The Boyz of Edtech | K–12 Education Insights

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Explore the latest education business trends, entrepreneurship, and school leadership insights with us. We bring you expert discussions on district leadership, edtech innovation, education policy insights, and K-12 education advancements. Join us for valuable perspectives on edtech trends, startup founders in education, and strategies for effective school operations and relationship building. Hosted by Dr. Rick Fernandez, Jacob Kantor, Jeff Piontek, Ryan Patenaude, Matthew Millstein, and powered by Old Soul.

  1. 2d ago ·  Video

    Designing Technology Around Kids: Agency, AI, and the Future of Learning with Michael Preston

    In this episode of The Boyz of EdTech, Rick Fernandez, Matthew Millstein, and Jeff Piontek sit down with Michael Preston, Executive Director of the Joan Ganz Cooney Center at Sesame Workshop. Michael shares the path that took him from growing up with Sesame Street and experimenting with an early home computer to working in New York City schools, helping launch what became Computer Science for All, and eventually leading an R&D center focused on helping the technology and media sectors design better experiences for children. The conversation explores what the computer science movement can teach education as AI reshapes how students learn and work. Michael argues that computer science was never simply about teaching a programming language. It was about helping young people understand how technology works, question outputs, experiment, iterate, and develop confidence in their own ability to create. Those same principles become even more important as AI makes it easier for students to outsource parts of the thinking process. Michael also challenges educators and EdTech companies to put children directly into the design process. Drawing on the Cooney Center's work, he explains why students should be partners from the earliest stages of product development, when their ideas can still meaningfully shape what gets built. The group discusses screen time, phone bans, oral language, human relationships, teacher involvement, evidence of learning, and the tension between technology that expands agency and technology that can quietly take it away. Looking toward the future, Michael argues that preparing students for an unpredictable workforce is less about identifying the perfect technical skill and more about developing rigorous curiosity, adaptability, agency, and a willingness to struggle with difficult problems. Reflecting on the legacy of Joan Ganz Cooney and Sesame Street, he leaves educators and product leaders with a larger design question: if technology can shape children's experiences at enormous scale, how can we intentionally design it around the kind of world, relationships, and opportunities we want children to have? Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ Key Moments 01:20 Michael's journey from early computing to education innovation 05:34 What Computer Science for All was really designed to give students 06:18 Why computer science remains relevant in the age of AI 10:36 Rethinking attention, learning stamina, and how kids learn today 13:04 Protecting student thinking and agency when using AI 16:07 Why children should help design the technology built for them 19:49 What students and teachers are saying about technology and AI 24:26 Protecting human relationships, oral language, and student voice 29:23 Preparing young people to use AI without outsourcing their thinking 32:41 What students need for a workforce we cannot fully predict 33:41 Building rigorous curiosity and comfort with uncertainty 38:07 What Sesame Street's legacy can teach today's EdTech designers 40:48 Resources and research from the Joan Ganz Cooney Center 41:30 Why EdTech leaders should include students in product decisions Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode:

    Designing Technology Around Kids: Agency, AI, and the Future of Learning with Michael Preston

  2. Oct 27 ·  Video

    From Cold Outreach to Real Conversations: Building a Smarter K-12 Go-to-Market Strategy

