Tyler Sellhorn: From the classroom to CX and beyond

Welcome to Escalations, a series where I’ll be sharing stories of some amazing careers that started in Customer Support. While many of these will be compiled into a book, I will also be regularly sharing stories here, too. If you like this content, please consider subscribing or sharing. 

Introduction: the starting point

Before Tyler Sellhorn was coaching customers, he was coaching kids—literally. A former secondary math teacher and football coach, Tyler’s early career was grounded in education, systems thinking, and team development. When the pace of the school system didn’t align with his personal ambition, he pivoted into customer success at Hubstaff.

His entry into SaaS wasn’t born of a perfect resume. It was born of resourcefulness. The district timeline for leadership roles didn’t match his readiness to lead, so he started applying for remote jobs in tech—a decision that would change his trajectory completely.

The growth path

Tyler’s first support-adjacent role was at Hubstaff, a remote-first SaaS company focused on time tracking and project management. He was placed in the gap between new customers and product value—and immediately recognized the power of human connection in that moment of early activation.

His teaching instincts kicked in: coach the user, document the patterns, and build systems. But what really sparked his career growth was the decision to measure that impact. He built a spreadsheet to track conversion and expansion rates for users who interacted with him—and found they were converting 5x more often than website-only leads.

That spreadsheet unlocked a new leadership role. And that role unlocked more. Tyler started podcasting about remote work, eventually landing a Head of Remote position at Polygon Labs. He never let go of his support roots—he just zoomed in and out of them, finding new opportunities at every level of the system.

Implementing this in your own career:

• Build in public—track your impact and share your results

• Use your core strengths (like teaching or coaching) in new contexts

• Volunteer for out-of-queue work that creates systems or scale

• Treat every support interaction as a trigger for improvement

Breaking through: lessons & key decisions

1. Expand your luck surface area

Instead of waiting for opportunities to arrive, Tyler took bite-sized actions to show up consistently. That meant commenting on LinkedIn posts, quoting thought leaders, and staying present in his digital spaces—long before he needed anything from them.

The result? Visibility. Network depth. And invitations to speak, consult, and collaborate that he never would have seen otherwise.

How You Can Apply It:

• Repurpose downtime to engage on LinkedIn

• Comment with insight, not just praise

• Build relationships before you need them

2. Track what matters

While his company had solid inbound lead flow from SEO, no one had linked human interaction to higher revenue. Tyler did. He connected early customer conversations to larger contract values and stronger conversion rates.

That single spreadsheet gave him the leverage to build a team, prove ROI, and move up.

How You Can Apply It:

• Identify which of your actions drive real business outcomes

• Document results, even informally, and share them upward

• Don’t assume leadership sees your impact—show them

3. Start acting like the role you want

Whether it was rewriting documentation, optimizing onboarding, or advocating for better knowledge tools, Tyler never waited for a promotion to lead.

The work spoke for itself. By the time an official role opened up, he was already doing it.

How You Can Apply It:

• Own part of the knowledge base or training process

• Spot problems and pitch simple solutions

• Start leading by doing, not by asking

4. Speak their language

To be taken seriously outside of support, Tyler learned to translate outcomes into metrics that mattered to the business.

That meant thinking in ARR, conversion rates, and product adoption—not just CSAT or ticket deflection.

How You Can Apply It:

• Frame your wins in terms of revenue, retention, or velocity

• Speak to your audience’s KPIs, not just yours

• Share before/after snapshots with concrete impact

5. Share power to grow influence

Throughout Tyler’s story is a core leadership principle: the best way to build authority is to give it away. His favorite leadership resource—Brené Brown’s "Power and Leadership" framework—draws a clear contrast between leaders who hoard power and those who expand it by sharing.

He referenced this article and PDF as foundational to his thinking: true leadership means working with, to, and within others—not exerting power over them.

How You Can Apply It:

• Hire and mentor people for their trajectory, not just their past

• Create clarity and confidence for your team

• Let go of control in favor of shared ownership and growth

Actionable takeaways

• Track and share your impact. That spreadsheet might be your first leadership tool.

• Act before you're asked. Leading starts with doing the work, not waiting for permission.

• Build your digital body language. Commenting and sharing online compounds over time.

• Hire for trajectory. The tryhards often outperform the overqualified.

• Center your values. Be an integrated person who leads from a place of service.

• Use leadership to expand others. The more you share, the more influence you create.

Where they are now & final words of advice

Today, Tyler is helping drive GTM strategy at Fillout while continuing his consulting and podcasting work. His career isn’t linear, but it is intentional: built on curiosity, service, and a systems mindset that loops every experience forward.

Do you have a story to tell or insights to share? Consider having a conversation with me so I can share something like this about you!