Vice President Sales Operations

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  • Chicago
  • Hours Full-Time
  • Start Date Flexible

About The Second City

The Second City is the premier brand in improv-based sketch comedy. Dedicated to entertaining, inspiring, and transforming through fearless comedy, the company’s ten resident stages in Chicago and Toronto, plus eight Touring Companies and a booming Theatricals division, entertain over one million theatergoers per year. The Second City Training Center, which includes the Harold Ramis Film School, is the largest school of comedy on the planet, with locations in Chicago, Toronto, and Los Angeles. Second City Works is the professional services side of the company, serving more than 600 clients –including nearly 25% of the Fortune 500– through hands-on learning, licensed and custom video, consumer marketing programs, and custom live entertainment.

Founded in 1959, The Second City continues to grow rapidly in size and influence by upholding five core values: performance; ensemble; diversity and inclusion; resiliency; and authenticity.

About the role

The VP of Sales Operations is a tremendous senior level sales opportunity for someone looking to make a big impact with a legendary brand. As the VP of Sales Ops, you will be responsible for sales operations across all locations and portfolios including Second City Works, the Second City stages and our Training Center.

This is a new and exciting role at The Second City where you’ll have the ability to leverage our unique assets to generate and optimize sales processes and workflows that advance productivity for our sales team. Our business gives us access to a plethora of potential future clients. It will be your responsibility to interpret and optimize that data and align workflow to generate B2B sales activity. You will partner with our President and executive team to ensure alignment, consistency, and performance expectations are being met by all revenue-generating individuals across the organization.

The goal for the VP of Sales Ops is to set the sales team up for success. You are an active, hands on collaborator who knows how to enable the team for customer success and track progress while meticulously keeping on top of pipeline and sales activity goals. You are a thought leader in cross-functional discussions with Marketing, Business Development, and Customer Experience, overlooking directly and indirectly a team of 15-20 employees. It goes without saying, but a “Yes And” attitude and ensemble-orientation is an absolute must.

This is a full time, exempt position reporting directly to the President.

Primary responsibilities

  • Enablement: tying sales and marketing to ensure sales team has optimal data and resources each and every day to maximize productivity and pipeline
  • Provide strategic advice to executive team on go-to-market plan
  • Establish and follow through on all revenue-generating KPI’s for full funnel reporting and monitor sales activity to drive accountability. Develop go-to-market scorecards, forecast, and report on lead generation activities to ensure that sales goals can be achieved.
  • Build and execute ideas to improve conversions and efficiencies, creating a material increase in productivity for the team
  • Lead execution of large-scale internal cross-functional projects that directly impact new business, cross-sell, and enable customer retention
  • Work closely with sales management to improve sales processes and to drive consistency across the sales organization. Assist sales management in understanding and resolving process bottlenecks and inconsistencies.

Qualifications and background

  • 10 plus years of proven experience in senior sales operations and/or enablement roles with exceptional organizational and task management skills.
  • Proven results of successfully increasing sales productivity to drive revenue
  • Previous direct selling experience is a plus. You have helped teams and people succeed in the past to reach and exceed their revenue goals
  • Previous demonstration of being a lateral thinker who likes building, growing, and scaling business as well as mentor teams who do not report directly to you
  • You are a granular thinker but thrive in ambiguity and managing multiple priorities, and have a collaborative and flexible approach, with a bias for action
  • Proven ability to succeed in a complex, fast-paced environment that offers intangible services/products
  • Feel a strong sense of ownership and accountability over your work. You’re strategic (but tactical enough) to be able to execute day-to-day
  • Entrepreneurial, decisive, and have the tenacity to “make things happen” backed by measured and clear communication and presentation skills


The Second City is 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 community.


Apply directly for this position.


The Second City is an e-verify employer. E-Verify is a web-based system that allows enrolled employers to confirm the eligibility of their employees to work in the United States. E-Verify employers verify the identity and employment eligibility of newly hired employees by electronically matching information provided by employees on the Form I-9, Employment Eligibility Verification, against records available to the Social Security Administration (SSA) and the Department of Homeland Security (DHS). Your employment is contingent upon employment authorization from e-verify.