Senior Director, Commercial Operations

Skillsoft Ireland Limited; Boston (MA); Hybrid; USD 215,000 - 235,000; Full time

Benefits offered by this job

Medical

Dental

Vision

Paid time off

Job summary

Skillsoft Ireland Limited is seeking a Senior Director, Commercial Operations to design and build the end‑to‑end commercial function—pricing, deal desk, contract negotiation, and RFP support—and to own and run the processes as a permanent part of the team.

Located in Boston, MA or on the East Coast with up to 20% travel, the role requires 12+ years in strategic transformation in SaaS/PaaS, leadership of a team, CPQ and pricing analytics expertise, and exceptional communication for executive

Qualifications

• 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.

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

Strategic transformation

Team leadership

Communication skills

Executive presentation

Analytical mindset

Education

MBA or advanced degree in quantitative or business field

Tools

CPQ systems

Contract lifecycle management

Pricing analytics

Job description

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.

Our Values

We are passionately committed to leadership, learning, and success. We embrace every opportunity to serve our customers and each other as: one team, open and respectful, curious, and agile.

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.

Additional Information

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection.As a government contractor subject to the Vietnam Era Veterans' Readjustment Assistance Act (VEVRAA), we request this information in order to measurethe effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categoriesis as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service‑connected disability.

A "recently separated veteran" means any veteran during the three‑year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Race

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey.Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiringprocess or thereafter. Any information that you do provide will be recorded and maintained in aconfidential file.

As set forth in Skillsoft’s Equal Employment Opportunity policy,we do not discriminate on the basis of any protected group status under any applicable law.

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey.Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiringprocess or thereafter. Any information that you do provide will be recorded and maintained in aconfidential file.

As set forth in Skillsoft’s Equal Employment Opportunity policy,we do not discriminate on the basis of any protected group status under any applicable law.

Skillsoft has my consent to collect, store, and process my data for the purpose of considering me for employment, and for up to 365 days thereafter.

About Skillsoft

Skillsoft (NYSE: SKIL) delivers transformative learning experiences that propel organizations and people to grow together. The Company partners with enterprise organizations and serves a global community of learners to prepare today’s employees for tomorrow’s economy. With Skillsoft, customers gain access to blended, multimodal learning experiences that do more than build skills, they grow a more capable, adaptive, and engaged workforce. Through a portfolio of best-in-class content, a platform that is personalized and connected to customer needs, world‑class tech and a broad ecosystem of partners, Skillsoft drives continuous growth and performance for employees and their organizations by overcoming critical skill gaps and unlocking human potential. Learn more at www.skillsoft.com