Allen Wolff

Birmingham, MI

Allen is Co-founder and Chief Financial Strategist of PlumDiggity, a financial and marketing firm. PlumDiggity offers operational, financial, and marketing strategies to accelerate corporate growth, structure, and culture. It specializes in early-stage technology companies.

Allen most recently served as CFO of 365 Retail Markets - the global leader in item-level MicroMarket technology. Allen assisted with securing 365’s equity financing of $1.2M in equity and $600K in debt, serving on the Company’s Operating Committee since early 2012. 365 has experienced over 400% annual growth.

Allen is involved with two social ventures. He is an early investor and advisor in Roozt, a curated eCommerce platform that connects online shoppers with trendsetting cause-related brands. Allen also worked at Crowdrise - a social charitable network co-founded by actor and philanthropist, Edward Norton. During his engagement at CrowdRise as “Game Changer” the company experienced +100% annual growth while securing its place in the event fundraising business.

Prior to Crowdrise, Allen co-founded PaySimple, a SaaS solution to automate the collection of accounts receivables. Since inception in December 2005, PaySimple has added thousands of clients fueled by a capital raise of over $30M in debt & equity. In addition to serving on the company’s board of directors, Allen held roles including President, CFO, and Executive Vice President.

Before PaySimple, Allen participated in more than a dozen private equity transactions representing more than $40M in invested capital during his tenure at SpaceVest, a $300M Venture Capital firm based in Washington, DC.

Allen began his career in the restaurant industry and owned a BD’s Mongolian Grill franchise in Bethesda, MD for over 14 years. He received his B.A. in Organizational Studies from the University of Michigan and his MBA in Entrepreneurship and Finance from the University of Maryland.

Allen resides in Birmingham, MI with his wife, Shelley, and two children, Jocey (12) and Bryce (10) and enjoys running, boating, and entrepreneurship.

  • Work
    • 365 Retail Markets
  • Education
    • University of Michigan
    • University of Maryland