The Reality of EdTech Jobs: Layoffs, Hiring Trends, and How to Actually Get Hired

The Reality of EdTech Jobs: Layoffs, Hiring Trends, and How to Actually Get Hired

In this episode of the Boys of EdTech, the crew is joined by Jenna Farone, Vice President of Education at Rockwood Search, for a timely and unfiltered conversation on the current state of the edtech job market. Jenna shares her journey into edtech recruiting, from entering the industry with no prior experience to building a strong network and becoming a trusted partner for both candidates and companies. She offers a behind-the-scenes look at how hiring really works in edtech today and why relationships matter more than ever. The conversation dives into the wave of layoffs and restructuring happening across the industry, unpacking what is actually driving these changes. From post-COVID overhiring and shifting budgets to evolving expectations around performance, the group explores why companies are becoming more selective and risk-averse in their hiring decisions. Jenna also shares practical advice for job seekers navigating this uncertain market. She emphasizes the importance of leveraging your network, being clear about your experience, and avoiding the common mistake of mass applying without a strategy. The discussion highlights how strong candidates differentiate themselves by understanding their strengths, asking the right questions, and treating interviews like a true two-way process. The episode also explores the role of AI in hiring, the importance of self-awareness in career decisions, and how both candidates and companies can make smarter, more intentional choices. Whether you are hiring, job searching, or simply trying to understand the market, this episode offers valuable insights grounded in real-world experience. 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 04:22 Adapting quickly in new jobs 07:53 Coping with a layoff 10:41 Discussing layoffs and AI impact 13:31 Business growth and funding challenges 16:39 Navigating partnership challenges 19:45 Understanding Sales Hiring Needs 24:59 Assessing Leadership in Job Search 28:38 Finding the right team fit 31:04 Challenges of Founder Led Sales 35:38 Founders doing their own sales 36:47 Technical founders avoiding sales 41:14 Finding strong job candidates 45:20 Finding a specialized recruiter Connect with Guest Jenna Farone: https://www.linkedin.com/in/jennafarone  Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38  Listen to the episode: https://youtu.be/sGgVHQL46Q8

Competing for the Future: How Dr. Rick Surrency Is Transforming Outcomes in Putnam County Schools

In this episode of the Boys of EdTech, the crew is joined by Dr. Rick Surrency, Superintendent of Putnam County School District in Florida, for a powerful conversation on leadership, innovation, and what it takes to truly compete in today’s K-12 landscape. With nearly 50 years in education, Dr. Surrency shares his journey from coach and classroom teacher to an elected superintendent navigating one of the most dynamic and challenging education environments in the country. He offers a unique perspective on leading in a choice-driven system, where districts must continuously evolve to meet the needs of students and families. The conversation dives deep into the district’s transformation, including a dramatic rise in graduation rates and the implementation of robust career and technical education programs. From aviation and advanced manufacturing to dual enrollment and STEM pathways, Dr. Surrency explains how aligning education with real workforce opportunities has given students a clear reason to stay engaged and succeed. He also addresses the realities of competition, funding challenges, and the growing impact of school choice, emphasizing the importance of trust, transparency, and community engagement. The episode highlights how forward-thinking leadership, strategic partnerships, and a willingness to embrace change can drive meaningful outcomes for students. If you are a district leader, edtech partner, or anyone invested in the future of education, this episode offers practical insights on building systems that prepare students for real opportunities beyond graduation. Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/ [https://www.linkedin.com/in/dr-rick-fernandez-40692434/] Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/ [https://www.linkedin.com/in/matthew-millstein/] Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/ [https://www.linkedin.com/in/thejacobkantor/] Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/ [https://www.linkedin.com/in/ryanpatenaude/] Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ [https://www.linkedin.com/in/jeffpiontek/] Key Moments 03:54 Why Dr. Surrency chose education 04:49 Rethinking innovation and student outcomes 06:20 Building CTE and STEM pathways for real careers 08:19 Challenges of school choice and funding shifts 10:15 Competing in a choice-driven education system 12:14 Supporting student mental health and safety 15:48 Navigating AI adoption in schools 17:27 Evaluating edtech through ROI and outcomes 18:53 Leveraging partnerships and consortium buying power 20:26 How districts can pilot new solutions 26:06 Why CTE is driving graduation success 28:28 Funding and sustaining CTE programs 30:24 Creating real career opportunities for students 33:34 AI tools improving district operations Connect with Guest Dr. Rick Surrency: https://www.linkedin.com/in/rick-surrency-221a69a5 [https://www.linkedin.com/in/rick-surrency-221a69a5] Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 [https://forms.gle/SRVhzpXikBombee38]

