[All remote jobs](https://jobicy.com/jobs.md)[![Skillsoft logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/cb747022-221.png)](https://jobicy.com/company/skillsoft.md)[Skillsoft](https://jobicy.com/company/skillsoft.md) # Senior Director, Commercial Operations Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/skillsoft.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 215k–235k / yrDepartment[Product & Operations](https://jobicy.com/categories/management.md)EmploymentFull TimeExperienceDirectorPublished14 Oct 2026Apply before13 Nov 2026Listing views46Application actions1Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Skillsoft is hiring a Senior Director of Commercial Operations to design, implement, and permanently operate integrated commercial processes across pricing, deal desk, contract negotiation, and RFP support. The role will define future-state workflows, systems requirements, and analytics across the deal lifecycle, including CPQ, approval workflows, and contract lifecycle management. It requires extensive SaaS or PaaS transformation experience, strong commercial-process expertise, and the ability to lead teams through live operational change. The successful candidate will combine strategic process design with hands-on ownership of exception handling, pricing and discount analysis, and continuous operational improvement. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a senior build-and-operate leadership role requiring 12+ years of transformation, commercial operations, analytics, and SaaS/PaaS experience. The incumbent must establish new processes and systems while influencing executives and managing live operational change. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$225,000US market range (per year)$200k–$270k0$297k AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. The employer discloses a credible annualized base-salary range of $215,000 to $235,000 USD, with a midpoint of $225,000 per year. Estimated US market compensation for a senior commercial operations leader with SaaS transformation, CPQ, pricing, and deal-desk ownership is approximately $200,000 to $270,000 annually; this is an AI estimate rather than verified salary research. ## Core skills Skills and capabilities most closely associated with this opportunity. [Commercial operations](https://jobicy.com/jobs?search_keywords=Commercial%20operations.md)[SaaS transformation](https://jobicy.com/jobs?search_keywords=SaaS%20transformation.md)[CPQ](https://jobicy.com/jobs?search_keywords=CPQ.md)[Deal desk](https://jobicy.com/jobs?search_keywords=Deal%20desk.md)[Pricing strategy](https://jobicy.com/jobs?search_keywords=Pricing%20strategy.md)[Discount analytics](https://jobicy.com/jobs?search_keywords=Discount%20analytics.md)[Contract lifecycle management](https://jobicy.com/jobs?search_keywords=Contract%20lifecycle%20management.md)[Process design](https://jobicy.com/jobs?search_keywords=Process%20design.md)[Business process improvement](https://jobicy.com/jobs?search_keywords=Business%20process%20improvement.md)[Commercial analytics](https://jobicy.com/jobs?search_keywords=Commercial%20analytics.md)[Approval workflows](https://jobicy.com/jobs?search_keywords=Approval%20workflows.md)[Change management](https://jobicy.com/jobs?search_keywords=Change%20management.md)[Team leadership](https://jobicy.com/jobs?search_keywords=Team%20leadership.md)[Executive communication](https://jobicy.com/jobs?search_keywords=Executive%20communication.md) Sample interview questionsHow would you approach designing Skillsoft's future-state commercial operating model?I would begin by mapping the current deal lifecycle, decision rights, systems, policies, handoffs, cycle times, and exception patterns. I would prioritize the highest-value friction points, define target processes and governance, then launch measurable pilots before scaling the operating model. What metrics would you use to evaluate pricing and discount effectiveness? I would track realized price versus list price, discount depth and variance, approval rates, win rates by price band, renewal and conversion outcomes, margin impact, deal-cycle time, and exception frequency. The measures should be segmented by product, customer type, region, channel, and deal complexity so policies can be improved with evidence. Describe how you would implement CPQ without disrupting live sales operations. I would use phased implementation with clear process ownership, a prioritized requirements backlog, pilot user groups, data-quality controls, and defined success metrics. Change management would include practical training, sales feedback loops, support coverage, and a governance process for rapidly resolving configuration or policy issues. How do you balance commercial flexibility with process control and policy compliance? I establish clear standard paths for common transactions and transparent guardrails for discounts, terms, and approvals. For legitimate exceptions, I create risk-based escalation routes with documented rationale, turnaround targets, and analytics that identify recurring exceptions that should become standard policy. How have you led transformation teams through ambiguity and competing stakeholder priorities? I align leaders on the customer and business outcomes first, clarify decision ownership, and break the transformation into sequenced deliverables with visible metrics. I maintain regular executive communication, involve frontline users in pilots, and use operational results to resolve disagreements and sustain adoption. Opportunity details ## About this role. 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. ### 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](https://nam12.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.skillsoft.com%2F&data=05%7C02%7CAlicia.Webb%40skillsoft.com%7C36d2da8de0194a56800708de643c71a1%7C50361608aa23494da2332fd14d6a03f4%7C0%7C0%7C639058407944984460%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=vKXEeOW14HJrrID0XOoQJVjVbwOsMZAEXYws7OBBySU%3D&reserved=0). 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. 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