StartEd resources

Evan Shy, CEO of Coding Temple, joins us to talk about the future of work and learning in the age of AI. From upskilling and proof of work to building learning into daily routines, Evan shares his take on how companies and individuals can stay ahead in a fast-changing labor market. He also opens up about his own leadership style and what’s next for workforce development.

These are the same themes we'll be exploring with a small group of CEOs, investors, and operators at the StartEd CEO Summit at EdTech Week 2026.

If this is relevant to what you're building, you can learn more or request an invite here.

Matt Kennard runs BetterLesson, a roughly 15-year-old company that has grown from a lesson-planning site into an outcomes-focused professional learning and strategic planning partner for districts. He reframes the sector's central problem around what district and state leaders actually need — post-secondary readiness and provable ROI on spending — and makes the case that a coming period of consolidation will reward companies willing to stand behind their student-outcome data. He also reflects on teacher career pathways, servant leadership, and AI as a durable tool rather than a fad.

These are the same themes we'll be exploring with a small group of CEOs, investors, and operators at the StartEd CEO Summit at EdTech Week 2026.

If this is relevant to what you're building, you can learn more or request an invite here.

Kermit Cook leads Penn Foster, an online school tracing its roots to an 1890 correspondence program for coal miners that today graduates more than 90,000 career-focused students a year. He shares how radically affordable, asynchronous learning is finally delivering on its long-promised outcomes with AI, why an AI writing-feedback tool moved the needle while an AI tutor didn't, and how employer scrutiny of training ROI is reshaping the market. He wraps with a leadership philosophy rooted in his years as a Teach For America teacher.

These are the same themes we'll be exploring with a small group of CEOs, investors, and operators at the StartEd CEO Summit at EdTech Week 2026.

If this is relevant to what you're building, you can learn more or request an invite here.

Owl Ventures' Amit Patel joins the CEO Spotlight to unpack the EdTech investing rebound and how AI is reshaping the sector. He walks through the cycle of consolidation and proliferation that follows any technology shift, what separates the companies getting funded from those stalling out, and how his firm evaluates whether a startup has a durable moat or risks being absorbed into the frontier models. He closes on what he looks for in a founder and how his global investment thesis has evolved over Owl's first decade.

These are the same themes we'll be exploring with a small group of CEOs, investors, and operators at the StartEd CEO Summit at EdTech Week 2026.

If this is relevant to what you're building, you can learn more or request an invite here.

Brought to you by the StartEd CEO Summit, where the leaders in these conversations meet in person. Explore the Summit.

I talk to hundreds of EdTech CEOs every year. Across many of them, I feel a recurring, quiet dilemma: the rumination over what a CEO “should” actually do.

There is a nagging sense of guilt that hits when you dive into the details of a product launch or a sales script. You’ve hired great leaders—experts in marketing, product, and success—to drive those functions. So, you tell yourself to stay at 30,000 feet. You focus on “strategy.” You delegate. You empower.

But then, you feel disconnected. You worry you’re losing the pulse of the business. You’re caught in the False Dichotomy: Are you a visionary leader, or are you a micromanager?

My recent conversation with Sara Leoni, CEO of Ziplines Education, offered the perfect antidote to this struggle.

The Player-Coach Mindset

Sara doesn’t see a conflict between vision and execution. She views leadership through the lens of her time as a D1 softball player at UNLV—a top-10 ranked team that fought its way to the College World Series. In that world, the best coaches weren’t just standing on the sidelines with a clipboard; they were “player-coaches” who knew exactly what it felt like to be in the dirt.

For Sara, being a CEO means:

• Aligning the Vision: Not just stating a goal, but making sure every person understands exactly what that vision looks like for them.

• Showing Up Off the Field: Building a team-first culture where “I’m only as good as my team” is a daily operating principle.

• Radical Transparency: Sharing the “brutal truths” alongside the wins. If you don’t share the bad, you aren’t leading a team; you’re kidding yourself.

Harmony in the “Dirt”

The “False Dichotomy” suggests that getting into the details is micromanaging. But Sara’s approach suggests that you achieve harmony by doing both.

You hire experts to lead their disciplines, but as the CEO, you are the bridge. You are the one who ensures that the 20-mile march—a principle from a book Sara recommends, Jim Collins’ Good to Great—is happening every single day, regardless of the “weather” in the market.

Respecting the Traction Gap

In the growth stage, many CEOs try to build a “rocket ship” overnight. They push for scale before they’ve truly crossed what Bruce Cleveland calls the “Traction Gap,” also the title of a book that helped inform Sara’s practices.

Sara’s leadership is built brick-by-brick. It’s about executing the basics day in and day out. It’s about having the discipline to stay in the “Player-Coach” role until the foundation is unshakable.

The takeaway for my fellow EdTech leaders? Don’t be afraid to get a little dirt on your uniform. If you’re ruminating on whether you should be in the details or in the clouds, the answer is usually: Yes.

Real leadership isn’t about choosing between strategy and tactics; it’s about the “harmony” found in doing both.

These are the same themes we'll be exploring with a small group of CEOs, investors, and operators at the StartEd CEO Summit at EdTech Week 2026.

If this is relevant to what you're building, you can learn more or request an invite here.

Brought to you by the StartEd CEO Summit, where the leaders in these conversations meet in person. Explore the Summit.