    In this episode of The Boyz of EdTech, Rick Fernandez, Matthew Millstein, and Jacob Kantor sit down with Bobby Offterdinger, CEO of TAM to Target, for a tactical conversation about what actually works when selling into K-12. Bobby shares his journey from elementary school teacher and reading specialist to instructional technology, EdTech sales, and eventually launching TAM to Target to help companies build more effective go-to-market strategies across education and the public sector. Bobby breaks down why more meetings do not automatically translate into more revenue. Successful EdTech companies still need product-market fit, message-market fit, sales acumen, and a clear understanding of district procurement. The group explores growing opportunities in CTE and career readiness, why some legacy products are leaving room for new competitors, and how founders can connect a specific district leader's pain point to a specific solution rather than overwhelming prospects with every feature their product offers. The conversation also gets practical about outbound sales. Bobby explains why phone outreach continues to outperform cold email for TAM to Target, how founders should test different messages before scaling volume, and why genuine curiosity and empathy are fundamental sales skills. They discuss researching prospects before meetings, choosing go-to-market channels based on the type and price of a product, and understanding why selling an enterprise-wide system requires a very different motion from selling a smaller solution below procurement thresholds. Bobby also shares how AI is reshaping the SDR function. Instead of expecting one person to research accounts, build lists, write outreach, call prospects, and manage every other part of prospecting, TAM to Target separates go-to-market engineering from the human conversations SDRs are best positioned to handle. The episode closes with a rapid-fire discussion on cold email, phone calls, sales signals, storytelling, and why the strongest K-12 sales conversations still come back to preparation, relevance, trust, and listening with empathy. Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/ Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/ Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/ Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/ Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/  Key Moments 03:26 Why Bobby launched TAM to Target 05:55 What separates meetings from actual EdTech revenue 09:53 Why CTE and career readiness are gaining momentum 14:00 Finding message-market fit before scaling outreach 16:01 Testing soft versus direct calls to action 16:28 Why phone outreach remains powerful in K-12 19:02 Replacing the product dump with curiosity and empathy 22:07 Matching your go-to-market channel to the type of product 24:12 The district pain points that change and the ones that stay constant 27:43 Why founders still walk into sales meetings unprepared 29:51 Rethinking the traditional SDR role with AI and go-to-market engineering 33:03 Using AI to create more time for human sales coaching 39:33 Why great salespeople get buyers to tell their own stories 43:33 Rapid-fire lessons on cold outreach, signals, and smarter prospecting Connect with Bobby OffterdingerLinkedIn: https://www.linkedin.com/in/bobbyoffterdinger Website: https://tamtotarget.com/  Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

    From Cold Outreach to Real Conversations: Building a Smarter K-12 Go-to-Market Strategy

  3. Oct 16

    Building an AI Brain for Schools: How BaboBot Is Rethinking Communication, Access, and Operations in K-12

    In the first edition of EdTech Unwrapped, The Boyz of EdTech welcome Mauricio Szajman and Axel Petochi, Co-Founders of BaboBot, to put their product in the hot seat. Mauricio and Axel walk Rick Fernandez, Matthew Millstein, and Jeff Piontek through BaboBot, an AI-powered information management platform designed to connect the systems and information schools already use and make that knowledge easier for families, students, and staff to access. Axel shares how the idea started at Babson College with a simple problem: finding out what was being served in the cafeteria. A small tool that texted students the daily menu quickly attracted roughly a quarter of the school, revealing a much larger problem around fragmented information. That early experiment eventually evolved into BaboBot, which aims to give school communities one place to ask questions and receive personalized answers based on the information relevant to them. During the live demo, Mauricio shows how parents can ask about events, field trips, forms, and their children, while administrators can explore attendance trends, safety information, staff schedules, and other operational questions. The platform connects information from documents, Google Drive, emails, websites, and school systems, provides citations with its answers, identifies conflicting information, and escalates unanswered questions to staff rather than simply guessing. The Boyz then dig into the questions school leaders and EdTech buyers are likely to ask, including onboarding, privacy, permissions, analytics, integrations, communication workflows, and differentiation from established platforms. Mauricio and Axel also share where BaboBot is headed, including WhatsApp access, deeper integrations, proactive communications, and automations that can turn school information into action. The broader vision is to move beyond another communication tool and create an AI-powered operating layer that brings siloed school data into one central brain. Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ Key Moments 00:59 How BaboBot connects school information in one place 02:25 How a college cafeteria problem inspired BaboBot 03:57 Live demo of the parent and family experience 10:45 What onboarding looks like for schools and districts 13:29 How users get access through existing school rosters 14:51 Protecting school data while using an LLM 16:15 Helping prospective families explore schools and programs 16:56 Inside BaboBot's administrator portal and knowledge base 23:26 Turning platform activity into useful district reporting 25:53 Personalizing information based on each user's role 27:31 The Boyz begin their product feedback 30:14 Meeting families where they already communicate 31:04 Building an AI brain that can turn school data into action Connect with Axel Petochi and Mauricio SzajmanAxel Petochi LinkedIn: https://www.linkedin.com/in/axel-petochi-7b86b91ab Mauricio Szajman LinkedIn: https://www.linkedin.com/in/mauricio-szajman Website: https://babobot.com/  Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/hnbrHwODgdM

    Building an AI Brain for Schools: How BaboBot Is Rethinking Communication, Access, and Operations in K-12

