Colleen Wilson

I have 12 years of experience working in large companies, startups and small businesses in a variety of leadership roles, from product development and management, business development, marketing strategy, training and development, insights and research, and coaching. I spent the first 9 years of my career at one of the largest financial services firms and most recently led product marketing for Square Capital, the fastest growing product at Square. 

My diverse background helped me develop a unique understanding of business from the lens of a customer, competitor, owner, and investor combined. Collaborate Chicago is a culmination of my experience in finance, tech, business school and working directly with startups, allowing me to apply all of this experience directly to entrepreneurs and startup teams.


Finance, SaaS, fintech, recruiting, telecomm, creative services, personal development


Right now I am focused on the interaction of female entrepreneurs and fundraising. If you are getting ready to pitch, or have just received funding, I’d love to talk with you and support your growth

Product and industry wise, I’m fascinated with how traditional high-touch industries (recruiting, coaching, lending, financial planning, etc.) are becoming more disrupted and made scalable via analytics and technology; I also love the challenge of offering a humanized experience through tech.


The Flourishing Center - Certificate in Applied Positive Psychology (CAPP)

Washington University in St. Louis - MBA

  • Focus areas: Strategy, Entrepreneurship, Organizational Behavior
  • ArchGrants Due Diligence Committee member
  • TRex Pro Bono Advisor

Saint Louis University - BSBA

  • Economics and Marketing majors
  • Magna Cum Laude


Advised, consulted, supported and coached over 1100 entrepreneurs and startups

Launched over 20 products and services

Led 35 product initiatives, cross-functional campaigns and rollouts

Developed and spec’d out Square Capital’s first partnership product

Led multi-market client segmentation study to inform new products and client experience delivery

Grew the Square Capital platform to over $400M in 2015, and $342M advanced in Q1 & Q2 2016

Delivered over 300 presentations, training and speaking engagements

Received 2nd place in my first pitch competition

Conducted due diligence for over 30 startups and served on the due diligence team for Square Capital, helping us secure funding from 5 new investors

Graduated in the top 10% of the MBA Class at Wash U and was chosen by my professors to receive the Neuwoehner award for my contribution to the classroom and program

Created the last two jobs I held (including successfully pivoting my career into tech)

Lived in 3 cities in 3 years...and don't plan to move any time soon!