Affinity Web Development Llc Jobs in Chicago, IL

The Role
We're looking for a visionary technology leader to head our Web Development practice, someone who can bridge the gap between ambitious digital strategy and flawless execution. In this role, you'll own the technical direction of our web platforms, lead a talented cross-functional team, and directly shape the digital experiences of the enterprise clients we serve.
This is a senior leadership position that reports to the VP, Digital Experience. You'll work alongside C-suite stakeholders, practice leads, and client teams, serving as the authoritative technical voice in a fast-moving, innovation-driven environment. If you thrive at the intersection of technology, strategy, and people leadership, and you bring an AI-native mindset to everything you build, we'd love to meet you.

What You'll Do

Lead the Team

• Manage and mentor a team of tech leads and senior developers, fostering a culture of craft, accountability, innovation and excellence.
• Attract top talent, develop career paths, and build team capabilities to match evolving client needs.
• Champion responsible and performant AI development practices, including robust CI/CD pipelines that support increased development velocity.
• Operate as the business leader of the web development discipline with a focus on driving profitability, optimizing utilization, and setting teams up for success with thoughtful project-level resourcing. 

Drive Technology Strategy

• Define and execute the web development strategy, including the architectural roadmap for platforms, integrations, and emerging technologies.
• Lead with an AI-native approach - leveraging AI tools and automation throughout the development lifecycle, from ideation to QA to delivery. Continuously assess and redefine how AI tools can enhance our practice. 
• Evaluate and recommend CMS and no-code/low-code platforms appropriate to each project's context. Architect scalable, secure, cloud-first solutions with strong command of AWS, Azure, or GCP environments and other CMS platform-specific cloud environments.
• Stay ahead of the curve on emerging frameworks, personalization technologies, accessibility standards, and omnichannel integration patterns.

Deliver for Clients

• Serve as the senior technical lead in client-facing engagements. You'll take complex architectural decisions, platform tradeoffs, and technical constraints and make them land clearly for non-technical stakeholders: clients, brand teams, and marketing lead. You'll consult with client technology teams, present recommendations with confidence, address concerns before they become blockers, and remain a trusted POC from kickoff through launch. You'll build relationships and affinity with clients and help drive growth. 
• Collaborate with CX, UX/UI, content, creative, and strategy teams to deliver seamless, high-quality digital experiences.
• Oversee multiple concurrent enterprise-scale projects, ensuring on-time, on-budget delivery without sacrificing quality.
• Translate complex business and marketing requirements into practical, scalable technical solutions.

Set the Standard

• Establish and enforce coding standards, security protocols, and compliance practices across all web platforms.
• Ensure adherence to data privacy regulations (GDPR, HIPAA, CCPA, etc.) and accessibility standards (WCAG) - experience in healthcare or other regulated industries is a plus.
• Understand and support our healthcare clients in a healthcare specific regulatory environment.
• Implement monitoring, analytics, and reporting frameworks to track platform performance and business impact.
• Support internal digital initiatives alongside client work, improving the efficiency and effectiveness of how we operate.

What You'll Bring

Experience & Background

• 10+ years in web development, with at least 5 years in a senior leadership role overseeing enterprise-scale platforms and teams.
• A proven track record delivering large-scale digital projects - on time, on budget, and with measurable business impact.
• Demonstrated experience managing developers across levels (junior through tech lead), including distributed and nearshore/offshore team structures.
• Experience in healthcare, life sciences, financial services, or another regulated industry is preferred, though not required.

Technical Expertise

• Technology-agnostic mindset: you evaluate platforms based on fit, not familiarity - while bringing hands-on depth with CMS platforms including WordPress, Drupal, and Sitecore, and no-code/low-code tools such as Webflow and Framer.
• Strong command of modern frameworks (React, Angular, Node.js, etc.), microservices architecture, API-first development, and DevOps/CI-CD practices.
• Solid grounding in cloud infrastructure (AWS, Azure, GCP), enterprise security, and compliance requirements.
• Mastery of AI tools and automation. Operates with an integrated workflow that includes Claude Code, Codex, or Cursor.  

Leadership & Communication

• Excellent communicator who can translate technical complexity for executive, marketing, and client audiences equally well.
• Strong stakeholder management instincts and comfort presenting in senior strategy discussions.
• Experience and interest in participating in new business and growth efforts. 
• A collaborative leader who earns trust across disciplines.

Candidates must currently live in the US and be legally authorized to work in the US without requiring visa sponsorship now or in the future. Verification of work eligibility will be required upon hire.

Perks and Benefits

• Competitive Salary
• Health, Dental and Vision benefit packages to fit all types of lifestyles
• Life, Short- and Long-Term Disability Insurance paid 100% by the company
• FSA / HSA Options
• 401(K) with a generous company match program
• Flexible Paid Time Off (aka- unlimited)
• Paid Parental Leave
• Hybrid and Remote work schedules available
• Employee Assistance Program (unlimited free telephonic counseling for a variety of issues such as mental health, financial support, and legal advice)
• Employee Referral Program