Sr Director, Application Engineering

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.

Location: Driving distance from Boston, MA

Skillsoft is seeking an Application Engineering Lead to build, run, and evolve our enterprise application landscape in support of company strategy and business transformation priorities.

In this role, you will have the opportunity to be accountable for engineering delivery and operational excellence across a portfolio of front-office, back-office, and employee experience platforms. You will ensure solutions are stable, secure, scalable, and aligned to enterprise process outcomes, while enabling faster delivery, lower cost, and higher quality.

As a senior leader within Digital & IT, you will work cross-functionally with Enterprise Business Solutions, Enterprise Architecture, Data / Integration / Automation, PMO, Security, and business stakeholders to convert priorities into measurable business outcomes. You will also lead the adoption of modern engineering practices, AI-enabled development, and application simplification to improve speed, efficiency, and value realization.

Key Responsibilities

Enterprise Engineering Leadership & Outcome Delivery

• Own engineering delivery and operational health for the enterprise applications portfolio supporting critical business capabilities and processes

• Translate approved business solutions into scalable, maintainable engineering execution plans

• Ensure delivery aligns to business priorities, architecture standards, security requirements, and governance frameworks

• Partner with PMO and Solutions leaders on prioritization, capacity planning, sequencing, and execution transparency

• Drive consistent execution that balances run, enhancement, and transformation initiatives

Application Operations & Lifecycle Management

• Lead end-to-end lifecycle management, including build, release, operate, enhance, and retire

• Ensure high availability, reliability, and performance of production systems

• Oversee incident, problem, and change management processes

• Maintain a strong focus on operational resilience, uptime, and business continuity

• Drive structured lifecycle planning including upgrades, patching, and decommissioning of legacy systems

Simplification, Automation & AI-Enabled Engineering

• Reduce application complexity through rationalization, standardization, and modernization

• Drive adoption of AI-assisted engineering practices to improve productivity, quality, and cycle time

• Enable automation-first delivery across testing, deployment, and operational processes

• Partner across teams to streamline workflows, reduce manual effort, and lower total cost of ownership

• Identify and scale opportunities for AI and automation within enterprise applications in a controlled manner

Governance, Risk & Compliance

• Ensure adherence to enterprise architecture, security, and engineering standards

• Support compliance requirements including audit readiness (e.g., SOX where applicable)

• Maintain disciplined release, change, and environment controls

• Ensure solutions are well-documented, testable, and supportable

• Partner with Security and Risk teams to proactively mitigate technical and operational risks

People Leadership & Capability Development

• Build and lead a high-performing, modern engineering organization

• Develop a skills-based team with strong capabilities across platforms, automation, quality, and AI

• Define clear roles, responsibilities, goals, and development plans

• Foster a culture of accountability, continuous improvement, and enterprise thinking

• Develop talent that can operate across technologies and business domains

Stakeholder Engagement & Value Realization

• Build strong, trust-based partnerships with business stakeholders and cross-functional IT teams

• Ensure delivery outcomes translate into measurable business impact

• Support adoption and value realization post-implementation

• Contribute to a management cadence that tracks outcomes beyond deployment

• Communicate clearly with senior stakeholders on progress, risks, and value delivered

Required Skills & Experience

• 10+ years of professional application engineering, delivery, or enterprise systems leadership experience

• Proven track record leading engineering teams supporting enterprise applications (e.g., ERP, CRM, HRIS, finance, or similar platforms)

• Experience operating in a fast-paced, resource-constrained environment requiring prioritization trade-offs

• Strong experience across application lifecycle management, release governance, and production operations

• Experience driving modernization, simplification, and automation initiatives

• Experience introducing or scaling AI-assisted development and engineering practices

• Demonstrated ability to partner across business, architecture, PMO, data, and security teams

Technical & Leadership Capabilities

• Strong understanding of SaaS platforms, integrations, and enterprise system architectures

• Experience with modern development practices, DevOps, CI/CD, and automated testing

• Strong analytical, problem-solving, and decision-making skills

• Ability to balance strategic thinking with hands-on execution leadership

• Excellent executive communication and stakeholder management skills

• Strong leadership presence with the ability to influence across functions

Target base salary range for this job requisition is anticipated to be approximately $220,000 - $240,000 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. MORE ABOUT SKILL

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