The 24-Month Career Pivot: From Tax Accountant to Customer Success to Account Executive

I spent more than a decade plus working in tax before moving into Customer Success and Account Executive roles at Thomson Reuters.

Within two years, I had earned Rookie of the Year, Circle of Excellence, and Customer Success Executive of the Year recognitions in back to back years.

Then, in the summer of 2026, I was tapped for an internal promotion into the Sales team as a Senior Account Executive.

Tax accountant to Customer Success Executive to Account Executive for Tax and Global Trade software.

Looking backward, the connections are pretty clear. Each role prepared me for the next.

Looking forward at the time? I couldn’t have told you exactly where it was all going. I didn’t see the last three years coming at all to be honest.

But I knew I wanted to keep learning, become more useful, and build a reputation people could trust. That gave me a direction even when I didn’t have the entire career mapped out.

Tax gave me a foundation

Corporate tax work teaches you to manage complexity, budgets, and strict timelines using your analytical and communication skills.

You’re balancing compliance deadlines, reviewing data, explaining issues to leadership, and coordinating with colleagues and outside consulting firms. Sometimes across multiple countries and time zones. Often with several deadlines competing for the same people and resources.

A spreadsheet can look fine until you discover a problem in the underlying data. A process can work for years until an acquisition, system change, or new requirement exposes its weaknesses.

You learn to ask questions. You learn where things can break. You learn why accuracy matters.

You also learn that technology is only as useful as the processes and people around it.

That experience came with me when I joined Thomson Reuters in Customer Success.

The Tax Directors, VPs of Tax, and CFOs I now served as customers were dealing with pressures I understood. I had worked inside their world. I knew why a software issue near a filing deadline could quickly become a much bigger business problem.

I understood the work behind the software.

That helped me ask better questions, understand the answers, and earn credibility.

Customer Success stretched me in a new direction

My tax background gave me a starting point. I still had plenty to learn.

In tax, much of my work revolved around producing an accurate result by a specific deadline. In Customer Success, I had to understand what the customer wanted to accomplish over time, what might prevent it, and how to keep progress moving.

I made a simple promise to myself:

Be the person the customer sees first, remembers most, and trusts completely.

That promise had to show up in how I worked.

Listen long enough to understand the problem

“What keeps you up at night?” became a useful starting question.

Then I had to listen.

A customer might begin by describing a software problem. Behind it could be a staffing shortage, an inefficient process, a difficult implementation, or pressure from leadership to accomplish more with the same resources.

Those details matter. They help you understand the consequences of the problem and what a useful solution would actually look like.

My experience in tax helped me recognize some of those pressures. Curiosity helped me understand the ones that were different from my own.

Define progress from the customer’s perspective

Meetings, account plans, and renewal dates were part of the job. I also had to ask what was improving for the customer.

Could the team complete its work more efficiently? Had a recurring issue been resolved? Did people understand how to use the software they were paying for? Were we making progress toward the goals we had discussed?

Those questions kept me connected to why the customer had invested in the first place.

Follow through across teams

I couldn’t personally fix every issue. Helping customers required support teams, product teams, implementation specialists, and colleagues with expertise I didn’t have.

My responsibility was to help connect that work.

Understand the problem. Find the right people. Clarify the next step. Follow up. Keep the customer informed.

When someone raised a concern, I wanted them to feel confident that I would stay with it.

That’s how trust develops over time. People see how you handle the difficult situations, especially when the answer isn’t immediate.

The recognition gave me confidence to keep building

In 2023, I received Rookie of the Year and Circle of Excellence recognition. In 2024, I received the Customer Success Executive of the Year award.

I’m proud of those awards. They represent a lot of work, a willingness to learn, and support from colleagues who helped me succeed.

They also gave me confidence that the transition was working. The experience I had accumulated in tax was creating value in a different role.

I kept building on it.

In 2025, I met with 28 customers in person across multiple states and industries. I developed Customer Success plans and explored how AI tools could help me prepare, organize information, and support enterprise relationships.

Getting into the room mattered.

It gave me time to ask follow-up questions, understand priorities, and learn more about how each department actually operated. Every conversation added to my understanding of the people and businesses we served.

Customer Success opened the door to Sales

In the summer of 2026, I was tapped to take that experience into the Sales team through an internal promotion to Senior Account Executive.

The responsibilities and expectations changed. I now had more to learn about developing opportunities, navigating buying decisions, and helping customers evaluate where to invest.

But I brought a useful foundation with me.

Tax taught me how these departments operate. Customer Success taught me how to build relationships, understand customer goals, and coordinate the work needed to help them succeed.

As an Account Executive, I can draw on both.

When I speak with a tax or finance leader, I can think through the process they’re trying to improve, the pressures on their team, and the practical questions that come with introducing new technology.

Who needs to be involved? What would implementation require? What does the team need to accomplish? How will they know the investment is working?

My time in Customer Success also shapes how I think about the commitment made during a sales conversation. The customer will eventually have to implement, use, and depend on what we discuss.

That perspective is valuable as I continue learning the Sales role.

My career changed because my experience kept becoming useful

I didn’t plan every step of this progression.

But I can see a pattern in it now.

I learned the work in tax. I used that knowledge to serve customers. I built relationships and earned trust. Those experiences helped open the next opportunity.

Each move required me to learn something new while finding ways to contribute with what I already knew.

That’s the part of a career pivot that can be easy to overlook.

You may feel inexperienced because you haven’t held the new title before. Yet you may already understand the industry, the customer, the process, or the problems better than you give yourself credit for.

At the same time, experience in one area doesn’t excuse you from learning another.

I had to learn Customer Success. Now I’m continuing to learn Sales.

Being willing to contribute and being willing to be coached have both mattered.

What this means for your next move

If you’re considering a career change, take inventory before you assume you need to start over.

What problems have you spent years solving?

Whose work do you understand?

What can you explain clearly because you’ve experienced it yourself?

Where could that knowledge become useful in a different role?

Then identify the gaps. Talk to people doing the work. Ask what success looks like, what’s difficult, and what you would need to learn.

My awards came within 24 months of moving into Customer Success. The foundation took more than a decade to build.

And that transition eventually led to another opportunity I hadn’t fully anticipated.

You don’t need to predict every step to make a thoughtful next move. You do need to understand what you bring, put in the work to grow, and give people reasons to trust you with more responsibility.

Download The 24-Month Career Pivot

I turned the lessons from my move into Customer Success into a free guide, The 24-Month Career Pivot.

Use it to identify your transferable strengths, consider what you need to learn, and turn a career idea into practical action.

Download The 24-Month Career Pivot: free PDF

For practical lessons on leadership, careers, and taking ownership of your work, subscribe to Ryan’s Leadership Lessons. You’ll also receive the guide in your welcome email.


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