My Journey in Tech and Beyond

I started coding in middle school, messing around with BASIC and writing simple programs just for fun. But things really clicked for me after Apple World 1996, where I got into web development. Something about the web—its immediacy, its interactivity—pulled me in, and I never really looked back.

During college at Boston University, where I majored in Computer Science, I took on freelance projects, which turned out to be my first real exposure to building software for actual users. After graduation, I joined a tiny startup called Bullhorn—just 10 people at the time. By the time I left, it had grown into a 300+ person company. I wore just about every hat imaginable, from coding a custom email server to racking physical machines in a data center.

I took inbound customer support phone calls, troubleshooting issues and learning firsthand how users interacted with our software. I created visual design mockups, ensuring a polished and user-friendly interface. On the engineering side, I wrote full-stack features—from styling the UI with CSS to designing and implementing database schemas. I also worked with then-cutting-edge Ajax in JavaScript to create dynamic, responsive user experiences. This experience shaped my approach to problem-solving, product thinking, and building systems that balance usability with technical efficiency. That kind of early-stage chaos taught me how to build things from scratch, solve problems with whatever was on hand, and work across disciplines.

After Bullhorn, I moved into backend engineering, focusing on Python at two different companies. Somewhere along the way, I transitioned into full-time management, realizing that my biggest impact wasn’t just in the code I wrote—it was in helping teams function at a higher level. Managing people let me shape healthy team dynamics, excellent communication, and high-leverage work.

I fell in love with mentoring new engineers and first-time managers. I geeked out on things like hiring processes, promotion frameworks, tech talks, and internal blogging. As I moved into senior leadership roles, I found myself drawn to the big, messy, ambiguous problems—the ones where there’s no clear solution. Things like shifting team culture, rolling out a new process across hundreds of people, or even navigating major layoffs. Those were some of the hardest things I’ve ever had to do, but they were also deeply engaging learning experiences. The irony is, the bigger the problem, the less I can write about it!

Beyond Work

Outside of work, I’m into basketball, ultimate frisbee, and the occasional RPG video game binge. I’ve also developed a love for photography, gardening, personal finance, and cooking. When I’m not diving into leadership challenges, you’ll probably find me coaching Little league, reading science fiction (Goodreads profile) or experimenting with a new recipe (cookbook link).

At the end of the day, I like solving problems—whether it’s in code, teams, or life in general.

My Working Style Profile

Myers-Briggs (ISTJ): Logical, structured, and detail-oriented; values stability, planning, and accuracy over spontaneity.
Strengths Finder (Analytical, Focus, Discipline, Futuristic, Relator): Data-driven problem solver who thrives on long-term planning, structured execution, and deep connections.
Enneagram (Type 8 - The Challenger): Independent and direct; challenges ideas, values autonomy, and resists control or rigid authority.
Insights Discovery (BRGY - Logical & Independent): Strategic and objective thinker who prefers working independently and values precision.
BlueEQ (High Self-Confidence & Resilience): Accountable, disciplined, and motivated; comfortable making tough decisions with a long-term focus.
My Worldview (Redefining): Challenges norms, seeks deeper understanding, and values intellectual curiosity and alternative perspectives.

Working with Me: A Guide to Navigating My Precise, Analytical, and Independent Thinking

If you work with me, you’ll quickly notice a few things: I value precision, thrive on logic, and am relentless in my pursuit of clearly defining the principles behind a decision or creating a structured framework for thinking about a problem. I enjoy breaking down complex challenges into organized solutions, and I don’t make decisions based on gut feelings or emotions. Instead, I gather data, assess the facts, and execute with a methodical approach. My closest team describes me as a “teddy bear wrapped in barbed wire”—I can come off as intense or intimidating, but at my core, I care deeply about getting things right and supporting the people around me. If you’re looking for someone who brings stability, organization, and follow-through, I’m the person you want in your corner.

