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The Second City · Sales

Account Executive, Group Sales

United States, Chicago · Job Posted March 22, 2026
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Job Description

Our Group Sales team is at the heart of how we connect organizations, communities, and audiences with the transformative power of live comedy. We are looking for a driven, creative, and relationship-first sales professional to lead and grow our group business. The Account Executive, Group Sales is responsible for building and maintaining a robust portfolio of group ticket accounts while continuously pursuing new business opportunities. This role demands equal parts discipline and creativity — honoring the fundamentals of consultative sales while embracing innovative strategies and technology to stay ahead of an ever-evolving marketplace. You will cultivate lasting relationships with clients, tourism partners, nonprofits, schools, social clubs, and community organizations. You will also be an evangelist for The Second City’s unique ability to deliver unforgettable group experiences — from company outings and holiday parties to team-building events and association gatherings.

Job Responsibility

  • Create, manage, and grow new group sales opportunities, through consistent and creative out bounding efforts
  • Develop and execute seasonal group sales campaigns aligned with the production calendar and organizational goals
  • Create customized proposals and group packages tailored to client needs, including private receptions, exclusive seating arrangements, and add-on experiences
  • Meet and exceed monthly, quarterly, and annual group sales revenue targets
  • Maintain meticulous CRM records tracking all prospect touchpoints, pipeline stages, and contract history
  • Coordinate with box office and operations teams to ensure seamless group booking experiences from sale through event night
  • Proactively manage renewals, follow-ups, and account retention to maximize repeat business
  • Represent The Second City at industry events, trade shows, and community gatherings to expand visibility and build new referral pipelines
  • Cultivate a strong personal network of event planners, HR professionals, hospitality contacts, tourism operators, and community leaders
  • Partner with Chicago-area destination management companies (DMCs), hotels, and convention bureaus to drive group traffic
  • Host site visits and hosted experiences at The Second City to give prospective clients a firsthand feel for our unique offerings
  • Build relationships with affinity groups, alumni associations, professional associations, and cultural organizations to create recurring group business
  • Proactively research and identify untapped market segments and underserved client categories with high group sales potential
  • Develop and pitch creative group packages that respond to emerging corporate and social trends
  • Collaborate with marketing to develop targeted outreach campaigns
  • Explore partnership opportunities
  • Pursue group business connected to major Chicago conventions, sporting events, and citywide festivals by identifying visiting organizations and conference attendees
  • Leverage CRM tools (Salesforce) to track pipeline, forecast revenue, and prioritize outreach with data-driven insights
  • Use social selling techniques on LinkedIn and other platforms to identify prospects, engage decision-makers, and build credibility within key industries
  • Employ digital prospecting tools (ZoomInfo) to build and maintain targeted lead lists
  • Work with the marketing team to develop group-specific digital content — email sequences, landing pages, and social campaigns — that convert inbound interest into booked business
  • Analyze ticketing and sales data to identify trends, spot opportunities, and refine outreach strategies throughout the season
  • Stay current on industry technology trends, testing new tools that can improve outreach efficiency and client experience

Requirements

  • 3–5+ years of experience in group sales, event sales, hospitality, entertainment, or a closely related field
  • Demonstrated track record of meeting or exceeding sales targets
  • Demonstrated success in building group sales relationships specific to the Chicago social entertainment market (sports, theater, live music, festival events, etc.)
  • Demonstrated ability and enthusiasm for working autonomously in a fast-paced environment
  • can create internal sense of urgency to meet goals successfully
  • Exceptional interpersonal and communication skills
  • Strong organizational skills with the ability to manage a high volume of accounts and prospects simultaneously
  • Proficiency with CRM platforms and digital prospecting tools
  • comfort learning new technology quickly
  • Entrepreneurial mindset with the creativity to identify new opportunities and the persistence to pursue them
  • Passion for live entertainment, comedy, and the arts
  • Availability for select evening and weekend events, including open nights and client entertainment
  • Bachelor’s degree in Business, Marketing, Communications, Hospitality, or a related field preferred
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