A former direct report once pulled me into a 1:1 with a Google Doc titled “Path to VP” already open on the screen. Multiple page scrolls worth of content. Color-coded. With a timeline.
We were three months into the role.
At this point into the role…The numbers? Nowhere near target. The campaigns? Half-launched. The cross-functional relationships? Non-existent (yet).
But the ambition? Off the charts.
👋 Hiii, it’s Kaylee Edmondson and welcome to Looped In, the newsletter exploring demand gen and growth frameworks in B2B SaaS. I write this newsletter every Sunday, and wildly, a few thousand of you read it each week. I’m grateful!
Here’s what nobody tells you about promotions in B2B SaaS: wanting one doesn’t mean you’ve earned one.
And honestly? Most people haven’t.
I’ve been on both sides of this. I went from marketing coordinator to VP of Marketing in 6 years, which felt fast. I’ve also managed people who thought they were crushing it while their metrics told a completely different story. And I’ve watched genuinely talented people hit a ceiling because their company just couldn’t promote them, no matter how much they deserved it.
The gap between where you think you are and where you actually are? That’s what I want to talk about today.
Let’s Get Real About Performance
You want a promotion. I get it. You show up every day, you work hard, you care about the outcomes.
But here’s the question: Are you actually doing the work at the next level?
Not the work you think the next level does. The actual work.
When I was at Chili Piper as Senior Director of Demand Gen, reporting to the CEO, I wasn’t just executing campaigns. I was in board meetings defending marketing spend. I was building annual plans with no template. I was making budget calls that impacted the entire company.
Nobody asked me to do those things before I got the title. I just started doing them because I saw the gap.
The people who get promoted aren’t the ones who execute their current job description perfectly. They’re the ones already doing parts of the job they want.
Some specific examples of what “doing the next-level work” actually looks like:
If you’re an IC wanting to become a manager:
You’re already mentoring junior team members (without being asked)
You’re creating documentation and process improvements that help the whole team
You’re thinking about team capacity and resource allocation, not just your own tasks
You’re bringing solutions to problems, not just flagging issues
If you’re a manager wanting to become a director:
You’re thinking about cross-functional impact, not just your team’s OKRs
You’re making strategic recommendations in meetings, not just reporting status
You’re building relationships with other department leaders
You’re defending your team’s work with data and business impact, not just effort
If you’re a director wanting to become a VP:
You’re having CEO-level conversations about business strategy
You’re influencing decisions outside your immediate scope
You’re thinking multi-quarter and multi-year, not just this quarter
You’re building and testing frameworks that could scale across the company
Most people skip these steps. They think time in role plus solid performance equals promotion. It doesn’t.
There’s this quote someone shared with me early on in my career that I loved so much I kept on a sticky note on the inside of my laptop for years.
Ownership is visible when a team member realizes potential
that others have yet to see.
Let me be blunt: if your numbers aren’t hitting, you’re not getting promoted.
I don’t care how many hours you work, how much you’ve “grown” this year. If pipeline is down, if conversion rates are flat, if you keep missing targets, you’re not ready.
And look, I get it. Sometimes the targets are unreasonable. Sometimes you inherited a mess. Sometimes the market shifted.
But here’s what separates people who get promoted from people who don’t: how you respond when things aren’t working.
The people who get promoted:
Diagnose why they’re missing targets and come with a plan to fix it
Ask for help or resources they need (specifically)
Make tough calls about what to stop doing
Show progress even if they’re not hitting the full target
Take ownership without making excuses
The people who don’t:
Blame the market, the product, the sales team, the budget
Keep running the same plays that aren’t working
Ask for a promotion while simultaneously asking to lower their targets
Confuse activity with impact
I’ve seen both. The difference is stark.
But What If You ARE Performing?
Now, the harder scenario: You’re actually crushing it. Numbers are up. You’re already operating at the next level. You’ve checked all the boxes.
And your company still can’t promote you.
Maybe there’s someone already in the role above you who isn’t going anywhere. Maybe the operating margins are too thin. Maybe there was a hiring freeze right before your review cycle.
This is when you have to make a choice: stay or leave.
And here’s the part that’s going to sting a bit: companies don’t pay for loyalty.
I’m not saying they should—I’m saying they don’t. Vivian Tu puts it perfectly: “The biggest raises you’re going to get in your career are when you switch companies.”
When I left Campaign Monitor to join Chili Piper, I got a 71% comp increase.
SEVENTY-ONE PERCENT. That’s insane.
Not because Campaign Monitor undervalued me, but because that’s how the market works. Your current company knows what they’re paying you. The new company has to compete for you.
