How To Rise Through The Startup Ranks

The absolute best way to learn how to navigate the startup world is to work with or for someone who is better than you. Preferably much better. And it doesn’t matter how many times you’ve been a success or a failure. You should never stop learning.

I’ve followed this pattern throughout my career: Work with someone better than me, then go start my own thing, repeat. Right now I’m coming off selling two companies and I landed working with someone who is way better than me. Even after 10 startups, I’m still learning.

I’ve also realized that it doesn’t matter if it’s our first startup experience or our eleventh, the skills we need to master to get from where we are to where we want to be, they don’t really change.

So here are those things we need to master to rise up through the startup ranks.

First: Make Money

The most obvious metric in startup is money, not in a greed way, but in a survival and growth way. Be responsible for that metric.

When our executive management meets each week to prioritize the list of features, projects, initiatives, and crises we need to tackle, the first question we ask is always the revenue question: How much money is involved?

Sure, the answer covers the important things, like customer experience, addressing new markets, staying ahead of the competition, and so on. But everything we do involves one or more of those things, so there’s always a dozen or more items deserving of the “top priority” designation. Something has to give, and the way we separate Priority 1 from Priority 1A is with revenue.

Here’s what we’re aiming for: Everyone at our company should be thinking about revenue. And the best of them do.

It doesn’t matter if we’re a company executive, a senior coder, or a low-level marketing associate, we’ve all got a hundred things to do and each one of them could be called top priority. The best people use the revenue question like muscle memory, allowing them to wade through a dozen things in a day without spinning out.

Second: Save Money

This is a tough skill for most entrepreneurs to get their brain around because saving money is not nearly as straightforward, or as sexy, as making money. But once a startup hits the growth phase, the quickest way to failure is failing to control burn. Even if our strategy is to raise money to unicorn levels, we need to have a plan for burn from the very beginning.

So just as our executive team is prioritizing the tasks that can expand our top line, we’re also prioritizing other tasks to expand our bottom line. That happens by shrinking all the costs. The most successful companies cut burn not by cutting resources, but by finding efficiencies.

And just as we want everyone in the company looking at revenue, we also want everyone in the company looking for efficiencies, anywhere they can find them.

Third: Don’t Wear a Lot Of Hats

I need to debunk a misplaced bit of conventional wisdom about entrepreneurs. After a certain point in the early phase of a startup, we don’t need to wear a lot of hats. In fact, once we bring aboard employees outside of the founding team, playing more than one role becomes extremely inefficient.

If we’re hired into sales, believe me, no one needs our opinions in engineering. If we’re in marketing, we don’t need to be out there closing deals. If we’re a coder, we shouldn’t be coming up with content ideas for blog posts.

I know this sounds counterintuitive to the traditional startup ethos of doing more with less, so let me just put the cliche another way:

Instead of wearing a lot of hats, we should wear one hat that we can wear in every situation.

What this means is we should know our core competency and how it relates to all the other touch points within the company, and we should know how the rest of the parts of the company impact our domain.

If we’re in sales, we should understand how the product is built in relation to how that defines our sales cycle. We should also be feeding back what we’re hearing from customers and potential customers in a way that isn’t noise.

If we’re in engineering, we should understand how our roadmap and release cycle impact the sales pipeline. We should also be listening to how our customers are consuming the product, and focusing our efforts on those features they find important.

Fourth: Be Less Hassle

A refined corporate organization spends roughly 50% of its time focused on customers, product, and revenue, and the other 50% of its time focused on the company itself. A corporate entity has that luxury.

In startup, this swings to 90% on the customers, product, and revenue and 10% on the company. This usually means shitty office space, minimum benefits, unsubsidized snacks and drinks, and less than premium equipment. Now, I don’t think a ton of startup employees complain about this, but it serves as an example for a higher level of discomfort.

With that near-laser focus on the product and customers, startups usually don’t even have the time to maintain more important resources like a central repository of company information, or a lot of internal training, or a wealth of product documentation.

In startup, every dollar spent taking care of the employee is two dollars not spent taking care of the customer.

The faster we can pick up on the leadership’s cues and start doing what they would do, or at least what we think they would do, the more valuable we become. We can make mistakes, as long as we can explain them. It’s rare you can go wrong with “I thought it was what you would do,” especially over “I didn’t know what to do.”

Fifth: Lead When It’s Not Expected

Every startup has Leadership and Ownership. Our startup probably has a neat little org chart, and our startup most definitely has options for shares of the company granted throughout the workforce.

But every startup also has lower case leadership and lower case ownership, and these belong to everyone, no matter where they are on the org chart or how many shares they hold.

We should never have a black box or waterfall or working-in-a-vacuum mentality. When I ask someone to do something, I’m not asking them to complete a task, I’m asking the to own the task, lead on it, and figure out what needs to be done to integrate what they’re doing into the bigger picture.

I understand there are mundane tasks like administrative paperwork. I’m not saying every Friday fridge cleaning needs a kickoff and a post-mortem, but it’s true startup to go beyond the call of duty without wasting a ton of time getting there. That’s leadership and ownership.

Sixth: Bring New Ideas

At one point at one startup a few years back we discussed the idea of having an old-school anonymous suggestion box that would serve both the company and the product. Not a bad idea, but I shot it down because I ultimately thought it would make people circumvent the avenue of open communication for those same exact ideas. Instead, we reminded everyone at the next all-hands that there was no such thing as a stupid idea.

And there really is no such thing as a bad idea, but man, fear of suggesting something stupid gets drilled into our heads some time after childhood and it stays there for the rest of our lives.

Keep an open mind and an open mouth. Ultimately, the main difference between success in the corporate world and success in startup is that in startup, we’re not looking for individual contributors or team players, we’re looking for difference-makers.

Those difference makes will exist outside of the status quo, and learning to be one of them starts with thinking outside of the status quo.