At Skillsoft, we propel organizations and people to grow together through transformative learning experiences. We believe every team member has the potential to be AMAZING. Join us in our quest to transform learning and help individuals unleash their edge.
Remote Boston, Massachusetts Area
Skillsoft is seeking an experienced, outcome-driven Portfolio & Transformation Leader to drive strategic execution across a portfolio of high-impact, cross-functional initiatives. In this role, you will have the opportunity to use your deep expertise in end-to-end business process transformation and technology-driven project delivery, and thrives at the intersection of business strategy, operations, and systems enablement.
The ideal candidate will have the experience in leading a centralized Portfolio Management Office (PMO), as well as, be responsible for prioritizing initiatives, aligning executive stakeholders, and ensuring measurable business outcomes—particularly those enabled by technology, whether through internal platforms, tools, or enterprise systems. With a proven ability to deliver clarity and structure in ambiguous, fast-changing environments, you’ll be a trusted advisor to senior leadership and a catalyst for organizational effectiveness.
Responsibilities:
Enterprise Portfolio Strategy & Execution
- Own and manage the enterprise-wide portfolio of business and technology initiatives across departments including Product, Engineering, Marketing, Sales, Finance, and Customer Support.
- Partner with C-level leaders to align strategic priorities, manage capacity, and track delivery against business goals.
- Define governance models and operating cadences to assess investment decisions, manage risk, and escalate critical blockers.
End-to-End Business Process Transformation
- Lead transformation programs that optimize and connect business processes across the lead-to-cash lifecycle and beyond.
- Guide teams through the assessment of current-state processes, development of future-state models, and implementation of iterative process improvements.
- Integrate technology and operational enhancements to improve efficiency, scalability, and business impact.
Technology-Driven Program Oversight
- Lead strategic initiatives involving internal systems, enterprise tools, or platform integrations to enable business capabilities.
- Partner closely with Product, Engineering, and IT teams to ensure projects are scoped, resourced, and executed in alignment with business needs.
- Oversee delivery of technology-enabled solutions that improve operations, enable scale, and support digital transformation objectives—across areas such as CRM, ERP, quote-to-cash, analytics, or workflow automation.
Customer and Commercial Operations Enablement
- Drive programs that improve the operational backbone supporting customer engagement, order processing, pricing, fulfillment, and post-sales support.
- Ensure technology investments and process improvements are tightly aligned to commercial and operational outcomes, including scalability, compliance, and customer responsiveness.
- Lead cross-functional alignment to evolve how systems and processes support internal users and external customer-facing teams.
Executive Engagement & Communication
- Facilitate workshops, alignment sessions, and executive governance meetings to ensure clarity, ownership, and accountability across initiatives.
- Deliver executive-ready dashboards, reports, and insights to support decision-making and highlight progress against KPIs.
Leadership & Capability Development
- Build and mentor a high-performing team of program managers, portfolio analysts, and transformation leaders.
- Foster a culture of ownership, transparency, continuous improvement, and cross-functional collaboration.
- Serve as a coach and thought partner to leaders and stakeholders across the organization.
Skills & Qualification Requirements:
- 12-15 years of experience leading enterprise-level programs, strategic portfolios, or business transformation initiatives with a Bachelor’s degree or commensurate experience
- SaaS industry experience with deep expertise in end-to-end business processes (e.g., lead-to-cash, quote-to-cash) and how they intersect with digital tools and platforms
- Recent experience and the ability to lead complex, technology-enabled initiatives, either involving enterprise platforms, product-aligned tools, or business system integrations
- Solid portfolio planning, capacity modeling, KPI development, and outcome measurement knowledge and experience
- Strong background in business case development, capacity planning, and portfolio prioritization frameworks
- Exceptional communication, facilitation, and stakeholder engagement skills and comfortable working across all levels of the organization including Executive presentations and ability to influence change
- Ability to drive clarity and progress in ambiguous environments with competing priorities
- Location: Remote Massachusetts Area
Desirable Qualifications:
- MBA or similar advanced business or technical degree
- Lean Six Sigma, PMP, or Agile certifications
- Familiarity with enterprise platforms such as Salesforce, Workday, NetSuite, Jira, or similar
- Experience working in SaaS, high-growth technology, or business transformation environments
Target base salary range for this job requisition is anticipated to be approximately $175,000 - $215,000 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 delivers online learning, training, and talent solutions to help organizations unleash their edge. Leveraging immersive, engaging content, Skillsoft enables organizations to unlock the potential in their best assets – their people – and build teams with the skills they need for success. Empowering 36 million learners and counting, Skillsoft democratizes learning through an intelligent learning experience and a customized, learner-centric approach to skills development with resources for Leadership Development, Business Skills, Technology & Development, Digital Transformation, and Compliance.
Skillsoft is partner to thousands of leading global organizations, including many Fortune 500 companies. The company features three award-winning systems that support learning, performance and success: Skillsoft learning content, the Percipio intelligent learning experience platform, which offers measurable impact across the entire employee lifecycle. Learn more at www.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.
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Skillsoft Boston, Massachusetts, USA Office
10 Post Office Square, Boston, MA, United States, 02109
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