protect renewals and drive cross-sell opportunities across existing customers. You will own signal design, data validation with SQL, and partner with Revenue Systems to connect product usage to CRM data.

You’ll work within GTM engineering to turn signals into scalable agent-first workflows and operational SOPs, enabling sales and account teams to own the processes.

Qualifications

• Background in RevOps or GTM engineering with automation

Responsibilities

• Design, build and ship AI agents and agentic workflows
• Protect renewals by monitoring renewal health
• Grow revenue with agentic cross-sell motions
• Define required signals and validate data with SQL
• Replace manual workflows with reusable AI pipelines
• Drive adoption with SOPs, demos and playbooks
• Own pipeline reporting and experimentation to improve revenue impact

Skills

RevOps/GTM operations

Low-code orchestration

AI/LLM workflows

SQL data validation

CRM (HubSpot)

Outbound/go-to-market

Cross-functional collaboration

Communication & demos

Tools

n8n

Make

Zapier

Python

TypeScript

SQL

HubSpot

Job description

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 ShareGate, 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

ShareGate’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 our 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 adding headcount.
• Drive adoption by turning everything you build into SOPs, demos and playbooks, so the team uses what you ship, not just appreciates it.

Your team

You’ll join a GTM engineering effort that already runs a signal-based, agent-first approach to new customer acquisition, and now points it at the customers we already have. The challenge: connect usage, support and renewal signals into agents that reduce the friction between signal and action. The tools, plays and channels will evolve; that mission won’t.

Our stack: low-code orchestration (n8n, Make, Zapier or similar), Python or TypeScript, SQL on our data warehouse, and our CRM (HubSpot).

What you’ll bring

• Background in RevOps, GTM/marketing operations, customer success operations or GTM engineering, with hands-on experience building automation;
• Hands-on experience with low-code orchestration (n8n, Make, Zapier or similar), plus working knowledge of Python or TypeScript for API integrations and data transformation;
• fluency with agentic tools and MCP connectors. Strong LLM workflow design (agent orchestration, tool use, evaluation), sound judgment on when AI adds leverage versus complexity, and a track record of shipping AI agents or LLM workflows to real users, not just prototypes;
• Working SQL to query and validate usage, support and renewal data., so you can build and trust the data behind your agents;
• CRM fluency (HubSpot a plus): enough to design agents on our data model and work with Revenue Systems on what you need;
• Understanding of subscription business metrics (renewal rate, net retention, customer lifetime value), and experience with or strong interest in outbound and signal-based go-to-market motions;
• The ability to work directly with Sales and Account Management, translate complex builds into plain language, and earn adoption through demos and handoff docs, without a PM to bridge the gap;
• Bonus: experience building AI-driven qualification or scoring systems; a B2B SaaS background with multiple product lines, ideally product-led or demo-led; published technical content that makes complex systems accessible.

What the job comes with

• Base salary: $110,000 - $140,000. This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate's region to align with local market conditions.
  
  • OTE: $120,000 - $155,000
• LTIP program, share in Workleap's long-term growth.
• RRSP + Family health insurance + telemedicine + annual wellness budget.
• Flexible vacation policy.
• Remote work, with access to our Montreal office.
• In-person gathering twice a year.
• Claude access, for everyone.

Note: The internal title for this role is GTM Architect.

What drives us

At Workleap, we build software that sits at the center of how people experience work, every day, at every level.

We move fast. Priorities shift, decisions get made with the information we have, and we iterate. If you thrive on intensity and ambiguity doesn't slow you down, you'll feel right at home.
We're builders. We do what it takes to move forward. AI is part of our toolkit. We use it to go faster and decide smarter, not to replace judgment.

If you want real impact and a place where your decisions matter, this is it.

How we hire

Transparency is how we hire — for you as much as for us.

Here's how it works: a first call with a recruiter, then a virtual interview with the hiring manager. You'll then complete a take-home case study, followed by a meet with future colleagues to discuss it together. Depending on the role, the process may vary slightly — your recruiter will walk you through it on your first call.

We use AI to support certain steps of the process, but every hiring decision remains human.

We can't wait to meet you.

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