The Second City - Head of People

1616 N Wells St, Chicago, IL 60614, USA Req #137
Tuesday, May 18, 2021

The Company

The Second City is the premier brand in improv-based sketch comedy and the world’s largest school of improvisation with theatres and training centers in Chicago, Toronto and Hollywood. We have full time touring ensembles, casts on Norwegian Cruise Lines, and a thriving B2B division focused on hands-on learning, digital content and consumer insight.  Founded in 1959, the company continues to grow rapidly in size and influence.   

For additional information on The Second City please visit:

Position Summary

Reporting to the COO, the Head of People will be the functional lead for all people and culture initiatives at The Second City. This strategic leader would be joining the company in the early stage of our culture transformation journey and will be responsible for designing and implementing HR best practices, effectively leading a high-performance HR team and cultivate a productive, diverse, equitable, and inclusive workplace to ultimately support the forward-thinking mission and vision of The Second City.


The successful Head of People candidate will be an enthusiastic and passionate leader with executive presence and an uncanny ability to persuade, influence and inspire people. This leader must be able to create plans that map how to accomplish the business goals and objectives as it is an integral operational and strategic executive leadership position within a company on a culture transformation journey in a financially challenged climate. The Head of People is confident leader with demonstrated experience collecting and synthesizing input from stakeholders, identifying opportunities for improvement, proposing creative and pragmatic solutions, and thoughtfully designing process rollouts through a change management lens.


The Head of People will provide HR leadership and oversight for full-time and part-time employees in all Second City locations (Chicago, Hollywood and Toronto, Canada).  This leader will drive HR strategy in all areas of Human Resources including talent management, talent acquisition, benefits administration, compensation, learning and development, labor relations and employee communications.

Primary Responsibilities

  • Be accountable and responsible for the development, performance and evaluation of the People Team and departmental strategies and objectives. 

  •  Translate the business strategy, and our vision and values into a People Strategy, encompassing attraction, recruitment, induction, engagement, reward, retention, cultural development and talent development.

  • Provide a framework and support for the Leadership Team in the development, achievement and evaluation of their business, people management strategies and objectives.

  • Be an active and effective member of the Leadership Team, ensuring the high visibility, focus and delivery of the People and Culture activity.  

  • Develop, implement and continuously improve HR Business Partnering and People Management

practice and performance.

  • Oversee Talent and Casting Directors, as well as casting, professional development and best practices in collaboration with the Creative Departments.

  • Provide clear and inspirational leadership to motivate and develop the HR team to deliver high-quality, customer‐centered services.  Ensure that the quality and standard of services provided is the highest possible within available resources and positively benchmarked against organizational targets and comparative organizations.

  • Development of People Policy, and related systems and practices, that support our culture, reflect our mission and values and are fully implemented and adhered to at all times. 

  • Plans, develops, organizes, directs and evaluates the company’s human resource function and HR team performance. 

  • Ensure that diversity, equity and inclusion is firmly embedded within the People strategy, policy and practice, and the value of differences is realized.

  • Drive employee engagement, talent management, and employee relations to maximize individual performance and effectively balance the needs of the individual, organization and manage risk.

  • Manage the implementation of our collective bargaining agreements and provide ongoing interpretation and administration of the final contracts. Manage and continuously build Second City’s relationship with Union representatives.

  • Brings new and innovative ideas, policy implementation and new employee programs that will enhance the company culture and employee experience.

  • Evaluate and improve the talent acquisition and on-boarding process across the company to shorten time-to-hire and time-to-productivity of new hires.

  • Design and direct the performance management process across the company

  • Design succession planning model and oversee succession management processes across the company.

  • Design and implement department-specific employee development programs that improves employee performance and ensures top talent for future company growth.

  • Enhance, develop and coordinate companywide employee and community communications and team-building initiatives.

  • Strategic and operational use of employee information, and related systems, to maximize resource efficiency including for talent management and cost control. Ensure relevant people metrics inform and support business decisions.

  • HR and People Management IT functions and systems adequately support the team’s activities and that HR, managers, and other employees are equipped and able to use.

  • Design and maintain comprehensive, cost effective employee benefits programs, including managing annual open enrollment.

Experience and Education

  • 12+ years of progressive HR leadership experience.

  • Bachelor’s degree in Human Resources Management, Business Administration, or related field is required.

  • SHRM-CP or PHR certification highly preferred.

  • Proven ability to work effectively with employees at all levels, and from diverse and unique backgrounds and experiences.

  • Flexibility and determination to develop processes that will be effective within a dynamic and creative environment.

  • Positive, flexible, and collaborative leadership style.

  • Strong knowledge of all HR disciplines, with expertise in talent management and learning and development.

  • Knowledge of all current local, state, provincial and federal labor and employment laws.

  • Working knowledge of HR Information Systems and ability to utilize those systems for maximum HR results.  Knowledge of Dayforce is a plus.

The Second City is an equal opportunity employer. We encourage applications from all individuals regardless of age, gender, race, ethnicity, religion, or sexual orientation, and evaluate all candidates based on merit.

Other details

  • Pay Type Salary
  • 1616 N Wells St, Chicago, IL 60614, USA