Job description
Company Description
Workleap is a Montreal-based tech company on a mission to make work simpler.
Since 2006, we’ve been building game-changing products that tackle HR and IT’s biggest challenges.
Workleap operates two distinct product lines:
- The Workleap Platform, an AI-powered HR solution designed to drive team performance and boost employee engagement.
- ShareGate, the leading Microsoft 365 migration and governance solution, trusted by IT professionals worldwide for its unmatched simplicity.
Today, more than 20,000 companies rely on Workleap products to grow, lead, and operate with confidence.
We’re builders at heart, with a clear purpose: to craft the simplest products that deliver exceptional value for our customers. Period.
Job Description
So, what will your new role look like?
As the Sales Enablement Manager – Workleap Platform , you will play a pivotal role in driving revenue growth by empowering our Sales Development Representatives (SDRs), Business Development Representatives (BDRs), Account Executives (AEs), Account Managers (AMs), and Customer Success Managers (CSMs) to win, upsell, and retain clients. You will design and implement enablement strategies that enhance our revenue teams, improve sales efficiency, and increase customer value. Your leadership in competitive insights will directly impact win rates and customer retention, driving Workleap’s growth.
Responsibilities:
- Develop and execute targeted enablement programs that enhance selling skills, product knowledge, and customer engagement for SDRs, BDRs, AEs, AMs, and CSMs.
- Maintain deep, ongoing insight into sales funnel constraints, churn drivers, product capabilities, and our ideal customer profile through tools like Hubspot, Gong, and strategic collaboration across Product, Sales, and Marketing.
- Lead competitive intelligence initiatives, leveraging Crayon and partnering with Product Marketing and Product Management to deliver clear, actionable resources that improve sales effectiveness and win rates.
- Own and continuously refine all sales enablement materials for the Workleap platform, alongside the design team, ensuring they’re engaging, actionable, and easily accessible.
- Provide ongoing coaching and guidance to Sales managers on enablement programs to drive adoption and maximize revenue impact.
- Define and track KPIs to assess the impact of enablement programs on win rates, asset utilization, training adoption, and customer retention.
- Support the onboarding of new Sales hires by providing relevant enablement materials and collaborating with Sales leaders to embed key knowledge and skills into onboarding plans.
A typical week?
- Align with the Sales Director on bottlenecks within the sales funnel.
- Review call data to spot recurring messaging misalignment.
- Review updates in Crayon to track competitor positioning, pricing changes, or feature launches.
- Deliver a presentation to the Sales team on how to leverage a new feature to address a common objection.
- Update reporting on utilization metrics of key assets (e.g., pitch decks, battlecards).
What does your future team look like?
You will report to the Director of Marketing, Workleap Platform, alongside one Senior Product Marketing Manager. You will work most closely with Sales (Business Development Representatives, Account Executives, Account Managers, and Customer Success Managers), Marketing (Growth and Brand), and Product (Product Management).
What are the next challenges awaiting your team?
- Scaling with limited resources: As the sole Sales Enablement Manager supporting the Workleap Platform, your ability to autonomously prioritize effectively will be essential to focus on the highest-impact initiatives.
- Keeping pace with product evolution: With frequent product updates, staying current and translating that into enablement materials will be a constant necessity.
- Improving competitive readiness: As the competitive landscape intensifies, we’ll need to continuously refine our battlecards, talk tracks, and positioning to help Sales reps win against more established players.
Qualifications
- 3+ years of experience in enablement, sales training, product marketing, or related revenue-driving roles, ideally within SaaS or technology-focused organizations;
- Proven expertise in building strong relationships with revenue leaders to create impactful enablement programs directly influencing sales performance and customer success outcomes;
- Deep familiarity with enablement best practices, methodologies, and tools;
- Demonstrated success working with sales, account management, and customer success teams, clearly understanding their unique enablement needs;
- Exceptional communication and interpersonal skills, capable of influencing and collaborating across all organizational levels;
- Strong results orientation with proven ability to manage multiple projects, priorities, and stakeholders simultaneously.
Who we are
We’re a team of curious minds and bold builders, brought together by a shared drive to make work simpler - and better - for everyone. Challenges fuel our creativity, fast-paced environments keep us sharp, and pushing boundaries is just part of how we operate. We believe the best ideas come from experimentation, rapid learning, and even the occasional discomfort - that’s where growth happens.
Since 2006, we’ve been rethinking the way teams work, blending creativity and tech to solve real problems in IT and HR. We move quickly, we learn constantly, and we always keep our customers at the center of what we do. If you’re a proactive thinker who takes ownership, loves to collaborate, and isn’t afraid to leap into the unknown - you’ll fit right in.
Additional Information
At Workleap, we build together, we trust each other, and we support each other in success or failure. You will be able to express yourself, evolve and develop your creativity in an environment that will adapt to your daily life and your needs.
We strive to create a healthy and inclusive work environment. This is everyone’s business.
Our Candidate Experience Flow at Workleap:
Phone Screen - Virtual Interview using Microsoft Teams - Work Sample - Job Offer
We are looking forward to getting to know you!
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