---
title: 'Senior Strategic Account Manager - Workleap at Workleap - en'
canonical: 'https://feeny.ai/job/senior-strategic-account-manager-workleap-workleap-en-canada-9wk4t77zfscq'
type: 'job'
last_seen: '2026-10-12'
---

# Senior Strategic Account Manager - Workleap at Workleap - en

- **Company:** Workleap - en
- **Location:** Canada
- **Work type:** remote
- **Posted:** 2026-09-28
- **Last confirmed live:** 2026-10-12
- **Apply:** https://job-boards.greenhouse.io/workleap/jobs/5247152007

## 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](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

Workleap's post-sale revenue is scaling — and its most complex accounts need a senior owner who can match the stakes. As a Senior Account Manager, you'll own a portfolio spanning mid-market to enterprise on the Workleap platform: protecting revenue, driving expansion, and acting as a genuine strategic partner to customers. This role exists now because we're executing a pricing migration across the entire book — a commercially sensitive motion that demands executive credibility, sound judgment, and the ability to hold a hard conversation without losing the relationship.

Your impact:

- Own the most complex, highest-ARR accounts in the portfolio by building and maintaining quarterly account plans, mapping stakeholders proactively, and building multi-threaded relationships that survive org changes on the customer side;
- Lead complex renewal negotiations and pricing migration conversations with confidence — knowing when to hold the commercial line and when flexibility is the right call, including through procurement and legal;
- Drive expansion from demonstrated value: use usage data and outcome metrics to build an ROI story customers can articulate in their own words, and initiate expansion conversations at six months — not eleven;
- Handle executive escalations with composure by documenting clear save plans, flagging risk before it surfaces reactively, and keeping the internal team aligned when accounts go sideways;
- Use AI tools (Claude, ChatGPT, or equivalent) daily to prepare for customer conversations, synthesize account data, draft renewal strategies, and move faster across a complex book — a habit, not a checkbox;
- Raise the team's floor by modeling strong account management habits — how to run a quarterly plan, how to prep an executive QBR, how to navigate a tough objection — so that junior team members grow through proximity;
- Give leadership a reliable, real-time view of the portfolio by maintaining CRM as a live document, with documented next steps on expansion pipeline and active mitigation plans on at-risk accounts.

## Your team

You're joining a structured, systems-oriented AM/CSM team where autonomy is expected and operational rigor is non-negotiable. Two Customer Success Managers share the portfolio with you; cross-functional collaboration with Product, Finance, and Legal is part of the job on complex accounts. The team doesn't run on heroics or tribal knowledge — it runs on clear plans, a live CRM, and a predictable cadence. This year's challenge: execute the pricing migration across the full book, build executive multi-threading in accounts that are currently too single-threaded, and operate with more leverage without adding headcount. The senior person in this team sets the standard everyone else follows.

## What you'll bring

- 4+ years in SaaS account management or customer success, with direct experience on enterprise or upper mid-market accounts;
- Consistent track record of meeting or exceeding NRR targets in complex books, including renewals involving procurement and legal stakeholders;
- Proven executive stakeholder management — multi-threaded relationships, not just the day-to-day champion;
- Rigorous CRM discipline: you treat CRM as a live document, not a reporting obligation;
- Daily use of AI tools (Claude, ChatGPT, or equivalent) for meeting prep, account research, and synthesis — a genuine work habit, not something you're exploring;
- Bilingual French-English (written and spoken);
- Bonus: SaaS HR tech experience, or familiarity with HR, People Ops, and C-suite buyers;
- Bonus: experience navigating a pricing migration or major packaging change with existing customers.

Most of this sounds like you? Apply.

What the job comes with

- Base salary: $100k - $120k / OTE: $170k - $200k. 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.
- 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.

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

## About Workleap - en

## Company Overview
- **One-liner**: Workleap is an AI-powered talent management platform that brings engagement, performance, and compensation into one connected system for small to mid-sized businesses.
- **Entity Type**: Private (Growth stage, series not publicly disclosed)
- **Headquarters**: Montreal, Quebec, Canada
- **Founded**: 2006
- **Founders**: Simon De Baene, Guillaume Roy, Sébastien Leduc

## Core Business
- **Primary Industry**: Human Resources Technology (HR Tech), Employee Experience, Talent Management
- **Target Customers**: SMBs and growing businesses with small or generalist HR teams (B2B)
- **Mission**: "To make work simpler" and help HR leaders ignite employee potential and boost business results.

