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Transitioning from a Large Company to a Startup

Big move? Learn how to successfully make your transition from a large sales org to a startup.

Much of this Duck Duck Go immortalizes the idea of moving to a startup but often wonders what it takes to be successful at one. I have been entrenched in a new role as a Sales Director at a Series A (now series B) startup, and quickly learned that the startup environment is vastly different from the sales world at an F500 monster.

So, I've decided to create your Guide to Making a Successful Transition from a Massive Sales Org to a Startup Sales.


Pressure Makes Diamonds

At a startup, your impact matters and the deals you close have a material impact on the bottom line of the company. The sales processes you put in place will help the entire org scale if they are sound.

In a sales org of 100+ people, you have an impact...but not really. If you don't hit your number, it affects your paycheck but that's about it. If you miss your number at a startup, it inhibits the entire company's growth. Be ready to handle that pressure. If you don't like the idea of having the organization's success riding on you and your team, don't go to a startup.

Be ready to build

In order to win in this environment, focus on building a sound and repeatable sales process. If you are the first AE, talk to salespeople that have been the first AE at other similar companies, understand their process, and build your foundation off of that. If you are not the first AE, go to the most successful AE on the team and learn every aspect of their sales process. Once you have that in place, don't be afraid to tweak things to be more effective.

Expect to Train Yourself

Building on this idea, expect to train yourself. Your startup doesn't have time to build out a months-long formal training to onboard you. I got 3 days of training and was told to get after it with my team. So how did I get up to speed? I got my hands dirty really quickly. After going through the surface-level training, I dove into all of the recorded calls I could get my hands on. We use Gong, so I listened to every demo our AEs and SDRs had run over the past 3 months. I learned quickly what worked and what didn't.

After that, it's time to rip the band-aid off. In my experience, there are 2 new-hire AE’s: the first is really hesitant and thinks they need to shadow just “one more call” before taking the reins. The other is ready after shadowing just a couple. Be the second AE. You were hired to sell so get your hands dirty. The only way you are going to get better is by getting reps, making mistakes, getting feedback from your manager, and implementing it. Don't wait. Start selling.

Get Comfortable with Not Knowing

Once you start selling you are going to have questions, one thing you need to understand about startups is that no one really knows what they are doing. Asking questions is good but don't expect to get concrete answers often. When that happens, trust your gut, document what you do, test, and be ready to make changes based on results.

If you truly have no idea how to handle a certain situation or solve a problem, go talk to someone outside of your business that has been through this. I promise you that you are not the first AE/Manager/Director/VP of Sales to face this problem. A playbook already exists so go talk to someone who has been there before, how they handled the situation, and how you can apply it to whatever you are dealing with.

Conclusion

Startups move at blazing speed. Meaning if you have an idea, it can (and often will) get implemented quickly. So, if you notice an opportunity to improve efficiency or effectiveness, speak up.

I give this advice with 1 caveat, however: have sound reasoning and backing for your recommendation. Don't fire from the hip. No one can afford a huge mistake because you were operating on a hunch. If you have sound reasoning though, don't hold back. No one cares about your tenure, they care about growing customers, growing revenue, and making money. You're at a startup now, it's time to speak up.

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