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TobinLeff offers you a team of twelve M&A advisors, exit planning consultants, and research analysts who are passionate about helping business owners realize the rewards of their hard work. Our partners have owned and exited their own companies, worked with big four accounting firms, and practiced business law. We have sat on your side of the table and will combine our business experience with deep M&A expertise to help you maximize and monetize your business value. 

Since our founding in 2010, TobinLeff has assisted nearly 200 clients with M&A transactions and exit planning solutions. 

David Tobin


Founder & Managing Partner

David is passionate about crafting and implementing plans for clients to convert business value into family wealth. He strives to help clients expand their view of possibilities, develop creative and sound solutions, and get deals closed.

David is a serial entrepreneur who has founded, grown, and [...]

In addition to founding, growing, and crafting exit strategies for his own four companies, David has worked with well over 100 companies to maximize and monetize business value.


Managing Partner

Scott has owned and run advertising, marketing, PR, and video production shops. He has led mergers and sales of for-profit and nonprofit corporations, run and sold a family-owned bank, produced a national PBS documentary, was President of a Carnegie Mellon University spin-out technology company, ran a $1.3 billion trust and investment management company, and spent close to [...]

Scott is not only successful in his M&A endeavors. He also produced a national PBS documentary, ran a $1.3 billion trust and investment management company, and worked on strategic plans and financial analyses for a decade at Robert Morris University.
Scott Leff
Bruce Bishop



Bruce brings more than 30 years of M&A and financial management experience to the TobinLeff team. As the U.S. CFO of global holding companies and large marketing communications agencies, he has spearheaded more than 30 M&A transactions. [...]

Bruce has directly worked with CEOs and senior-level management to boost revenues and enhance overall profitability and margins.


Research Analyst

Kelly is a Research Analyst for TobinLeff. She graduated from the University of Illinois with a degree in economics and received her MBA in finance from North Central College. She previously worked as a business analyst for Citi Residential Lending.

Kelly lives in Naperville, IL with her husband and two children.

Kelly Chen
Chuck Gottschalk



Chuck is a forward-thinking operations expert with a keen eye for growth. With experience both as an entrepreneur and as a corporate executive, he first brought his deep financial analysis skills to the TobinLeff team in 2018.

A practiced architect of business strategy and management [...]

Having worked at a “big four” accounting firm, a tech startup, and a family office, Chuck has been both an entrepreneur and corporate executive, with extensive involvement in all aspects of M&A transactions.


Senior Designer & Market Research Analyst

Heather is a Senior Designer and Market Research Analyst with TobinLeff. She has over fifteen years of experience working with small, midsize, and Fortune 500 companies, designing award-winning B2B and B2C marketing materials. Her expertise includes extensive work in digital, print, packaging, publishing and web, as well as marcom plans and research. Heather believes well-executed design, research, and communication are key to helping a business connect with its clients [...]

Heather Huether
Mary McKinney Flaherty



Mary’s passion and focus is helping founders and business owners understand and navigate the financial, legal, and emotional complexities of selling and transitioning the companies they have built and grown  [...]

Mary applies the lessons of a 20-year career in law, corporate governance, and investment analysis to build value and develop deals that are built to last. 



Roy is a 30 year veteran of sales, advertising, public relations, and marketing communications. The agency he founded in 1995, Third Degree Advertising and Communications, returned an average of 33% per year through 25 years of operation. He exited the company in 2018 following a merger structured by TobinLeff [...]

Roy is an author, entrepreneur, and certified Rhythm Systems Affiliate and Coach. He has received multiple honors for his work in advertising, business and recovery coaching.
Roy Page
Gregg Tobin



Since 2003, Gregg has facilitated the sale of 220 businesses. In addition, he has sold seven companies that he started or bought, giving him both the buyer’s and seller’s perspective when facilitating client transactions.

Gregg prides himself on getting deals done while simplifying the [...]

Gregg has facilitated the sale of 220 businesses, on top of selling the seven companies that he started or bought. This uniquely gives him both the buyer’s and seller’s perspectives when facilitating client transactions.



Janet brings nearly three decades of experience in building award-winning businesses. She co-founded Airfoil Group, a marketing communications agency primarily serving the technology sector. She led the company from startup to the Inc. 5000 list and worked with renowned clients like Microsoft, PayPal, LinkedIn, eBay, [...]

Janet has built a highly successful career by helping others create their own success stories – as individual executives, entrepreneurial startups, non-profits, or large-scale corporations.
Janet Tyler
Hannah Vaughn


Marketing Director

Hannah has been around content and communications her whole life, growing up working in her family’s marketing firm. Since then, she’s successfully navigated the marketing world. Working with retail brands, tech startups, nonprofits, and financial and M&A firms, she understands nuances across industries and tailors marketing and design strategies that specifically fit client needs.

She attended Lipscomb University in Nashville on a Presidential Scholarship, graduating early [...]



Holt has been in business since his teens. Starting with about two hundred dollars, he grew a consortium of multimedia, packaging, and marketing communications companies that included a spin-off brand providing organizational and strategic growth consulting, including exit and succession planning, for the faith-based industry. His production facility was honored in Mix Magazine’s [...]

Holt is a rockstar in both music and M&A. He started a business in his teens and then grew a consortium of marcom companies that sold in 2016, while also releasing multiple albums and leading a theology think tank.

Holt Vaughn

TobinLeff meets you where you are in your exit planning journey. You only get to sell your company once. Trust our exceptional, experienced, strategic team and wide network to maximize your exit payday. Contact us today to discuss your business options — or just to talk M&A. We welcome the opportunity to get to know you and explore if we can add value to your plans.