The War Room

Comprehensive Guide for Moving to a Startup

Badger Gang,

UrAss is back to drop some knowledge on making the move from a massive sales org to a startup.

I see some form of this question all the time in here "Im thinking about moving from my company and going to a startup, what should I expect". If this is something you find yourself asking, follow along.

For context, I am moving from a pretty well known public company with about 2000 sales people. I was managing a mid market team of 12 and we sold a SaaS product. I moved to a 70 person company with a 10 person sales team and am now the director of sales. Ill give you the 5 things that have stood out to me most in making this change.

1) Pressure makes diamonds - in a massive org you really only matter to yourself, your goals, your paycheck etc. You only have minimal impact on the business.

In the startup world you MATTER. The revenue you close can make or break the company (especially really early stage startups - dont get me started on how we define a startup, different convo). You have real implications on the success of the business. I love this pressure and thrive knowing the impact I can make, BUT not everyone is cut out that way. If you dont want that pressure, dont move to a startup.

2) Expect to train yourself - I have had your run of the mill onboarding and training experience in my first week but the only way I will succeed in leading this team is by getting my hands dirty, figuring out the process on my own and asking those that are winning. The process isnt fully baked and wont be spoon fed to me. Which leads me to my next thought...

3) Have your own process or be ready to build - massive orgs know what it takes to win, as an AE or manager you are purely there to execute the plan that is laid out. If you do, you close a ton and make a bunch of money. At a startup there is no process yet, its your job to define it.

I tend to believe there are 2 types of salespeople in this world, those that create the process and want to figure out how to win, and those that are fantastic at executing the plan that others have laid out. Both are great, just different and if you are the latter you will struggle at a startup.

4) Get comfortable with no one knowing you - One major (dis)advantage of a massive firm is that your prospects know you, you dont need to educate them on who you are and what you do. You just need to show them why you are better than what they currently do.

At a startup no one knows who the fuck you are and what you do yet, so be ready to break down that wall and educate your prospects.

5) Fast paced is an understatement - Everything moves quick, you need something done and its turned around in like 24 hours. Product and engineering actually listen to you and build what you ask for, and it happens quickly. If you are frustrated with red tape and bullshit slowing you down, startup life might be for you.

If you're still with me, I appreciate you. Hope this helps anyone thinking about making the jump.

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