Jay Padzensky: Balancing Ambition with Authentic Service

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

Jay began his professional life in education and youth services—teaching English abroad, working with at-risk youth, and serving in the Peace Corps. That path, while meaningful, left him feeling burned out and underpaid. Eager for change, he applied for a frontline support role at Treehouse. It was a leap into the for-profit sector, but it also felt like a chance to help people in a new way.

He quickly realized that the same empathy and de-escalation skills he’d honed working with students and at-risk youth translated seamlessly into solving customer issues. Listening, validating concerns, and adapting on the fly—these qualities became his foundation in support.

The Growth Path

From answering tickets at Treehouse to becoming a manager at Abstract, CoinTracker, and beyond, Jay steadily took on more leadership responsibility. Early on, he’d ask, “What else can I do?”—taking on side projects, learning operations, and helping shape support processes. Though his energy sometimes bordered on overzealous, it showcased his drive to grow quickly and prove himself in a new field.

At Abstract, Jay’s appetite for cross-functional collaboration deepened. He became the product-and-support bridge, helping engineering and product teams consider the customer experience from the outset. Eventually, the CEO asked him to step into a full support leadership role—an opportunity that changed his trajectory entirely.

Implementing This in Your Own Career

• Build relationships outside your immediate team (Product, Engineering, etc.)
  

• Volunteer for projects that stretch your skill set
  

• Communicate your goals clearly to managers and mentors

Breaking Through: Lessons & Key Decisions

1. Adjust Your Expectations

When Jay first joined the Peace Corps, he thought he’d be changing lives on a grand scale. In reality, he found it more impactful to focus on helping one or two people at a time. That same mindset carried over into his support career—big ambitions are great, but you build lasting change through smaller, consistent wins.

By embracing more realistic goals and taking victories where he could find them, Jay avoided the burnout that often comes with overextending. In his early support roles, he learned to tackle what was directly in front of him—like answering tickets and creating small process tweaks—while trusting that bigger changes would come naturally as he gained influence.

How You Can Apply It

• Start every project by clarifying a smaller, specific outcome
  

• Recognize that even modest improvements can build momentum over time
  

• Celebrate each success, no matter how incremental
  

2. Identify Transferable Skills

Shifting from teaching and nonprofit work into technology might seem like a leap, but Jay quickly realized his true differentiator was empathy. Having de-escalated volatile situations with at-risk youth, he was well-equipped to calm frustrated customers and rapidly assess their needs.

That ability to validate a person’s experience, even when you can’t fix their issue immediately, is gold in support. Jay’s nonprofit background also trained him to remain flexible: he had no qualms about picking up new tools or learning new systems on the fly.

How You Can Apply It

• Think beyond job titles: map out the soft skills you’ve developed in other fields
  

• Practice active listening by repeating back what someone says before offering solutions
  

• Use real-world stories in interviews to show how you handle tough or complex interactions
  

3. Own Your Success (Even If It Feels Uncomfortable)

Early in his tech career, Jay worried he was “behind” compared to peers who had spent years in the industry. Determined to catch up, he took a proactive, almost relentless approach: “What can I fix? Where can I add value?” Whether it was curating a knowledge base or improving an internal workflow, he made sure leaders saw what he was contributing.

This mindset led to rapid advancement, from frontline support into management. Still, Jay emphasized that you need to strike a balance: it’s easy to become overzealous and create more work for others if you try to overhaul everything at once. The key is to show consistent results and communicate progress often.

How You Can Apply It

• Look for “small wins” that demonstrate your initiative (e.g., revamping a single FAQ page)
  

• Track every project: note the original problem, your solution, and the final outcome
  

• Share your progress regularly—leaders aren’t mind readers, so it’s on you to highlight your achievements

4. Embrace Iteration Over Perfection

In the rush to prove himself, Jay sometimes launched full-scale projects without fully grasping the existing context. Over time, he learned to adopt a more iterative mindset—start small, gather feedback, and refine. This approach saved him from spending hours on grand plans that didn’t align with the team’s true needs.

Rather than pushing huge initiatives right away, Jay now pilots a feature or process first, then measures impact. If it solves a real problem, he scales it up. If not, he moves on without having wasted massive time or effort.

How You Can Apply It

• Validate your ideas in small test groups before rolling them out to everyone
  

• Ask your team, “Has this been tried before?” and learn from past attempts
  

• Keep lines of communication open so you can pivot quickly if something isn’t working

Actionable Takeaways

• Stay Agile and Curious
  Continue to seek out unmet needs, and offer to help tackle them. This shows initiative and adaptability.
  

• Learn to Listen First
  Start every interaction by validating the other person’s concerns. This builds immediate trust.
  

• Track Both Numbers and Narratives
  Show how your contributions drive improvements—whether in ticket volume or customer satisfaction.
  

• If Growth Is Blocked, Move On
  Don’t be afraid to seek roles where your ambition is nurtured and fairly compensated.

Where They Are Now & Final Words of Advice

Today, Jay is a Customer Support Manager at SmugMug. He devotes his efforts to helping his team members grow—whether that means mastering support or leveraging their skills for roles in product, engineering, or beyond. Although Jay didn’t set out to make support his lifelong calling, he has found an ideal balance of financial stability and genuinely helping people develop.

By staying open-minded and harnessing the empathy he first practiced in nonprofits, Jay has turned support leadership into a true career path—one that fosters both personal growth and meaningful impact.

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!