Caroline Sizer

Vice President, Portfolio Analytics

2024

Gridiron Capital is an investment firm focused on partnering with founders, entrepreneurs, and management teams, and creating value by building middle-market companies into industry-leaders in branded consumer, B2B and B2C services, and niche industrial segments in the United States and Canada. We help transform growing companies by winning together through hard work, partnerships grounded in shared values and a unique culture that comes from hands-on experience building and running businesses. As a team led by former operators and entrepreneurs, we know what it takes to run successful businesses on a day-to-day basis.

Member

2024

An invite-only networking group of founders, investors, and senior leaders in the tech sector, where we support the "Females in Finance" initiative.

Member

2019

The world’s largest global community for women in venture capital to connect, collaborate, and create opportunities.

Board Director

2022 - 2024

The nation’s leading pop, dance, and hip-hop music festival series, hosting over 100,000 college students and young professionals annually, touring 30+ college campuses across the US, and activating a small army of 1,200+ college student ambassadors.

Board Observer

2022 - 2024

Bakery concept founded by James Beard award-winning pastry chef Christina Tosi. Since its founding as a standalone bakery in 2008, Milk Bar has transformed into a multi-platform lifestyle brand, spanning traditional retail, e-commerce, live experiences, and media, with locations in New York City, LA, DC, Boston, WA, and Las Vegas.

Vice President, Investing and Portfolio Management

2017 - 2024

Private investment firm made up of builders, innovators, partners and founders who focus on companies across sports and entertainment, media and marketing, food and lifestyle, and technology. By combining a deep understanding of a founder’s mission with the strategic resources of our network, RSE elevates businesses at inflection points. Connect with us at rseventures.com and @RSEVentures. -- Select investments: Magnolia Bakery, VaynerX, Relevent Sports Group, ResQ, Breakaway Music Festival, Atomo, Momofuku, Milk Bar, Fuku, &pizza, Bluestone Lane, Drone Racing League, NextVR, Resy (acquired by American Express in 2019), and SkOUT Secure Intelligence (acquired by Barracuda).

Board Observer

2018 - 2023

Mission-driven, culture carrying pizza company dedicated to better flavor, quality ingredients, and community betterment. Proud to differentiate themselves, &pizza is doing more for their workers by providing a livable wage, a socially conscious vision, and real action to help advance real social progress. &pizza has locations across the East Coast in New York, Philadelphia, Boston, Washington DC, Baltimore, and Virginia.

Board Observer

2021 - 2023

Australian-inspired coffee and café hospitality business founded by former Melbournian, Nicholas Stone. Known for introducing the “Flat White” and “Avocado Smash” to the United States, the brand has enjoyed rapid adoption from consumers who are looking for superior coffee, an elevated experience, and healthier menu options.

Associate

2017 - 2017

Senior Analyst

2015 - 2017

Advisory firm that provides financial and strategic planning services to small- and medium-sized businesses, enterprise nonprofits, and government entities.

Analyst

2013 - 2015

Economic consulting firm that provides economic, financial, and strategy consulting to law firms, corporations, and government agencies. Main Practice Areas: Bankruptcy, Energy, Strategy & Analytics, and Commercial Damages