Director Software Development Manager Jobs in Chicago, IL

POSITION SUMMARY 

The Senior Director, Software Development is responsible for leading the engineering organization for Follett Software's library portfolio, including K–12 library products, international library management solutions, and shared platform capabilities that support the portfolio. This role brings together engineering leadership across multiple library products and shared platform capabilities – serving K-12 school libraries and international library management – with accountability for delivery, modernization, and operational performance across the portfolio.

The Senior Director provides strategic and operational leadership across the full software development lifecycle, including planning, architecture, development, testing, release, maintenance, and continuous improvement. They will lead development managers and engineers responsible for delivering secure, scalable, and reliable software that serves educators, librarians, administrators, and school districts across domestic and international markets.

This leader partners closely with Product, Design, QA, Cloud Engineering, Technical Support, and customer-facing teams to translate business priorities into engineering execution. They drive technical strategy and architectural modernization while balancing product innovation, platform stability, customer commitments, and operational excellence across all the library suite.

POSITION SCOPE 

Engineering Leadership and Delivery

• Lead the engineering organizations for domestic and international Library Management products and the wider Destiny platform, ensuring strong delivery, team health, and operational continuity across all product lines.
• Establish and execute an engineering vision aligned to product strategy, customer needs, and company goals, while owning delivery of the roadmap across Library Management and the shared Destiny platform from planning through release and follow-through.
• Provide technical and organizational leadership across architecture, modernization, engineering standards, and operational excellence, with attention to scalability, security, performance, reliability, and maintainability.
• Ensure leadership continuity through critical business periods, especially the back-to-school season, including release cadence, escalation ownership, cross-team coordination, and customer-impacting issue management across all products.

Cross-Product and Cross-Functional Partnership

• Partner closely with Product, Design, Security, QA, Cloud Engineering, DevOps, Technical Support, and other customer-facing teams to improve product outcomes, resolve escalations, and strengthen end-to-end execution.
• Operate effectively across distinct product contexts—including Destiny Library Manager/Resource Manager and Accessit Library—while identifying opportunities to strengthen shared platform capabilities and connected experiences across the broader library ecosystem. Represent engineering priorities, tradeoffs, and delivery status clearly and credibly to executive and cross-functional stakeholders.

Organizational Leadership and Talent

• Lead organizational design, talent planning, hiring, coaching, and succession across all three product lines, fostering a culture of accountability, collaboration, learning, and continuous improvement.
• Develop and grow development managers and senior engineers, providing regular coaching, clear performance expectations, and meaningful career development opportunities.
• Identify and nurture individual strengths and specialized abilities to drive career development and team satisfaction.
• Partner with recruiting to attract top engineering talent and build retention strategies that recognize achievement and create advancement pathways.
• Create and maintain a positive, inclusive, secure and collaborative engineering culture that promotes open communication and a sense of belonging.

Operational Excellence and Governance

• Maintain strong operating rigor and organizational clarity through durable documentation, clear ownership, and effective communication of key product, team, customer, vendor, and operational context.
• Use metrics, judgment, and business context to manage priorities, resources, budgets, risks, and team performance, and to drive sound engineering decisions.
• Ensure regular, transparent communication with teams about organizational updates, changes, and expectations, facilitating open dialogue and encouraging feedback.

Modern Engineering Practices and AI Adoption

• Champion adoption of modern engineering practices, including AI-enabled and Spec-Driven Development approaches, by building clarity, accountability, and strong technical leadership across the organization.
• Advance engineering maturity across the portfolio through modern development practices, appropriate use of AI-enabled workflows, and clear technical and delivery standards.Other duties as assigned.

