Erin O'Leary 🍀, MBA, CMAA

Co-Founder

Boston, Massachusetts, United States27 yrs 10 mos experience
Most Likely To SwitchHighly Stable

Key Highlights

  • Expert in maximizing business exit values.
  • Proven track record in M&A negotiations.
  • Dedicated to empowering business owners.
Stackforce AI infers this person is a Mergers & Acquisitions expert with a strong entrepreneurial background.

Contact

Skills

Core Skills

Mergers & Acquisitions (m&a)NegotiationIntegration

Other Skills

Analytical SkillsBusiness AnalysisBusiness ValuationCRM DatabasesCoachingCross-functional Team LeadershipCustomer ServiceDeal StructuringEntrepreneurshipFinanceFinancial AnalysisFinancial ServicesFundraisingLeadershipManagement

About

Serial entrepreneur and global consultant turned into $4-25M M&A (sell-side mandate) advisor and top LinkedIn voice. I am honored to empower business owners by giving them their freedom. Navigating one of the most significant milestones in business owner’s lives is selling their company, and it is anything but easy. It is a journey wrought with obstacles and challenges along with emotional highs and lows. This is why I do what I do. I’ve been there myself, many times. And I also know that when freedom comes - freedom provided by the time & money you receive when you sell - it is worth the journey. My sellers set the rules of engagement, whether it is securing top dollar, finding the ideal fit in a buyer, or structuring an internal transfer that aligns with their goals. I bring deep market knowledge, industry insights, and M&A expertise to every transaction, ensuring you get the best possible outcome: **Business Valuation:** Accurately assessing your business's market value. **Market Positioning:** Showcasing your unique value proposition to attract premium offers. **Negotiation Mastery:** Securing the best deal for you with expert negotiation. **Deal Structuring:** Crafting win-win agreements that close deals. **Seamless Execution:** Leading the M&A process so you can focus on your next chapter. Selling a business is more than just a transaction—it's a personal journey. I’m dedicated to understanding your goals and tailoring my approach to meet your unique needs. If you're not ready to sell now, I can help you identify value drivers specific to your firm and raise your enterprise value for a future sale. Let’s connect if you’re a business leader, wealth advisor, CPA, CEO, founder, or event planner looking for a speaker!

Experience

27 yrs 10 mos
Total Experience
8 yrs 5 mos
Average Tenure
9 yrs 3 mos
Current Experience

Penn state smeal college of business

3 roles

President, Alumni Society Board & Penn State Alumni Council

Promoted

Jul 2025 – Present · 11 mos

President Elect, Alumni Society Board

Apr 2019 – Jul 2025 · 6 yrs 3 mos

President, Smeal Club Happy Valley, Penn State Smeal College of Business

Mar 2017 – Jan 2021 · 3 yrs 10 mos

Fidelity paper & supply corp.

Sales and New Business Development Consultant

Feb 2015 – Jul 2015 · 5 mos · PA, MD, OH, MA

  • Fidelity Paper & Supply is a top national source for typical packaging products ranging from bubble and shrink wrap to plain or printed corrugated boxes and tape. However they specialize in Pharmaceutical/Industrial packaging which includes die-cut foam briefcases for high tech equipment as well as more sophisticated packaging solutions. Further Fidelity has JIT/next day delivery capabilities within the state of PA and bordering states allowing clients to capitalize on their ISO 9000 certified warehouse to achieve better operations management and reduce the cost associated with dedicating warehouse space to packaging. (Also the profit and loss statement of your company will show better returns immediately when your company only pays for the packaging your use and need during any given month.)
  • My role is to develop strong business relationships with companies who use packaging of any type. These include: Fortune 500 companies such as Johnson & Johnson, Colgate-Palmolive, Victoria Secret, and Over Head Door (current clients) as well as smaller companies such as printing companies, manufacturing companies, food companies, etc.
  • As a new member of this organization my goal is to provide the highest quality packaging solutions available with the best service possible (JIT in PA with next day delivery) for the most competitive price.

Assetmark, inc.

