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.
Senior Director, Commercial Operations
Skillsoft is redesigning its end-to-end commercial processes and building an integrated commercial function covering pricing, deal desk, contract negotiation, and RFP support. As Senior Director, Commercial Operations, you will have the opportunity to join at the design stage; build the new commercial processes, analytics, and systems, then own and run them as a permanent member of the function. This is a hands-on build-then-operate role in the commercial organization, not a rotational transformation position.
Key Responsibilities:
- Assess end-to-end commercial processes, policies, and resources across the deal lifecycle, and design and document the future state, including pricing, discount, and conversion analytics.
- Define enabling systems requirements and support implementation across CPQ, approval workflows, and contract lifecycle, with AI as a radical enabler of process speed and productivity.
- Support pilots in live operations and refine designs based on results; may flex across adjacent initiatives early before moving full-time into the function.
- Responsible for owning and running core commercial processes within the function as process owner and subject-matter expert, managing exception handling and driving continuous improvement in speed and quality.
- Deliver ongoing pricing, discount, and deal data evaluations that inform commercial decisions and policy.
Skills & Qualifications to Be Successful:
- 12+ years of a strategic transformation experience with and analytical process, technology and business experience in SaaS or PaaS environments
- 2+ years leading a team and driving outcomes
- Hands-on process & technology business experience
- Robust knowledge of the Commercial-space with exposure to deal desk, contracts, pricing systems, as well as Configure, Price, Quote (CPQ)
- Strong modeling and analytics ability with change execution in live operations
- Polished written and verbal communication & collaboration skills with Executive Presentation skills
- Location: Boston, MA or East Coast with the ability to travel up to 20%
Preferred Skills & Experience
- MBA or Advanced Degree in a quantitative or business field
Target base salary range for this job requisition is anticipated to be approximately $215,000 - $235,000 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 uses AI-enabled tools to screen applications. Recruitment and hiring decisions are made by Skillsoft personnel and are not based solely on automated processing.
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 of strategic transformation experience with analytical, process, technology, and business experience in SaaS or PaaS environments
- 2+ years leading a team and driving outcomes
- Hands-on process and technology business experience
- Knowledge of commercial operations, including deal desk, contracts, pricing systems, and Configure Price Quote (CPQ)
- Strong modeling and analytics ability with change execution in live operations
- Strong written, verbal, collaboration, and executive presentation skills
- Ability to work in Boston, Massachusetts or on the East Coast
- MBA or advanced degree in a quantitative or business field
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 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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Skillsoft Offices
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Employees work remotely.
