How to get promoted at a startup

I went from a nameless, entry-level associate, stapling papers in a windowless room, to a CFO at a Series C startup - in exactly nine years. Looking back at it, I don’t think I got everything right, and I probably pissed off a handful of people along the way. But right, wrong, or indifferent, if you’re going for speed, here’s the playbook on how to get promoted at a startup.

TL;DR:

Previous to my startup endeavors I worked at a PE firm, where my excel skills were maybe a B+ (OK, a C+ plus) compared to my co workers. I was a serviceable (and perhaps overpaid) role player. All hustle and tenacity, but probably undersized for the role, and punching above my weight. I was the Matthew Dellavedova of Leveraged Buyouts.

But this was me, same excel skills, on day 2 at my first startup, spinning up our quota deployment model:

Startups produce innovative products that solve for a customer need in a hyper-specific way. People at startups need to do the same thing for the org.

I took my excel skills, which were forged in the fire of Discounted Cash Flow models and Net Income to EBITDA bridges, and applied them to marketing pipeline forecasts and ARR waterfalls.

I created my own unique SKU within the startup, which got me into projects that I didn’t even fully understand yet, just because they needed someone to build a forecast (WTF is a data center build out?)…which got me interacting with execs very early on (you want me to give that same presentation to your direct reports?), which got me into meetings I wasn’t ready to be in (what date is the board meeting?).

And it all started with selling a SKU that others didn’t. Building your own SKU creates a virtuous cycle, presenting more and more opportunities to step it up.

This is crucial to identify at the outset. Figure out who your role is most aligned to serve within the org, and be relentless in doing whatever you can to make their lives easier. Every role has ONE key customer. And everything you do must ultimately put their needs first.

This goes back to another startup adage:

It’s why startups focus on one segment, or one persona, and hammer it home before moving onto another customer base.

In some roles, like as a Sales Ops Manager, my main customer was the VP of Strategy & Operations. And her main customer was the CEO. My job, therefore, was to arm her with whatever metrics she needed to feel prepared to wow her main customer, the CEO.

In some roles, like as a Director of FP&A, my main customer was the CFO. 100% of my quarter was, in some way / shape / form, all leading to his presentation at the board meeting. That was the Super Bowl. Full stop.

And sometimes, like as a Chief of Staff, it was a straight-line to serving the CEO. I researched every single person he was going to meet with and had a bio on his desk, in his suitcase, or ready to verbally explain while standing at adjoining urinals. I virtually stalked every person he met with, and took it one step further to attempt to predict what their underlying asks would be.

In every one of these roles I filtered all work through the lens of “does this serve my customer”.

Did the CMO ask me to recut the marketing program budget by geography for a meeting she has later this week? That’s fine, but it will never come at the expense of the revenue analysis I needed to do for the CFO.

Please note that this strategy does present a level of platform risk. I’ve seen it first hand.

A CEO I was serving unexpectedly left the company, and a very smart person on my team remarked:

I had no idea what he was talking about.

But he instantly realized that for the last two years he and his team had left a wake of bodies in their path as they kicked down doors for the CEO. Now, to keep their (well paying) jobs, they had to go back into the “market” and win the business of the new CEO or executive stakeholder.

We’ve all seen 2x2 slides like this, where the company pitching somehow magically appears in the top right hand corner every time.

How do they get themselves to the PowerPoint promised land? By carefully choosing the vectors they compete on.

You need to do the same.

For me, I was the guy who could tell a story with numbers. Now, I wasn’t the best story teller - there were people in marketing who could weave together an amazing narrative, supported by our underlying branding. And I wasn’t the best with numbers - there were people in the data and analytics group who could build a model that analyzed customer cohorts while frying an egg.

But I was in the ~90th percentile in both.

I stacked two talents - storytelling and modeling - and planted my flag. That meant you could come to one individual who could do a pretty kickass job at both, avoiding the hustle and bustle of needing to ask two managers to ask two sets of teams to cook up something, and then combine their work into one deliverable. I was a one stop shop.

What hours do you work? Do you check your email after 7PM? Do you respond to people on weekends? How fast can people expect you to turn around work? Do you reply to emails faster than your colleagues, with thoughtful responses?

I worked for a CEO who liked to get work done on Sundays between 2 and 6 PM. I realized this after just a few weeks on the job. So I made the commitment to be available at those times, even though I hated it.

It caused a lot of stress, anxiety, and ruined a lot of mindless NFL football.

People will tell you this stuff doesn’t actually matter in your career. They’ll say that working harder and later than others isn’t a real way to get ahead.

It’s not the end all be all; true. But it is part of a larger mosaic to getting promoted. And if the phone rings and you pick up, people remember that.

Sure, the people who don’t pick up might be happier.

But they didn’t get promoted fast.

What’s better than a 42 year old, intelligent VP of FP&A with +15 years of experience, super comfortable in their role, running the same, predictable process each quarter, who delegates 100% of the work across a team of eight people, and rarely needs to crack open an excel workbook?

A hungry, FP&A Manager, who’s 60% of the price, 85% of the knowledge, eager to prove themself, and will stay up until 2AM aligning-left all the shapes in a PowerPoint presentation themselves.

