Senior Strategic Account Manager - Workleap

Workleap Inc.; Montreal (administrative region); Hybrid; CAD 100,000 - 120,000; Full time

Benefits offered by this job

LTIP

Health insurance

Telemedicine

Wellness budget

Remote work

Montreal office access

In-person gatherings

Claude access

Job summary

Workleap is seeking a Senior Account Manager in Canada to own a portfolio spanning mid-market to enterprise on the Workleap platform. You will protect revenue, drive expansion, and act as a strategic partner during a pricing migration across the entire book.

Join a structured AM/CSM team with two managers, cross-functional collaboration with Product, Finance, and Legal, and daily use of AI tools to prepare renewal strategies and strengthen relationships.

Qualifications

• 4+ years in SaaS account management or customer success for enterprise/upper mid-market
• Proven track record of meeting or exceeding NRR targets in complex books
• Executive stakeholder management with multi-threaded relationships
• Rigorous CRM discipline: live CRM
• Daily use of AI tools for meeting prep and research
• Bilingual French-English (written and spoken)
• Bonus: SaaS HR tech experience or familiarity with HR and C-suite buyers
• Bonus: experience navigating pricing migrations with customers

Responsibilities

• Own the most complex, highest-ARR accounts with quarterly plan development and stakeholder mapping
• Lead renewal negotiations and pricing migration conversations with procurement and legal
• Drive expansion using ROI data and initiate six-month expansion conversations
• Handle executive escalations with clear save plans and alignment
• Use AI daily to prepare for conversations and synthesize account data
• Maintain a live CRM with next steps on expansion and mitigation plans
• Model strong account management habits for junior team members

Skills

SaaS AM

Executive mgmt

NRR targets

CRM discipline

AI tools usage

Bilingual FR-EN

Pricing migration

Tools

CRM software

ChatGPT

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

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.

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.