District technology leaders field hundreds of messages a day, and most pitches never make it past an executive assistant. The ones that do get through did their homework, used the right channel, and made it easy for a buyer to say yes. Getting that far is only the beginning, though. Getting an AI product through procurement and into a signed contract takes something else entirely, the kind of thinking usually reserved for a prenup.
Diane Doersch spent years on the buying side of that table. She taught for nearly a quarter century in the classroom before moving into district technology leadership, serving as Chief Technology and Information Officer for Green Bay Area Public School District in Wisconsin. She later chaired the board at CoSN and worked at Digital Promise, stepping away in early 2026 into what she now calls her rewirement.
In this episode, Diane covers what moves a sale through K-12 procurement, from the research done before opening an email to the security question she feels she should never have to ask. She also makes her case for treating an AI vendor contract like a prenup, breakup language included, and shares a moment from a vendor floor when vendors skipped past her to pitch the man standing beside her, and how that kind of assumption can end a vendor relationship before it starts.
What You'll Learn
Why a tech leader’s peer network can make or break a vendor’s reputation before a single email is read
How something as simple as over-personalized outreach can tip into “creepy”
How AI’s arrival sent already-approved tools back through vetting, and why Diane treats the resulting contract like a prenup
What Diane expects to see on security and privacy before she’ll move forward with a vendor
How assuming who holds the final say on a buying team can quietly cost a vendor the relationship
The reason Diane treats every vendor relationship as a marathon, not a sprint, even after a lost first round
Why It Matters
Budgets are uncertain, AI has reset the vetting process, and district tech leaders are reading contracts more closely than before. For EdTech marketers, relationships, timing, and transparency now matter as much as the product. Diane's experience makes clear that the buying process starts long before an RFP goes out and continues long after a contract is signed.
Resources Mentioned in this Episode:
Diane's own podcast, featuring candid conversations with EdTech leaders about the moments and challenges that shaped them.
K-12 Community Vendor Assessment Tool (K-12CVAT)
CoSN's vendor risk assessment questionnaire, which Diane references when discussing how vendors can show their security practices up front.
The professional association for K-12 technology leaders, where Diane served as Board Chair.
The organization where Diane worked before retiring in early 2026.
"Stop Building Solutions in Search of Problems": A Principal's Case for Slower EdTech
All Things Marketing and Education earlier episode with Dr. Kip Glazer, whose approach to vetting AI tools Elana references in this conversation.
Elana Leoni, Host
Elana Leoni has spent nearly two decades helping education organizations grow through strategic marketing and storytelling. Over the past nine years, she has built and scaled Leoni Consulting Group, an education marketing agency that has partnered with more than 50 education and EdTech brands. Earlier in her career, she led marketing for Edutopia (The George Lucas Educational Foundation).
Diane Doersch, Guest
She/Her
Fractional CTO | Advisor and strategist | Former CoSN Board Chair | WIT founding board member | Former school district tech leader | Podcaster @ Beneath the Water
About All Things Marketing and Education
What if marketing was judged solely by the level of value it brings to its audience? Welcome to All Things Marketing and Education, a podcast that lives at the intersection of marketing and you guessed it, education. Each week, Elana Leoni, CEO of Leoni Consulting Group, highlights innovative social media marketing, community-building, and content marketing strategies that can significantly increase reach, relationships, and revenue.
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