Account Executive, Group Sales

The Second City•Chicago, IL

About The Position

Dedicated to entertaining, inspiring, and transforming through innovative live experiences, The Second City is the premier brand in improv and sketch comedy. With sold-out shows playing on resident stages in Chicago, Toronto, and New York; Second City’s Touring Theatrical companies also entertain 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 brick-and-mortar locations in Chicago, Toronto, New York and a virtual division offering accessible classes online worldwide. 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. For additional information on The Second City please visit: www.secondcity.com. The Role 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.

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 — you're genuinely energized by building relationships
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

Nice To Haves

Bachelor's degree in Business, Marketing, Communications, Hospitality, or a related field preferred

Responsibilities

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