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# GTM Engineering – ShareGate

AI Summary Workleap is seeking a GTM Architect to build AI-driven workflows that improve renewal retention and cross-sell outcomes for ShareGate customers. The role combines low-code automation, SQL validation, CRM design, and Python or TypeScript integrations to connect product, support, and renewal signals with Account Management and Sales actions. This embedded GTM engineering position owns reusable agentic pipeline modules, performance reporting, controlled experiments, and enablement materials for end users. Success requires strong LLM workflow design, commercial judgment in a subscription SaaS environment, and the ability to drive adoption without a dedicated project manager.[Apply for this job](#job-application)[View company](https://jobicy.com/company/workleap.md)ShareRemote from[Canada](https://jobicy.com/job-region/canada.md)SalaryCAD 110k–140k / yrDepartment[Software Engineering](https://jobicy.com/categories/engineering.md)EmploymentFull TimeExperienceSeniorPublished6 Nov 2026Apply before6 Dec 2026Listing views30Application actions2Application toolkit

## Make your next move.

Prepare your resume, explore your fit, and draft a cover letter for this opportunity.

Opportunity details

## About this role.

### 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](https://workleap.com/), our newest solution built to make every manager more effective, and [ShareGate](https://sharegate.com/), 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.

Most of this sounds like you? Apply.

### 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.

By applying, you confirm that you have read and agree to our [privacy policy](https://workleap.com/trust-center/privacy).

#LI-Remote

Show more

[Apply now >](https://jobicy.com/jobs/159410-gtm-engineering-sharegate.md)

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## Role DNA

A quick view of the complexity, pace, ownership and collaboration implied by the job description.

### Job Complexity

5/5EasyHard

### Pace & Pressure

5/5RelaxedFast-paced

### Autonomy Level

5/5GuidedFull ownership

### Communication Load

5/5IndependentCollaborative

AI insightThis is a senior, cross-functional build role requiring production-grade AI agent design alongside data, CRM, automation, and GTM expertise. The employee must operate through ambiguity, quantify commercial impact, and secure adoption from Sales and Account Management independently.

## Salary analysis

Estimated compensation compared with the broader CA market for similar roles.

Estimated job median (per year)Market rateC$125,000CA market range (per year)C$115k–C$145k0C$159.50k

AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. The employer discloses a CAD 110,000–140,000 base-salary range; the yearly cadence is inferred from the full-time Canadian professional-role context because no explicit pay period is stated. A reasonable estimated Canadian market range for this senior GTM engineering and AI automation role is CAD 115,000–145,000 annually, excluding OTE, long-term incentives, and benefits.

## Core skills

Skills and capabilities most closely associated with this opportunity.

[GTM engineering](https://jobicy.com/jobs?search_keywords=GTM%20engineering.md)[Revenue operations](https://jobicy.com/jobs?search_keywords=Revenue%20operations.md)[AI agent orchestration](https://jobicy.com/jobs?search_keywords=AI%20agent%20orchestration.md)[LLM workflow design](https://jobicy.com/jobs?search_keywords=LLM%20workflow%20design.md)[Low-code automation](https://jobicy.com/jobs?search_keywords=Low-code%20automation.md)[n8n](https://jobicy.com/jobs?search_keywords=n8n.md)[SQL](https://jobicy.com/jobs?search_keywords=SQL.md)[Python](https://jobicy.com/jobs?search_keywords=Python.md)[TypeScript](https://jobicy.com/jobs?search_keywords=TypeScript.md)[HubSpot CRM](https://jobicy.com/jobs?search_keywords=HubSpot%20CRM.md)[API integrations](https://jobicy.com/jobs?search_keywords=API%20integrations.md)[Customer retention](https://jobicy.com/jobs?search_keywords=Customer%20retention.md)[Cross-sell strategy](https://jobicy.com/jobs?search_keywords=Cross-sell%20strategy.md)[Pipeline analytics](https://jobicy.com/jobs?search_keywords=Pipeline%20analytics.md)[Experimentation](https://jobicy.com/jobs?search_keywords=Experimentation.md)

Sample interview questionsHow would you design an AI workflow to identify renewal-risk accounts and route useful actions to Account Managers?I would first define leading indicators from product usage, support activity, contract dates, and account history, then validate their reliability in SQL. I would create a scored risk model with explainable reasons, use an agent to synthesize account context and suggested next actions, and push structured alerts into HubSpot. I would measure precision, intervention adoption, renewal outcomes, and false-positive rates, then iterate on thresholds and prompts.

Describe how you decide whether a workflow should use an LLM agent instead of deterministic automation.

I use deterministic automation for stable, structured, high-volume decisions with clear rules. I use an LLM when unstructured context, research, summarization, prioritization, or personalized language creates meaningful leverage. For agentic workflows, I constrain tools and outputs, add evaluation criteria and human review where risk is material, and monitor quality continuously.

How would you build a cross-sell motion for customers who may fit a second product line?

I would define the ideal-fit attributes and combine them with product usage, firmographic, support, and relationship signals. A workflow would score and prioritize accounts, enrich each account with relevant context, generate personalized outreach hypotheses, and capture engagement and qualification outcomes in the CRM. I would route verified interest to the appropriate seller with the evidence, recommended messaging, and full account context.

What steps would you take to validate data before automating decisions from it?

I would map the source systems, definitions, ownership, refresh cadence, and join keys for each signal. Using SQL, I would check completeness, duplicates, freshness, outliers, and agreement with known records in the CRM. I would document assumptions, establish monitoring for data-quality failures, and avoid automating irreversible actions until the data has been validated against real outcomes.

How would you drive adoption of a new GTM automation among Sales and Account Management teams?

I would involve representative users early, design the workflow around their existing tools and decisions, and demonstrate concrete time savings or revenue impact. I would provide concise SOPs, enablement demos, feedback channels, and visible reporting on usage and outcomes. I would also iterate quickly on friction points so the automation becomes a trusted part of the team’s process rather than an extra task.

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