Sr Director, Application Engineering

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 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 .

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.