Inside Sales Representative

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  • Chicago
  • Hours Full-Time
  • Start Date Flexible

About Second City Works

Second City Works is the professional services side of The Second City, the world’s leading comedy theatre and school of improvisation. We serve 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. When businesses engage Second City Works they develop unique insights and skills to better collaborate and create with their colleagues and customers. Working with leading international clients across various industries, including tech, CPG, financial services and healthcare, over 4 million employees view our video content globally, and we maintain a Net Promoter Score of 82. We are adding to our Sales Enablement team to expand our impact and match market demand for our solutions. To know more about us, visit

About the role

The Second City has been an iconic institution for 60 years. Our award winning shows, training center, together with Second City Works, enable us to share our talent and techniques with locals, visitors and businesses alike. To reflect that, we will be adding someone to our Inside Sales Team to expand our network and enhance our position as a strategic partner to both current and prospective clients.

This is an individual contributor role where you will identify and qualify high potential prospects for the business. Because we know our unique product, services and uncanny delivery will exceed all expectations, one of the main priorities of the inside sales representative is to educate prospective customers about the value and breadth of Second City’s offerings. You will have direct client alignment to evaluate and understand their needs and make offerings with your product knowledge. You will be the primary influencer specifically in prospecting and qualifying phases.

Second City Works is comprised of enthusiastic and performance-driven individuals. The ideal Inside Sales candidates are hungry to over achieve on goals.

Success in this role is measured by hitting and exceeding monthly sales goals, consistently staying ahead of daily metrics, and handling rejection in stride, all in an ensemble-focused environment. It goes without saying, but a “Yes, And” mindset is critical.

This is a full-time, exempt position reporting to the VP of Sales Operations.

Primary responsibilities

  • Building effective relationships: Drive increased revenue for new & existing products with superior relationship building skills
  • Opportunity Identification: Displace competitors & win wallet-share
  • Articulating Value Propositions: Drive increased revenue for new & existing products
  • Quota Achievement: Drive solid funnel through good opportunity prospecting
  • Sales Forecasting: Regularly track and provide accurate sales activities utilizing sales tools
  • Closing the deal: Consistently move the customer or prospect towards commitment and provide service that exceeds customer expectations
  • Knowledge sharing: Consistently contribute to the strength of the ensemble, sharing personal expertise, and collaborating to design creative solutions
  • Tracking: Record all sales activities in CRM system


Minimum skills and qualifications

  • BA
  • Minimum 2 years inside sales experience
  • A generalist knowledge of the full product portfolio with the ability to orchestrate transactional deals
  • Strong account relationship skills
  • Highly developed interpersonal, organizational and communication skills
  • Strong data management abilities
  • Experience in Salesforce (certified admin a plus)
  • Well-versed in Google Suite, Microsoft Office and WorkPress
  • Ability to effectively prioritize tasks and time within a fast-moving environment.

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 community.