Charting New Horizons: Stephen Rosenthal’s Journey with Big Band Software

Just eight months ago, Stephen Rosenthal was wondering what an exit might look like and took a step by engaging with Big Band Software. Fast forward to today, he’s not only successfully partnered with Big Band but has also chosen to remain in his role at DocLib as CEO, continuing to drive its growth and bring his vision to life. From a pre-med student with dreams of becoming a surgeon to a tech entrepreneur reshaping an industry, his journey has been anything but conventional.

A pivotal moment came when he transitioned from selling medical devices to diving headfirst into tech, joining his father’s business to tackle its most pressing challenges. Not one to shy away from risk, he took the ultimate leap—buying out his father and his business partner to make DocLib his own. Recognizing the opportunity to scale beyond its niche, Stephen found in Big Band a partner whose vision and values aligned with his own.

 The rest is history, but you can hear it for yourself:

Can you tell us first how you first got involved in - and ended up buying DocLib?

Depends on how far back you want to go! I went to school with my sights set on becoming an orthopedic surgeon. This started with a Biology / Pre-Med degree and ended when I realized I couldn’t start my career as a surgeon until my 30s! An opportunity to sell medical devices sprung up and I was able to work my way into Stryker Orthopedics selling their trauma line. This quickly burnt me out and I decided to pivot into tech. I had always told myself that I would not work for my father and that I needed to prove myself on my own instead of working within his business. This all changed when he gave me the awesome opportunity of coming on to help figure out sales and marketing for his software product, DocLib. But I had a longing to work on the biggest problems in his business which at the time were not just sales growth. This led me to starting my own consulting business and bringing DocLib on as a customer. After a year of this, the opportunity presented itself to buy out my dad and his business partner. I leveraged it all and bought his business!

What made you think - after successfully growing a business you’d bought - that it might be time to sell and get help for the next legs of growth?

Believe it or not, I was not ready to sell! It was all Chris Reedy’s good looks and charm. In all seriousness though, I had planned to sell this business in 2027 or beyond at the right price. My decision to sell is very closely linked to who Big Band is as a company and what they offered. I believe the offer they made was phenomenal and worth looking into.

Can you talk a little bit about your team and the work culture you’ve prioritized there?  How have you done this - including key team members?

I am a STRONG believer that business is not worth doing without prioritizing relationships. We have hired a police officer, a hotel clerk, and everything in between. I believe that we are designed as people to be in community with one another and are not designed to simply build the biggest empire for ourselves to enjoy. One of my closest friends, Jeshal Mistry, has served as our Director of People & Culture since day 1 of my involvement with DocLib and we have immensely benefited from his leadership in this area. He has a knack for applying the concepts I just mentioned to each decision in our business. He is my right hand man in the business and we allow our prioritization of people to influence and guide each of our decisions. We have made plenty of mistakes along the way but by God’s grace we have been able to build a business to be proud of. Here is a link to a great video about our culture.

What initially drew you to engage with Big Band?

I had not heard of Big Band until a SaaS Academy Intensive in February. SaaS Academy is a great organization to learn everything you might need to know about running a successful software business with great content, community, and events. Big Band is a Partner of this organization and it is through my work with SaaS Academy as a client that I first met Chris and was introduced to Big Band. What drew me to Big Band was their unique perspective on continuing to build the businesses they buy. I have had some experience both first and second hand in private equity and in general, there is negative sentiment about what happens to your business after it is sold. Big Band has shown a commitment to building for the long term and has undergirded this verbal commitment with action.

What aspects of Big Band’s vision or strategy convinced you that this was the best move for your company?

Circling back to the prioritization of people, I saw Big Band’s long term focus as essential in continuing to build the right type of company. There is certainly a strong prioritization on financial health as this is essential to Big Band’s business model however, there is also a recognition of the types of investments that are required for sustained growth.

What excites you most about staying on with Big Band Software / as the CEO of DocLib?

