Head of Engineering

Selby Jennings; Chicago (IL); On-site; USD 180,000 - 240,000; Full time

Job summary

Selby Jennings is seeking a senior engineering leader in Chicago to guide architecture, delivery, and strategic initiatives across core platform systems.

The role focuses on scalable, secure, and reliable engineering with strong collaboration with product and business teams, mentoring engineers, and shaping organizational practices for growth.

Qualifications

• Experience in fintech, payments, financial infrastructure, banking tech or regulated industries.
• Strong leadership and people-management capabilities.
• Proven ability to design scalable, reliable systems and engineering standards.
• Experience with security considerations and regulatory compliance.

Responsibilities

• Remain actively involved in architecture, design, code reviews, and critical engineering initiatives.
• Own engineering execution and delivery across multiple initiatives.
• Partner with product and business stakeholders to prioritize work.
• Mentor engineers and manage hiring, career development, and team growth.
• Establish and maintain engineering standards, processes, and operational excellence.
• Lead troubleshooting of complex production issues and system challenges.

Skills

Fintech domain

Leadership

Architectural design

Performance & scale

Security & compliance

Job description

• Remain actively involved in architecture, design, code reviews, and critical engineering initiatives


• Contribute directly to the development of core platform functionality and business-critical systems


• Drive decisions around scalability, reliability, security, and performance


• Lead troubleshooting efforts for complex production issues and system challenges


• Establish and maintain engineering standards, best practices, and development processes


• Own engineering execution and delivery across multiple initiatives


• Partner with product and business stakeholders to prioritize and organize work effectively


• Mentor and develop engineers at all levels of experience


• Manage hiring, performance, career development, and team growth


• Create accountability and clear ownership across projects and teams


• Foster a culture of transparency, collaboration, and operational excellence

Key Responsibilities

Technical Leadership

• Remain actively involved in architecture, design, code reviews, and critical engineering initiatives


• Contribute directly to the development of core platform functionality and business-critical systems


• Drive decisions around scalability, reliability, security, and performance


• Lead troubleshooting efforts for complex production issues and system challenges


• Establish and maintain engineering standards, best practices, and development processes

Team Leadership

• Own engineering execution and delivery across multiple initiatives


• Partner with product and business stakeholders to prioritize and organize work effectively


• Mentor and develop engineers at all levels of experience


• Manage hiring, performance, career development, and team growth


• Create accountability and clear ownership across projects and teams


• Foster a culture of transparency, collaboration, and operational excellence

Organizational Impact

• Build scalable processes that improve execution without creating unnecessary bureaucracy


• Ensure engineering efforts align with business objectives and strategic priorities


• Partner with executive leadership on organizational planning and technical strategy


• Help shape the future structure and growth of the engineering organization

Desired Skills and Experience

• Experience within fintech, payments, financial infrastructure, banking technology, or other regulated industries


• Familiarity with transaction processing, payment workflows, risk systems, or money movement platforms


• Experience scaling engineering teams through periods of rapid company growth


• Background working in startup or high-growth environments


• Experience building mission-critical systems that handle significant transaction volume


• Exposure to compliance, security, or regulated operational environments