Full-Time

Sales Enablement Manager

Workleap Platform

Posted on 8/9/2025

Workleap

Workleap

201-500 employees

AI talent management platform for HR

No salary listed

Remote in Canada

Remote

Category
Sales & Account Management
Required Skills
Hubspot
Requirements
  • 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.
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.

Workleap provides an AI-powered talent management platform designed to improve the employee experience in hybrid work settings. It combines performance management with compensation management (added after acquiring Barley) to connect how well employees perform with how they are rewarded, creating a holistic view of talent development. The platform helps HR teams and business leaders streamline various parts of the employee lifecycle—from onboarding to performance reviews—through an integrated suite of tools that boost engagement and develop high performers. Compared with competitors, Workleap offers an all-in-one HR technology solution that ties performance directly to compensation, enabling data-driven decisions and easier talent development across the organization. The company’s goal is to help organizations optimize talent management, increase employee engagement, and improve retention by providing a unified, AI-assisted platform tailored for hybrid work environments.

Company Size

201-500

Company Stage

Growth Equity (Venture Capital)

Total Funding

$91.7M

Headquarters

Montreal, Canada

Founded

2006

Simplify Jobs

Simplify's Take

What believers are saying

  • HR tech market grows to $81.7B by 2030 at 13.2% CAGR for AI platforms.
  • Peter Dougherty as CRO scales global sales with Lightspeed experience.
  • Fall 2024 launch empowers HR with engagement and growth features.

What critics are saying

  • Slack launches native HR analytics, eroding Workleap's integration edge.
  • BambooHR captures SMB share, driving Workleap customer churn.
  • Barley founders' cultural clashes delay compensation integration past October 2025.

What makes Workleap unique

  • Workleap integrates Slack AI agent for real-time team performance insights.
  • Barley acquisition unifies performance and compensation management seamlessly.
  • Pingboard adds industry-leading org charts for hybrid team visualization.

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Benefits

Remote Work Options

Flexible Work Hours

Wellness Program

Growth & Insights and Company News

Headcount

6 month growth

3%

1 year growth

1%

2 year growth

4%
PR Newswire
Feb 18th, 2026
Workleap launches AI agent for people managers in partnership with Slack

Workleap has launched a Human Capital agent built in partnership with Slack, using Slack's Real-Time Search API and Model Context Protocol. The agent provides people managers with real-time visibility into team performance, engagement and coaching moments by analysing Slack conversations alongside Workleap's existing HR data. The integration allows managers to access team signals from Slack channels and messages, combined with performance goals, engagement insights and historical review data. Slack admins control access permissions, with Workleap only viewing what individual users can already see. The Montreal-based company says the integration enables more accurate performance reviews, sharper engagement insights and faster access to workplace information. The feature is rolling out to all Workleap customers through February 2026, with plans for future AI-assisted actions within Slack workflows.

PR Newswire
Feb 9th, 2026
Workleap names Peter Dougherty as chief revenue officer to scale global expansion

Workleap, a Montreal-based tech company, has appointed Peter Dougherty as Chief Revenue Officer to lead its next phase of global expansion. Dougherty brings over 15 years of SaaS scaling experience, most recently serving as President of Spreedly, where he led a go-to-market reset. Previously, Dougherty spent more than a decade at Lightspeed Commerce, holding senior executive roles with P&L responsibility for approximately $350 million in annual revenue and overseeing over 1,000 employees globally. At Workleap, he will align sales, marketing and customer success teams across the company's two product lines: the Workleap Platform and ShareGate. Founded in 2006, Workleap serves more than 20,000 companies with its HR and IT solutions. The appointment follows last year's addition of CFO François Deschamps.

BetaKit
Jul 7th, 2025
Workleap Acquires Barley for $5.4M CAD

Workleap, a Montréal-based HR platform, has acquired Toronto's compensation planning software Barley to add compensation management features. Barley's six-person team, including founders Jafar Owainati and Billy Mainguy, will join Workleap. Barley launched in 2023 after raising $5.4 million CAD. Workleap, which rebranded in June 2023, plans to integrate Barley by October and will launch Workleap AI soon to analyze employee data.

PR Newswire
Nov 25th, 2024
Workleap Fall Launch: Empowering Hr Leaders With New Features For Employee Growth And Engagement

MONTRÉAL, Nov. 25, 2024 /PRNewswire/ -- Workleap, a leading Canadian software company behind products that empower 20,000 companies in more than 100 countries to build better employee experiences, announces its fall platform release introducing new solutions and integrated features into an all-in-one simple-to-use platform. This release marks a new milestone in Workleap's ongoing commitment to transform the employee experience by empowering HR leaders to drive organizational performance and achieve business goals. Workleap's comprehensive platform helps HR lead organizations to thrive in the modern setting of hybrid, remote, and distributed work environments. The consolidated solution for understanding employee engagement, driving performance, and developing employees is the best add-on to your existing HRIS and HR technology, allowing companies to add simple experiences across the employee lifecycle. Bringing these functions together in one platform, Workleap enables HR professionals to create a more responsive, agile and employee-centric work environment

PR Newswire
Dec 6th, 2023
Workleap acquires US-based Pingboard, an employee experience SaaS company recognized for its industry-leading Org Chart and Employee Directory capabilities

/PRNewswire/ -- Workleap, a leading software company behind products that improve the employee experience for 20,000 companies in more than 100 countries, has...

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