What Makes a Vendor Partnership Actually Work: Lessons from Independent School Leaders

Key insights from our March Connected Schools webinar on trust-based vendor relationships

For school leaders, selecting a new technology platform is a significant commitment, one that affects daily operations, staff confidence, and long-term budgets. The demos look polished, the sales conversations go smoothly, and everyone promises exceptional support. But what actually determines whether a vendor partnership holds up over time?

That was the question at the center of our most recent Connected Schools webinar, "Trust as Your School's Strategic Advantage, Part 2: Partnership in Action." The panel included two experienced independent school technology leaders alongside their vendor partners:

School leaders:

• Bill Stites, Director of Technology at Montclair Kimberley Academy
• Molly Rumsey, Director of Information Services at Harpeth Hall School

Vendor partners:

• Marshall Singer, Co-Founder and COO of Ruvna
• Keith Krass, VP of Partnerships and Global Strategy at Veracross

What emerged was a candid, experience-driven look at what separates vendors worth staying with from those worth leaving.": 

Relationships Are the Foundation, Not a Feature

Both Bill and Molly have spent decades at their respective schools, and both have worked with enough vendors to know what to look for. When asked what matters most in a partnership, neither started with features or pricing.

"Partnerships are built on relationships, and those relationships are built on trust," Bill said. "I need to trust that we're both aligned with what we need to achieve on both sides of the platform."

Molly echoed that sentiment, adding a practical dimension: "I know that I can get a person. When I need it, I can get a person, and I can get them quickly, and often it's the same person."

That consistency matters more than it might seem. Molly noted that rotating account representatives, a frustration she'd experienced with other vendors, forces schools to re-educate their contacts repeatedly, eroding the institutional knowledge that makes a partnership actually functional. 

Having a dedicated representative who knows your school, your systems, and your team is not a nice-to-have. For schools operating with lean technology staff and complex operational needs, it's essential.

Honesty During the Sales Process Predicts Everything That Follows

One of the more candid moments in the conversation came when Bill described what actually sold him on both Ruvna and Veracross during their respective evaluation processes.

"It was the level of honesty that came out of the evaluation process that sold me more on the vendors than necessarily the feature sets," Bill said. "If I understood what they could do, if I understood what they couldn't do clearly, and if I understood what was on a roadmap that was clearly defined, I could have a solid plan going forward."

Marshall reinforced this from the vendor side, describing a recent conversation with a prospective school partner: "Being super open and saying, no, we're not going to be able to help you just yet, but here's what I see as our roadmap. Providing that transparency around what you can do and how it'll provide them value is just so important."

The pattern both sides described is consistent: vendors who overpromise during the sales process create problems that compound over time. Vendors who are straightforward about limitations,  and clear about where they're headed,  build the kind of credibility that sustains a long-term relationship.

What Happens When Things Go Wrong

Any vendor can describe their support process in favorable terms. What's harder to evaluate upfront is how a partner actually responds when something doesn't go as planned.

Molly shared a specific example from her experience with Veracross. A grade calculation issue that surfaced after a significant system change, resulting in incorrect grades being published to parents. The situation required quick action, clear communication to families, and close coordination with her vendor contact to resolve.

"Because I knew I could get them, and I wasn't in an endless ticket cycle, I was able to put out the SOS and I got the help that I needed," she said.

Bill described a similar moment with Ruvna.  A drill that surfaced a timing mismatch between when Veracross updated attendance data and when Ruvna pulled it.  Once the problem was identified, it was resolved with a straightforward configuration change.

"We identified the problem, and once we were able to identify the issue, we were able to address it very, very quickly."

Both stories point to the same principle: problems will happen in any technology partnership. What defines the relationship is how quickly and transparently they get resolved.

Vendors That Know Independent Schools

One thread that ran throughout the conversation was how much it matters that a vendor genuinely understands the independent school environment, not just K–12 education broadly, but the specific culture, governance, and operational rhythms of independent schools.

"They don't just know schools, they know independent schools, which are different beasts," Molly said. "Both of these vendors understand our essence and how we work, and that is incredibly critical for us."

Keith reinforced this from the vendor side, noting that this kind of familiarity shapes how Veracross builds and improves their products. "It's actually trusting you to say, this is what I know my colleagues need, this is what schools should be focusing on," he said. School partners like Bill and Molly, he noted, help vendors understand what actually matters across the independent school community, not just at a single institution.

Trust, it turns out, runs in both directions. When vendors genuinely know the environment their clients operate in, and when school leaders trust their vendors enough to share honest feedback, product development, support, and day-to-day partnership all improve. It's that mutual investment, more than any feature set, that determines whether a vendor relationship stands the test of time.

Practical Advice for Schools Evaluating Vendors

As the conversation wrapped up, Bill and Molly offered guidance for school leaders currently navigating a vendor evaluation.

Bill's advice was straightforward: do your homework before the demos begin, know your non-negotiables, and don't default to the lowest-cost option. "Do not always go for the cheapest solution. Look at the cumulative costs — the software costs, the time costs, the people costs."

Molly echoed the importance of knowing who you can count on when it matters. Having a dedicated contact who knows your school and can be reached quickly, she noted, is something she looks for in every vendor relationship.

Marshall's advice from the vendor side was equally practical: ask what the implementation process actually looks like from day one to go-live, request access to someone technical who can speak to the product in depth, and don't rely solely on vendor-provided references. "Talk to other schools," he said. "Go find them yourself. Ask your network."

The common thread in everything Bill, Molly, Marshall, and Keith shared is that the best vendor partnerships function less like software transactions and more like ongoing professional relationships, ones built on honesty, consistent communication, and a genuine investment in each other's success.

Want to hear the full conversation? Watch the complete recording of "Trust as Your School's Strategic Advantage, Part 2: Partnership in Action" on our webinars page.