## Products & Services
- **[Workleap Platform](https://workleap.com/)**: An AI-powered HR suite that includes employee engagement surveys (Officevibe), performance reviews (Performance), and compensation management (Compensation). Designed as a unified system to replace fragmented HR tools.
- **[ShareGate](https://workleap.com/)**: A Microsoft 365 migration and governance solution for IT professionals, focused on simplicity and security. Operates as a separate product line under the Workleap umbrella.

## Market Standing
- **Valuation**: Not publicly disclosed.
- **Key Metrics**: 70,000+ leaders worldwide use Workleap; 20,000+ companies across the entire customer base; 375+ employees.
- **Notable Investors/Partners**: Not specifically listed. Investors are not publicly disclosed.
- **Growth Signals**: Significant customer growth (from "over 70,000 leaders" on the about page), investment in AI features (manager agent, survey summaries), and expansion of the ShareGate product line. The company has a remote-first talent model, hiring across Canada.

## Competitive Advantages
- **Purpose-built for Small HR Teams**: Workleap is designed specifically for smaller or generalist HR teams that lack the resources of enterprise HR departments, offering simple, high-adoption tools.
- **Unified AI Platform**: Combines engagement, performance, and compensation in one system, reducing the "DIY chaos" and clunky legacy tools common in HR tech.
- **High User Satisfaction**: Praised on G2 for fast implementation, ease of use, and high adoption rates.
- **Strong Market Position in M365 Ecosystem**: ShareGate is a leading tool for Microsoft 365 migration and governance, providing a strong, separate revenue stream and brand recognition among IT professionals.

## Strategic Focus
- **AI-First Management Agent**: Developing a proactive "manager agent" that drafts 1:1 agendas, surfaces signals, and helps drive performance reviews, making great management a repeatable process.
- **Product Expansion**: Continuing to unify engagement, performance, and compensation into a single, intelligent platform.
- **Remote-First Culture**: Committed to a remote-first policy (work from anywhere in Canada, up to 150 days abroad annually) with twice-yearly in-person gatherings, aiming to attract top talent without geographic constraints.
- **ShareGate Growth**: Scaling the ShareGate product line for M365 administration and security.

## Why Work Here
- **Remote-First & Flexibility**: Work from anywhere in Canada; work up to 150 days per year abroad. Office in Montreal is optional except for two annual in-person gatherings. [workleap.com](https://workleap.com/careers)
- **Comprehensive Benefits**: Group insurance, $1,300 health & wellness allowance, telemedicine & EFAP, financial support for new parents, home office allowance, internet reimbursement, and delivered meals. [workleap.com](https://workleap.com/careers)
- **Competitive Compensation**: Competitive salary, annual performance bonuses, 5% RRSP contribution, and referral bonuses. [workleap.com](https://workleap.com/careers)
- **Learning & Growth**: Training, conferences, language courses, and a focus on career development.
- **Engineering Culture**: Emphasis on written, asynchronous communication; proactive communication principles; and a strong focus on sustainable, high-performance collaboration. [workleap.com](https://workleap.com/careers)
- **Values-Driven**: "Walk the talk" on employee experience, with a strong internal focus on caring for own team before serving customers.

## Sources
1. [Workleap About Page](https://workleap.com/about)
2. [Workleap Careers Page](https://workleap.com/careers)
3. [Workleap Job Board (Greenhouse)](https://job-boards.greenhouse.io/workleap)
4. [Workleap Homepage](https://workleap.com/)
5. [Workleap LinkedIn](https://ca.linkedin.com/company/workleaphq)

## Other roles at Workleap - en

- [Senior Product Designer - ShareGate](https://feeny.ai/job/senior-product-designer-sharegate-workleap-en-canada-zamjye1qcg9b) — Canada
- [Partner Development Manager, EMEA - ShareGate](https://feeny.ai/job/partner-development-manager-emea-sharegate-workleap-en-canada-pafw3wqg18kr) — Canada
- [Marketing Analyst, Attribution - ShareGate](https://feeny.ai/job/marketing-analyst-attribution-sharegate-workleap-en-canada-e5a2pg1eyj26) — Canada
- [Sales Development Representative — ShareGate](https://feeny.ai/job/sales-development-representative-sharegate-workleap-en-canada-k031nqkcw2a4) — Canada