Skillsoft
Direct Greenhouse career site

Senior Director, Commercial Operations

Pay
$215,000 – $235,000 per year
Location
Remote (US)
Listed
Today

About the role

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

Pay and benefits

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.

More About Skillsoft

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.

About Skillsoft

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.

Read the original posting

From Skillsoft's careers page, first listed on Rolev.ai on November 12, 2026. Rolev.ai is not the employer.

How Rolev.ai helps with this application

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Common questions

What is the salary for the Senior Director, Commercial Operations role at Skillsoft?

The Senior Director, Commercial Operations posting at Skillsoft states compensation of $215,000 – $235,000 per year. Final pay may depend on location, experience, and interview evaluation on Skillsoft's official career site.

Where is the Senior Director, Commercial Operations job at Skillsoft located?

Yes, this Senior Director, Commercial Operations opening at Skillsoft is listed as Remote (US). Always check Skillsoft's application page for specific state eligibility or relocation policies.

How do I apply for the Senior Director, Commercial Operations position at Skillsoft?

This listing links directly to Skillsoft's Greenhouse application page. You can apply directly on Skillsoft's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Greenhouse application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.