With a career spanning classroom teaching, edtech sales, consulting, and nonprofit leadership, Thomas shares his journey from growing up in San Diego to becoming a trusted advisor across K-12 and beyond. He reflects on how early experiences, strong mentorship, and a commitment to giving back shaped his path and continue to influence his work today.

The conversation dives into the evolution of education leadership, highlighting the importance of mentorship pipelines, cultural understanding, and developing future leaders who can sustain meaningful change. Thomas shares insights from his work with CALSA and other organizations, emphasizing the role of community, representation, and intentional leadership development in transforming education systems.

The group also explores the changing dynamics between school districts and edtech providers, unpacking why relationships, storytelling, and problem-solving must take precedence over traditional sales approaches. Thomas offers a compelling perspective on how vendors can become true partners by focusing on impact, embracing performance-based models, and aligning with district needs.

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
02:58 Transition from teaching to edtech sales

05:11 Why hitting quota defines success in edtech sales

06:40 Growth story of CALSA and leadership development

09:48 Mentorship as the foundation of leadership pipelines

12:07 Cultural awareness and diversity in leadership

17:26 Building trust between districts and edtech partners

24:18 Three key shifts in edtech: AI, performance contracts, partnerships

29:01 Current challenges and opportunities in school systems

32:09 Innovation vs. defense mindset in education leadership

38:17 Launch of K-12 Impact Academies and training future leaders

40:27 Keys to success in edtech sales and leadership

Connect with Guest
Thomas Davis: https://www.linkedin.com/in/thomas-aurelio-davis

Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

Listen to the episode: https://youtu.be/Ld2CtmkKKFE

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

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/
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 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

Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

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

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

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/
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

01:28 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

Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

In this episode of the Boys of EdTech, Rick, Ryan, and Jeff are joined by Amanda Lanicek, CTO of Springtown ISD, for a candid and urgent conversation on navigating a major data breach in K-12 education.

Amanda walks through her real-time response to the Instructure incident—from immediately disconnecting APIs and securing systems to communicating transparently with staff and families. She shares the tough reality of operating with limited resources while making high-stakes decisions that impact student safety and district trust.

The conversation dives deep into where vendors fell short, especially around communication and transparency, and what districts actually need in moments of crisis. Amanda emphasizes the importance of proactive security measures like MFA, geofencing, and continuous education—not just for staff, but for students and parents as well.

Beyond the breach itself, the episode explores broader implications for edtech: build vs. buy decisions, the future of cloud vs. on-prem infrastructure, and how districts should rethink partnerships moving forward. The group also highlights the human side of leadership—empathy, community collaboration, and showing up for others during high-pressure situations.

This episode is a must-listen for district leaders, edtech vendors, and anyone responsible for protecting student data in an increasingly complex digital landscape.

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

01:09 First response: securing systems and disconnecting access

02:40 Where vendor communication broke down

04:06 Preparing schools for phishing and cyber threats

06:02 Security basics every district should implement

07:25 What effective crisis communication should look like

09:05 Why acting early matters more than avoiding disruption

11:29 How breaches spread through connected systems (APIs explained)

13:39 Real-world risks: phishing, scams, and data misuse

15:05 Build vs. buy: rethinking edtech reliance

16:52 How districts make high-stakes decisions during crises

18:10 Safer alternatives for data sharing and integrations

21:58 The power of community and shared best practices

27:23 Teaching digital safety to students and families

34:56 What makes a great (and terrible) cold email

Connect with Guest:
Amanda Lanicek: https://www.linkedin.com/in/amandalanicek

Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

In this episode of the Boys of EdTech, Matthew and Jacob are joined by Rob Dickson (Wichita Public Schools) and Kris Hagel (Peninsula School District) to explore the rise of “vibe coding” and what it means for the future of edtech.

The conversation dives into how district leaders are increasingly building their own solutions using AI—often in hours instead of months—and why this shift is challenging the traditional edtech vendor model. From custom-built apps tailored to specific district needs to saving hundreds of thousands of dollars through internal innovation, the guests share real-world examples of what’s now possible.

Rob and Kris unpack the broader implications of this movement, including the idea that software has reached a maturity point and is evolving beyond human-centered design. They also explore how AI is flattening the software stack, enabling districts to rely less on complex integrations and more on intelligent systems closer to the data.

The episode also addresses critical concerns around data privacy, cybersecurity, and decision-making—highlighting the balance between leveraging AI’s power and maintaining human judgment in education. As districts rethink build vs. buy decisions, this conversation offers a glimpse into a future where educators are not just consumers of technology, but creators.

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

01:23 Kris Hagel’s first experience building with AI
03:24 The shift beyond traditional software models
04:00 Building for your district vs. building to scale
05:20 Rise of inbound AI-built solutions from individuals
07:21 Going viral and saving $250K through internal builds
10:18 Are edtech vendors becoming infrastructure providers?
12:09 Real-world applications and AI-driven workflows
13:21 The future of decision-making: build vs. partner
16:02 Data privacy and security challenges in AI adoption
17:11 Flattening the software stack with AI
18:07 What’s next: AI agents and automation in schools
19:20 Intelligence vs. understanding in education
20:43 Why this moment is different for district leaders

Connect with Guests
Rob Dickson: https://www.linkedin.com/in/showmerob
Kris Hagel: https://www.linkedin.com/in/krishagel

Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38