Vice President, Second City Works (B2B Division)

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  • Chicago
  • Hours Full-Time
  • Start Date Flexible

Position title: VP, Second City Works (B2B Division)

Position location: Chicago, Illinois

Position type: Full time


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 soon 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 soon 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.

About the role

The Second City is looking for a visionary leader to oversee, transform and scale the global Second City Works business vertical. This role will manage the P&L for SCW (Second City Works) and be responsible for all aspects of the operations including product development and planning, inbound and outbound sales strategy and implementation, management of the global sales force, client relations, and overall excellence in delivery and production. This is a tremendous opportunity for a senior level sales and planning professional looking to make a significant impact with a legendary brand.

In this role you will leverage our unique assets to generate and optimize sales and update internal processes and workflows that advance productivity for our sales team and align with the needs and expectations of our clients. Our brand position and 65 years of unparalleled success in building the next generation of comedic talent and supporting corporate clients with their learning and development needs ensures us access to an endless pool of existing and potential partners. The leader of SCW will interpret historical and current market data to optimize product and workflow to drive B2B sales activity.

This is an active, hands-on position. A successful candidate must demonstrate the proven ability not only to sell and achieve annual targets, but also to design sales strategy and process, including meticulous tracking and reporting of pipeline and sales activity. They must also show managerial excellence, enabling, developing and driving the sales and customer success teams of 10-15 professionals. And, critically, a candidate for this role must showcase a team-oriented ensemble approach, with the ability to thrive in high-pressure environment and work in tandem with other business heads across the organization including Marketing, Production, Creative and Training Center.

This is a full-time, exempt position, reporting directly to the Chief Operating and Revenue Officer.

Primary responsibilities

  • Manage SCW P&Ls, including Chicago, Toronto, NYC and global
  • Review, design and update the SCW product offering in consultation with Creative and Production
  • Set and achieve annual sales targets and other KPIs, and provide weekly forecasting
  • Work with Production, Marketing, and Finance to optimize margins on the business
  • Manage a global sales team of approximately 20 people
  • Regularly review, analyze, and report performance data to Leadership Committee, CEO, COO/CRO and CFO
  • Actively monitor sales activity and maintain excellent Salesforce hygiene to drive accountability
  • Provide strategic advice to the Leadership Committee on go-to-market strategies
  • Build inbound and outbound client pipeline and drive incremental conversions and productivity for the sales team
  • Identify new B2B revenue streams for the company (sponsorships, etc.)
  • Oversee client relationships, leading to strong renewals
  • Develop and implement improved sales processes that drive consistency across the organization.

Qualifications and background 

  • 10 plus years of proven experience in senior sales operations and/or enablement roles with exceptional leadership, organizational and task management skills
  • Proven results of successfully increasing sales productivity to drive revenue
  • Previous direct selling experience is a plus
  • Experience training and developing a sales team and driving accountability to revenue goals
  • Entrepreneurial instincts with a success record of growing, building, and scaling a sales business
  • Detail-oriented with ability to adapt and thrive in complex, ambiguous and ever-changing market conditions
  • Collaborative and flexible approach, with a bias for action
  • Proven ability to succeed in a complex, fast-paced environment
  • Feel a strong sense of ownership and accountability over your work; be strategic (but tactical enough) to execute day-to-day
  • Decisive, and have the tenacity to “make things happen” backed by measured and clear communication and presentation 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.

The Second City follows CDC guidelines and recommendations regarding safety measures to navigate the Covid-19 pandemic. To work at The Second City you must show proof of being fully vaccinated against SARS-CoV-2. Applicants with medical or religious exemptions will be considered