In management literature, Sir John Kay’s book Obliquity posits that the most complex goals are best achieved indirectly. Kay argues that the most profitable companies are rarely the ones most focused on profit. Instead, profit is the second-order (or even third-order) effect of pursuing a high-level purpose excellently.

I saw this principle in action during a conversation with Karl Rectanus, the founder of LearnPlatform (acquired by Instructure) and current CEO at Really Great Reading (RGR). Karl argues that while departments like Product, Sales, and Finance are critical, they should not be aligned around profit. They should be aligned around impact—the measurable difference made in the life of a student or leader.

“We believe that if we aligned those things around customer impact... that would give us an unfair advantage.” — Karl Rectanus

By focusing on the customer’s success (the oblique goal) instead of platform usage (the direct goal), the financial success follows. At LearnPlatform, this focus resulted in significant growth because impact acted as the “governor on scale”—the mechanism that ensures growth is sustainable and rooted in value.

The Impact Metric: Quantifying Second-Order Effects

To prevent “Impact” from becoming an empty buzzword, Karl insists on a quantitative proxy: the Impact Metric.

• First-Order Effect (Usage): The customer buys and uses the platform.

• Second-Order Effect (The Oblique Goal): The customer achieves their ultimate objective (e.g., improved literacy).

• Third-Order Effect (The Result): The business achieves financial scale and sustainability.

For LearnPlatform, the metric was “decisions made.” They didn’t just measure minutes spent on the system; they measured how many data-informed decisions educators were making. When this metric became the North Star:

• Sales stopped asking for “purple buttons” and started asking for features that drive administrator and educator decisions.

• Product prioritized the “decision engine” over secondary features.

• Trust was built because the company was obsessed with outcomes, not just subscription fees.

Front-Line Leadership: Rectanus meets Musk

Despite their different industries, there is a striking parallel between Karl’s leadership and the philosophy described in Erik Jorgensen’s The Book of Elon Musk. Their approach to “presence” is identical.

Karl emphasizes that you cannot have quality time without quantity time. A leader must be present to understand ground-level challenges. This mirrors Musk’s “sleeping in the factory” era at Tesla and SpaceX. In both cases, the leader’s job is to serve the team by identifying and removing barriers.

Karl calls this conviction. You can fake confidence, but you cannot fake the conviction that comes from being “in the dirt” with your team, seeing the impact of your product first-hand.

The Feedback Loop: Outcomes Over Content

In the current EdTech landscape, the “answer” isn’t just selling content or platforms; it’s the feedback loop of learning, motivation, and data.

This is the ultimate second-order effect. If you focus solely on content consumption, you become a commodity and risk becoming irrelevant. If you focus on the learner’s success, you are a partner.

This is a shift that major platforms like Udemy (which acquired my last company) and Coursera are navigating. Having seen this from the inside, it is clear that minutes watched does not equal learning outcomes. As the market matures, the industry’s value will shift from content libraries to verified impact. Karl is now applying this principle at RGR, the first literacy outcomes company, where the goal isn’t to sell reading programs, but to improve the trajectory of U.S. literacy rates.

The Takeaway

Whether you are building a rocket or a reading platform, alignment comes from looking past the product to the impact. When you measure second-order effects, your team becomes more purpose-driven and starts working for a mission.

Karl suggests that “Impact for Scale” provides an unfair advantage in today’s environment. Looking at your own organization: What is your Impact Metric? What is the one data point that gets everyone excited about the mission?

These are the same themes we'll be exploring with a small group of CEOs, investors, and operators at the StartEd CEO Summit at EdTech Week 2026.

If this is relevant to what you're building, you can learn more or request an invite here.

Brought to you by the StartEd CEO Summit, where the leaders in these conversations meet in person. Explore the Summit.

In growth-stage companies, we frequently celebrate individual miracles: the late-night push to save a client, or the heroic effort to ship a product on time.

In my conversation with Dana Stephenson, CEO of Riipen, our discussion turned toward a fundamental leadership discipline. It is a perspective anchored in Peter Senge’s The Fifth Discipline, the masterpiece on organizational learning. While Senge details five distinct component technologies that build a resilient enterprise, it is the final discipline — Systems Thinking, that serves as the vital, integrative engine. Without a deliberate systems foundation, an organization demands individual “heroics” to execute the basics.

Dana applied this systems-thinking lens to two distinct architectures:

• The Macro System (The Experience Trap): The catch-22 “to get a job you need experience; to get experience you need a job”— is a broken linear sequence. As AI automates entry-level rungs, we can no longer rely on sequential “handoffs” between college and career. Today, nearly half of college graduates are underemployed, while 8.3 million students compete for just 2.5 million high-quality internships. Riipen’s fix was systemic: closing the loop by integrating project-based industry work directly into the classroom curriculum.

• The Micro System (Internal Operations): Internally, Dana recognized that relying on staff heroics prevented scalable growth. He replaced individual fire-fighting with a structured, rigorous internal Operating System, proving that you must diagnose the process before you blame the person.

Whether you are launching a new product or scaling a global enterprise, heroic fixes to systemic problems will always yield diminishing returns. Stop counting on heroics to overcome structural flaws. Focus on the system first.

These are the same themes we'll be exploring with a small group of CEOs, investors, and operators at the StartEd CEO Summit at EdTech Week 2026.

If this is relevant to what you're building, you can learn more or request an invite here.