The business of empowering educators at scale

In this edition of the Business Insights Series, I had the pleasure of speaking with Luke Sheppard, founder of TeacherTee, a multifaceted agency that helps remote English teachers train, find work, and build flexible careers online. 

What began as a one-person mission to make travel and remote work sustainable quickly turned into a global teacher empowerment movement. TeacherTee isn’t your average recruitment platform. As shown on their site, they provide far more than just job placement. 

Their services span TEFL certification, resume and interview support, demo class preparation, mentorship, and even career guidance tailored to lifestyle goals like travel. It’s part training provider, part job placement partner, part mentor hub, and deeply rooted in a digital nomad ethos.

Luke’s personal journey from feeling stuck in the corporate rat race to rediscovering purpose while teaching from Colombia shaped the mission of TeacherTee: to help others experience that same freedom, flexibility, and confidence in their careers. 

In the past five years, he’s grown TeacherTee from an idea shared over Xbox games and WhatsApp messages into a trusted agency that processed over 1,500 teachers and is gearing up to scale threefold.

Our conversation covered the reality of growing a niche education business in a crowded global market: from building backend systems that don’t buckle under growth, to leading with values, to managing the transition from do-it-yourself to strategic delegation. 

From niche positioning to automation challenges, from riding out client losses to scaling with friends and family on the team, our conversation explored it all. And what stood out most was how clarity of mission can serve as a compass through all the chaos of building something real.

Let’s dive in.

From Freelance Teaching to Global Support Platform

Luke’s journey into entrepreneurship didn’t begin with spreadsheets and investor decks. It began with a plane ticket and a curiosity for travel. After teaching English online while living in Colombia, he started fielding messages from friends who wanted to do the same. That’s when it clicked.

“I just became possessed, more or less, about just getting it set up.”

What started as casual advice over texts and voice notes quickly turned into something much bigger. Luke began by pointing friends to TEFL courses and job boards, but quickly found himself building an informal system to help them launch remote teaching careers. Within a few weeks, the volume of requests made it obvious: there was no central place that offered aspiring ESL teachers everything they needed in one go. No trusted go-to hub. No clear roadmap.

So, he built one.

That spontaneous surge of demand turned into TeacherTee: a business helping teachers get qualified, placed, and supported in their online teaching careers. As Luke described it, the company handles everything from training to CV prep, interview coaching, demo classes, and even post-placement mentoring.

TeacherTee’s approach has always been to support teachers at every stage of their journey. Rather than offering one-off training or placements, they commit to walking alongside teachers from certification through mentorship and beyond. 

TeacherTee has since evolved into a multifaceted agency offering TEFL certification, recruitment services, and ongoing mentorship. Their partnerships with large online language platforms form a steady revenue model while supporting global ESL teacher mobility. They’re also now building out new programs like the TeacherTee Accelerator Academy, which takes that teacher-first philosophy even further.

That teacher-first identity is the thread running through every service and every strategy. It’s also the reason TeacherTee continues to grow by word of mouth, reputation, and results.

Why Niches Win in the ESL Market

One of Luke’s biggest messages to the teachers they work with? Pick a niche.

“If you want to start charging higher rates, you want to focus on one area.”

That advice goes beyond better pay. It speaks to identity, clarity, and relevance in a saturated market. The ESL world is crowded with generalists, teachers offering everything from phonics to test prep to casual conversation classes. But when everyone offers everything, it’s hard to stand out. Luke sees this as one of the most overlooked mistakes in the freelance teaching space.

“Business English is definitely the fastest growing area right now, it’s what we hear the most demand for from employers.”

He encourages teachers to think of themselves not as service providers but as specialists with solutions to specific problems. The example he gave? A tech manager preparing for a promotion who needs to nail their presentations in English. 

That teacher’s role includes delivering language instruction while also supporting learners in building the communication skills they need for real-world professional success. And when teachers market themselves that way, clients are willing to pay significantly more for the right fit.

