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There is a growing gap between how education is marketed to and how it is actually experienced inside schools.
Leaders are navigating full days that require constant context switching, balancing relationships with students and teachers, operational demands, and long-term decisions about tools and systems.
At the same time, marketers and vendors are trying to break through with messages about value, innovation, and now, AI.
In this episode, Elana Leoni sits down with Chris Lehmann, founding principal of Science Leadership Academy, to ground that gap in reality. Chris shares what his day actually looks like, how he evaluates vendors, where marketing efforts fall apart, and what earns his attention over time. The conversation then moves into AI, where the tension between possibility and risk is not theoretical. It is showing up daily in classrooms, policies, and conversations about integrity.
This episode is a candid look at what it means to engage education leaders in a way that is useful, honest, and sustainable.
What You’ll Learn1️⃣ Why most education marketing fails to reach decision-makers
A principal’s day is fragmented and high-volume, leaving little room for cold outreach. Messages only land when they align to an immediate need or build on an existing relationship.
2️⃣ How trust is built in schools over time
Leaders engage with organizations that consistently provide useful, relevant value. Ongoing responsiveness, thoughtful content, and real partnership matter more than one-off campaigns.
3️⃣ Where AI is creating tension in classrooms right now
Schools are working through academic integrity, student learning, and appropriate use in real time. Leaders are cautious of messaging that overlooks the complexity and tradeoffs involved.
Quick Wins from the Lightning RoundFast, direct answers from Chris, no filtering:
→ Most overused phrase: Student achievement
→ Biggest red flag: Anything labeled “now with AI” without real substance
→ You know a vendor is overselling when: They claim to solve everything
→ Most underrated strategy for improving learning outcomes: Reading
→ Word that will define the next school year: Authenticity
→ Where we would invest more budget: Teachers
What This Means for MarketersSchool leaders are solving problems in real time with limited capacity. Most marketing misses because it ignores that context. Generic messaging, cold outreach, and overpromising, especially around AI, erode trust quickly. What works is relevance and consistency. Understand how schools operate, contribute value before asking for attention, and build relationships that can hold up over time.
New York City Public Schools announced one of the most restrictive AI policies in the country, and LAUSD followed with a quiet moratorium of its own. For any company selling AI-powered tools into K-12, this isn't background noise anymore. It's a sign that the ground rules are being rewritten in real time, and positioning needs to keep up.
At the same time, October is arriving with a full plate. Conference season, award deadlines, and the usual run of thematic days are all stacking on top of each other. It's worth asking a harder question before the calendar takes over: which of these deadlines actually matter, and which ones are just habit?
This field notes episode covers what's moving fast right now, the AI policy shifts landing in New York City and Los Angeles, the conference and award deadlines worth prioritizing this fall, and what actually earns a response on LinkedIn.
What You’ll Learn
1️⃣ Why NYC and LAUSD's AI policies matter beyond their own districts
New York's policy sounds like a blanket ban, but it's more nuanced than the headlines suggest. Teachers can still use AI to plan lessons, translate, and communicate with families, they just can't use it to grade, decide who graduates, or counsel a student in crisis. LAUSD's own moratorium on student use of generative AI arrived quietly enough that it reportedly surprised its own school board. When the country's largest districts move first, others tend to follow.
2️⃣ What's worth prioritizing on a packed fall conference and awards calendar
DA Awards entries close October 1st, EdTech Week runs October 13th - 14th, FETC's prices increase October 30th, and SXSW EDU's Launch competition deadline is November 1st, on top of national conferences like NCTM in Denver and CGCS in Boston. This episode breaks down which deadlines are worth building a strategy around, rather than trying to hit everything.
3️⃣ What new findings say about getting a response to a LinkedIn connection request
Richard Vanderblom's poll and analysis found that a "helpful" message, one that references something specific about the person's post, is what actually gets a response. It's a small shift, but one that changes how outreach on the platform should be built.
