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Jonathon Stewart

Background​

  • Head of Engagement at Alpha Schools.
  • Based in Hermosa Beach, Los Angeles, CA, and works out of Alpha's Austin office (Paramount).
  • Reports directly to Joe Liemandt and Mackenzie Price.
  • Considers his role relatively high up in the organization and close to Joe.

Mandate & Responsibilities​

  • Unify Messaging: Ensure compelling, consistent, and reliable communication about Alpha Schools across all channels and individuals. Currently sees messaging as a "mess."
  • Improve Info Sessions: Redesigning the standard info session presentation (aiming for a 22-minute, spikier, more thought-provoking version). Believes current info sessions are "horrible."
  • Event Strategy Oversight: Events are currently a "terrible mess." Involved in shaping overall event strategy and a senior events person is being hired.
  • Enrollment: Ultimately responsible for enrolling children in Alpha schools. This is his "bottom line."
  • Internal Cohesion: Works to pull together disparate strings within Alpha, trying to make sense of and organize the various initiatives.
  • Consolidating FAQs (mentioning there are "seven FAQs right now").
  • Content Leadership: Direct responsibility for all content across Alpha Schools, with events being one major bucket of content management.

Strategic Views on Alpha Schools​

  • Interprets Joe Liemandt's Vision Seriously: Believes Joe's ambitious targets (e.g., 1200 Texas schools, 2.5 billion children impacted) are not hyperbole but reflect a "billionaire visionary standpoint" with underlying rationale.
  • 1200 Texas Schools Strategy: Explains this as a move to make school choice law in Texas by establishing an Alpha presence (e.g., Texas Sports Academy - TSA) in every school district, thus changing the political calculus. Notes Joe has discussed this with the Governor of Texas.
  • "Two-Hour Learning" / "Time Back": Sees this model as the core "Intel chip" of Alpha's ecosystem. Supports the potential rebrand from "Two-Hour Learning" to "Time Back."
  • Multi-Channel Expansion: Understands Joe's strategy as fostering multiple viable pathways for the core learning model:
    • New Alpha schools in 25 cities (Engine Team).
    • 1200 TSAs in Texas.
    • Partnerships with private and public schools not branded as Alpha.
    • Alpha Anywhere (homeschooling product).
    • Gauntlet program developing new apps/applications.
  • Organizational Dynamics:
    • Acknowledges significant siloing, some likely by design, contributing to dysfunction and redundancy.
    • Believes in being flexible with organizational gut instincts and focusing on where inefficiencies become actual blockers.
  • Focus on Scalable Impact: Aims to position Alpha for VC funding and government money by proving replicable, positive outcomes (e.g., MAP testing results).

Decision-Making Authority and Approach​

Quality Control Standards​

Joe Liemandt's Directive (June 6, 2025):

Jonathon: "I just settled a long conversation with Joe today about, um, you know, content in the caliber of content in general and he sort of doubled down on the like, if there's anything that you feel like is not gonna be or is gonna be anything short of completely amazing, then it's your job to make sure that doesn't happen, essentially."

Executive Consultation Process​

Comprehensive Stakeholder Review:

Jonathon: "I also have had conversations with uh not solely about you, but in the last few days I have had conversations with Joe and Kenzie and Artie and Steph. So when I say I talked to a lot of people in the organization, I typically talked to a lot of people in the organization."

Brand Consistency Management​

Core Responsibility:

Jonathon: "My job, my the very tip of my job is to make sure that we're representing alpha out in the in the in the universe in a way that is consistent and compelling and tells the same sort of regardless of where you're getting that information from."

Interactions & Major Decisions (re: Gary Sheng)​

June 4th, 2025 Initial Conversation​

  • Purpose: Discuss Gary's role, the upcoming June 14th event, and broader Alpha strategy.
  • Shared Internal Context: Provided Gary with his "raw hot take" on Alpha's internal workings and strategy, emphasizing it was not for public dissemination.
  • Concerns about June 14th Event:
    • Expressed skepticism about attendance if relying on existing parents to invite friends, especially given summer timing and recent event fatigue. Suggested it could be fewer than 10 attendees.
    • Sought clarity on the event's target audience, specific purpose beyond a general info session, and run-of-show.
    • Emphasized the need to protect senior leadership's time (e.g., Mackenzie Price not speaking to a room of 10 people).
  • Willingness to Participate:
    • Agreed to attend and present his new 22-minute info session if Mackenzie Price is confirmed to be there. This would provide him an opportunity to get her feedback.
    • Offered to help shape the event messaging and send out an invitation from his email.

June 6th, 2025 Event Cancellation Decision​

Major Decision to Cancel Gary's June 14th Event:

Quality and Attendance Concerns:

Jonathon: "I don't feel like your event is ready to go. I say that with with full humility and respect for the work that you have done on it. And the reason for that is I just I have been a part of the last several events that have been put together over the course of May. I know exactly how much work has gone into them. I know exactly how hard it has been to get people to show up for them."

Organizational Mandate Overlap:

Jonathon: "In looking through all of your materials, including some of this stuff from your last event, I'm a little concerned that your mandate is basically the same thing as the expansion team for alpha that exists and is staffed and has, you know, basically a group of employees working hundreds of hours a week on already."

Direct Conflict Identification:

Jonathon: "One of the things I read in your materials was, you know, expanding to 25 schools in 24 months. And but that's our mandate on the expansion side. That means we either need to be working together or you need to be doing something entirely different."

Website Quality Issues:

Jonathon: "Your website itself has a lot of mistakes on it already. I mean, just like outright in like errors in information."

