Budget crunches, look-alike products, and vendors that rarely talk to each other are making it harder than ever for school leaders to decide what to buy, and harder for EdTech companies to stand out. Add AI to the mix, and the sales conversation gets more complicated: fast product cycles, thin data privacy answers, and a market flooded with tools claiming the same features.

Dr. Kip Glazer has a front row seat to all of it. She is principal of Mountain View High School in Silicon Valley and author of Ready to Lead with AI: A Practical Guide for School Leaders. Between running a comprehensive high school, fielding vendor pitches, and writing her pointed "Dear EdTech Companies" series on LinkedIn, she has developed a clear, specific sense of what earns her trust and what ends a conversation before it starts.

In this conversation, Kip walks through what happens on her side of the sales process: the identity crisis AI is creating for leaders used to being the most knowledgeable person in the room, why boutique vendors survive on service rather than efficiency, and why she would rather refer a company to a better fit than force a mismatch.

What You'll Learn

1. Why "stop building solutions in search of problems" became the rallying cry behind Kip's "Dear EdTech Companies" series, and what she wants vendors to ask before they build
2. The specific deal breakers that end a sales conversation for her, from vague answers on student data privacy to AI labels slapped onto tools without real substance
3. How a single referral, or a single decline, moves through a principal's professional network and reaches far beyond one school

Why It Matters

EdTech companies are operating in one of the toughest sales environments in recent memory: shrinking budgets, longer approval cycles, and a wave of AI tools arriving faster than schools can vet them. Kip's account makes clear that a school leader's decision rarely stops with one person. Her professional network amplifies both her confidence and her hesitation, so a single strong or weak interaction can shape how ten other schools see a company. For marketers and sales teams, the lesson is that trust functions like currency across an entire referral network, and price becomes a secondary question once trust is established. Companies willing to say "we are the wrong fit for you, here is who might serve you better" build the kind of credibility that outlasts any single sale.

Resources Mentioned in this Episode:

• Ready to Lead with AI: A Practical Guide for School Leaders
• Kip's book, written specifically for school leaders navigating AI, safety, and the emotional weight of leading through disruption.
• Dear EdTech Companies (Part 1)
• The post that kicked off Kip's LinkedIn series calling out EdTech companies for building solutions in search of problems.
• Dear EdTech Companies, Part 9: On AI Washing
• Kip's take on what changes the moment a product claims to be AI powered, and the tougher questions buyers start asking.
• What Principals Actually Pay Attention To
• Our earlier episode with Chris Lehmann offers another school leader's perspective on evaluating EdTech and building trust, worth comparing against Kip's take.
• Thinkering Collective
• One of the Substacks Kip reads regularly for long-form thinking on education and technology.
• Mark Racine
• Another Substack in Kip's regular reading rotation.
• Center for Humane Technology
• Rounding out Kip's Substack reading list, focused on the broader impact of technology on human behavior.
• Kip Glazer's website
• Speaking topics, articles, and more from Kip.
• Connect with Kip: LinkedIn