Sr. Director, Renewals Operations

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 building an integrated commercial function that unifies pricing, deal desk, contract negotiation, and adjacent commercial capabilities, governing price and discount on a ~$250M Enterprise ARR base. As the Director, Renewals Operations, you will have the opportunity to co-lead the future-state design of this function and end-to-end commercial process redesign, then build and run it as its operating leader. This is a design-and-operate full-lifecycle role where you shape the function, pilot its priority capabilities, and carry it into steady-state ownership.

Key Responsibilities:

Serve as the future operator of an integrated commercial function unifying pricing, deal desk, contract negotiation, and adjacent capabilities, governing price and discount on a ~$250M Enterprise ARR base

Co-manage future-state design of the function and end-to-end commercial process redesign.

Integrating today's fragmented pricing, deal desk, contracts, and RFP resources into one function.

Redesign commercial processes for speed and productivity with AI as a radical enabler.

Define enabling systems requirements across CPQ, approval workflows, and contract lifecycle.

Responsible for driving measurable ARR and productivity improvement through stronger pricing, discounting, and deal management by owning commercial policy, approval frameworks, and exceptions.

Lead with an AI-first mindset. Use data, automation, and tooling, including Claude, to optimize the commercial processes, monitor KPIs, and continuously raise the bar on performance.

Build and lead the function's team; partner and collaborate at the executive level with Sales, Legal, and Finance.

Skills & Qualifications to Be Successful:

12+ years of experience running a SaaS/PaaS integrated commercial operations organization with a Bachelor’s degree or equivalent experience

6+ years leading teams that own deal desk, pricing, or discount governance at scale.

Experience managing pricing and discount governance at scale, as well as commercial policy design.

Process redesign expertise with an AI/automation-forward orientation

Strong analytical command of deal, discount, and margin economics

Executive presence and cross-functional authority across Sales, Legal, and Finance

Location Preference: 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

Industry-specific experience in learning technology or enterprise SaaS MBA or Advanced Degree in Finance

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.