Strengths: A Strategic, No-Nonsense Problem Solver

I operate with a long-term vision and high personal standards. I’m analytical, systematic, and disciplined—someone who enjoys assembling facts, structuring information, and identifying patterns. I don’t need constant check-ins to stay on track; if you give me a problem to solve, I’ll take it seriously, dig into every possible angle, and provide a well-reasoned path forward. I don’t get overly swayed by sentiment—my decision-making process is rooted in logic and practicality.

As a leader, I set clear expectations, delegate heavily, and take a hands-off approach, trusting my team to take ownership and drive outcomes. I value efficiency and accuracy, and I have little patience for unnecessary bureaucracy or inefficiency. My expectation is that my team always does what’s best for the company, takes full responsibility for their work, and embraces a certain level of scrappy, non-scalable effort when needed to meet leadership where they are and assume good intent. If you need honest, critical feedback, I won’t sugarcoat it—but it will always be geared toward achieving the best possible outcome. I appreciate regular 1:1s where we share notes in writing, including feedback, materials to align on, and as an external brain/memory for future reference.

I can count the number of people I haven’t gotten along with in a work context on fewer than five fingers. I prioritize building strong professional relationships and fostering trust and psychological safety with my peers and closest teams, which has consistently led to productive and collaborative working environments.

How to Work Best with Me

Be clear and factual. I respect logic and objectivity, so the best way to work with me is to present well-reasoned arguments supported by data.
Don’t take my directness personally. My feedback is about improving the work, not a personal critique. If I challenge an idea, it’s because I want the best possible outcome.
Give me space to think. I’m not a fan of extemporaneous discussion—I prefer time to process before making a decision. If you need a fast response, providing key details upfront will help.
Be prepared to adjust plans. While I value structure and planning, projects inevitably evolve. Helping me see the strategic benefits of a shift in direction will make the transition smoother.
Build a working relationship over time. I work best with people I know well and trust. If we haven’t worked together before, expect to invest if really getting to know each other before we hit full stride.

In short, I’m the kind of person you want leading a critical project, managing complex problems, and ensuring follow-through on key initiatives. I’m analytical, disciplined, and strategic—but also independent and structured in ways that may require adaptation from teammates who operate with a more fluid, emotionally driven approach. If we align on expectations and approach work with clarity and purpose, I’ll be a reliable and effective collaborator.

Frequently Asked Questions

What are your expectations for your direct reports?

Build strong relationships with your product and design partners, as well as your direct reports.
Deliver on sprint and quarterly commitments at least 90% of the time.
Take ownership of one or two impactful initiatives per year.
Come to 1:1s engaged, ideally with a written agenda.
Proactively follow up on action items.
Communicate effectively in writing.

What can you expect from me, as a manager?

Dedicated and reliable weekly 1:1 time, where I’ll bring topics to discuss.
Transparent and timely information sharing, when appropriate.
If I ask you to attend a meeting, I’ll ensure it’s well-run and valuable.
High autonomy—most decisions will be yours to make.
Flexible work hours, location, and vacation policies.
I almost never ping people outside of business hours.

What do you need from your manager?

Weekly 1:1s with my boss, ideally with written notes.
Maximum transparency, especially on context from executive leadership.
Meetings that start on time, follow an agenda, and have clear written takeaways.
Dedicated focus time for deep work, with the flexibility to decline meetings when needed.

What motivates you?

I thrive on projects and initiatives where I can:

Set and execute against long-term goals.
Think deeply and refine ideas before making decisions.
Collect data and evidence to guide strategy.
Improve processes through iteration.
Provide guidance and mentorship to others.

How would your team describe you?

Unflappable, practical, informal, and disciplined.

What is your biggest weakness?

If I don’t write something down, I’ll likely forget it.

What’s the most surprising thing you’ve learned about yourself?

I’m introverted, but I gain energy from spending time with people I know well. It takes me a few months to feel fully comfortable with a new team or business partner and about six months to build deep trust.

Let’s Work Together

Chase Seibert