That belief inspired the creation of the TeacherTee Accelerator Academy, a program designed to help teachers identify, position, and market themselves in high-value niches. It supports TeacherTee’s broader goal of increasing both the volume and quality of teacher placements as they scale.

Teacher specialization goes beyond career advice. It’s a platform-defining strategy that leads to measurable outcomes, like 3-4x increases in hourly rates for teachers. It also creates value alignment with platform partners who want more specialized, experienced candidates. And for Luke and his team, it creates a roadmap to deliver meaningful, long-term impact.

Growing a Business with Friends, Family, and Purpose

While many founders are advised to keep business and personal relationships separate, Luke’s journey looks different, and intentionally so. From the beginning, he’s surrounded himself with people he trusts implicitly, including family and close friends. That familiarity contributed to building a culture grounded in mutual support and collaboration.

“My parents  help me with more real personal things… just like general sort of administrative stuff.”

Their support has allowed Luke to focus more on building systems and partnerships. Having family involved in the operational backbone ensures that smaller, essential tasks don’t fall through the cracks. It also reinforces the mission-driven culture that runs through TeacherTee.

“I’ve got two of my best friends out here… both working for me doing recruitment.”

By bringing trusted people into the business, Luke created a circle of loyalty that became foundational during tough times. When a major client pulled out, one that had previously made up a significant portion of TeacherTee’s revenue, the team regrouped quickly. They focused on what they could control and took clear steps to rebuild the business pipeline.

“We’re not taking that as an option to be laying people off… we need everybody to be literally building their way now.”

Over the next three months, they brought in four to five new clients, diversified their income sources, and stabilized monthly revenue. That response came from having a team that was emotionally invested in the mission and willing to adapt quickly to new challenges.

The decision to work with friends and family reflects a focus on trust capital, prioritizing relationships built on loyalty, mutual respect, and shared commitment. Luke’s approach proves that when people believe in what they’re building together, they step up when it counts. Hiring familiar faces has never been the end goal. Luke’s focus is on cultivating a resilient culture of ownership, accountability, and unwavering belief in the shared vision.

Scaling: Metrics, Momentum, and Major Moves

Luke shared that TeacherTee has processed over 1,500 teachers in the past 20 months and is currently averaging about 150 teachers per month.

“By 2025, 2026… we would be processing around 500 teachers a month. That’s the plan.”

Behind that number is a team preparing for scale with care. They know that growth includes more than simply increasing teacher numbers. It also requires creating systems and support structures that help those teachers thrive once they’re on board. That’s what TeacherTee is quietly building toward.

Their vision is grounded in an ecosystem of interlocking services. And recently, that ecosystem has grown in bold new directions.

Since our conversation, Luke and the TeacherTee team have entered an entirely new chapter: one marked by rapid momentum and a major business model shift.

First, the TeacherTee Accelerator Academy has become a full-fledged mentorship and coaching program that’s tripled their monthly recurring revenue. With a sharper focus on niche development and Business English, the Academy is now helping freelance teachers specialize, build personal brands, and land premium clients on their own terms.

Second, TeacherTee has officially launched its own B2B Business English platform. Rather than simply placing teachers with third-party schools, they now directly match teachers with corporate clients under the TeacherTee brand. This means they’ve shifted from being a recruitment agency to becoming the direct supplier. Check out the platform here.

As a result of this rapid success, recruitment services have been paused entirely. TeacherTee is now focused on two clear tracks: empowering teachers to thrive as freelancers or to teach through their fast-growing B2B model.

To support this expansion, the team has brought on six new hires and is actively scaling. It’s a bold new phase for the company, and a testament to how fast things can move when vision meets execution.

“We’re a multifaceted agency. We’re offering recruitment, training, and mentorship all under one roof. It’s a mix of models that work together under the TTT brand.”

This multi-model approach helps them serve teachers at different stages of readiness. But with each new layer comes operational strain. Luke and his team are working to make sure that what’s growing doesn’t outpace what’s working.

Meeting increased demand means thinking in systems: how teachers get matched to schools, how information is shared between departments, how support continues after placement. Every moving part needs a better backend.

