How to get promoted at a startup

A 12 step playbook on how to climb the ladder

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:

1. Craft your own SKU

2. Know your customer

3. Define the field you compete on

4. Set your SLAs

5. Compete on pricing, and value

6. Spend time on your packaging

7. Know the moment

8. Plug the gap

9. Be interested

10. Be interesting

11. Swim in the right pond

12. Ask for it

1. Craft your own SKU

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.

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2. Know your customer

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:

If you try to make everyone happy, you make no one happy.

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:

“Shit, we just lost our number one customer.”

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.

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3. Define the field you compete on

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.