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Justin Vondra

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.

✨ Change is Coming to the SISThe SIS and ERP space is one of the hardest to sell into because these systems are deeply embedded. Asking a school to migrate from a system they've been using for 20+ years is difficult. It’s more than just selling the product; it's about guiding them through a significant change. Schools are cautious, and there’s always a hesitance to adopt new technology. You need a high level of trust and a clear value proposition.

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.

✨ Change is Coming to the SISFor years, the SIS space has been stagnant, with long-standing systems in place that haven't evolved much. But the last five years have introduced significant changes, especially with the rise of distance learning and hybrid models. Schools are now looking for flexibility and tools that can better support student engagement. The focus has shifted towards interoperability, with institutions demanding systems that work seamlessly with third-party solutions.

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.

✨ Finding a Champion in Higher EducationEducation is a relationship-driven industry, not transactional. It’s about building strong connections, understanding what institutions need, and being a partner in their journey. Schools are not just looking for a vendor; they want someone who understands their challenges and helps them navigate complex decisions. This focus on relationships is why it’s so important to show up and present, in their offices, at conferences, and engage with decision-makers in meaningful ways.

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.

✨ Finding a Champion in Higher EducationIn sales, especially in this space, having an internal champion is critical. You need someone who understands these solutions and the problems they solve, advocating for you within the institution. That person helps you navigate the internal challenges and decision-making processes. Without an internal champion, it’s difficult to move the deal forward. They help translate the institution's pain points into a business case, making it easier to prove your product's value.

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.

✨ Creating Relevant Content is KeyCuriosity is one of the most important traits for success in sales. You need to be constantly learning—about the industry, the institution, and the technology. It’s not just about selling a product; it’s about understanding your customer’s world and bringing their vision to life.. Curiosity leads to better questions, deeper insights, and stronger relationships with clients.

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.

✨ Creating Relevant Content is KeyContent marketing has become critical. Traditional sales channels like cold calling or mass emails are saturated. Institutions are bombarded through these communication mediums, so your content has to stand out. It’s not just about pushing a product—it’s about providing value with every touch, demonstrating thought leadership, and proving you understand their challenges. The collaboration between sales and marketing is key here. Together, we create content that speaks to our expertise, the institution’s needs, and helps build trust.

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 in similar environments, can generate the required reporting, 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.

✨ Navigating Long Sales CyclesSales cycles in the SIS space can take 6, 9, even 12 months. It’s a long process, and you have to stay close to and support the institution throughout. You can’t make assumptions. You need to understand their budget, their decision-making process, and any internal barriers. Procurement can take months after you’re selected as the preferred vendor. Staying curious, staying engaged, and being a true partner in their evaluation process is how you make it through these long cycles. One of the biggest hurdles is understanding the institution’s procurement process. You could be selected as the preferred vendor, but if you don’t understand the steps to get through procurement, you could be stuck for months. It’s about being hyper-aware of what they need—budget, timelines, internal approvals. If you can stay close and help them navigate those hurdles, you’ll have a better chance of success.

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.

✨ The Future of SIS and ERP SystemsThe days of the monolithic ERP systems are over. Now, institutions want systems that integrate with specialized third-party solutions. Interoperability is crucial—schools want technology that works together seamlessly. Many institutions are moving toward cloud-based systems, but SaaS SIS isn’t fully mature yet. There’s still work to be done in ensuring these systems are adaptable, accessible, and provide a positive user experience. The transition to SaaS-based SIS and ERP systems is happening, but it’s not fully baked yet. Institutions are moving away from on-premise models, but they’re cautious. They want assurances around data security, compliance, and performance. The switch to SaaS offers more flexibility and scalability, but it’s a slow shift, and there are still challenges in making sure these systems are mature and fully capable of meeting institutions' needs.

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 conversations with key evaluation stakeholders with clear, actionable takeaways and can immediately provide value, that’s a strong signal that, from a technical standpoint, you’re in good position.  With that said, becoming the technical preference is only half of the battle as education, in general, presents a number of procurement hurdles depending upon the type of institution. 

Demonstrating an understanding of their environment through proof of concept can also drive momentum. Again, another key factor is identifying a strong internal champions—someone advocating for you within the institution. It’s 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.

✨ Leadership and Team BuildingCuriosity is the number one trait I look for in salespeople. I want someone who’s eager to learn, who doesn’t think they’ve figured it all out yet. The best salespeople are those who ask questions, who are constantly learning about the industry and their customers. It’s also about action—being prompt in follow-ups, staying disciplined, and being proactive in building relationships. Discipline and action often win over talent.

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.

✨ Leadership and Team BuildingSales and marketing need to work hand in hand. The amount of content out there is overwhelming, and it’s easy for institutions to feel bombarded. That’s why the content has to be valuable. We need to prove we understand their challenges and can offer real solutions. Marketing helps drive that message, but we work closely together to make sure the content resonates and adds value to the customer experience.
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🔥 Rapid fire questions
Direct or through channel partners?
Direct. This is dependent on stage but owning your brand and the relationships early can influence the outcome more directly. However, the right channel partners also carry a significant opportunity to broaden reach.
A good event or good content?
Event. Personal interaction is irreplaceable, and I value the chance to connect with customers face-to-face.
Inbound or outbound marketing?
Outbound. I enjoy building go-to-market strategies and reaching out to potential clients.
Quantity or quality?
Quality. Fewer, well-built and targeted interactions are far more effective than sheer volume.
Education or technology?
Education. That’s why we’re here.
In-house marketing team or agency?
This is a tough one! In-house. It can allow for better collaboration and alignment with the company’s goals, though, outside perspective offers its own, unique value to any organization.
Discipline or talent?
Discipline. Action and consistency win every time.
Thanks, Justin. This was a great conversation—appreciate your time!

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