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Skillsoft

Account Executive, Mid-Market

Remote

Canada

Mid level

Freelance

22-12-2025

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Skills

Communication Leadership Sales CRM Training Organization

Job Specifications

At Skillsoft, we propel organizations and people to grow together through transformative learning experiences. We believe every team member has the potential to be AMAZING. Join us in our quest to transform learning and help individuals unleash their edge.

Skillsoft is seeking an experienced, motivated, and successful Mid-Market Account Executive based in Canada to manage a portfolio of existing accounts. As a Mid-Market Account Executive, you will have the opportunity to be responsible for driving the success of our innovative products by building positive relationships with customers across Canada through digital and in-person communication.

Responsibilities

Exceed quarterly and annual targets for retention and growth, including quota, GRR, NRR, cross-sell, and upsell for assigned Canadian accounts
Consult with economic buyers, champions, and other stakeholders to understand each customer’s workforce upskilling and reskilling needs, business challenges, and key goals
Develop and execute account strategies aligned with customer workforce transformation needs, leveraging key customer and Canadian industry data points
Establish strong customer partnerships throughout the lifecycle (e.g., onboarding, adoption, expansion, renewal) and leverage internal resources appropriately to meet customer needs
Generate, update, and close renewal and expansion opportunities to ensure forecast accuracy and meet targets
Provide guidance, tools, resources, best practices, and business reviews across multiple Skillsoft products and solutions, ensuring each customer achieves measurable value, leading to renewal and expansion
Meet all CRM requirements including account health, account plans, close plans, activities, contacts, communications records, NPS, etc.
Manage renewal timelines effectively, including reassessing needs, issuing prompt and accurate quotes, responses, and proposals, and executing contracts in accordance with Canadian business practices

Skills Required

Here’s What We Are Searching For:

5+ years of professional experience in sales, account management, customer success, and/or customer renewals role with an Associate’s degree or commensurate experience
Proficient in Microsoft Office products and experience using tools to conduct virtual client meetings and presentations

Qualification Requirements

Demonstrated experience with renewal and upgrade forecasting, quoting, opportunity management, pricing, and contracting
Experience in managing customer relationships in a B2B environment with strong knowledge of Solution/Consultative Selling
Ability to prospect and manage a designated territory to maximize revenue growth
Solid understanding of the stages involved in a sales cycle and how to leverage each stage to advance the sale
Ability to work with cross-functional departments and roles to manage all aspects of the customer life cycle
Excellent ability in analyzing opportunities for cross-sell and upsell potential within existing books of business
Strong relationship-building and consulting skills and able to manage multiple relationships within an organization
Operates with a sense of urgency and has a positive, winning attitude
Excellent written / verbal communication skills to interact with all levels of leadership

Desirable Requirements

Sales experience in a technology-oriented field is highly preferred
Bachelor’s degree or professional Certifications
Working knowledge of Salesforce.com and familiarity with MEDDPIC

More About Skillsoft

Skillsoft delivers online learning, training, and talent solutions to help organizations unleash their edge. Leveraging immersive, engaging content, Skillsoft enables organizations to unlock the potential in their best assets – their people – and build teams with the skills they need for success. Empowering 36 million learners and counting, Skillsoft democratizes learning through an intelligent learning experience and a customized, learner-centric approach to skills development with resources for Leadership Development, Business Skills, Technology & Development, Digital Transformation, and Compliance.

Skillsoft is partner to thousands of leading global organizations, including many Fortune 500 companies. The company features three award-winning systems that support learning, performance and success: Skillsoft learning content, the Percipio intelligent learning experience platform, which offers measurable impact across the entire employee lifecycle. Learn more at www.skillsoft.com.

Thank you for taking the time to learn more about us.

If this opportunity intrigues you, we would love for you to apply!

NOTE TO EMPLOYMENT AGENCIES: We value the partnerships we have built with our preferred vendors. Skillsoft does not accept unsolicited resumes from employment agencies. All resumes submitted by employment agencies directly to any Skillsoft employee or hiring manager in any form without a signed Skillsoft Employment Agency Agreement on file and search engagement for that p

About the Company

Skillsoft (NYSE: SKIL) is a global leader in corporate digital learning, focused on transforming today’s workforce for tomorrow’s economy. The Company provides enterprise learning solutions designed to prepare organizations for the future of work, overcome critical skill gaps, drive demonstrable behavior change, and unlock the potential in their people. Skillsoft offers a comprehensive suite of premium, original, and authorized partner content, including one of the broadest and deepest libraries of leadership & business skil... Know more