Being able to “span” multiple price points in the org is a real thing. As a Manager I was willing to sweep the floors, water the plants, and make sure the headers in a presentation didn’t jump from slide to slide. I was also capable of building an M&A business case that would determine a multi million dollar outcome. My older colleagues were also eager to do the latter, but much less willing to do the former.

Make your deliverables “look and feel” a specific way. This sounds ridiculous, but if someone receives a PowerPoint slide that you made, or an excel model you built, they should know it came from you.

People share documents within the org, and having a bread crumb that links back to you is sneaky powerful. If you do it right, it’s like having your personal brand tentacles touching all parts of the org (ew, that sounds weird). And even if people try to “re-purpose” your work, your co workers will instantly know who it came from. (Nice try, Jim).

At one company I was notorious for a very specific box and bullets slide with green bullet points. By the end of the year, the buggers permeated presentations from Marketing to Engineering.

Half the battle in life is just showing up. The other half is recognizing when it’s a big moment, and knowing you need to really show up.

I’ve worked with a lot of people who know they are meeting with the CEO in the morning, and don’t do anything special to prepare. They treat it like every other meeting they have that week.

But think about it - let’s say the average CEO has 10 thirty-minute meetings per day. That’s 50 blocks per week. And say you are presenting in one of those 50 blocks. What do you do to make sure your block is in the top 5% of blocks the CEO had that week? How do you remain memorable? How do you present something more valuable than the rest?

Here’s how - you prepare for it, you script it, you even practice the pauses in between sentences. You may even be so lame to script out a joke. Cringe? Absolutely. But IDGAF.

Yes, it’s only one 30 minute block. Big whoop. But kicking ass in that one 30 minute block opens the door to getting invited to two thirty-minute blocks per week, which opens the door to three thirty-minute blocks per week, and eventually you are in 10% of the CEO’s blocks, which… you guessed it - helps you get promoted.

Identify what your boss hates the most. Maybe it’s managing share grants in Carta, which are tedious and a grind to pump out. Take those off their plate.

Also, identify what your boss feels the most insecure about. Maybe she constantly forgets people’s names whom she’s already met. Become a human rolodex.

Both are easy routes to ingratiate yourself.

Take that “thing” they hate and make it disappear. Then, when you go on vacation someday, or get sick, they’ll stumble upon that dreaded thing of the past again, and remember how much better you’ve made their life.

Doing these types of things makes you their comfort blanket. And the comfort blanket gets invited to important meetings and taken on important trips.

Does your boss like hunting? Nice, you once heard Joe Rogan say something about a cross bow. Does your boss like cars? That’s awesome, your grandfather once restored a ‘63 (or was it a ‘66?) Mustang. Is the VP of your department a “foodie” (yuck)? Congrats! You are watching Jiro Dreams of Sushi this weekend.

I’m not saying lie - people sniff that out. What I’m saying is you need to have something relatable to say, because it shows you are actively listening and engaging in someone else’s interests. It shows you are going the extra mile to forge a connection. People like to talk about hobbies they identify with, because it’s just that - part of their identity.

What’s your go to joke if you are taking clients out to dinner and trying to have a good time? What’s your go to story? Mine was about me and my wife getting hit by a Cat 5 Hurricane on vacation, the day after I proposed, and getting airlifted out by the US military (all true). I’ve told the story at least ten times. And I can stretch it out over the entire length of appetizers at Del Friscos.

Be memorable and someone people want to bring out to dinner.

This may be the hardest one to be honest with yourself on - sometimes the pond gets too crowded with people who all do the same thing, and you have to pick up your rod and fish elsewhere.

The ideal scenario is you enter as a big fish in a small pond, and that pond keeps growing due to the success of the business. But eventually you need to be real with yourself and look around to assess if the pond now has multiple people competing on your same vectors. That’s just what happens as a company gets bigger and people’s roles become more specific.

It’s happened to me. And it sucks in the moment, but once you embrace it, you can go downstream again, with an updated playbook, take on a bigger role, and climb a new ladder.

It’s VERY difficult to go from the guy behind the guy behind the guy to THE guy all at the same company. There can only be one CPO at a company. Does yours look like they are leaving any time soon? Be real about it.

Plus, you’ll probably get a big pay bump in the process that beats the breaks off your current company’s inflationary level raise. New employees get PAID. And they get new equity grants. Existing employees get mehhh raises.

Seriously - staying you may get a raise of 5% to max 10% per year. But when you leave you can usually achieve 25% or more if you take on a larger role.

Is this right? IDK. But demz the rules of the road. I didn’t make ‘em. And it’s easier to get promoted if you are applying your skills in a place where they are in in high demand. And that will usually call for switching ponds every few years.

Do all the things above, and then be blatantly obvious about what you want. Your boss should know that it is your goal to move up. Make it a point to check in as to if you are knocking off whatever items they’ve identified for you to accomplish to get there. Yes, it’s uncomfortable, but we aren’t playing this great game we call “work” for “fun”.

You want to take all objections off the table.

And you want to leave no doubt of your ambitions.

I harken back to the greatest movie of the 21st century: