The Real Support Leadership Career Path: What I Wish Someone Had Told Me

I spent 11 years working my way up the support leadership career path from frontline support to Director. I want to walk you through what really happened at each step—and what I wish someone had told me before I got promoted. (Spoiler: I learned most of it the hard way.)

TRANSITION 1: Plugin Support Agent → Support Supervisor (2012-2019)

The 7-Year Setup

What I Thought:

• I finally got the title that, honestly, everyone had already treated me like I had anyway.
• Now I could finally roll up my sleeves and start fixing all the broken processes I’d been complaining about for years.
• This was going to be easy, right? The team already saw me as a leader. Or at least, that’s what I told myself.

What It Actually Was:

• The second I got the title, everything changed. Suddenly, it felt like I was standing on the other side of the fence.
• People who used to vent to me about management started looking at me like I was management. Honestly, I wasn’t sure how to act around them either.
• Having informal influence ≠ having formal authority.
• I had to earn everyone’s trust all over again, but this time, it was a whole different ballgame.

The Lesson I Wish Someone Had Told Me:

• Just because people respected what you had to say as a peer doesn’t mean they’ll automatically listen to you as their supervisor.
• If I could do it over, I’d spend my first month listening 80% of the time and only changing things 20% of the time. I did the opposite, and let’s just say, it did not go as smoothly as I hoped.
• Your former peers are watching to see if you’ll “become one of them” (management) or if you’ll stay “one of us.”
• I wasn’t the best or the most technical support agent out there, but honestly, that doesn’t have much to do with being a good leader.
• You can’t be both. Pick leadership. Just don’t forget to do it with empathy.

The Skill That Unlocked The Next Level:

• Learning to audit support interactions for patterns instead of just “good agent” vs “bad agent.”
• I started looking at the bigger picture: systems, not just people problems.
• That shift from ‘this person is bad at their job’ to ‘this workflow is setting people up to fail’ – that’s what made me valuable as more than just ‘the person who’s good at support.

The Specific Moment I Realized I’d Changed:

• I had to fire someone. Someone I’d considered a friend before I became their Supervisor. Since I’d never had to fire anyone before, my boss actually handled it, but I was still there in the room, part of the process. That’s when I learned I could be friendly with my team, but I had to be careful not to get too close. It was a weird shift for me. My best friend at the time (and still now) was someone I’d met at a previous job, and she’d been my boss back then. Then I was her boss when I had to fire my first team member. Maybe I’m still a little naive, because I do think it’s possible to be friends with people who work for you. But I’m a lot more careful about it now than I used to be, and I try not to lose my caring or empathy.

TRANSITION 2: Support Supervisor → Support Manager (2019-2021)

Managing Managers (Sort Of)

What I Thought:

• More teams = bigger title = more impact
• I figured I could just take what worked with one team and copy-paste it everywhere else.
• Now I’d really be able to make things happen. Or at least, that’s what I thought.

What It Actually Was:

• My job turned into: Why is Team A doing it this way and Team B doing it completely differently?
• Coaching other leaders, which is definitely not the same as coaching agents.
• It was less about coaching agents and more about asking, ‘Why don’t these workflows talk to each other?’
• I stopped being the person who swoops in to fix the problem. Instead, I had to figure out why the problem kept coming back in the first place. (Spoiler: it usually wasn’t the people.)

The Lesson I Wish Someone Had Told Me:

• Consistency across teams matters more than perfection within a single team.
• Your job is now “make sure this works when I’m not looking.”
• You’ll probably feel less useful and further away from the real work. That’s totally normal.
• You don’t have to know everything. You just need to surround yourself with people who know the things you don’t.
• If you’re still the go-to person for the day-to-day tickets, you’re missing the point.
• Again – listen first, act second.

The Skill That Unlocked The Next Level:

• I had to start thinking about how the whole operation, how the whole company worked, not just how to manage a team.
• I had to learn how to build systems that could run without me hovering over every detail. And I had to get better at handing off work to others instead of trying to do it all myself.
• Learning to earn the trust and respect of team members who didn’t already know and respect me.
• I started speaking the language of executives: metrics, trends, capacity. Not just talking about coaching and morale with team leads anymore.

The Specific Moment I Realized I’d Changed:

• Agents had stopped coming to me for help with technical or customer problems. Now, managers were coming to me with manager problems, and the leaders above me were asking me to make much bigger decisions. Suddenly, I was the one researching different support platforms to bring our teams together and figuring out how to make that move. I was presenting my research to leadership and convincing them what was best for everyone, not just my team. Looking back, maybe part of why that hit me so hard was imposter syndrome. I kept thinking, ‘Who am I to be making these decisions? I was just sitting next to these people last month.’ It took me way too long to realize that being promoted doesn’t mean you suddenly have all the answers. It just means you’re the one responsible for finding them, or finding the people who have them.

TRANSITION 3: Support Manager → Director (2021-2023)

The Title Finally Caught Up

What I Thought:

• This was just making it official, right?
• Not much would change, since I was already doing the work anyway. Or so I thought.

