Sales Manager, New Business — Workleap

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 We’re looking for a Sales Manager to lead the new business team at Workleap. Reporting directly to the VP of Revenue, you’ll own one of the most important bets we’re making right now: bringing the Workleap Agent to market and building the team, systems, and culture to do it well. This isn’t a quota-management role. It’s a coaching, strategy, and execution role — you’ll lead from the front, set the standard for what great looks like, and make sure the field and the go-to-market strategy are always in sync. Your impact: Drive quarterly new business ARR targets by building the conditions for every AE on your team to perform at their best — not just tracking numbers, but actively removing blockers and sharpening the play; Coach a team of AEs across SMB, Mid-Market, and Enterprise segments through consistent pipeline reviews, call shadowing, and growth conversations that actually move people forward; Own the sales strategy end to end — define it, implement it, and iterate on it to improve conversion rates and deal velocity; Deliver reliable, data-driven forecasts to the VP of Revenue so leadership can make clear decisions with confidence; Build a tight feedback loop between sales, marketing, and product so what the field hears directly shapes how Workleap evolves; Integrate AI tools into the team’s daily workflow — from Gong for call intelligence to Claude for prep and enablement — to raise the ceiling on what a lean team can do. Your team You’ll lead a team of 5 Account Executives covering English and French Canadian markets across SMB through Enterprise. The timing is deliberate — Workleap made a calculated move away from being a suite of HR point solutions and went all-in on something bigger: an agentic HR platform that works alongside managers, not just sits in their stack. The Workleap Agent is that product, and your team is on the front lines of bringing that story to market for the first time. You’ll inherit a team with real wins, real pipeline, and real momentum — and the challenge is to turn that into a repeatable, scalable machine. What you’ll bring +2 years of sales leadership experience in B2B SaaS — HRtech or adjacent is a strong asset; A strong track record as an AE or in business development with consistent quota overachievement — you know what good looks like because you’ve lived it; A reputation as a genuine sales coach who can lift a team’s capabilities fast, not just manage performance after the fact; Discipline around pipeline management and CRM forecasting — you work with data, not around it; Clear, direct communication that lands equally well with your team and at the leadership table; Comfort operating in a fast-moving environment where information is imperfect and priorities shift; Daily fluency with AI tools — Claude, Gong, HubSpot, Microsoft 365 — as real work accelerators, not experiments you’re still warming up to. Most of this sounds like you? Apply. What the job comes with 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. #LI-Remote