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.
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.
Skills Required
- 10+ years of professional application engineering, delivery, or enterprise systems leadership experience
- Proven track record leading engineering teams supporting enterprise applications (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
- 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
- Excellent executive communication and stakeholder management skills
- Strong leadership presence with the ability to influence across functions
What the Team is Saying
Skillsoft Compensation & Benefits Highlights
How does Skillsoft ensure its pay and bonus plans are competitive?
Skillsoft’s compensation is supported by employee feedback around market-rate pay, bonus opportunities, benefits and total rewards. The company pairs compensation with flexibility, learning access and career development programs that employees describe as part of the overall value of working there.
- Market-aligned pay and bonus opportunities: Employees describe Skillsoft’s compensation as competitive, especially in roles with bonus potential. Employees surveyed on external review sites cite “salary plus bonus potential” as market rate, quarterly bonus access in sales and a strong compensation plan. A marketing employee cited “great pay,” while a solution design architect described Skillsoft as offering a “very competitive benefits and total compensation package.” (Comparably; Glassdoor)
- Performance-based rewards: Skillsoft employees point to bonus opportunities as part of the company’s rewards approach. A software engineer said their bonus was “excellent,” while sales employees cite quarterly bonus access as part of their compensation package.
- Benefits as part of total rewards: Skillsoft’s total rewards are also supported by employee comments about health benefits, insurance benefits, flexible time off, remote work and work-life balance. Employees surveyed on external review sites cite health benefits and insurance benefits as strengths, while other employees highlight great benefits, remote-first work and flexibility as part of the employee experience. (Comparably; Glassdoor)
- Growth and learning as added value: Skillsoft’s rewards approach is connected to its employee growth culture. The company provides employees with access to Percipio, Aspire Journeys, role-based pathways, instructor-led training, coaching and CAISY® simulations. Employees describe Skillsoft as a place with “continuous learning opportunities across the tech stack” and “no better place to learn and grow.”
● External signals:
○ Compensation and bonus: Employees on external review sites cite market-rate salary plus bonus potential, quarterly bonus access in sales, a strong compensation plan, “great pay” and an “excellent” bonus as compensation strengths. (Comparably; Glassdoor)
○ Total rewards: Employees on external review sites describe Skillsoft as offering “great benefits,” a “very competitive benefits and total compensation package” and benefits that support work-life balance, flexibility and employee growth. (Glassdoor)
○ Health and insurance: Employees on external review sites cite health benefits, insurance benefits and good health plans as strengths of Skillsoft’s employee experience. Mental health benefits are also listed among Skillsoft’s employee benefits. (Comparably)
○ Flexibility as a reward: Employees on external review sites connect rewards not only to pay, but also to remote work, flexible hours, flexible time off, independence and management that avoids micromanaging. (Glassdoor; Comparably)
Bottom line: Skillsoft supports competitive pay through market-rate compensation, bonus opportunities and a broader total rewards experience that includes benefits, flexibility and career development.
Skillsoft Insights
What We Do
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 and supports a global community of more than 105 million learners. Learn more at skillsoft.com.
Why Work With Us
We help the world's biggest companies build better workforces — and we invest just as much in our own people. Learning new skills is a core part of your job here. We're fully remote, spread across the globe, and united by a shared belief that learning changes careers.
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Skillsoft Offices
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Employees work remotely.
