Rachael Rose

Vice President of Inventory Strategy & Operations, Compass International Holdings

Compass

Aug 2026 - Current (1 month)

Chief Revenue Officer (CRO)

Uscreen

Jul 2025 - Current (1 year 2 months)

Uscreen is a video monetization platform helping creators build sustainable businesses through memberships, on-demand content, and community. Leading a full GTM transformation by rebuilding the revenue system from the ground up while keeping the business growing. What we're building: - Enterprise pipeline more than doubled in a single quarter, with total pipeline value growing 3x; including closing more new enterprise deals in Q4 2025 than the prior two years combined - Driving 28% YoY growth in new Platform MRR following a full GTM restructure in the first 90 days - Reducing churn and downgrades by double digits, exceeding board targets across both metrics - Redesigning the full GTM org: dual SMB + Enterprise motion with aligned compen

Senior Vice President and General Manager

Techstars

Oct 2022 - Jul 2025 (2 years 10 months)

Techstars is the world's leading startup accelerator, investing in and accelerating founders across 100+ programs globally. Inherited a highly siloed organization operating like a collection of independent programs. Built a unified, scalable operating model, without losing the individual character that makes each program uniquely work. What we built: - Managed $70M in annual corporate partner renewals, exceeding an 82% retention target consistently across the portfolio - Oversaw 38 accelerator programs globally, driving excellence in founder experience and investment returns across ~450 startups annually - Led 146-person team across Investments, Accelerator Operations, Global Mentorship, and Partnerships, building a culture of servant l

President, Customer Value

Compass

Jan 2022 - Oct 2022 (10 months)

Promoted to national scope to drive growth and engagement across Compass's full agent network of 30,000+ agents. - Designed and launched 8 national programs achieving an NPS of 9/10 - Drove 18% YoY improvement in agent performance through Customer Success programs - Delivered 183% increase in agent engagement — with 100% retention of the national agent base - Teams included: Agent Development Instructors and Advisors, Curriculum Development, Marketing, Operations & Production and third-party Real Estate Coaches)

Regional President - Illinois, Indiana, Minnesota and Wisconsin

Compass

Feb 2018 - Dec 2021 (3 years 11 months)

Launched Compass's Midwest region from zero infrastructure and scaled it into the company's highest-performing market. - Grew region from 13 to 4,000 agents across four states — 3,000+ in Chicagoland alone - Recruited 1,000 agents and 40 staff across four states in under a year - Scaled regional P&L to $160M annually — fastest region to profitability in company history - Achieved #1 market share in Illinois and recognition as #1 Top Workplace in Chicago by the Chicago Tribune - Led 150 staff across Agent Experience (Onboarding, Operations and Customer Success), Marketing (Regional brand management & Marketing Agency for Agents), Revenue (Agent contract renewal), Real Estate Managing Brokers & Sales Managers, Transaction Management & Compl

GTM Advisor & Educator

Various

Dec 2017 - Aug 2026 (8 years 9 months)

I advise great companies and CRO students at the University of Chicago on GTM strategy, talent management and scale. ► University of Chicago Professional Education | Instructor of "Customer Lifecycle Management" course ► Chief | Member ► Techstars Portfolio Companies | Mentor ► VentureSCALE | Mentor

Head of Practice Sales

Outcome Health

Apr 2017 - Dec 2017 (9 months)

Built and scaled a national sales organization across eight healthcare practice verticals. - Led 65 sales professionals to exceed national market penetration targets by 127% - Launched Sales Enablement program driving 34% productivity increase and 57% improvement in sales retention - Rebuilt recruiting pipeline — hired 21 top-performing FTEs in 60 days - Led team of 8 leaders and 65 sellers driving growth and national market penetration in the Health Care Provider network. - Healthcare Practice Areas included Oncology, Neurology, Rheumatology, Primary Care, Gastroenterology, Dermatology, Eye Care, Cardiology, and Infectious Disease

Franchise Director, Provider Solutions

Outcome Health

Jul 2016 - Apr 2017 (10 months)

VP of Sales, Groupon Getaways

Groupon

Apr 2015 - Jul 2016 (1 year 4 months)

Responsible for over $90 million in bookings a quarter; as well as the development and growth of 6 sales leaders and 55 sales professionals. Our goal is to provide consumers with undeniable value; and hotel partners with quality incremental guests when they want them. - 16% increase in billings YoY - 8% increase in features launched YoY - 33% increase in deals closed/Rep YoY - 17% increase in Sales Rep activity YoY - 13% reduction in Rep attrition

Regional Sales Director

Groupon

Oct 2013 - Apr 2015 (1 year 7 months)

• Responsible for over $64 million in Gross Bookings a quarter • Effectively manage and lead 5 Divisional Sales Manager and 67+ sales representatives • Sandler Trained

Divisional Sales Manager - Illinois & Wisconsin

Groupon

Jun 2012 - Oct 2013 (1 year 5 months)

Hired as an Outside Senior Account Executive for the Western Suburbs of Chicago. Within one year I was moved to the downtown sales territory where I averaged 134% to goal over my first year of sales. 7 months later I was promoted to to a Divisional Sales Manager (DSM) of the City of Chicago, the Southern Suburbs of Chicago and Rockford, IL. In this role I developed a team of 12 representatives, taking them from 87% of goal to over 160% of goal within four months. As of April, 2013, I manage 25 representatives across Illinois and Wisconsin. My responsibility and success has been in growing books of business month over month while also acquiring new business and improving overall sales strategy, continuously developing the representatives

Senior Account Executive - Outside Sales, Chicago

Groupon

Mar 2011 - Jun 2012 (1 year 4 months)

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Manager of Key Account Managers

Regency Office Products

Dec 2008 - Mar 2011 (2 years 4 months)

Regency Office Products is a (supplier of big/small ticket products to large/medium/small businesses in the Chicagoland area) with over $300 Billion in annual sales. In each of the last five years, annual sales have grown by 27%. Print Solutions Managzine ranked Regency as the second fastest growing print distributor of 2009. Director of Key Account Managers; Direct business to business sales position providing office products, printing, promotional products and programs, shredding and other value added services to C-level employees and their staff. Responsibilities include retaining and growing existing target account base while overseeing a sales force of 8 employees across 9 states focused on the heavy plate marketplace. Recruit, trai

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Director of Public Relations

JAINN

Jun 2007 - Jul 2008 (1 year 2 months)

www.jainn.net

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Key Account Manager

Regency Office

Dec 2006 - Dec 2008 (2 years 1 month)

Monthly retention percentages averaged 99.8%, (the highest rate ever achieved). Responsible for the company's most important clients in the Chicago land area; monthly revenue exceeded $170,000 (Sales Representative) 2005-December 2006 Top Sales Representative in the Chicago market, 6 months in a row Prospect, build and maintain customer relationships and purchasing habits Average fifty in-person cold calls and fifty phone calls per day Arrange an average of ten appointments per week with office managers and C-level decision makers

Account Executive

Weber Shandwick

Jun 2004 - Oct 2005 (1 year 5 months)

Draft memos and news releases, manage a team of interns, build and maintain client relationships, develop client partnerships, execute grassroots campaigning, conduct company’s communication audits, petition signings, act as liaison between client and consumer, strategize media plans, present and place news stories in the media, and develop long term crisis management strategies on a client to client basis.

Intern

Powell Tate

May 2003 - Aug 2003 (4 months)

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