Cracking the SIS Code: VP of Sales Justin Vondra on Driving Meaningful Impact in Higher Education

We're really glad you're here. Could you start by sharing a bit about yourself and your journey into the EdTech space?

Sure, thanks for having me. I’m based in central Wisconsin, where my wife Brittany and I raise our four kids—Aria (7), John (6), James (4), and Bella (3). It’s a busy life, filled with coaching and participating in their activities like soccer, hockey, wrestling, and swimming. I work remotely from home and travel frequently, but I love the flexibility it offers to keep me present and involved in their lives.

Great! Can you talk about how you got into EdTech?

Yes, like many, sales found me, and so did EdTech. There’s a large local EdTech provider in my hometown who specializes in student information and ERP systems, and through meaningful personal connections, I got my start there on the support side. I began by supporting ERP customers, handling technical consulting and on-site implementations. This experience opened my eyes to the challenges schools face in digital transformation. I saw opportunities to help institutions improve processes, staff experiences, and most importantly, student outcomes. That excitement led me to move from support into sales, where I could work more closely with schools to implement solutions.

<div class="highlight"><span class="highlight-pearl">✨ The Art of Problem-Solving</span>Fall in love with the problem, not the solution," has become our mantra at Pivodio. My co-founder Yi and I adopted this from Uri Levine's book, and it’s transformed how we think. The biggest mistake I made was focusing too much on building solutions without truly understanding the problem. Everything starts with the problem, and it's the users—not us—who decide if the solution works. This perspective has been the foundation of our growth and resilience.</div>

Did your background in support and consulting give you an advantage when you transitioned into sales?

Absolutely. Empathy plays a big role. If you can speak their language and truly understand their pain points, it’s not just about selling—it's about building relationships and solving real problems. Understanding their world makes all the difference in how effective those conversations are.

For those starting out in sales and marketing in EdTech, especially in higher ed, what are key things to understand about building relationships in this space?

Higher education is very relationship-driven, not transactional. You have to understand the environment—financial aid, student retention, enrollment challenges. HigherEd is undergoing major shifts, with institutional initiatives, educational models, consolidation and closures all shifting the landscape . You can quickly access valuable information on strategic goals and challenges, as much of it is public. True understanding helps you better connect and build relationships with institutions.

What are the key events or conferences you find valuable for networking and connecting with the right people?

It’s tricky, and for each organization to decide where they fit best. Sometimes the events you expect little from end up being the most valuable, and others that are highly recommended can fall short. It’s about understanding who you serve best in education—whether it’s K-12 or HigherEd, public or private, community colleges, or other segments . Events like EDUCAUSE are great for technology in higher education, but my suggestion would be to focus solely on where you can make the most impact and offer thought leadership, rather than just following the crowd.

That’s a key takeaway for marketers—choosing the right events based on your target audience, not just the event’s popularity.

Exactly. I’d add that seeking feedback from your customers on which events they attend can also be a helpful way to decide where to invest your time and resources.

Before we started recording, I mentioned my interest in the ERP and SIS space, especially given how challenging it is to sell into higher education. It’s tough to convince an institution to migrate from a system they’ve used for 20-plus years. Could you share how you approach guiding institutions through the process of considering change or re-evaluating their long-standing systems?

Sure. It's a challenge, and Academia by Serosoft has been in higher education for 16 years, so we’re no strangers to the complexities. Education is generally slower to adopt new technologies or evolve internal processes. Many institutions are still using systems that were implemented decades ago. When I talk to institutions, they often admit they weren’t sure if their system was the right choice 30 years ago, and they still aren’t sure now, but options were limited back then.

Many vendors haven’t significantly evolved their products, that’s largely because of complexities associated with their architecture, but also because these systems touch so many stakeholders while offering so much functionality. As an industry, we need to be pushed to offer more adaptable solutions, stronger partnerships, and products that evolve with an institution’s strategic goals, instead of rigid structures that remain stagnant.

For some institutions, especially mid-sized and smaller private ones, the traditional vendors haven’t offered systems that meet them where they are —whether it’s non-traditional models, distance learning, hybrid learning , or operational flexibility. That’s where we see our biggest opportunity. We're engaging with institutions that are now more open to re-evaluating, especially with the rise of AI, new student engagement tools, and demands for adaptable and user-friendly platforms.

So, would you say that the SIS space, which has been stagnant, is now facing shifts that are creating opportunities for new vendors to make a difference?

Yes, absolutely. Especially in the past five years, we’ve seen institutions adapt rapidly to changes in distance learning, hybrid models, and how they engage with students. These changes have driven growth in education technology overall. Interoperability has become key, with many institutions integrating third-party solutions into their ecosystem. Gone are the days of monolithic ERP systems—we’re now seeing a best-of-breed approach with specialized tools that need to work together seamlessly.

