My Chief Product Officer once asked me a question I couldn't answer. At that time, I was a product manager. I had spent years in customer support. I had climbed from Tier 1 all the way through the department and into product. I thought I had figured out how this whole thing worked.

Then he asked: "Alex, why would we invest engineering resources in building a chatbot to solve 20% of support issues when we could just fix the product friction causing those issues instead?"

That ended up being a question that took me years to find a satisfying answer to.

But this article isn’t about the question itself.  It's about what I learned on the way to answering it. Because climbing from Tier 1 to product gave me a perspective on support that I never could have seen from the inside.

The Climb

Quick rundown of my career: I began as a tier 1 support agent on a 10-person team. I worked up to tier 2, then moved to tier 3 on a 30-person team at a different company. Later, I started again at T3 at an enterprise company with a 500-person support department, working my way through Operations engineer, Analyst, Program Manager. Eventually, into their product team as a Product Manager.

Every one of those jumps resulted from the same playbook. A set of career strategies that my mentors gave me along the way. The most important thing I did was find those mentors because they taught me the following lessons.

The Playbook 

1. Pair every problem with a cost and a solution.

I was lucky enough to have a mentor, early on, who rewired how I approached problems. While I was complaining about a process one day and she told me something I never forgot: "No one likes complaints. Always pair them with a solution."

So instead of "this process is broken and it wastes so much time" I started showing up with "we spend roughly 10% of our labor capacity on this single issue, and here's how I think we fix it." Same observation. Completely different reaction from leadership.

Support employees feel problems first. But when you are able to bring a problem, how much it's costing, and a way to fix it, you become someone the business wants to invest in.

Your director, your VP, your CPO, cannot act on feelings. So my advice is to start by estimating, even if the numbers aren't perfect. A rough estimate beats a strong opinion every single time. Even if your proposed solution isn't great, people appreciate that you're trying to solve it instead of just complaining about it.

When I moved to the new enterprise company, I put that into practice on day one. I saw operational issues in the department and put together a presentation my first week. Not a list of problems. A solution: "SOP Creation & Management". I found the company-branded PowerPoint template, made it look like it belonged, and that became my path into operations engineering. Change management and knowledge management packaged into something leadership could greenlight.

It’s easy to forget that your boss's job is hard too. When you bring them a problem paired with a solution, you're making their life easier and you're giving them a win they can celebrate with the department. But honestly, the bigger play here isn't about making yourself look good. It's about raising up the people around you. Help your teammates solve problems. Share credit. Make your manager's job easier without keeping score.

This builds social capital, but only if it's genuine. The moment people sense you're doing it because it benefits you, the trust evaporates. You have to actually care about making the people around you successful. When you do, leadership notices. You become the common thread across everyone's success stories. Fostering growth in others and empowering them to succeed is a leadership trait, and it makes you a natural candidate for promotion without ever having to ask for one.

2. Seek out mentors deliberately.

Don't wait to be noticed. Start with someone you recently worked on a project with or chatted with in the break room. "Hey, I want to grow my career and I feel stuck. Can I get 30 minutes?" Most people will say yes. And even if they're not the right person, they usually know someone who'd love to help.

Mentors don't just teach you how the business works. They become your champions. When a promotion opens up, they're the ones in the room saying your name. Every single promotion I got was because a mentor I had cultivated went to bat for me. The learning matters, absolutely. But the relationship is what actually moves your career.

3. Do the shit part of the jobs above you.

I don't mean do your boss's job so they don't have to. I mean when someone above you asks for help with something tedious or unglamorous, treat it as an opportunity to learn the skills required for the next rung.

Here's how this played out for me. COVID hit. Our department's analyst got fired and we couldn't get the budget to replace them. So I raised my hand "If you pay for a SQL course, I'll learn it and do the analytics for the department," and they said sure. I don't think they expected much.

Suddenly, I was generating the reports our director used in leadership meetings. I was sitting in weekly ops meetings with product managers, directors, and C-suite. I was learning firsthand how leadership thinks, what metrics they care about, and how they make decisions.

The key is to be strategic about it. Ask your mentors: "What skills do I need for the role I want?" Then look for every opportunity to build those skills, whether your boss is delegating because they want you to grow or because they just don't want to do it themselves. Either way, you're building a portfolio of work at the next level up.

