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.
North America Services Leader
Skillsoft is hiring an experienced North America Market Services Sr. Director to make an impact and drive ARR growth, improve retention, drive a great customer experience, and guide teams through change with clarity and pace. We are seeking a strong operator, coach, and change agent who can turn strategy into repeatable execution across five North America markets. This role is comprised of a combination of Sales, Professional Services Delivery, Solutions Consulting/Pre-Sales, and Customer Success.
This Services Sr. Director will have the opportunity to be a player / coach and deliver regional results and own the Customer Experience and growth engine for North America. Overseeing the regional Market Solutions Leaders and ensuring consistent, disciplined execution across the customer lifecycle to include presales, adoption, expansion and renewal. This role operates as an executive people leader, global practice owner, and partners closely with the North America VP of Sales as the region's primary Go To Market change leaders for the region sustaining team confidence, clarity, and pace through continued change.
Key Responsibilities:
Lead the Geographical Market Solutions Teams
- Manage, coach, and develop the MSLs across the geography; set clear performance standards and accountability.
- Ensure Market Solutions Leaders (MSLs) execute the end-to-end customer solution lifecycle (Sale → Value → Expand → Renew) with MEDDPICC rigor and value-realization discipline.
- Build a high-performance, coaching-first culture aligned to Skillsoft's Enterprise Leadership Skills; build team capabilities systematically.
- Guarantee the MSL’s align Solutions Partners across markets to match opportunity size, complexity, and urgency.
Coach Solutioning Capability and Lead Through Transformation
- Coach MSLs and their teams on advanced solutioning - executive discovery and problem framing, solution architecture and design, value narrative and business case development, and platform and ecosystem expertise
- Steer the team through an organization in transformation: guide teams through evolving roles, new operating models, and shifting customer expectations with clarity, confidence, and pace
- Support MSLs in developing the CSM function as a strategic advisor capability - fluent in skills intelligence, data-led insight, executive engagement, and outcome-based partnership rather than reactive account management
- Collaborate with and support the MSLs in developing Solution Partners as expert customer-facing advisors - deep in product and platform, disciplined in solution design methodology, and credible with C-suite buying committees
- Drive adoption of AI-enabled workflows and tooling to expand strategic capacity and reduce administrative load
Deliver Regional Revenue and Customer Outcomes
- Co-own regional targets with the North America Geo Sales Leader (AVP): ARR growth, retention, expansion, NPS, and platform conversion.
- Oversee regional performance management cadences to drive continuous improvement and results; escalate and resolve at-risk accounts; enable growth across accounts.
Own the Regional Component – Shared / Channel Teams
- Define the charter and target operating model for global shared/channel solution teams.
- Establish rules of engagement between shared CSM pools, MSLs, direct sales, and channel partners.
- Build channel enablement content and playbooks for solution positioning through partners.
- Design coverage tiers so tier-2/tier-3 customers receive scalable, high-quality solution support.
- Report on channel-sourced ARR and shared-team utilization to the Global Solutions Leader.
Drive Cross-Regional Consistency
- Serve as a member of the Global Solutions Management team alongside peer GMSLs, the Solutions IP Team lead, and the Program Manager.
- Responsible for ensuring global standards are applied in-region while allowing appropriate local tailoring for market realities.
- Share regional insights back into the global system — customer patterns, competitive intel, and solution feedback — to inform IP and roadmap.
Cross-Functional Leadership
- Partner with the Solutions IP Team to translate defined solutions and POVs into repeatable, market-ready plays.
- Interlock with Professional Services regional leadership on clean presales-to-delivery handoffs.
- Partner with Product, Marketing, and Enablement to close feedback loops from field to global functions.
- Support the Program Manager in keeping data clean, systems used, and operating rhythm consistent.
Required Skills & Qualifications
- 12+ years of progressive management experience in enterprise PaaS spanning some combination of Sales, Customer Success, Solutions Consulting/Pre-Sales, and/or Professional Services.
- Overseeing Professional / Managed Services and Solutioning (or consulting) experience with demonstrated results driving long-term customer growth with services engagements based on business cases.
- Proven track record of delivering ARR growth, retention, and expansion in a platform and solutions-based selling motion.
- Proficient in Salesforce and Business Intelligence (BI) tools.
- Deep fluency in MEDDPICC (or equivalent), value-based selling, and end-to-end customer lifecycle management.
- Experience as a practice or system builder — designing repeatable processes, tools, or capability models adopted at scale.
- Possess a strong operational rigor with proficiency in forecasting, pipeline inspection, and data-driven outcomes
- Have a deep familiarity with North America market dynamics.
- Executive presence with proven ability to engage C-suite customers and internal senior leadership.
- Location: East Coast US Highly Preferred with the ability to travel
Preferred Skills & Experience
- Experience operating in a matrixed global organization and collaborating with strong partnership across Product, Professional Services, Revenue Operations, and Marketing.
- Familiarity with the Learning technologies and L&D functions, learning/talent ecosystems, and AI-enabled workforce transformation.
Target base salary range for this job requisition is anticipated to be approximately $215,000 - $239,000 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.
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