Matt Strauss

Advisor, Entrepreneur, Speaker & Board Member

I specialize in helping: Entrepreneurs, Executives and Business Leaders.

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Running a business can feel like a lonely road, but it doesn’t have to be.

That’s why I launched my advising and speaking practice—to empower leaders to thrive as business owners, navigate career transitions with confidence, avoid costly mistakes, and truly enjoy the journey.

How I Help

Executive Advising & Coaching

  • Leadership Evolution
    Personalized executive coaching to help leaders grow from their current stage to their next level of effectiveness and impact.
  • Go-to-Market Strategy & Sales Acceleration
    Guidance on messaging, positioning, and sales execution—plus warm introductions to accelerate growth.
  • Channel Partner Development
    Build or expand a scalable referral partner network to drive consistent revenue and market reach.
  • Fundraising Strategy & Investor Alignment
    Tactical support on pitch refinement, deal structure, and access to strategic capital partners.
  • Product Launch & Process Optimization
    Support with launching new offerings or refining internal operations for greater efficiency and scalability.
  • Social Impact Business Design
    Strategize or pivot toward a mission-aligned business model that blends profit and purpose.
  • Team Growth & Leadership Transitions
    Navigate hiring, restructuring, and executive transitions with clarity and confidence.
  • Matt’s Process: Exploring Executive Coaching Fit

    1. Discovery Call (30 Minutes)
    A focused conversation to explore your goals, challenges, and vision—ensuring strong alignment and the potential for real impact.

    2. Proposal Review
    If there’s a mutual fit, Matt will share a customized proposal that ties executive coaching to your business growth, leadership development, and strategic priorities.

    3. Kickoff Session
    Together, you’ll define your “current self” and set measurable benchmarks for the “next-level leader” you’re working to become—laying the foundation for your executive coaching journey.

    4. Weekly Coaching & Strategic Support

    Ongoing 1:1 sessions to tackle your biggest challenges, delegate key projects for Matt to lead or support, celebrate wins, and stay accountable as you evolve into your future self.

    Speaking & Workshops

    Book Matt for a speaking session to inspire your team, energize your customers, workshop with your employees, experiment new processes, or create innovative ideas.

    Impact

    8+

    Executives or Entreprenuers Coached

    $10+ mil

    In Revenue and Investments Raised

    320+

    Jobs Placed

    About Matt

    Matt has over 10 years of experience in venture capital and entrepreneurship. Those ten years were filled with ups, downs, moments of depression, and triumphs. Matt often believed that Fridays were the hardest days—the ones with the most 'no's in sales, the toughest customer challenges, as if life was testing his resolve. Those moments led him to some of the lowest points of his life. But through it all, he learned that overcoming those challenges is what built success.

    Now, Matt hopes to be there for you, especially during the tough times. Whether you're growing a company, managing a team, or navigating a career change, know that you’re not alone in facing challenges. Resilience and perseverance are the keys to breaking through.

    Matt's passion for helping others was shaped by his parents' and siblings' influence. While mentoring young people from under-resourced communities in Chicago, he saw firsthand the systemic barriers that make it difficult for job seekers to access opportunities. Recognizing the need for change, he set out to bridge these gaps in workforce development.

    That’s why he founded RiseKit—a platform that connects nonprofits, employers, government agencies, and community foundations, making it easier to identify, train, and support job candidates. Matt and his team are driven by the belief that a person’s zip code should not determine their future. He is always eager to collaborate with innovative, like-minded leaders who share his vision for creating lasting social impact.

    Matt is also a founding board member of Of Color, Inc. He resides in the Chicago suburbs with his wife, Brooke Strauss. Brooke and Matt  are often spending time with family, watching Liverpool or Chicago sports, enjoying live music, theater, or traveling. 

    Testimonials

    "Matt is one of the Founding Board Members of Of Color, Inc. We are a 501c3 in Chicago's south side serving opportunity youth, homeless veterans, and other vulnerable populations. As one of the founding board members, Matt was instrumental in getting Of Color, Inc off the ground through his connections, advice and board governance."

    Renita White

    Of Color, Inc

    "I have known and worked with Matt for over five years. Matt is someone with a huge heart who has found his passion in life by working with and lifting up the underserved communities. Matt brings over-the-top and exceptional sales ability in sharing his vision and getting buy-in from Corporations, Family Offices, Foundations, and Venture Capital. Matt has developed managing and organizational skills to supplement his drive and vision, and is someone I am honored to have invested in RiseKit and Matt!"

    Scott Kallick

    Investor & Business Coach

    Portfolio

    RiseKit

    RiseKit brings together employers, social services, workforce and education leaders to connect untapped talent with family-sustaining wage employment.

    Of Color, Inc.

    We believe people of all colors can be leaders in their own lives when given the proper resources to enhance their own economic and education goals.

    Dion's Chicago Dream

    Feeding Families, Building Communities, Fuel Hope.

    Puberry

    Revolutionizing Health Education starting with Puberty.

    Blog: Check out the impact across my portfolio

    Contact me to learn more about anyone in my portfolio.

    40 Under 40 Award

    Award

    City of Chicago Renews

    City of Chicago Partnership

    RiseKit Raises $4.75 Million to Help Companies Solve Labor Shortages by Scaling Their Community Hiring Initiatives

    Fundraise, capital, investors.

    RiseKit Leadership Update: Josh Glantz Joins as CEO, Matt Strauss Transitions to President

    CEO Transition

    Dion's Chicago Dream's Amazing Mission and Leader

    Dion on the news!

    A Brief Parent’s Guide to Supporting Their Child’s Mental Health

    A Brief Parent’s Guide to Supporting Their Child’s Mental Health

    Reach out to Matt
    to Learn More

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