The fastest path up is not doing your current job better. It's doing the shit part of the jobs above you. Because once you're doing that work, you're already operating at that level. The title just hasn't caught up yet.

And once you're doing it, lock it in. Go to your performance reviews with a career development plan. Get the prerequisites for the next role in writing from HR. Gather every single thing you'd need to be eligible for that promotion, documented and agreed to. That way when the position opens, there's no "well, you haven't done X yet." You already have the receipts.

4. Own your career roadmap.

Figure out where you want to be in five years. Identify the roles that would get you there. Then go to your manager and say: "This is what I want. What would I need to do to get there?"

If they give you a plan, execute on it. If they can't give you a plan, it's time to find a company that can.

I'll tell you how this played out for me. I hit a dead patch. My current company wouldn't promote me because I was too valuable at my current level. So I told them I was disappointed, and that the main reason I worked as hard as I did was because I was focused on growth. If there were no more rungs left to climb, I'd have to look for other avenues forward.

So I went out and interviewed. I got an offer from another company with a skip-level title bump and better pay. Before I accepted, I went to my director and told her about the offer. She said she wanted to promote me, but wasn’t able to get the raise approved. I understood, and I sent my resignation. 

That same day, several of my mentors went to HR independently when they heard I had resigned. It wasn't an organized effort. It was a genuine response from people who had grown to care about my success over years of working together. By the end of the day I had the skip-level promotion, a 20% pay increase, and stock options to stay. The lesson here is important: my direct manager wanted to promote me but couldn't make it happen on her own. It took the collective weight of people across the organization saying "you cannot lose this person" to get it done. That's why lesson two matters so much. Your manager is not the only person who determines your career. The relationships you build across the company are what carry you when it counts.

Mentors become your champions when it matters most. And being honest about leaving because you want more responsibility is not a black mark. Loyalty to a company that invests in your growth is valuable. Loyalty to a company that doesn't is just stagnation.

What the Playbook Built 

That playbook is what took me from Tier 1 to the product team. Let me show you what it produced, because it's also where the answer to my CPO's question was hiding.

As the analytics person, leadership would ask me questions I couldn't answer because our taxonomy was garbage. So I rebuilt it. Six months later we had 90% coverage with85% accuracy. I then went to every product manager and said: "I can show you exactly how much your domain contributes to customer friction." I found a few champions, celebrated wins together at the all-hands, and adoption snowballed.

The relationship between support and product flipped. Product stopped waiting for support to push complaints at them. They started pulling intelligence from us. CS owned the taxonomy, built the dashboards, ran Voice of the Customer reporting. That feedback loop is what got me promoted into product.

Once I was on the product team, I finally cracked a mystery I'd been sitting on for four years. An annual pattern in contact rates that everyone dismissed as seasonality. I correlated per-user contact rates against the number of active experiments each user was enrolled in. The correlation was undeniable. The annual volume cycle was the product team's own development rhythm creating friction in predictable waves. Experimentation in Q1, pruning in Q2, growth in Q3, cost optimization in Q4.

Nobody in support could see this because they didn't have visibility into the product roadmap. Nobody in product could see it because they only tracked contact rates at the individual experiment level. They couldn't see the cumulative effect of enrolling the same users in dozens of experiments simultaneously. I could see it because I had spent years in both worlds. I knew what to measure and I knew where to look.

And that's when I finally understood the answer to my CPO's question.

The Results

You don't choose between fixing the product and building the chatbot. You do both. Products never reach a "fixed" state. Every feature launch, every experiment, every update generates friction. Support keeps customers around while product ships, and the data from support tells product what to ship next. When that loop is running, you get product velocity and retention at the same time.

I only understood that after I had climbed from one side to the other. The playbook got me there. The perspective is what made it all make sense.

That's what eventually led me to start Make Data Speak Human. We help CS teams build that intelligence loop without spending six months doing it by hand. But you don't need our tool to start.

You need initiative, a spreadsheet, and the willingness to learn skills that aren't in your job description.

The signal is already in your queue. It's been there the whole time. Go find it.