At Skillsoft, we believe skills fuel growth. Our mission is to empower every organization and every learner to turn constant change into continuous growth. As part of the team, your skills will help organizations understand what skills they have, what they need next, and how to apply them in ways that drive real performance and progress.
Skillsoft is seeking an experienced Sales Enablement Director to lead and execute scalable enablement programs that embed solution-selling behaviors across Sales, Business Development Reps, Customer Success and Partner teams. In this senior individual contributor role, you will have the opportunity to translate go-to-market strategy into programmatic enablement systems that improve discovery quality, value articulation, and deal execution at scale. This role drives impact through programs, systems, and manager enablement, not individual one-to-one seller coaching.
Key Responsibilities
- Establish and operationalize a consistent solution-selling standard focused on discovery, problem framing, stakeholder alignment, and value narratives.
- Lead end-to-end enablement programs from design through rollout, reinforcement, and iteration.
- Facilitate high-impact virtual sessions and development of courses including workshops, practice labs, and cohort-based learning.
- Design manager-led coaching and reinforcement models; no ongoing one-to-one seller coaching is required.
- Partner with Sales, BDR, Partners, Marketing, Product, and RevOps leaders to drive adoption.
- Track enablement effectiveness using adoption, proficiency, and leading performance indicators.
- Design certification and proficiency standards tied to observable behaviors, required skill gains, and business outcomes.
- Deliver executive-ready updates and recommendations.
Successful Attributes
- Consistent solution-selling behaviors across roles and regions
- Improved discovery quality and value-based deal execution
- High manager adoption of coaching and inspection models
- Enablement programs that scale without individual dependency
Required Skills & Experience
- 12+ years in Sales Enablement, Sales Effectiveness, or related fields
- Deep expertise in solution selling and consultative sales motions
- Proficient in
- Proven success leading program-based enablement initiatives
- Excellent communication skills with strong facilitation, program management, and stakeholder influencing skills
Preferred Experience
- Prior experience as a seller or sales-adjacent leader
- B2B Enterprise level enablement experience
- Familiarity with MEDDPICC, Force Management, or similar
Target base salary range for this job requisition is anticipated to be approximately $175,000- $200,000 annualized.
We also offer Enterprise benefits including but not limited to: medical, dental, vision, and paid time off
The company may modify salaries, salary ranges and/or Pay Plans from time to time as it deems necessary.
Skillsoft (NYSE: SKIL) is a global leader in AI-native skills management for the human + AI era. By unifying learning, real-time skills intelligence, and workforce insights, Skillsoft helps enterprises build their Skillforce™ — humans and AI working together to drive measurable business outcomes. Through personalized, interactive learning across leadership, technology, and compliance, Skillsoft enables organizations to close critical skill gaps and accelerate transformation. Skillsoft is trusted by thousands of organizations worldwide, including 60% of the Fortune 1000, and supports a global community of more than 105 million learners. Learn more at 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 position will be deemed unsolicited in nature. No fee will be paid in the event the candidate is subsequently hired as a result of the referral or through other means.
Skillsoft is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.
Skills Required
- 12+ years in Sales Enablement, Sales Effectiveness, or related fields
- Deep expertise in solution selling and consultative sales motions
- Proficient in leading program-based enablement initiatives
- Excellent communication skills
What the Team is Saying
Skillsoft Compensation & Benefits Highlights
How does Skillsoft ensure its pay and bonus plans are competitive?
Skillsoft’s compensation is supported by employee feedback around market-rate pay, bonus opportunities, benefits and total rewards. The company pairs compensation with flexibility, learning access and career development programs that employees describe as part of the overall value of working there.
- Market-aligned pay and bonus opportunities: Employees describe Skillsoft’s compensation as competitive, especially in roles with bonus potential. Employees surveyed on external review sites cite “salary plus bonus potential” as market rate, quarterly bonus access in sales and a strong compensation plan. A marketing employee cited “great pay,” while a solution design architect described Skillsoft as offering a “very competitive benefits and total compensation package.” (Comparably; Glassdoor)
- Performance-based rewards: Skillsoft employees point to bonus opportunities as part of the company’s rewards approach. A software engineer said their bonus was “excellent,” while sales employees cite quarterly bonus access as part of their compensation package.
- Benefits as part of total rewards: Skillsoft’s total rewards are also supported by employee comments about health benefits, insurance benefits, flexible time off, remote work and work-life balance. Employees surveyed on external review sites cite health benefits and insurance benefits as strengths, while other employees highlight great benefits, remote-first work and flexibility as part of the employee experience. (Comparably; Glassdoor)
- Growth and learning as added value: Skillsoft’s rewards approach is connected to its employee growth culture. The company provides employees with access to Percipio, Aspire Journeys, role-based pathways, instructor-led training, coaching and CAISY® simulations. Employees describe Skillsoft as a place with “continuous learning opportunities across the tech stack” and “no better place to learn and grow.”
● External signals:
○ Compensation and bonus: Employees on external review sites cite market-rate salary plus bonus potential, quarterly bonus access in sales, a strong compensation plan, “great pay” and an “excellent” bonus as compensation strengths. (Comparably; Glassdoor)
○ Total rewards: Employees on external review sites describe Skillsoft as offering “great benefits,” a “very competitive benefits and total compensation package” and benefits that support work-life balance, flexibility and employee growth. (Glassdoor)
○ Health and insurance: Employees on external review sites cite health benefits, insurance benefits and good health plans as strengths of Skillsoft’s employee experience. Mental health benefits are also listed among Skillsoft’s employee benefits. (Comparably)
○ Flexibility as a reward: Employees on external review sites connect rewards not only to pay, but also to remote work, flexible hours, flexible time off, independence and management that avoids micromanaging. (Glassdoor; Comparably)
Bottom line: Skillsoft supports competitive pay through market-rate compensation, bonus opportunities and a broader total rewards experience that includes benefits, flexibility and career development.
Skillsoft Insights
What We Do
Skillsoft (NYSE: SKIL) is a global leader in AI-native skills management for the human + AI era. By unifying learning, real-time skills intelligence, and workforce insights, Skillsoft helps enterprises build their Skillforce™ — humans and AI working together to drive measurable business outcomes. Through personalized, interactive learning across leadership, technology, and compliance, Skillsoft enables organizations to close critical skill gaps and accelerate transformation. Skillsoft is trusted by thousands of organizations worldwide, including 60% of the Fortune 1000, and supports a global community of more than 105 million learners. Learn more at skillsoft.com.
Why Work With Us
We help the world's biggest companies build better workforces — and we invest just as much in our own people. Learning new skills is a core part of your job here. We're fully remote, spread across the globe, and united by a shared belief that learning changes careers.
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Employees work remotely.