QUALIFICATIONS 

Required

• Bachelor's degree or equivalent experience in Computer Science, Software Engineering, Information Technology, or a related field.
• 12+ years of software development leadership experience, including significant experience in senior engineering leadership roles with responsibility for multiple teams and/or product lines.
• Proven success leading large or multi-product engineering functions, including direct reports who are themselves people leaders.
• Strong experience delivering and supporting commercial software products in a SaaS, web application, or hybrid software environment.
• Strong technical foundation in modern software engineering practices and sufficient depth to credibly guide teams working across diverse technology stacks, including Java, J2EE, .Net and service integrations, SQL Server, JavaScript, Git-based workflows, and Jira or similar development tools.
• Experience leading modernization efforts in environments that include legacy technologies such as Java, J2EE, .Net, JBoss, WildFly, SQL, jQuery, or third-party UI frameworks, while moving teams toward more scalable and maintainable approaches.
• Familiarity with Azure or comparable cloud platforms, CI/CD practices, automated testing, release management, and secure software development principles.
• Demonstrated ability to balance strategic thinking with operational execution in a fast-paced, multi-product environment.
• Strong leadership skills with the ability to influence across functions, communicate clearly with technical and non-technical audiences, and lead through change.
• Experience setting direction through metrics, managing budgets and resources, and making data-informed decisions.
• Strong judgment, emotional intelligence, and a track record of building healthy, accountable, high-performing teams.

Preferred

• Familiarity with AI development techniques, coding agents, Spec-Driven Development, and AI-embedded CLI/IDE tooling.
• Experience in EdTech, K-12 software, library systems, resource management, or other education-adjacent software environments.
• Experience leading engineering across international or multi-market product lines, including awareness of regional compliance, data residency, or localization considerations.
• Experience supporting customer-facing products with complex implementation, integration, and support considerations.
• Experience leading teams through seasonal or customer-critical operating periods with high continuity requirements.
• Experience driving adoption of modern engineering practices such as AI-enabled development, spec-driven workflows, or similar operating models.

WORK ENVIRONMENT 

• This role is remote and only open to candidates currently located in the United States and able to work without sponsorship. 
• It requires a suitable space that provides a private and quiet workplace.
• Work hours and schedules may be adjusted as needed to meet the requirements of the position, the needs of the organization, and collaboration with teams operating outside of the U.S., including overlap with their working hours when necessary.

PHYSICAL REQUIREMENTS 

• Perform tasks in a home office environment with frequent virtual meetings, communications, and interruptions, requiring effective time management and prioritization.
• Prolonged sitting with sustained visual focus on digital screens, requiring the ability to interact at a typical working distance.
• Frequent use of keyboard and mouse, involving repetitive hand movements and fine motor skills for typing, navigating, and handling materials.
• Occasionally adjust position or move within the workspace to reach, retrieve, or access items, involving bending, twisting, or reaching, and occasionally lifting or carrying items weighing up to 10 pounds.
• Travel requirements: Minimal (less than 10%)

This job description is intended to convey information essential to understanding the scope of the job and the general nature and level of work performed by job holders within this job. However, this job description is not intended to be an exhaustive list of qualifications, skills, efforts, duties, responsibilities or working conditions associated with the position. Duties, responsibilities, and activities may change at any time with or without notice. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions of the job.

At Follett Software, our people come first.
We're deeply committed to supporting the well-being, growth, and success of every Team Member. That commitment shows up in a thoughtfully designed, comprehensive benefits package that helps you thrive—at work and in life. Here's what you can expect:

• Fully remote work, giving you the flexibility to do your best work from anywhere in the continental U.S. (unless otherwise noted)
• Subsidized healthcare plans, including orthodontic coverage, with HSA option that includes employer matching
• Company-paid disability and life insurance, with the option to enhance coverage through voluntary plans
• Robust Paid Time Off, including Flex PTO for salaried roles, paid parental leave, company holidays, and paid volunteer service time
• Retirement savings with employer match, vesting every pay period
• Flexible Spending Accounts for healthcare and dependent care
• Optional supplemental coverages, such as accident, hospital, and critical illness insurance, identity theft and credit monitoring, and legal protection services
• Meaningful recognition and tangible rewards that celebrate achievements, fuel motivation, and recognize both individual and team success