If you’re performing at the next level but can’t get promoted, it’s time to test the market. Not out of spite, not to prove a point—just because it’s the strategic move for your career.
Some signals it might be time to move on:
You’ve been told “not this review cycle” for 2+ cycles
The company is contracting or laying people off
You’ve outgrown the scope of what’s possible in your current role
You’ve asked what it would take to get promoted and got vague answers
Your manager left and you don’t have a champion anymore
Some signals to stay and keep building:
You’re learning a ton and have clear growth runway
You have a manager who’s actively invested in your development
The company is growing and creating new roles
You’ve gotten specific, achievable goals for promotion
You’re building skills or experience you won’t get elsewhere
Only you can decide which situation you’re in. But be honest with yourself.
Taking Ownership of Your Career (Because No One Else Will)
The real talk: your professional development is YOUR job, not your company’s.
Sure, good companies invest in their people. They should. But you can’t wait around for them to do it.
I spent the first few years of my career waiting for someone to tell me what to learn next. Then I realized nobody was coming. So I started:
Building my own curriculum:
Subscribed to newsletters that stretched my thinking (shout out to the marketing communities keeping me sharp)
Found podcasts that actually taught me something (not just interview shows, but tactical breakdowns)
Took courses that gave me hands-on experience with new tools and frameworks
Joined communities where people were solving problems I hadn’t encountered yet
Seeking out hard projects:
Volunteered for the stuff no one else wanted to do (0-1 builds, system overhauls, messy migrations)
Asked to shadow people in roles I wanted to understand better
Offered to help other departments with their marketing challenges
Creating my own opportunities:
Started documenting my frameworks and sharing them (which eventually became the backing for DemandLoops)
Built relationships with people outside my company who could challenge my thinking
Ran experiments on the side to test ideas I couldn’t try at work
The best career insurance you have is being so good at what you do that you have options. That doesn’t happen by accident.
What Actually Gets You Promoted
Based on my experience going from coordinator to VP, and managing people through their own progressions, here’s what actually moves the needle:
1. Solve problems your boss has
Not the problems you think they should have. The actual problems keeping them up at night.
When I was a coordinator, I noticed our marketing ops were a mess. So I built a documentation system and process flows—not because anyone asked me to, but because I saw my boss struggling with it. That got me noticed.
2. Make your impact impossible to ignore
This isn’t about self-promotion (though that helps). It’s about making sure your wins are visible and measurable.
Own your metrics. Report on them consistently. Tie them to business outcomes. Make it easy for your boss to advocate for you.
3. Build cross-functional relationships
Promotions often require buy-in from people outside your immediate team. If the sales leader, product lead, or CEO doesn’t know who you are or what you do, you’re at a disadvantage.
Show up in other people’s meetings. Offer to help with their initiatives. Build a reputation that extends beyond your manager.
4. Get comfortable being uncomfortable
Every promotion I’ve gotten came after a period where I was doing work that scared me. Work I wasn’t sure I could pull off.
If you’re entirely comfortable in your role, you’re probably not pushing hard enough.
5. Ask for feedback (and actually use it)
Not in your annual review. Regularly. From your manager, from peers, from cross-functional partners.
Then—and this is the important part—actually do something with it. Come back three months later with examples of how you’ve improved.
When To Have The Conversation
If you’re reading this thinking “okay, but I AM doing all of this,” then it’s time to have a direct conversation with your manager.
Not a “when will I get promoted” conversation. A “what specifically needs to happen for me to get promoted” conversation.
The questions to ask:
What are the gaps between my current performance and the next level?
What specific outcomes would demonstrate I’m ready?
What’s the timeline for this happening?
What’s the approval process? Who needs to be convinced?
If you get vague answers, red flag. If you get specific, measurable goals, you have a path. Then execute on those goals and check back in regularly. Don’t wait for the next review cycle.
Promotions are earned, not given. And sometimes, even when you’ve earned them, you don’t get them.
That sucks, but it’s the reality of working at startups where budgets are tight, roles are undefined, and companies are figuring it out as they go.
Your job is to control what you can control:
Perform at the level you want to be at
Make your impact visible
Build relationships that matter
Invest in your own development
Know when it’s time to move on
The good news? If you do all of this, you’ll have options. Whether that’s a promotion at your current company or a better opportunity somewhere else.
But you have to do the work first.
See ya next week,
Kaylee ✌
Some resources that helped me:
Lenny’s Podcast (for product-adjacent thinking)
Elena Verna’s growth frameworks
Tactical podcasts like Marketing Against the Grain
Taking courses on Maven in areas I wanted to grow
And even earlier this year I enrolled in GTM Engineering School