  4. Oct 9

    Beyond Badge Scans: How to Win the EdTech Conference Season

    In this episode of The Boyz of EdTech, Rick Fernandez, Matthew Millstein, and Ryan Patenot take a practical look at Q3 and Q4 in the K-12 EdTech market and why these months can be critical for building momentum. With districts settling into the school year and the holiday season approaching, the conversation explores how EdTech companies can use this window to strengthen relationships, create opportunities, and position themselves for pilots and partnerships in the new year.The Boyz dig into one of the biggest investments on the EdTech calendar: conferences. Rather than attending every event or measuring success by badge scans and LinkedIn photos, they discuss how companies can choose conferences based on their ideal customer profile, existing relationships, and business objectives. Rick shares the district and association perspective, explaining why meaningful partnerships are built around mutual value, trust, education, and creative ways for vendors to participate in the community. Matthew and Ryan break down what effective conference execution looks like before, during, and after an event. They discuss setting meetings in advance, using conference communities and LinkedIn to identify attendees, following up while conversations are still fresh, and recognizing the difference between genuine opportunities and 'party pipeline.' They also explain why reciprocity, curiosity, and asking for the next step are stronger signals than simply collecting contacts. The conversation closes with tactical advice for both new and experienced EdTech sales professionals. From prioritizing existing CRM opportunities and studying conference agendas to dividing and conquering networking events, clearing calendars, leveraging customer advocates, and staying fully present, the message is clear: conferences deliver value when there is a strategy behind showing up. Success is less about being everywhere and more about knowing who you need to meet, why the relationship matters, and what should happen next. Connect with the BoyzRick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ Key Moments 00:34 Why Q3 and Q4 matter for building EdTech momentum 03:16 Using conference season to prepare for Q1 opportunities 04:32 Measuring whether a conference was actually worth the investment 07:16 Creating mutual value between education leaders and partners 11:04 Choosing quality over quantity when selecting conferences 13:35 Building a conference strategy before buying a booth 15:15 When and how to follow up after a conference 17:55 Understanding the difference between pipeline and 'party pipeline' 20:11 Knowing when a conversation is ready for the next step 25:00 Using reciprocity to identify genuine business interest 29:04 Building connections before arriving at a conference 30:52 What to do when you walk into an event knowing no one 35:37 Why teams should divide and conquer at networking events 37:10 Clearing your calendar and staying fully present at conferences 43:21 Practical strategies for building momentum in a new EdTech territory Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/4hABnJycfGI

    Beyond Badge Scans: How to Win the EdTech Conference Season

  5. Oct 2

    Rethinking School for the Age of AI with Jennifer Womble

    In this episode of The Boyz of EdTech, Rick Fernandez, Jacob Kantor, and Jeff Piontek sit down with Jennifer Womble, Conference Chair and EdTech Advisor for the Future of Education Technology Conference (FETC), for a wide-ranging conversation about where education is headed and what schools need to rethink along the way. Jennifer shares her unconventional path into education, from studying economics and criminology to becoming a teacher, working at the state and national levels, and developing a broad view of the education ecosystem. The conversation explores a fundamental question: What is school actually preparing students for? Jennifer argues that education cannot simply train students for jobs that may look completely different in the future. Schools need to develop lifelong learners who can think critically, solve problems, communicate, adapt, and understand their own learning. As AI accelerates change, those durable human skills, along with curiosity, metacognition, autonomy, and agency, become even more important. Jennifer also explains why successful technology adoption starts with community, strategy, and trust. Rather than beginning with a product, districts should involve families, educators, businesses, and other stakeholders in defining what learning should look like. The group discusses cybersecurity, responsible AI implementation, outcomes-based contracting, parent communication, and why EdTech companies need to listen before they sell. Jennifer emphasizes that AI should amplify strong curriculum and pedagogy rather than become the foundation itself. The conversation then turns toward what comes next, from AI-powered creativity and immersive learning to CTE, esports, cybersecurity, accessibility, and new approaches to assessment. Jennifer shares what FETC is seeing across districts and why some of the most exciting innovation is happening in career and technical education. The episode closes with a vision of schools that combine competency-based learning, multiple learning environments, human connection, and emerging technology while keeping curiosity, belonging, and student growth at the center. Connect with the BoyzRick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ Key Moments 03:54 How a nontraditional background shaped Jennifer's perspective 07:52 Rethinking the purpose of school and preparing lifelong learners 15:11 Why AI is forcing districts to examine deeper systemic challenges 17:45 Building AI strategy with community involvement from the start 22:09 Why EdTech companies need honest district feedback and co-building 27:42 Trust, listening, and stronger partnerships between districts and vendors 30:22 The risks and realities of outcomes-based contracting 38:02 Rethinking how districts communicate learning with families 40:54 Teaching AI wisdom, critical thinking, and responsible use 46:45 How AI can expand creativity and student problem-solving 50:20 What FETC is seeing across AI, CTE, immersive learning, and cybersecurity 56:21 Why CTE is becoming one of the most innovative areas in education 58:17 Integrating AI into authentic, project-based learning experiences 01:03:20 Competency-based learning and the future redesign of school Connect with GuestJennifer Womble: https://www.linkedin.com/in/jennwomble  Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38  Listen to the episode: https://youtu.be/fFFMguo46v0