I have so much to learn. Jason, Kevin, Chris, and Chloe have a wealth of knowledge that I long to glean from. The financial proficiency is top notch at Big Band. I work directly with Jason on this front and his history with GoDaddy, Lead Pages, WebPt, and others give him the credentials for an honorary doctorate in financial management of software companies rooted in reality. The rooted in reality part of this statement needs to be underlined. Jason has a strong sense of how to keep a company financially healthy and how to leverage financial health for growth. I have learned and am continuing to learn so much from Chris and Chloe about acquisitions especially since there are some awesome opportunities to build out DocLib with more acquisitions. I get to work directly with them on deal mechanics for the businesses we have targeted and am actively learning how to build a robust closing memo! Kevin introduced me to the concept of a Quarterly Business Review and has had great, constructive feedback for me. The Quarterly Business Review is a powerful tool and I wish I had been doing them prior to our deal. It has provided alignment for our leaders and focus on the most important priorities in our business. It also brings some brilliant minds together to stress test each of our goals and the assumptions behind how we will meet them.

What opportunities do you see for your product/team as part of Big Band Software?

Moving into new markets is the top opportunity we see at DocLib as a part of Big Band. We can move with confidence and grow DocLib out of the singular niche it has served for 3 decades. Proper execution of this opportunity will propel DocLib into the next level as a software company and I see Big Band and their expertise as essential in bringing this opportunity to fruition.

What is a piece of advice you would give Founders as they are thinking about a potential exit partner?

When thinking about an exit for your business, I have one recommendation . . . Do your homework. I know Kevin has a great resource in planning for an exit and you should check that out but once the process is started, you do not want to lose momentum by doing your homework for the first time. Make sure you find some top notch professionals to support your deal. You need a good lawyer that has experience in these deals and that you can keep in line to ensure the deal gets done. Don’t be afraid to compromise and don’t sweat the small stuff with your deal. You need a good accountant that can help you navigate what each of the deal terms means for you financially and has the heart of a teacher to help you understand holdbacks, working capital, tax implications, rollover equity, and much more. Look for people with experience in your industry / deal size, and ensure it is someone you can trust. There will be challenges in getting a deal done. It will feel like the deal might die. It’s ok. Put one foot in front of the other and keep pushing it along. 

What’s been harder than you thought about the acquisition - either the process or executing within Big Band? (Yes, we’re really asking that question in public, because we want to know and others will, too.)

There are two answers that come to mind for this question. One is very tactical and one is very theoretical. Tactically speaking, I struggled a bit with the role of Big Band’s board in my deal. It was not clear to me prior to signing the Letter of Intent that the Big Band board could keep the Big Band leadership team from executing on a transaction. Ultimately this did not come to fruition otherwise our deal would not have been done! I think Kevin in particular really helped me navigate this bump we hit in our process and provided clarity on how to overcome the obstacle. Secondly, I have been challenged with my mindset post acquisition. I am a scrappy entrepreneur and entrepreneurship is what I love. Selling my main business has been a challenge for me since a part of what I do professionally has dramatically changed. I appreciate Big Band and how they operate post sale but it is still a big shift away from my previous mode of operating. This, of course, is not all negative but it is one of the biggest adjustments / challenges in executing within Big Band. Keep in mind, I am also unique in this position as all other business leaders within Big Band’s portfolio were not the owners / operators of their businesses pre-acquisition. They are newcomers to the business.

Stephen’s decision to partner with Big Band Software wasn’t just about numbers—it was about aligning with a team that shared his vision for long-term impact and people-first leadership.

As CEO of DocLib under Big Band’s umbrella, he’s poised to guide the company into new markets and levels of success, all while maintaining the culture and values that make DocLib exceptional. His advice to other founders considering their next steps? Do your homework, find partners who align with your vision, and never stop learning. With Big Band, Stephen is doing just that—building off of a foundation of success with a team that believes in him.

THE PLAYLIST (What We're Watching, Reading, and Listening to)

• Brent Beshore - A reflection on the what it takes to run a successful holdco–from the head to the heart 

• Run Your Career as a Business - Stephen Rosenthal talks identifying your ICP, creating meaningful products and services and exchanging value to drive results in your business

• CRO to CEO - Ash Didwania, CEO of Workzone, reflects on shifting your growth mindset from short to long term

IRL (Where You Can Find Us)

• Several members of the Big Band team flew to Chicago for the SaaS Academy events October 23-25 and 27-29. We were happy to connect with countless founders and are eager to follow-up with more attendees to talk about their potential dream exits and how the Band can help today.

Join The Band

We’re building our database with the best leaders and operators out there. If you know exceptionally talented people that may one day want to work with us, please have them get in touch with us at [email protected] or fill out the form on our Connect page.

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