How to join a startup and succeed

Startup jobs are not like other jobs

It’s the beginning of the new year, and that means that all across the startup world there are thousands of new employees eagerly beginning their startup experience. As a two time startup employee, I thought I would take this opportunity to share my guide to joining and succeeding at a startup.

If you haven’t already read my post on what to do BEFORE you join a startup, and how to find a good startup to work for, I suggest you start there.

Consider this my guide for how you should go about joining a startup, after you have selected the right one.

Shut up and listen for the first month or so

I hope this doesn’t come across as too harsh, but the most important thing a new startup employee can do for the first month is to SHUT UP AND LISTEN. If I had a nickel for every 15 year veteran who came into my company from Salesforce or AWS or Oracle who sat down on their first day and started spouting ideas and contributing “value”, I wouldn’t have to do this shit anymore.

The truth is that no one can contribute value, particularly in a startup, before they understand how things work, what has been done successfully already, and what hasn’t worked in the past.

Instead of trying to add value, ask questions. Listen deeply to the answers, without trying to think of a cunning response that will make you seem smart. Make notes about the things that are difficult and causing friction. Empathize with your co-workers! The startup grind is really, really hard sometimes, and the best way you can do to get in with your new crew is to listen to what they have done and built so far, and the challenges they have faced to get there. Nod and make nice noises.

Now, I am not advocating that you don’t do anything in your first month… that would be suicide. All I am saying is that you shouldn’t assume you can provide any answers of value before you understand what’s going on. The more senior you are, the longer you will have to listen to make informed decisions (because your decisions span more of the company).

As you are listening, be sure to take notes for later. What is tough? What could be improved? Where can you add value in the future? Don’t try to improve or add value yet, just think about it. Refine. Ponder.

But also, work…

Focus on completing tasks, not establishing plans

You might have thought from my first point that the best course of action at a startup is to just sit back, take it all in, and learn. NO! Your new team is probably short-staffed, and now they have to train your newbie ass, too! I’m sure you are awesome, or they wouldn’t have hired you, but that doesn’t mean that you aren’t a pain for a little while as you are being trained.

The best thing that you can do is take some of the work off of your team. Even if you aren’t trained up, this isn’t hard to do. As you learn and listen, look for opportunities to take on rudimentary or frustrating tasks. Are you in sales? Go pretend you are a BDR for a while and research companies to prospect, or make some basic entry level calls with a call script. Marketing? Monitor the social channels, pack boxes for the field marketing team, clean out the marketing closet, clean up a slide deck, interview a customer. Engineering? Well, I don’t know, but my guess is that there has to be some kind of rudimentary engineering work that no one wants to do - go find it and take care of it!

There is nothing more annoying than having a new employee come in and announce (after a month of being on board) that they have a plan! Who cares. This is a startup, show me what you have completed, and then you will get a gold star.

I should note that this advice extends alllll the way up the food chain. I am relatively senior-ish at this point (Sr. Director), and the first thing I did in my new job was clean up the (very dirty, very cluttered) office. My new team saw that I was willing to get my hands dirty, and I established my credibility with them via action. I proved that I was devoted to the team, and right there with them in their day to day startup struggle. Another important part of this: I meant it. I wanted to do it because I LIKE them. At startups, people matter, so it’s important that you are motivated by helping people.

Plans are important, and they DO need to be made, but that’s something that should be done over time, collaboratively with the team. Maybe at an offsite. It’s much more crucial to complete a task than to plan in the first couple months.

Provide value, don’t suggest it

If this is your first job at a startup, then it can be a little jarring coming from a big company. In bigger companies, ideas are much more powerful than actual work. I mean, sure, someone needs to do the work at the end of the day, but it’ll probably get farmed out to contractors, or rolled down the hill to more junior staff.

At a startup, ideas are also VERY important, but only when combined with execution.

I’ll give you an example. I am in marketing, and one of the first things I noticed (when I was listening in my first two months) was that the sales team didn’t have a good way to find customer stories that were relevant to specific prospects. In other words, how do I find a slide deck explaining what we have done for customers in retail?

I discovered this because my boss had suggested I clean up all of the customer example slide decks that were floating around in various powerpoint and design formats. As I collected all of the decks from different members of the sales team, I heard 2-3 people complain that they wanted to have a better way to find other pertinent examples they didn’t know about.

Now, if I were at a big company, I would have gone to my boss and pointed out that we didn’t have a good way of organizing the slide decks, and that we should make a repository and index. That idea would probably get me some cred, and then someone would do the work to make it happen.

At a startup, pointing out a problem, or suggesting a better process is pointless. There are a thousand things missing. There are so many processes that can be improved. Noticing the problem is important and valuable, but only 1/10th as valuable as coming with a SOLUTION. In fact, it can often be seen as very condescending for new startup employees to say “At Oracle, we had a xyz that did 123 and solved this problem perfectly.” The insinuation being: this problem is easy to solve, how come you guys haven’t figured it out yet? Well, this isn’t Oracle. We don’t have that yet because we’ve been solving 100 other more difficult and important problems. We know what needs to happen, we just haven’t gotten around to it.

So, instead of pointing out the issue with the slide decks, I went out on my own and created a comprehensive list of every customer example with all of the different facets of their story, from industry to department, use case, and even the competitor we took out at that company. I put that up on our Wiki, then linked to every one of the newly cleansed and sparkly decks that I had also fixed.

In my second month on the job, everyone on the sales team knew my name, knew I was the guy to go to for customer references, and mentally catalogued me as someone that GETS SHIT DONE. If I had merely suggested the idea, it probably would never have gotten done, with no positive affect on my career.

Startups are hard to join but rewarding

Working at startups is tough, but at the end of the day it’s actually much simpler than big companies. There’s less politics, and more direct conversation. Take advantage of that to deeply understand your new company, find out what they need, and then go and solve the problem. Don’t spend hours on plans. Don’t suggest or point out what needs to be fixed. Don’t tell everyone what you did at your old company.

Go in, listen, find a problem, and fix it. That’s the secret to startup success.