Senior Strategic Account Manager - Workleap

Workleap Inc.; United States; Hybrid; USD 100,000 - 120,000; Full time

Benefits offered by this job

LTIP program

RRSP + health insurance + telemedicine

Flexible vacation policy

Remote work with Montreal office

In-person gatherings twice a year

Claude access

Job summary

Workleap Inc. in Montreal seeks a Senior Account Manager to own a portfolio from mid-market to enterprise. You’ll protect revenue, drive expansion, and act as a strategic partner during a pricing migration.

You will join a structured AM/CSM team, collaborate with Product, Finance, and Legal, and leverage CRM and AI tools daily to prep for conversations and renewal strategies.

Qualifications

• 4+ years in SaaS account management or customer success at enterprise or upper mid-market.
• Proven track record of meeting or exceeding NRR targets in complex books.
• Executive stakeholder management with multi-threaded relationships.
• Fluent French-English (written and spoken).

Responsibilities

• Own the most complex, highest-ARR accounts with quarterly plans and multi-threaded relationships.
• Lead renewal negotiations and pricing migrations with procurement and legal.
• Drive expansion using ROI and usage metrics to articulate value.
• Handle executive escalations with clear save plans and risk mitigation.
• Maintain a live CRM with next steps on expansion and at-risk accounts.

Skills

SaaS account mgmt

Executive stakeholder mgmt

CRM discipline

AI tools usage

French-English bilingual

Pricing migration

HR tech familiarity

Tools

Claude

ChatGPT

Job description

Company Descriptionthe company 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: the company 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 rolethe company'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 the company 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 the company'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 Senior Account Manager - Enterprise.

What drives us

At the company, 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.

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