    Rethinking School for the Age of AI with Jennifer Womble

  6. Sep 17

    What Makes an EdTech Company Built to Last with John Gamba

    In this episode of The Boyz of EdTech, Rick Fernandez, Matthew Millstein, Jacob Kantor, and Jeff Piontek sit down with John Gamba, Entrepreneur in Residence and Director of Innovative Programs at the University of Pennsylvania. John shares his journey from building some of the earliest branded websites to founding, funding, and scaling education ventures, including a successful exit to Blackboard, and ultimately bringing those lessons back to Penn to mentor the next generation of education entrepreneurs.John breaks down what separates promising EdTech ideas from companies that can create lasting impact. His framework focuses on three fundamentals: engagement, pedagogical alignment, and ease of adoption. The conversation explores why strong technology alone is not enough, why founders need evidence behind their claims, and how responsible AI, research, and measurable outcomes should shape product development. John also explains why the footnotes supporting a company's claims may be more important than the flashy slides in its pitch deck. The group then digs into the business mechanics behind sustainable EdTech growth. Instead of chasing district logos and annual recurring revenue at all costs, John advocates for paid pilots, milestone-driven expansion, and a greater focus on net recurring revenue. They discuss why landing a district is only the beginning, how customer experience determines whether a pilot becomes a renewal, and why companies need to intentionally map the entire journey from initial conversation through onboarding, implementation, measurement, and expansion. Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ Key Moments03:30 Building and exiting an EdTech company to Blackboard 05:05 Bringing entrepreneurship and innovation to Penn GSE 07:15 What John looks for in promising EdTech companies 11:20 The three fundamentals of successful EdTech products 14:35 Why evidence and research belong at the center of the pitch 19:10 Giving superintendents visible wins through technology 23:25 Shifting the focus from ARR to sustainable district growth 27:10 Why successful pilots should lead naturally to expansion 31:30 Mapping the complete customer journey after the sale 36:15 Why customer experience matters as much as customer acquisition 40:05 Paid pilots, milestones, and commitments to growth 44:25 The leadership qualities John looks for in founders 47:10 Balancing humility, coachability, and the will to succeed 50:30 How mentorship and coaching shape stronger entrepreneurs Connect with GuestJohn Gamba: https://www.linkedin.com/in/johngamba Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/TGCkPgC94gY

    What Makes an EdTech Company Built to Last with John Gamba

  7. Sep 14

    Beyond the Sale: What School Leaders Really Want from EdTech Partners with Dr. Davion Lewis

