Sales Manager, New Business - Workleap

Company Description

Workleap is a Montreal-based tech company, founded in 2006. 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.

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 bringing the Workleap Agent to market and building the team, systems, and culture to do it well. This is a coaching, strategy, and execution role — you'll lead from the front, set the standard, and ensure the field and go-to-market strategy are aligned.

Your Impact:

• Drive quarterly new business ARR targets by building the conditions for every Account Executive (AE) to perform at their best, 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.
• Own the sales strategy end-to-end: define it, implement it, and iterate to improve conversion rates and deal velocity.
• Deliver reliable, data-driven forecasts to the VP of Revenue.
• Build a tight feedback loop between sales, marketing, and product.
• Integrate AI tools into the team's daily workflow—from Gong for call intelligence to Claude for prep and enablement.

Your Team

You'll lead a team of 5 Account Executives covering English and French Canadian markets across SMB through Enterprise. You'll inherit a team with real wins, pipeline, and momentum, with the challenge 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.
• A reputation as a genuine sales coach who can lift a team's capabilities fast.
• Discipline around pipeline management and CRM forecasting.
• Clear, direct communication skills.
• Comfort operating in a fast-moving environment with shifting priorities.
• Daily fluency with AI tools (Claude, Gong, HubSpot, Microsoft 365).

What the Job Comes With

• LTIP program, sharing 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.

How We Hire

Transparency is how we hire. The process includes a first call with a recruiter, a virtual interview with the hiring manager, a take-home case study, and a meeting with future colleagues to discuss it together.