Navigating Success: Heather Klassman

Thought-Leadership Insight with Heather Klassman

We caught up with Heather Klassman – current Portfolio CEO at CORA Group, to talk about her career progression, vertical market software (VMS) expertise, our Jonas ABC’s, M&A thought leadership and much more. Read all the insights in this interview.

Background & Career

What Was Your Career Background Prior to Joining Jonas?

I have a background in food science and began my professional career as a Registered Dietitian, working in hospitals and senior living communities, focusing on food and nutrition. Later, I transitioned into the business and technology side, managing menu planning software as a value-added service. I became an end user of Computrition software, which is one of Jonas’ business units, and built meaningful connections with the team there. One of those connections was with Matt Otchet (current CEO of CORA Group), who eventually offered me a job at Jonas working on an initiative focused on senior living food service—an ideal blend of my nutrition background and newfound interest in technology.

Can You Describe Your Career Progression Since Joining the Team?

I joined Jonas 11 years ago as a Product Manager, overseeing development and product roadmaps for a new initiative. I was employee #2 and deeply involved in all functional areas of the business and it helped shape my leadership skills. After several years, I became President of that organization. I raised my hand at every opportunity to take on more, and so from there, I transitioned into a Group Leader role. As Group Leader I strategically oversaw several additional companies and became involved in integrations to grow my portfolio. Most recently I stepped into a Portfolio CEO position, I now oversee 11 businesses and continue to be focused on the operational excellence of my portfolio business units while also working in an M&A capacity. Each role allowed me to grow, learn, and take on more responsibility.

Were There Any Experiences You Gained Through Working with Jonas, that Allowed for a Successful Career Transition Into The Roles You Have Here?

Absolutely. Every role I’ve held has added to my skill set and VMS knowledge. One in particular, was a huge learning experience. It taught me how to use data to make tough decisions, when to cut losses, and how to share those experiences to help others. Your approach to failures and tough conversations can lead to recognition and advancement, and saying ‘yes’ to new challenges has always helped me grow. I’ve even presented these learnings internally, which has helped others avoid similar pitfalls. It’s part of the culture at Jonas—we embrace experimentation and learning, even from failure.

What About Jonas Kept You Engaged in the Work Here and Willing to Continue Your Career With the Company?

The autonomy I’ve had at Jonas has been a major factor in my engagement. I’ve had the freedom to explore, test, and grow ideas—and I’ve always felt supported. Our culture values curiosity, experimentation, and continuous learning. Over the years, I’ve had opportunities to evolve across functions and take on new roles, which keeps the work exciting and meaningful.

Industry Leadership Insights

In Your Opinion, What Makes Jonas a Great Home For Vertical Market Software Companies?

Jonas is a great home for VMS companies because of our commitment to long-term success through our buy-and-hold forever principle. That offers unmatched stability for employees and customers. We don’t aim for short-term profits, we’re ultra focused on creating long-term value. Our decentralized structure allows acquired companies to maintain their identity, brand, and culture while gaining access to best practices and a vast VMS network and strategic support. David Santora, one of our owners who successfully sold his business to Jonas, often refers to his exit as, “getting to sell your home and still live in it.”

How Do You Personally Stay Ahead of Industry Changes and Disruptions?

I stay ahead by staying close to two key groups—our business leaders and our customers. Leaders within the businesses I oversee have deep industry knowledge, and I trust their insights. I also prioritize regular customer engagement through interviews and surveys to understand trends, pain points, upcoming needs, and keeping on top of regulatory changes. Combining this feedback with real-time data helps me guide innovation and long-term strategy.

What are the Most Important Leadership Qualities Needed to Succeed in Vertical Market Software Today?

Successful vertical market software leadership requires industry knowledge, strategic vision, a customer-first mindset, and strong operational execution. You either need deep subject matter expertise or you need to surround yourself with a team that has it. You must be able to anticipate industry shifts and know how to respond. Strong operators can turn good companies into great ones—by implementing smart processes, collecting the right data, and making informed decisions.

M&A Strategy

How Does Jonas Set Up Our Acquired Companies For Success?

There are a number of items to discuss here. Jonas sets up our acquired companies for success by allowing them to retain independence (their unique culture, brand identity, key personnel, etc) while tapping into a larger ecosystem of support. Businesses get access to proven playbooks, best practices, and a vast network of leaders across 175+ VMS companies. Whether it’s tackling integration, optimizing a tech stack, or improving sales structure, someone else has likely been there. It’s not just the CEO—directors and team leads can connect across departments. We foster collaboration that lifts everyone up. While many organizations look at data points, we analyze metrics at their most granular level to provide businesses with the information necessary to make data-driven decisions. As mentioned earlier, the Jonas investment approach prioritizes long-term thinking over short-term gains, providing companies with the stability and time needed to develop defensible strategies and strengthen customer and partner relationships.

What Do You See As the Most Critical Factors For Successful M&A Transactions in the Software Space?

The most critical factor is cultural alignment. If the acquired and acquiring companies share values—openness, humility, collaboration—it makes integration smoother. You also need leadership buy-in on both sides. Everyone must believe in the vision and be committed to shared success. A well-defined integration with a strong communication plan is also essential to keep both internal and external stakeholders informed and alleviate customer concerns.

What’s an Example of a Past Acquisition That Delivered Unexpected Value or Lessons?

The Ineo acquisition stands out. The leader there was incredibly receptive to our playbook and data-driven approach. The experience taught me how valuable it is to identify the right people early, those who are collaborative, flexible, and aligned with the shared goal. It gave me the opportunity to create what I call a ‘recipe for success’—key traits of successful integrations, both from the integration manager and the seller. We even presented our shared experience at Jonas GROWs, offering a two-sided view of the process.

What Would You Say to a Business Owner Who is Thinking of Selling?

If you’re looking for a permanent home for your business, we’re a great fit. We’re focused on long-term growth, not quick turnarounds. We value the expertise and culture that founders have built and aim to preserve it while offering support. We have a strong track record of acquiring and growing many vertical market software businesses successfully—so sellers can feel confident throughout the process, from diligence through to integration.

What’s a Key Lesson You’ve Learned From Scaling a Software Company That You Wish You Had Known Earlier?

Nothing is ever final—whether it’s product design, internal processes, or data strategies. Everything evolves. You have to stay agile and be ready to pivot based on customer needs, market trends, or new technologies. Leaders who can recognize when to change direction—and do it effectively—are the ones who succeed.

Future Outlook

What Makes You Excited About the Future of Jonas?

What excites me most is the opportunity our growth creates for our people. As Jonas expands, new responsibilities emerge giving team members a chance to stretch their skills and step-up into new roles. Our culture emphasizes talent development and retention, enabling people to build long term careers across many different roles within Jonas. This has become a strategic advantage, given talent is one of our greatest assets.

Recent Posts