Inside Sales Representative

Back to All Careers
  • Toronto
  • Hours Full-Time
  • Start Date Flexible

The Second City is the premier brand in improv-based sketch comedy. Dedicated to entertaining, inspiring, and transforming through fearless comedy, the company entertains over one million theatergoers annually. The Second City Training Centre, which includes the Second City Film School, is the largest school of improvisation on the planet, with locations in Chicago and Toronto.


Second City Works, the B2B side of The Second City, focuses on providing organizations hands-on and virtual learning and development, corporate entertainment, and an on-demand library of over 300 comedic workforce education videos, focusing on topics such as talent management, diversity & inclusion anti-harassment and ethics & compliance.


About the team

Second City Works is the professional services arm of The Second City. When businesses engage Second City Works, they develop unique insights and skills to better collaborate and create with their colleagues and customers. Engagements with our clients can take a variety of forms: workshops, keynotes, customized video, corporate entertainment, and more. We are adding to our sales team to expand our impact and match market demand for our solutions.


About the role  

This is an Inside Sales 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.

This role will be based at Second City’s brand-new theatre and offices at 1 York St. in the heart of the city centre.


Primary Responsibilities  

  • Identify, engage with and close clients – primarily in the small/medium-sized business (SMB) space, through inbound leads, account prospecting, and uncovering opportunities where Second City Works could be a strategic long-term partner
  • Tell the story of Second City Works: who we are, our capabilities, and how we are uniquely equipped to improve engagement and connection with any business’s employees or customers
  • Manage all phases of the sales lifecycle across a variety of sales scenarios (new prospects, re-activations, growth within existing accounts)
  • Partner with Client Services and Creative Talent to customize client programs and solutions, ensuring that we deliver on our promises



  • 2+ years of consistent Inside Sales success, including managing and obtaining an annual quota of $600k+
  • Experience selling products or services over the phone and/or virtually while navigating multiple stakeholders across an organization
  • Successful experience selling within the talent/HR/learning category
  • Extensive knowledge of the Canadian business landscape, including selling into various industries.
  • Proven reliability to self-manage schedule, targets and timelines
  • Communication skills that make other people envious; collaboration skills that make teammates thankful
  • Experience with consistent account research and communication through tools such as: LinkedIn, ZoomInfo and Outreach
  • Demonstrated sales success due to inquisitiveness, resilience and/or likeability. Preferably all 3.
  • Must have experience and thorough knowledge of Salesforce, Zoom, Microsoft Outlook, Microsoft Excel and Microsoft PowerPoint.
  • Preferred knowledge of Outreach, ZoomInfo, LinkedIn and Loom


The Second City is an open, inclusive workplace and welcomes 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. 


All candidates for this role will be asked to authorize a background check and must be 21 and older. All candidates for this role must be able to legally enter the United States. 


Apply for job directly here.