Mergers and Acquisitions Specialist, Acquisition Deal Team to National Strategic Liaison

Jan 2015 – Aug 2018 · 3 yrs 7 mos · State College-DuBois Area

  • Aris Corporation, acquired by AssetMark, formerly offered high net worth asset management solutions as well as retirement plan investment management and other customized portfolio options to regional and national Investment Advisors. My role is as a deal team partner, I worked internally and externally to integrate assets, reduce redundancies, facilitate the transition team handoff, and immigrate clients and assets. Later as a Strategic Consultant Liaison , I "launched" new strategists onto the finserv platform, including marketing plan & sales strategy development to communicate with existing Client Advisors and reach out and develop new Advisor Relationships via in-person national sales meetings.
Mergers & Acquisitions (M&A)NegotiationNetworkingIntegrationProduct Launch

The state theatre in state college, pa

Chairman Of The Board

Jun 2013 – Jan 2019 · 5 yrs 7 mos · State College, PA

  • The State Theatre is a substancial contributor to the rich, cultural diversity of the university town of State College, PA. The State Theatre hosts everything from community dance and theatre to national acts of all genres.

Pegasus capital

Founder, M&A Advisor, Business Broker

Apr 2012 – Present · 14 yrs 2 mos · Boston, Massachusetts

  • As a boutique, mainly sell-side advisory, we work with founders, families and (often) other trusted advisors to successfully sell lower-middle market, privately held companies with enterprise value $3-25M. Our team gets the max value exit for stakeholders. Recognizing it is not just what you get, it is what you keep. We are founders, attorneys, wealth managers and CPA's, collaborating with our client's best interests in mind.
  • Why? Pegasus Capital was founded because business owners deserve better. Business owners who are in the $3M-25M space are typically sophisticated in their businesses yet underserved professionally. You want the same level of credentials (if you are selling to PE's with MBA's you should have an MBA with experience representing you) to level out both sides of the negotiations table.
  • Do you know your (business') worth?
  • Do you know the levers to enterprise value?
  • And even if you are transitioning in 3, 5 or 10 years - do you know how to prepare for an optimal exit?
  • What if someone comes to you prior, wanting to buy your firm, do you know how to proceed and negotiate with them while protecting yourself & your firm?
  • We help founders and their families get max exit value, by understanding the process and how to optimally position themselves to benefit from the process of selling their firm.
  • Using high-level financial insights we craft successful strategies and tactics to synchronize and maximize profitability and enterprise value.
  • By developing a strong financial IQ (based on unique KPI's) other performance factors, business owners can transition from being an Owner/Operator (where owners are intimately involved in every aspect of the business' operation which ultimately leads to burnout) into becoming a CEO or a financial owner, not an emotional owner. Financial owners can sell their firms for top dollar or transfer internally in the best way possible.
Analytical SkillsBusiness AnalysisFinanceFinancial AnalysisMarketingNegotiation+1

The salvation army

Board Member

Jan 2008 – Jun 2012 · 4 yrs 5 mos

  • Assisted in the design, implementation and execution of support programs to assist community members in need.

Penn state coaches vs. cancer

Major Sponsor

Jan 1999 – Jan 2012 · 13 yrs

  • Major Sponsor | Supporter | Noted Speaker at Events
  • Networking, speaking at events, and participating in fund-raising events.
  • Publicly addressed sponsors at various events, giving presentations with the intention of sponsor development and retention.
  • Contributed to the growth of this organization from start-up to $1.5M in donations.

Nittany

Owner | Founder | President

Aug 1998 – Sep 2019 · 21 yrs 1 mo · State College, Pennsylvania Area

  • Launched and developed strategies & branding of this "Penn State Proud" officially licensed enterprise, written up by Inc. Magazine, Fortune Small Business Magazine, The Wall Street Journal, and State College Magazine. Duties included oversight over all operations of 2 retail stores, 1 production plant, and 3 online stores.

Old state clothing company

Owner

Aug 1998 – Sep 2015 · 17 yrs 1 mo · 101 East Beaver Ave State College, PA 16801

  • Provider of quality Penn State Gifts and Clothing

Education

Penn State University

BA

Penn State Smeal MBA Program

Penn State University

M.B.A — Finance & Marketing

Penn State University

Bachelor of Arts - BA — Communication and Media Studies

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