Why It Matters
Education marketers are heading into one of the busiest stretches of the year with less room for error than usual. Districts are rewriting AI policy in real time, marketing calendars are more crowded than usual, and the platforms relied on for organic reach keep changing what earns attention. None of this is a reason to freeze. It's a reason to get more deliberate, know which policy shifts touch a given product, spend fall's limited time and budget on the deadlines that matter most, and build outreach around what's genuinely earning a response right now.
Resources Mentioned in this Episode:
EdTech go-to-market plans tend to get written as if there's one playbook that works everywhere. But anyone selling into more than one state learns quickly that isn't true. A message that lands in one state can fall flat two counties over, and a funding mechanism that unlocks budget in one place might not exist somewhere else. In K-12, treating all fifty states like fifty different countries isn't an exaggeration. It's closer to how procurement, funding cycles, and decision-making work.
Bryan McCorkle, SVP of Revenue at NovoDia, an AI curriculum infrastructure company for K-12, has built his career inside that reality. Across stops at Amira Learning, PowerSchool, and ClickSoftware, he's learned to read a market before he ever pitches it: what problem a district is actually living with, what data proves the demand is real, and what it takes to turn a signed contract into a product teachers and students use.
In this conversation, Bryan walks through the four questions he says every company has to answer before it can talk about go-to-market, how he verifies real demand using legislative calendars and district heat maps, and why he's banned himself from ever saying "circling back."
What You'll Learn
Why It Matters
Budgets are tighter, audits are more common, and districts are taking a harder look at whether the tools they're paying for are being used. For EdTech marketers and sales leaders, that means a repeatable go-to-market plan matters as much as a good product. Knowing exactly what problem you solve, being honest about what you don't solve, and picking a market you can win and repeat are what separate a deal that closes from a product that gets used. The idea that all fifty states behave like fifty different countries is a reminder that a one-size-fits-all plan rarely survives contact with a real district budget cycle.
Resources Mentioned in this Episode:
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
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:
LinkedIn just made a real change to how it ranks content, and it's aimed squarely at AI-generated posts. Captions are getting penalized for running too long, hashtags are being deprioritized, and the platform is now rewarding accounts that show up consistently rather than accounts that post the most. For education marketers already stretched thin, this changes what "good" LinkedIn content actually looks like heading into the busiest stretch of the year.
At the same time, EdTech just closed out the first half of 2026, and the industry felt it. Several companies made layoffs as they reconciled H1 numbers against annual goals, a reminder that marketing budgets and headcount are under real scrutiny right now. It's also a good moment to ask a harder question: which parts of your own marketing mix are you keeping simply because you've always done them, and which ones actually have the data to back them up?
This field notes episode covers what's moving fast right now: LinkedIn's new rules on AI content and consistency, what recent layoffs signal about EdTech budgets, where national conferences like ISTE fit into a shifting events landscape, subject line ideas worth testing before back-to-school email sends, and a full calendar of what to put on your radar for August and September.
What You’ll Learn
1️⃣ Why LinkedIn is rewriting the rules on content, and why it matters more than a ranking tweak
Long, AI-sounding captions and heavy hashtag use are getting penalized, while accounts that post consistently (two to three times a week) are getting rewarded. On top of that, posts are increasingly getting indexed and cited by AI search tools like ChatGPT and Google AI Mode, so what you publish today can still be surfacing your expertise months from now.
2️⃣ What the wave of EdTech layoffs after H1 signals about marketing budgets right now
Several companies cut staff as they reconciled first-half performance against annual goals, a sign that marketing investment is under real scrutiny. It's a good prompt to look at your own mix and ask what you're keeping simply out of habit versus what the data actually supports.
3️⃣ What's actually worth putting on your August and September marketing calendar
From back-to-school timing that varies wildly by region, to where national conferences like ISTE fit as attendance shifts toward smaller, regional events, to the literacy, attendance, and gratitude moments worth planning around before October's conference season ramps up.
Why It Matters
Education marketers are heading into back-to-school season with less room for error than usual. Budgets are under closer scrutiny after a round of EdTech layoffs, the platform that most B2B education brands depend on just changed what it rewards, and the traditional conference calendar that used to anchor a lot of go-to-market planning is shifting under everyone's feet.
