Robert Montgomery

Senior Manager, Special Events for the Chicago Cubs

Greater Chicago Area

About

Dynamic, engaging and collaborative self-starter with high-level communication and logistics coordination skillset. Proven experience in large-scale event planning, management and execution, public speaking, process streamlining and implementation, critical and strategic thinking, and organizing and leading teams.

Experience

  • Chicago Cubs (Full-time · 4 yrs)
    • Senior Manager, Special Events
      Feb 2026 - Present · 5 mos

    • Manager, Special Events
      Jul 2022 - Present · 4 yrs

  • Manager of Special Events and Initiatives at Adler Planetarium
    Mar 2019 - Jul 2022 · 3 yrs 5 mos

    • Project manager and key stakeholder in the Adler Planetarium’s Annual gala ‘Celestial Ball’ which raises over $1.8 million dollars annually for the institution. • Responsible for the planning, logistics, and on-site execution of a variety of events at the Western Hemisphere’s oldest planetarium. Events are focused on appealing to the Adler’s major donor base. • Works closely with the marketing and business strategy team to align event purpose and messaging with the Adler’s overall brand and business strategy in a given calendar year. • Responsible for the management and professional development of the Events Coordinator in the Development department. NOTABLE PROJECTS Celestial Ball, 2020 & 2021 • Lead project manager and night-of logistics manager for the Adler Planetarium’s first ever all digital gala. Worked to pivot all resources available to the department and institution to creating an engaging virtual event that appealed to both our major donor base, as well as the wider Adler audience. • Able to pivot the entire 2020 event to an online format with a budget cut of ~80%, and a three month turnaround window. • Responsible for working with an outside vendor to manage the filming, editing, and overall production of a virtual event with no experience in film production. Celestial Ball, 2019 ‘The Future Is Now’ • Lead project manager and onsite logistics manager for a 750 person gala at the Adler Planetarium. Responsible for working with a variety of vendors to ensure all aspects of the event are in line with donor and leadership expectations. The event raised over $1.8 million dollars in funds for the Adler’s mission. • Coordinated with a volunteer board and volunteer leadership as well as internal Adler stakeholders to create a program rooted in the Adler’s mission and highlighting the work the institution does in STEM and STEM education in Chicago. Responsible for creating this event within a set budget.

  • Half Acre (5 yrs 3 mos)
    • Events Coordinator
      Sep 2015 - Jan 2019 · 3 yrs 5 mos

      • Collaborate with the sales team to manage and execute all local, national and international festival, sampling and invitational travel opportunities. • Manage, staff, and coordinate a small team of part-time employees to deploy as support for events at over 1,000 local accounts. • Serve as primary operations employee for all major releases, parties and company sanctioned events at the brewery. • Coordinate and manage the ‘Hoppy Brew Crew’, Half Acre’s volunteer base. NOTABLE PROJECTS The Big North I, II, & III — Annual Anniversary Party, 2050 W. Balmoral Avenue • Lead coordinator in creating, curating and day-of operations for a 1,500+ attendee party at the Half Acre Beer Company production facility. • Organized and ran all aspects of the event including; beer, food, music, activities, volunteer staffing and scheduling, and the lay-out of the space three years in a row. • Highlights of The Big North include: Axe throwing, live tattooing, drum circle, roaming balloon animal artists, a castle made entirely of empty beer cartons, live airbrushing of the company truck, and the destruction of a 3,500 can pallet of empty aluminum cans by an employee dressed in a dinosaur costume. Photos available upon request. Far & Away — Invitational Festival, Harris Theater Rooftop Pavilion • Lead coordinator in curating and running a beer invitational featuring breweries from around the country and globe in the Harris Theater Pavilion in Millennium Park with over 65 beer and vintners represented and a total attendance of over 1,700 people. • Responsible for communication with brewery representatives regarding lodging and activities surrounding the event. • Managed set-up of the space and equipment for the event on the day-of, as well as all staffing of Half Acre employees and our volunteer core. • Coordinated with a hired production company to run attendee check-in, and the logistics of loading in and out of a prestige Chicago location in an 18-hour timeframe.

    • Private Events Manager
      Nov 2014 - Mar 2016 · 1 yr 5 mos

      • Responsible for responding to requests and negotiating contracts private event bookings. • Manage onsite facilitation of planned events within the industrial brewing facility. • Self-managed position bringing in new revenue streams of roughly $25,000 per quarter.

    • Hospitality
      Nov 2013 - Sep 2015 · 1 yr 11 mos

      • Worked as a host, bartender, server, and beer guide in the customer facing operations of one of Chicago’s largest breweries. Responsible for giving public and private tours for groups ranging from two to 80. • Responsible for daily opening and closing procedures as well as knowing all facets of the company to better serve our customers.