“One of our biggest battles here is back-end processes and trying to get things as efficient as possible.”

The shift to remote work has fundamentally altered how educational services are delivered. Remote work continues to be a dominant force, expanding the global talent pool and enabling teachers to work with students worldwide without geographical constraints. That focus on efficiency is driven by a clear vision to empower teachers through smarter, more sustainable systems. Luke and the team are refining the way they work because they believe operational excellence can directly support teacher success at scale. From automation to streamlined intake pipelines, they’re building smarter, not just bigger.

To meet the 500-teacher monthly goal, the TeacherTee crew is taking strategic steps: minimizing repetitive admin work, improving coordination across departments, and preparing the team for growing waves of demand. They’re strengthening the business from the inside out.

The energy here is proactive, not reactive. Luke and his team are building confidently toward what’s next, aligning systems and structure with their mission to deliver meaningful outcomes for every teacher who joins the journey. Their efforts reflect a clear and focused momentum, one that’s rooted in preparation, values, and a belief in thoughtful growth.

Leading Without Letting Go

Luke’s evolving approach to leadership reflects a growing awareness that building systems goes hand in hand with building people. Research shows that effective delegation is a sign of trust, and trust has a ripple effect: when leaders empower others, teams take greater ownership and often produce stronger results. Luke is embracing this shift through thoughtful handoffs and shared responsibility.

Luke is still deeply involved in operations, but his focus is shifting. What began as a solo journey powered by instinct and hustle is evolving into a leadership role defined by trust, collaboration, and strategic delegation. This next phase is all about building the kind of team that can grow the vision beyond what one person could ever accomplish alone.

“Now in the last couple of weeks, managed to get a team… people who are experts in separate fields who are all helping me.”

Rather than seeing delegation as a loss of control, Luke sees it as an opportunity to build something stronger. It’s about bringing in people who are not just capable, but energized by the chance to contribute their strengths. That shift is opening up new possibilities across the business, from refining operations to expanding marketing reach.

“I am learning how to delegate more, which I think is a really important skill, which you need to do as a startup founder, for sure.”

So far, he’s successfully transitioned key responsibilities like recruitment and mentorship to trusted team members. And now, areas like marketing and system optimization are the next exciting chapters. Luke is actively seeking out experts who can elevate these areas and bring fresh thinking into the fold.

“I’m definitely going to be putting a lot of trust in people… especially in areas like marketing where I don’t have a clue at the minute.”

This stage of growth brings both infrastructure development and a deepening of leadership. Luke is making space for others to thrive, and in doing so, he’s positioning TeacherTee to scale in a way that’s both smart and sustainable. It’s a purposeful transition from founder-led to founder-empowered, where leadership means enabling others and focusing on the big picture.

Conclusion: A Blueprint in Progress

TeacherTee’s story is still unfolding. What’s already clear is that Luke is creating a platform rooted in care and intentionality, where teachers are valued, supported, and seen as central to the success of the whole system. Every service, process, and decision is rooted in that core belief.

Throughout our conversation, one theme kept resurfacing: intentionality. Whether it’s helping teachers carve out their niche, staying steady in uncertain moments, or refining operations into something scalable and smart, Luke’s approach is refreshingly grounded. His story offers real, applicable lessons for any founder who’s trying to grow without compromising their original mission.

“We don’t want to lose the quality just because we’ve got the quantity.”

That mindset is a powerful reminder. Growth goes beyond hitting performance metrics. It means scaling in a way that strengthens the values at the heart of the business: trust, quality, and purpose. And doing that successfully takes more than ambition. It takes structure, strategy, and a clear sense of direction.

If you’re feeling the weight of growth, but you’re committed to doing it on your terms, this is your invitation to pause and get the right support around you.

Serenichron is ready to support founders like Luke with:

• Process automation that maintains personalization
• Scalable systems design for education platforms
• Strategic marketing roadmaps that resonate with niche audiences
• Organizational structure advisory
• Custom analytics setups for performance clarity

Let’s explore how you can scale without the burnout.