None of this is a reason to freeze. It's a reason to be more deliberate: know what you're measuring and why, know what LinkedIn actually rewards right now instead of what worked a year ago, and know exactly when your audience is heads-down in back-to-school mode versus ready to hear from you. The marketers who take the time to recalibrate this summer will be in a much stronger position once the fall buying cycle picks back up.
Resources Mentioned in this Episode:
Most EdTech companies pitch schools before they understand how decisions get made inside them. School budgets are tight, sales cycles are long, and trust is hard to earn and easy to lose. In a market this crowded, the vendors who succeed are rarely the loudest ones. They are the ones who understand what a school leader is weighing before they ever pick up the phone.
Smita Kolhatkar has sat on both sides of that equation. She spent 15 years in high tech before becoming an educator, and today she is Assistant Head for Innovation, Responsible AI and EdTech at Gideon Hausner Jewish Day School in Palo Alto. She evaluates new products constantly, built her school's AI Tinkery program to teach AI literacy from kindergarten up, and has a clear, specific list of what earns her trust and what ends a conversation before it starts.
In this conversation, Smita walks through her actual buying process: the no-gos that end a pitch immediately, why conference expo halls still outperform months of email outreach, and why a single "no" from her can quietly close the door at several other schools too. It's a clear look at what that decision-making looks like from the other side of the table, for anyone marketing or selling into K-12.
What You'll Learn
Why It Matters
EdTech companies are working in one of the toughest sales environments in years: tighter budgets, longer sales cycles, and a market flooded with AI tools faster than schools can evaluate them. What Smita describes is not just one school's experience, it is a window into how school leaders across the country are making these calls right now. She is not only a buyer, she is a connector: when something works, it moves through her professional network, and when something falls flat, that travels just as fast. For EdTech marketers and sales teams, the lesson is that a sale is never just to one person. The trust built or lost in a single conversation compounds across an entire network of schools.
Resources Mentioned in this Episode:
Most early-stage EdTech companies build in a familiar order: product first, sales next, marketing whenever there's budget left over. It's an understandable instinct in a sector where school budgets are tight and every dollar needs to prove itself quickly. But that order also means many companies spend years chasing the credibility they could have built from day one.
Karen Borchert, founder and CEO of Alpaca, a school culture and teacher retention platform, took the opposite approach. When she started the company four years ago, her first hire wasn't an engineer or a salesperson. It was a marketing leader, brought on the payroll before Borchert herself was. That decision has shaped how Alpaca has grown into a trusted name among school leaders with a small team and a category that didn't fit neatly into anyone's existing playbook.
The conversation traces how that early bet on marketing played out: a listening-first culture that shaped Alpaca's brand before it ever built software, a resource library that earned trust with principals long before any sales conversation began, and the hard lessons about when long-term brand building needs to give way to a more direct sales motion.
What You’ll Learn
Why it Matters
Most EdTech marketers are told to prove ROI fast, which often means marketing gets treated as something to add later, once there's revenue to defend it. Alpaca's experience complicates that narrative. Every dollar the company put into brand and listening before it had a sales team became the foundation that made later sales conversations easier, not a distraction from them. For marketers working with tight budgets and skeptical school buyers, the lesson isn't to skip short-term tactics like conferences or paid outreach. It's to recognize that the trust those tactics eventually convert depends on credibility built well before anyone asks for a demo.
Resources Mentioned in this Episode:
There is a real tension building in K-12 right now. The "no screens" conversation that started with cell phone bans has moved into legislative territory, with 17 states introducing screen time bills in 2026 alone and four already enacting laws that go beyond phones to target district-issued devices and classroom technology directly. If your product sells into schools, this is no longer a trend to monitor. It is a business reality to plan around.
At the same time, summer is not a selling season, and pretending otherwise is a fast way to lose trust with the educators and administrators you need on your side come fall. The question is not whether to show up in July. It is how to show up in a way that actually serves the people already using your product and the ones about to start.
