Sr Director – People and Culture

Salary: $135,000-$155,000 based on skills and experience, bonus eligible About The Second City Dedicated to entertaining, inspiring, and transforming through courageous comedy, The Second City is the premier brand in improv-based sketch comedy, with sold-out shows playing on stages in Chicago, Toronto, and New York City, and our Touring and Theatrical companies entertaining an additional one million theatergoers a year around the globe. The Second City Training Center is the largest school of improvisation-based arts on the planet, with locations in Chicago, Toronto, and New York. Second City Works, the B2B side of Second City, has brought award-winning improvisation and audience-driven techniques to over 600 Fortune 1000 companies, challenging businesses seeking a more collaborative culture to innovate through development programs, original digital and video content, campaign consultation, private events, and more. For additional information on The Second City please visit: About the Role The Senior Director, People & Culture will serve as a strategic leader and trusted advisor to the executive team at The Second City, driving initiatives that align people strategy with business objectives. This role will oversee all aspects of people operations, focusing on organizational design, talent management, employee engagement, and DEI. The ideal candidate will be passionate about fostering an inclusive, creative culture while optimizing organizational effectiveness. Key Responsibilities Strategic Leadership & Executive Partnership Serve as a key advisor to the CEO, CFO, and other senior leaders to align people strategy with business objectives. Provide strategic counsel and data-driven insights to support decision-making and long-term planning. Collaborate with senior leaders to drive growth, enhance operational success, and implement change management initiatives. Lead, mentor, and develop a team of three direct reports, fostering a high-performing and engaged HR team. Provide ongoing coaching and professional development opportunities to build leadership capabilities. Set clear goals, measure team performance, and ensure alignment with organizational objectives. Organizational Design & Workforce Planning Lead organizational design efforts to ensure teams are structured for scalability, efficiency, and long-term success. Partner with business leaders to conduct workforce planning and identify talent gaps. Implement workforce models that support both immediate and long-term business needs. Talent Acquisition & Development Oversee recruitment strategy to attract, hire, and retain top talent in a competitive market. Develop robust onboarding and leadership development programs that foster career growth. Culture & Employee Experience Champion Second City’s unique culture, fostering an inclusive, collaborative, and engaging work environment. Develop and maintain an employee engagement calendar that includes events, programs, and cultural initiatives. Implement initiatives that enhance employee satisfaction and retention, using data and feedback to inform improvements. Performance Management & Leadership Coaching Oversee a transparent and effective performance management process. Provide leadership coaching to managers and senior executives, fostering a high-performance culture. Partner with leadership to set clear goals, drive accountability, and promote continuous feedback. Diversity, Equity & Inclusion (DEI) Lead and drive Second City’s DEI strategy, ensuring equity and inclusion are embedded across all people programs. Partner with stakeholders to create inclusive hiring, development, and retention practices. Track progress through key metrics and hold leaders accountable for DEI goals. Compensation, Benefits & Total Rewards Partner with the CFO to design competitive and equitable compensation, commission and benefits programs. Ensure total rewards strategies align with business objectives and employee needs. Develop and manage employee recognition programs to celebrate accomplishments and milestones. Employee & Labor Relations Manage complex employee relations matters, ensuring fair and consistent resolution. Partner with legal and leaders to negotiate collective bargaining agreements for The Second City talent and teachers. Provide counsel to managers on employee relations issues, performance management, and conflict resolution. Ensure compliance with all federal, state, and local employment laws and regulations. Change Management & Business Transformation Lead organizational change initiatives, ensuring effective communication and stakeholder alignment. Provide training and resources to support employees through periods of change. Monitor change adoption and continuously assess the impact of transformation efforts. HR Operations & People Analytics Oversee HR operations, ensuring the implementation of efficient processes and systems. Leverage people analytics to measure effectiveness, track key HR metrics, and inform strategic decisions. Continuously seek opportunities to optimize people operations and enhance employee experience. Qualifications & Skills 8+ years of progressive HR leadership experience, with at least 3 years in a leadership role. Proven success in leading people strategies in creative, fast-paced environments. Strong business acumen with experience in organizational design, talent management, and employee engagement. Demonstrated success in leading DEI initiatives and driving inclusive workplace cultures. Experience managing and developing high-performing teams. Exceptional leadership and executive coaching abilities. Strong understanding of compensation strategy, performance management, and compliance. Proficient in HR systems, people analytics, and data-driven decision-making. Excellent communication, problem-solving, and decision-making skills. We are an open, inclusive workplace and welcome applicants who bring along with them diverse life experiences, including every permutation of economic and cultural backgrounds, orientation, ethnicity and points of view. We strive to continue our efforts to work with people who may otherwise be marginalized or underrepresented in our business and around our local community. #J-18808-Ljbffr