What It Actually Was:

• But the title change made people take me seriously in a way they just hadn’t before.
• Suddenly, I found myself in a whole new set of meetings, with a whole new set of expectations.
• Working more closely with external partners (BPOs, vendors, other departments).
• Director-level work, but not always with director-level access

The Lesson I Wish Someone Had Told Me:

• Titles matter more than you think—not for your ego, but for what doors they open.
• “I need to talk to the director” is a real thing customers, vendors, and execs say
• If you’re already working at the next level, ask for the title. It’s not just about vanity—it’s strategic.
• You’d be surprised how many conversations get easier just because your email signature changes. Seriously.

The Skill That Unlocked The Next Level:

• Managing a BPO team of ~20 agents across multiple brands
• Owning vendor relationships directly, not just “coordinating with the vendor.”
• Executive-level reporting and communication
• Strategic planning, not just putting out fires all day.

The Specific Moment I Realized I’d Changed:

• I’d been working with our BPO partners for a while, but suddenly, I was the one deciding which agents from our BPO team went to which brand, how many each brand got, and when. Even if those brands weren’t technically under my umbrella, I was basically making most of the decisions for our BPO team.

BONUS TRANSITION: Director at StellarWP → Senior Manager at hosting.com (2023-2025)

The Lateral Move That Wasn’t

What I Thought:

• I figured I’d be promoted from Senior Manager to a Director-level role in no time.

What It Actually Was:

• A serious learning opportunity.
• 75-person global operation, 30K tickets/month, 1M+ customers
• There was more complexity, more scale, and honestly, more strategic impact than I ever had as a Director. Funny how that works.
• An acquisition waiting to happen. (Spoiler: it did, and it didn’t end well for me.)

The Lesson I Wish Someone Had Told Me:

• Don’t get too hung up on titles if the scope of the work is bigger.
• “I led X-size team doing Y at Z scale” matters way more than “Director” vs “Senior Manager”
• The work is your resume, not the title. Don’t forget that.

The Skill That Actually Mattered:

• Everything I’d built in my previous roles had prepared me for this level of complexity.
• Global teams, acquisition integration, executive partnership, operational redesign
• This is where all those ‘systems thinking’ muscles I’d been building finally paid off. It was like training for a marathon without realizing it.

On Imposter Syndrome and Taking Your Time

Here’s something nobody talks about enough: imposter syndrome doesn’t go away when you get the title.

Agent → Supervisor: ‘I’m not actually qualified to manage these people.’

Supervisor → Manager: ‘I barely figured out one team, now I’m supposed to lead multiple?’

Manager → Director: ‘They’re going to figure out I’m just making this up as I go.’

At every level, I felt like I was faking it. Like someone was going to tap me on the shoulder and say, ‘Actually, we made a mistake.’

What I learned: Everyone feels this way. The difference is whether you let it stop you.

And here’s the thing: acting despite the imposter syndrome? That’s not fake. That’s courage.

Also, there’s no ‘right’ timeline. I took 7 years to go from Agent to Supervisor. Some people do it in 2. Neither is wrong. I needed those years—not just to learn support, but to deal with life. To figure out who I was outside of work. To build a foundation that could handle the weight of leadership.

If you’re taking longer than you think you should, maybe you’re not behind. Maybe you’re exactly where you need to be.

What I’d Tell My 2012 Self

A Letter to Elise

You’re going to spend 7 years as a frontline agent before you get the supervisor title. And honestly? You’re not going to feel behind. You’re going to be… comfortable.

You’ll come in every day knowing what to expect. You’ll be good at your job. You’ll have stability when life outside of work feels chaotic. And that’s going to be exactly what you need.

Here’s what nobody tells you: Sometimes staying put isn’t a lack of ambition. Sometimes it’s self-awareness. You needed those 7 years—not just to learn support, but because you were dealing with things in your personal life that needed your energy. Having one part of your life feel predictable and manageable? That wasn’t settling. That was smart.

Those 7 years weren’t wasted. They taught you:

• What actually breaks in support (so you knew what to fix as a leader)
• What frontline agents actually need (not what managers think they need)
• How to earn respect without a title (which made the title easier when it came)
• That there’s no shame in staying somewhere until you’re actually ready to leave

The actual secret to moving up the career ladder?

• Don’t be afraid to take your time and do what’s best for you, personally and for your career.
• Bring solutions, not just problems, to leadership.
• Don’t be afraid to let people know the work you’ve done.  It’s awesome to highlight your team’s successes, but don’t forget to shine a light on your own, too.

Also, 2012 Elise, you’re going to get laid off in 2025. It’s going to suck. But you’ll have built enough that you’ll know exactly what you’re worth.

Trust the process. And document everything. Seriously.

All my love,

2026 Elise 💜

What’s your support leadership story? What did you wish someone had told you before your first promotion? I’d love to hear it!