This field notes episode covers what is moving fast right now: the legislative landscape around EdTech and screens, what smart marketing looks like in a non-buying season, what is working on LinkedIn this summer, and a few posts from district leaders and educators worth paying close attention to.
What You’ll Learn
1️⃣ Why the no-screens movement has moved from conversation to legislation
What started as cell phone bans has expanded into bills targeting district-issued devices and classroom technology in 17 states in 2026 alone. For EdTech companies, this is no longer a sentiment issue. It is a product positioning and sales reality that requires a clear, proactive stance.
2️⃣ What smart marketing actually looks like in a non-buying season
July is not a selling window, but that does not mean going quiet. The brands that show up well right now are shifting into implementation and support mode, meeting educators where they are and building the kind of trust that converts when procurement opens back up.
3️⃣ Why LinkedIn carousels are one of the biggest underused opportunities right now
Carousel posts make up less than 5% of content on LinkedIn and still drive some of the highest reach and engagement of any post format. The bar for standing out is low, and the data-backed best practices are straightforward.
Why It Matters
Education marketers are heading into one of the most complex back-to-school seasons in recent memory. Legislation is reshaping what schools can buy and use. Budgets are tighter. Educators are more skeptical of vendor outreach than ever. And AI is changing how content gets surfaced and who gets trusted as a credible voice in the space.
Showing up in July with the same playbook as the rest of the year is not just ineffective. It signals that you do not understand how schools actually operate. The marketers who will be in the best position come fall are the ones using this window to support, listen, and build credibility in ways that compound over time.
Resources Mentioned in this Episode:
Selling into schools is rarely as straightforward as most teams expect.
District leaders are navigating competing priorities, long approval cycles, staffing challenges, and increasing pressure to justify every decision. At the same time, EdTech companies are trying to build trust, move deals forward, and prove their value in a crowded market.
Nancy Livingston, CEO of the National Summer School Initiative (NSSI), joins Elana for an honest conversation about what actually drives K-12 purchasing decisions and why so many organizations misunderstand the realities of selling into education.
Drawing from experience on both sides of the table, Nancy shares what surprised her most after moving from district leadership into sales, where deals typically stall, and why trust-building looks very different in education than in other industries.
The conversation explores the tension between empathy and momentum, the hidden complexity of procurement, and the role marketing plays in helping districts feel informed, confident, and ready to move forward.
If your team is trying to better understand how decisions really happen inside schools, this episode offers a grounded look at the process behind the partnership.
What You’ll Learn
Why it Matters
Too many organizations approach education sales as a faster-moving commercial process. But school systems do not make decisions in isolation, and they rarely move quickly without trust, alignment, and internal clarity.
Nancy’s perspective is a valuable reminder that successful partnerships are built through patience, responsiveness, and a real understanding of how districts operate. For marketers especially, this shifts the work away from pushing urgency and toward creating the kind of credibility and education that helps decisions move forward over time.
Hello, World!
Most education brands know email should be their strongest channel and yet it rarely delivers on its potential. Between inconsistent sends, generic copy, and the pressure to sound “professional,” messages that could build real connection often end up sounding like noise.
Email strategist Liz Wilcox joins Elana to share how education organizations can shift from transactional messaging to meaningful communication. She breaks down why simplicity outperforms polish, how to build trust through steady, human touchpoints, and what the best senders are doing differently.
She outlines her “follower, friend, customer” framework, a 20-minute approach to writing newsletters that actually get read, and the mindset shift from selling to serving. Liz also explains how a strong onboarding sequence sets the tone for every future interaction—and why owning your mistakes in email can make people trust you more, not less.
If you’ve ever hesitated to hit send or wondered what to say next, this episode will reset how you think about email.
What You’ll Learn
Quick Wins from the Lightning Round
Why It Matters
The difference between noise and connection isn’t design or frequency; it’s trust. Liz reminds us that effective email marketing comes from showing up consistently, sounding like a real person, and making every message worth opening. When we stop chasing perfection and start focusing on relationships, email becomes less of a tactic and more of a long-term advantage.
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