    In this episode of The Boyz of EdTech, Rick Fernandez and Matthew Millstein sit down with Dr. Davion Lewis, Superintendent of Essexville-Hampton Public Schools, to explore the realities of district leadership, community trust, and what education companies need to understand before approaching school leaders. Dr. Lewis shares his unconventional path into education and reflects on stepping into his first year in Michigan with a major challenge already waiting for him: rebuilding community support for a school bond that had previously failed by just 51 votes.Dr. Lewis breaks down how research, listening, board alignment, and community involvement shaped his entry into the district and ultimately helped turn the bond effort into a grassroots initiative. He also discusses the pressure new superintendents face to make changes quickly, why early wins matter, and how leadership stability can create the conditions for long-term improvement. From navigating conflict with a school board to recognizing when a decades-old problem might not be the right battle to fight, he offers a candid look at the judgment required to lead a district effectively. The conversation also delivers a practical message for edtech companies: do your homework and become a partner, not simply a vendor. Dr. Lewis explains why companies need to understand district budget cycles, state funding priorities, contracts, implementation realities, and the people surrounding the superintendent. He shares concrete ways providers can add value beyond their product, including internships, community involvement, professional development, and proactive implementation support. The episode closes with a discussion of Essexville-Hampton's academic success and why continuity in teachers, principals, superintendents, and boards may be one of the most important ingredients for sustained improvement. Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ Key Moments 03:10 Taking on a school bond after arriving in a new district 05:30 Building credibility by having skin in the game 08:10 Turning a failed bond into a grassroots community effort 10:30 Building a superintendent's first 100-day entry plan 13:45 Why today's superintendent role requires more than instructional expertise 16:15 Knowing when to move quickly and when to slow down change 19:05 Building credibility through early wins and healthy conflict 23:20 What edtech vendors misunderstand about district buying cycles 25:40 Why providers should understand state funding before making a pitch 28:35 The difference between an edtech vendor and a true district partner 35:05 Why the cheapest solution is not always the best partnership 39:10 Making implementation easier instead of creating more work for districts Connect with GuestDr. Davion Lewis: https://www.linkedin.com/in/davionrlewis Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/1KiFSgtvvrw

    Beyond the Sale: What School Leaders Really Want from EdTech Partners with Dr. Davion Lewis

  8. Sep 11

    Banning AI Won't Prepare Students for the Future with Jean-Claude Brizard

    In this emergency edition of The Boyz of EdTech, Rick Fernandez, Matthew Millstein, Jacob Kantor, and Jeff Piontek are joined by Jean-Claude Brizard, President and CEO of Digital Promise, for a timely conversation about New York City's newly announced restrictions on AI tools in schools. Drawing on more than two decades of experience inside the New York City education system, Jean-Claude questions whether broad restrictions address the real challenges schools face with artificial intelligence.The conversation explores the potential consequences for equity, instruction, procurement, and workforce readiness. Jean-Claude argues that students with access to AI at home will continue learning how to use it, while students who depend on schools for access risk being left further behind. Rather than treating AI primarily as a technology problem, the group discusses why schools should rethink instructional design, elevate pedagogy, and move students beyond answer-getting toward analysis, productive struggle, collaboration, curiosity, and other durable skills. Jean-Claude also examines the procurement and implementation challenges behind education technology. He explains why districts need stronger systems for evaluating whether products are safe, effective, aligned with instructional priorities, and properly implemented. The discussion highlights Digital Promise's work around AI and EdTech assurance labs, continuous efficacy measurement, and the need for shared accountability between districts and providers. The episode closes with a broader look at workforce readiness and global competitiveness. Connect with the BoyzRick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ Key Moments 02:14 Why a last-minute AI policy creates implementation challenges 05:12 The equity risks of limiting AI access in schools 08:05 Why EdTech procurement needs stronger evidence and evaluation 12:18 Preparing students for an AI-driven workforce 15:30 Moving from answer-getting to deeper thinking and analysis 18:42 Why instructional design matters more than banning the tool 22:15 What the graphing calculator debate can teach us about AI 28:10 Spending, strategy, and improving student outcomes 34:36 Why schools struggle to replicate successful practices 39:15 The challenge of removing AI from modern EdTech products 43:30 Building continuous AI and EdTech assurance systems 49:20 Why technology should support the instructional program 54:18 Shared accountability through outcomes-based contracting 58:12 Why AI literacy and computational thinking need to start early Connect with GuestJean-Claude Brizard: https://www.linkedin.com/in/jean-claude-brizard-0080a810 Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/oEtxATz0hcE

    Banning AI Won't Prepare Students for the Future with Jean-Claude Brizard
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Explore the latest education business trends, entrepreneurship, and school leadership insights with us. We bring you expert discussions on district leadership, edtech innovation, education policy insights, and K-12 education advancements. Join us for valuable perspectives on edtech trends, startup founders in education, and strategies for effective school operations and relationship building. Hosted by Dr. Rick Fernandez, Jacob Kantor, Jeff Piontek, Ryan Patenaude, Matthew Millstein, and powered by Old Soul.

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