Creating Safe Spaces for Real Conversations in EdTech with Tiffany Law

In this episode of the Boys of EdTech, the crew is joined by Tiffany Law, COO of the Institute for Education Innovation (IEI), for a candid conversation on what it really takes to build meaningful connections between district leaders and edtech partners. Tiffany shares her unconventional journey into education, transitioning from a 27-year career in the restaurant industry to helping build IEI from the ground up. Along the way, she reflects on the lessons learned from stepping into a completely new space, embracing mistakes, and finding her footing in a fast-moving and often overwhelming edtech landscape. The conversation dives into what makes IEI different. Instead of traditional conferences, IEI creates intentional, closed-door environments where district leaders can speak openly about their challenges, learn from one another, and connect with partners in a way that feels authentic and pressure-free. The focus is not on flashy presentations or big budgets, but on real problems, real conversations, and real solutions. Tiffany also breaks down how IEI structures its events to level the playing field between large companies and smaller innovators, using curated matching, real-time feedback, and highly qualified one-on-one meetings to ensure that every interaction is meaningful. If you are in edtech or district leadership, this episode offers a behind-the-scenes look at how trust, transparency, and thoughtful design can transform the way partnerships are built in K-12. 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 02:36 Transitioning from restaurants to education 03:36 Building IEI from the ground up 05:12 What makes IEI different from traditional events 07:47 Inside IEI event structure and formats 11:30 Why closed-door conversations matter 12:44 Creating safe spaces for district leaders 15:33 Connecting the right people through curated matching 18:28 How real-time feedback shapes conversations 22:44 Leveling the playing field between vendors 23:53 Why solutions matter more than budgets 28:23 How partners qualify and prioritize conversations Connect with Guests Tiffany Law: https://www.linkedin.com/in/tiffany-law-coo Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

The Why Behind the Work: How the Boys of EdTech Are Shaping K-12 from Every Angle

In this episode of the Boys of EdTech, the crew flips the script and takes a step back to answer a question they have never fully addressed: who are they, what do they actually do, and most importantly, why do they care so deeply about K-12 education? From former superintendents and operators to go-to-market leaders and relationship builders, each member shares their journey into edtech and the unique role they play in helping districts and companies work better together. The conversation highlights how success in K-12 is not about selling products. It is about understanding real problems, building trust, and creating meaningful impact for students. The episode also dives into personal stories that shaped their perspectives. From early nonprofit work supporting schools globally to growing edtech companies from scratch, to firsthand experiences navigating school systems as students. These stories ground the conversation in a shared mission: improving outcomes for students, especially those who need it most. If you have ever wondered what actually happens behind the scenes in edtech, or why relationships matter more than demos, this episode gives you an inside look at the people driving those conversations every day. 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 01:15 Supporting districts and edtech alignment 02:22 Translating complex solutions into clear value 03:49 Opening doors and driving meaningful conversations 04:11 Scaling EdTech companies and go-to-market strategy 05:50 Jeff Piontek’s background in education and leadership 07:10 Why education is the foundation of the future 07:58 Matthew’s nonprofit journey and impact on global education 09:17 Connecting EdTech solutions to real student outcomes 11:14 Supporting underserved student populations at scale 24:08 The mission to close equity and achievement gaps 48:04 Personal experiences shaping passion for education 50:22 Why relationships, not sales, drive success in K-12 Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

From “Hotmail for Schools” to Student Safety at Scale: The Evolution of EdTech with Gaggle’s Founder

In this episode of the Boys of EdTech, the crew is joined by Jeff Patterson, Founder and CEO of Gaggle, for a deep dive into the origins of student safety technology and how the edtech landscape has evolved over the past two decades. Jeff shares his entrepreneurial journey—from starting businesses as a child to building early edtech tools in the late 90s—and the pivotal moment that led to Gaggle’s creation. After a simple conversation with a teacher about the risks of student email, Jeff saw a clear gap in the market and built one of the first safe, school-controlled communication platforms. The conversation explores how edtech has shifted from basic tools to critical infrastructure for student safety, including monitoring communication, identifying risks, and supporting student well-being. The group also discusses the responsibility that comes with handling student data, the balance between innovation and protection, and why trust is everything in K-12. Along the way, the episode blends humor, real talk, and hard-earned lessons about building in education—where relationships, long-term value, and solving real problems matter far more than hype. Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/ [https://www.linkedin.com/in/dr-rick-fernandez-40692434/] Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/ [https://www.linkedin.com/in/matthew-millstein/] Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/ [https://www.linkedin.com/in/thejacobkantor/] Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/ [https://www.linkedin.com/in/ryanpatenaude/] Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ [https://www.linkedin.com/in/jeffpiontek/] Key Moments 01:28 Neighbor jokes and opening banter 02:50 Jacob’s “shoe shed” and personality moment 03:16 Jeff Patterson’s early days in edtech 04:02 Entrepreneurial journey and early failures 05:13 Discovering education as a market opportunity 06:26 The teacher conversation that sparked Gaggle 08:18 Why student email was a safety concern 11:34 Identifying the gap in school communication tools 16:22 Building the first version of Gaggle 17:18 “Hotmail for schools” concept explained 22:18 Evolution of edtech over time 29:44 Shifts in communication, safety, and responsibility Connect with Guests Jeff Patterson: https://www.linkedin.com/in/jeffhpatterson [https://www.linkedin.com/in/jeffhpatterson] Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 [https://forms.gle/SRVhzpXikBombee38]