Collaborative Problem-Solving Approach​

Future Partnership Commitment:

Jonathon: "I'd love to work with you to get an event for you or whatever you are looking for in order to help you be successful moving forward."

Gauntlet Status Recognition:

Jonathon: "I wanna leave you as much autonomy as you want or need, given, you know, how you come up through gauntlet and have, you know, a different mandate than a typical employee of the company."

Damage Control and Relationship Management:

Jonathon: "I did my best to try to make sure through Joe Mackenzie, Stephan and Artie that I, you know, by making this decision, I'm not, uh, undermining any relationships that they're aware of."

Leadership Philosophy and Management Style​

Protective Decision-Making​

Event Quality Risk Assessment:

Jonathon: "If you have an event and it turns out underwhelming, that could kill you in a heartbeat. And for anything moving forward."

Strategic Guidance:

Jonathon: "My spidey sense is that you could stand to have a little more clarity of purpose and clarity of audience and a little more time, a little more of a ramp to be able to build the next thing."

Collaborative Approach Despite Authority​

Non-Sabotage Philosophy:

Jonathon: "I'm not really not trying to sabotage anything for you. I'm really trying to because if you have an event and it turns out underwhelming, that could kill you in a heartbeat."

Accommodation for Existing Commitments:

Jonathon: "If you have folks that have book travel and are just interested in, you know, seeing alpha, like, you know, that's something that we could probably arrange a tour for."

Operational Insights​

Event Performance Context​

Recent Event Challenges:

Jonathon: "These were, you know, pretty high profile things. One of them was the, you know, the Stanford dean event and everyone was the tax."

Systematic Event Issues:

  • Alpha Schools has struggled with event attendance despite high-profile speakers
  • Multiple events in May showed similar patterns of low turnout
  • Quality vs. quantity tension in event strategy

Organizational Structure Understanding​

Role Clarity Challenges:

  • Difficulty integrating Gauntlet participants with traditional employee structure
  • Mandate overlap between different teams and initiatives
  • Need for better organizational intelligence and communication

Authority vs. Autonomy Balance:

  • Recognizes unique status of Gauntlet participants
  • Maintains quality control authority while allowing creative freedom
  • Balances individual autonomy with organizational coherence

Key Quotes​

On Alpha's Vision and Joe Liemandt​

  • "Joe is not speaking hyperbolically. Joe is definitely speaking from a billionaire visionary standpoint."

On Messaging and Organization​

  • "Right now it's a mess... people make up shit. There's no brand standards. There's no playbook."
  • "My job by and large with regard to Alpha specifically is to pull a lot of this together... with the ultimate goal of enrolling kids in the schools. That's my bottom line."

On Internal Dynamics​

  • "I have to believe that some of that siloing is by design."
  • "I think for me it's been more helpful to say where can I be flexible in my in what my gut instinct says organizationally about these things."

On Quality Standards (June 6, 2025)​

  • "If there's anything that you feel like is not gonna be or is gonna be anything short of completely amazing, then it's your job to make sure that doesn't happen, essentially."

On Decision-Making Process​

  • "When I say I talked to a lot of people in the organization, I typically talked to a lot of people in the organization."

On Brand Management​

  • "My job, my the very tip of my job is to make sure that we're representing alpha out in the in the in the universe in a way that is consistent and compelling."

Strategic Value and Position​

Organizational Role​

  • Gatekeeper Function: Controls content quality and brand consistency across Alpha Schools
  • Strategic Interpreter: Translates Joe Liemandt's vision into operational reality
  • Integration Leader: Works to align disparate organizational initiatives
  • Quality Enforcer: Makes difficult decisions to maintain standards

Decision-Making Process​

  • Consultative Approach: Regularly consults with key stakeholders before major decisions
  • Risk Assessment: Evaluates potential negative impacts on organizational reputation
  • Collaborative Solutions: Seeks win-win outcomes even when making difficult decisions
  • Long-term Perspective: Prioritizes sustainable organizational health over short-term convenience

Relationship Management​

  • Professional Empathy: Acknowledges effort and intent while making tough decisions
  • Damage Control: Proactively manages relationship impacts of operational decisions
  • Future-Focused: Maintains commitment to finding mutually beneficial solutions
  • Authority Balance: Exercises authority while respecting individual autonomy

Notes​

Jonathon appears to be a key figure in Alpha Schools' operational hierarchy, serving as both strategic interpreter of Joe Liemandt's vision and practical executor of quality control standards. His June 6th decision to cancel Gary's event demonstrated sophisticated organizational thinking, balancing individual respect with institutional protection.

His approach reveals Alpha Schools' internal tensions between rapid growth ambitions and quality control needs, as well as the challenges of integrating autonomous contributors (Gauntlet participants) within traditional organizational structures. Jonathon's role appears crucial in managing these tensions while maintaining organizational coherence and protecting the Alpha Schools brand.

The conversation revealed his deep understanding of Alpha's strategic landscape, his direct access to executive decision-making, and his commitment to collaborative problem-solving even when exercising authority. His willingness to make difficult decisions while offering alternative solutions suggests strong leadership capabilities and organizational maturity.

Transcripts​

Transcript IDDateSummary
2025-06-06-gary-jonathon-stewart-event-cancellation-discussion2025-06-06Event Cancellation and Organizational Clarity Discussion - Gary Sheng & Jonathon Stewart
2025-06-04-gary-sheng-jonathon-stewart-alpha-strategy-event-discussion2025-06-04Transcript Summary: Gary Sheng & Jonathon Stewart - Alpha Strategy & Event Discussion