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