What Makes a Vendor a Partner: Insights from School Leaders on Vendor Evaluation

If you've ever sat through a vendor demo that felt more like a sales performance than a genuine conversation, you're not alone. Independent school administrators are constantly navigating a marketplace full of platforms promising to transform everything, often in ways that feel disconnected from the real complexity of running a school.

That tension was at the heart of our most recent Connected Schools webinar, "Trust as Your School's Strategic Advantage, Part 1: The Evaluation Framework." We brought together three experienced school leaders: 

• Stacy Valentine, Chief Technology Officer at Mary McDowell Friends School
• Charles Polizano, Director of Technology at Poly Prep Country Day School
• Scott Chrysler, Director of Operations at Hammond School

Their conversation offered something genuinely useful: a candid look at how experienced administrators vet partners before any contract is signed.

It's About More Than the Product

Every panelist circled back to the same theme early on: functionality is table stakes. What actually determines whether a vendor relationship succeeds is everything surrounding the product.

For Scott, who oversees a wide range of operational systems at Hammond School, the framing was straightforward. 

"To our constituents, to our parents, to our families, it's not a vendor," he said. "Anything that we bring on is us."

That perspective shifts the evaluation conversation significantly. It's not just whether a platform works well in a demo; it's whether the company behind it will represent your school well when something goes wrong.

Stacy approaches vendor evaluation similarly, thinking of it as a relationship that requires investment on both sides. She looks for vendors who take the time to genuinely understand her school's culture, mission, and resources before offering solutions. 

"There really has to be an investment on the vendor's behalf to get to know you," she shared.

For Stacy, a vendor who jumps straight to pitching is a red flag from the start: "If I spend five minutes telling you about our needs, our culture, our makeup of our school, and the first thing you start doing is trying to sell me some AI-powered model system, then that tells me immediately that we're probably not a good fit for each other."

Training and Implementation Are Non-Negotiable

One area where the conversation got particularly practical was around training and implementation. Charles raised something that resonates with most independent school administrators: professional development time is precious, and platforms that require extensive ongoing training quickly become liabilities.

"No matter what we do in terms of setting up, that's a really easy kind of part of the process," he noted. "It's finding the time to really get the teachers, get staff involved with training."

He looks for vendors who have thoughtful models for onboarding staff that work within the rhythms of a school calendar, not against them.

Scott added another dimension: flexibility. Vendors who can only work standard business hours, or who show up on campus without notice, aren't operating with a real understanding of how schools function. "We've got two weeks in March that you have to do three months' worth of work," Charles pointed out.

 Vendors who can't adapt to that have already demonstrated they don't truly understand independent school operations.

Red Flags Worth Knowing

The panelists were candid about what causes them to disengage from a vendor conversation entirely. For Charles, auto-renewal clauses are an immediate dealbreaker. "If you refuse to take auto-renewal clauses out of your contract, I'm not going to sign a contract with you."

Scott pointed to a subtler but equally important signal: the vendor who won't take no for an answer. In his experience, persistent cold outreach and high-pressure tactics are a reliable indicator that a vendor prioritizes the sale over the relationship. "Don't come blaring down my door telling me I absolutely have to have you because you're the best thing," he said.

For Scott, the best vendor relationships tend to start with a referral or a genuine conversation, not a cold pitch.

Stacy brought up something increasingly relevant: the rush to incorporate AI into every product. She recently experienced a situation where a vendor asked to help reduce costs came back with a proposal centered on AI-driven automation that would have required significant staffing changes. "It totally got lost in the message of what I was trying to do." Her point isn't that AI is unwelcome, but that vendors need to understand when it's appropriate based on the relationship they've built, not as a default sales strategy.

Internal Buy-In Makes or Breaks Adoption

The conversation also moved into how these leaders build internal alignment around vendor decisions. The consensus was that involving stakeholders early and genuinely leads to significantly better adoption outcomes.

Charles shared an example of piloting a classroom technology product by sitting in on classes himself before making any decision.

"They felt like they were part of the decision-making process and it made adoption so much easier."

When faculty and staff feel heard throughout an evaluation process, they're more likely to embrace whatever solution is ultimately chosen.

Scott described his evaluation process for safety and operations platforms as one shaped by understanding the problem from the ground up. When he identified accountability as a critical gap at Hammond School, the path forward was built around operational need first, not a product category. That approach led him to a solution that genuinely fit his school's reality.

What Makes a Vendor a Partner

What this conversation made clear is that the best vendor relationships don't feel like vendor relationships at all, and for Scott, the proof is in whether a vendor actually acts on your input.

"If you could find somebody that's actively asking for your advice, and then you can see it implemented, it's amazing," he shared.

He contrasted this with platforms that collect feedback and let it sit untouched for years. The difference, in his experience, is vendors who make you feel like you have a genuine stake in the direction of the product.

"When you can find somebody that is responsive and engaged, it really makes it a tremendous amount of fun to be involved in it and to feel that not only are you being listened to, but you actually do have a stake in the direction of where it's going."

That feeling, of being heard and seeing results, is ultimately what separates a vendor from a true partner. So how do you find one? The panelists had clear advice.

The Advice Every Administrator Should Hear

All three panelists pointed in the same direction: lean on your network.

Scott encouraged administrators to participate in professional organizations where peers openly share what's working and what isn't. "Educators want to share their information with people," he said simply.

Charles added a specific question worth asking every prospective vendor: do you have educators on staff? "You have to understand a school to be in a school." He also recommended always asking for a product roadmap, wanting to know whether the company has a clear vision and can realistically deliver on what they're selling today.

Stacy's advice was more relationship-oriented: schedule regular check-ins with your current vendors, not just when something goes wrong. "Those regular 10 or 15-minute meetings once a month really has made a huge difference." Proactive communication transforms a transactional relationship into a genuine partnership, and ensures that when the right moment comes, your vendor already understands what your school needs next.

Watch the full webinar recording to hear more from Stacy, Charles, and Scott. 

And join us on March 25th for Part 2, where we'll hear from a school leader and vendor partner about what trust looks like in action.