At the same time, long-standing vendors are trying to adapt by transitioning from on-premise models to the cloud. But SaaS-based SIS solutions are still maturing. Over the next few years, we’ll see this model continue to evolve, offering more flexible solutions for institutions.

Beyond the functional and infrastructure aspects, like SaaS models, what are the other concerns institutions have when considering newer SIS vendors?

Data security and compliance are always top concerns, especially when moving to the cloud. Some institutions still prefer on-premise systems because they offer fine-tuned control over performance, which can be difficult to give up. So, when considering a transition, institutions want to know about uptime, business continuity, disaster recovery, and security.

But beyond that, they need proof that the system works and can integrate well with their existing ecosystem. Interoperability is critical right now—institutions want to know if a new SIS will integrate seamlessly with their current tools. They're looking for use cases, proof of concept, and testimonials from peers in the community, as education is heavily relationship-driven. Institutions trust each other’s experiences more than anything.

Absolutely. And because of how education operates, it's important to take a constructive approach. Now, let's talk about your role. The SIS space is one I respect due to its complexity—not just closing the deal but managing the intricate processes afterward. What's your biggest challenge in selling to the diverse North American higher education market?

I'll quickly touch on my role and the biggest challenge. I joined Academia by Serosoft about 13 months ago. Throughout my career, I've noticed many institutions lack the flexibility and functionality they truly need in their student data systems. Academia, built on enterprise-grade open-source technologies, offers the flexibility that many traditional systems don’t, which got me excited about this role. My focus has been on building a go-to-market strategy, showcasing the value we offer, collaborating with marketing, and delivering impactful outreach to clients.

The biggest challenge is creating visibility for a fresh face in a market dominated by long-established players. SIS and ERP transitions are massive undertakings for institutions, and no school makes that decision lightly. The complexity lies in demonstrating the value and flexibility our solution offers while overcoming the resistance to change and navigating internal decision-making processes. However, we've made significant strides in positioning ourselves as emerging leaders in the space.

Is there a particular market segment where you feel you can best support institutions?

Yes, without getting too specific, we see great potential with more unique institutions—those that have prestigious brands, presence across regions, non-traditional student populations, hybrid learning models, or specific operational structures. These institutions often feel underserved by existing solutions because they have been. Our product allows for differentiation by supporting their specific needs, whether it's in the academic models or operational procedures. Understanding these nuances and meeting them with the flexibility they deserve while aligning the proper solutions is key during the evaluation process.

You've been a leader in EdTech sales. How do you view your relationship with marketing?

It's highly collaborative—sales and marketing work hand in hand every day. Content has become critical in sales, especially with the traditional channels being so oversaturated. Clients receive a constant barrage of emails, social messages, and cold calls. To stand out, we focus on delivering valuable content that showcases our expertise and demonstrates that we understand and can solve their problems. Collaborating closely with marketing on content and messaging is crucial to creating that differentiation.

Content marketing is definitely a long-term game. How do you and your team generate content ideas or experiments?

At Academia by Serosoft, we aren't siloed—sales and marketing exchange ideas constantly. Organizational chat tools help us share insights in real-time. If I notice a recurring theme in conversations with clients or trends emerging in the market, I immediately share that with marketing. We then brainstorm ways to address those topics through content—whether it’s a webinar, white paper, or thought leadership piece. It's all about delivering value and ensuring that everything we produce helps our clients and prospects take actionable steps.

Given that EdTech sales cycles are long and complex, especially for SIS, what signals help you identify when a deal might be close to closing? What are the early signs that indicate it’s worth investing more time with a potential customer?

If you walk away from a conversation with clear, actionable takeaways and can immediately provide value, that’s a strong signal. Demonstrating and understanding of their environment through proof of concept can also drive momentum. Another key factor is identifying a strong internal champion—someone advocating for you within the institution. It’s also essential to understand internal barriers early on, like procurement timelines or budget constraints. Sales cycles in education can be lengthy, so being curious, asking the right questions, and staying close to their day-to-day needs are critical to guiding them through the process.

Absolutely. Now, about your fellow EdTech sales team members—what traits do you value most when hiring or working with them?

Curiosity is key. It shows a willingness to learn, not only about sales techniques but also about the education sector itself. I also look for action-oriented people—those who follow up promptly and execute tasks effectively. Discipline is equally important; it’s what drives consistent follow-through and results.

Are those traits different from what you’d expect in a marketer?

Not really. Creativity and action are crucial in both sales and marketing, and I think the overlap is increasing. Both roles require curiosity and a strong work ethic to succeed.

Great point. Now for a classic question: What advice would you give your 20-year-old self?

Take care of your health—both physically and mentally. Build your network early and nurture those relationships because they will prove valuable down the road. Also, stay confident in your skills and path. It’s easy to overestimate how much and in what ways people perceive you, so focus on and stay true to your goals without being swayed by outside pressures.