The War Room

How did you transition from SMB to Enterprise AE roles?

I'm the first AE for the company I work for and I'm welcoming another AE in a couple days. My CEO wants me to get cracking at larger enterprise deals and I feel like there's a ton of stuff that's different between the two.

How did you transition from SMB to Enterprise? Which is better? What's the first couple of things I need to know getting into Enterprise sales?

I've done SMB mostly for the last 5 years or so and I love that velocity. I want to experience and learn this art too.

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WR Lieutenant
Head of Sales
The big differences are:

1) The pricing means more people need to say okay to make the purchase

2) The more people means competing interests both within the same department and from other departments involved

3) You cannot be the sole focus of the deal from your side. Multithread others within your company to strengthen momentum over longer sales cycles

4) You'll be responsible for keeping everyone honest to milestones. You need to use mutual decisions plans to collaborate with the buyer side

5) Larger deals with more people involved means greater complexity. Complexity is great way for deals to end up in status-quo, no decision. You're ability to be an elite enterprise rep will come from reducing complexity wherever you can

6) Enterprise deals balloon and blossom at the top. Your ability to connect and establish credibility with execs is what gives you leverage to charge premiums and avoid deals stalling. Get comfortable with that mindset.

7) Be comfortable with how legal, procurement, security, IT, etc. all work. You don't need to be the expert, but it's a bad look when you can't speak well to something like indemnification or SOC II compliance.

8) People don't want to look bad and be that person who made a shitty purchasing decision. A secret weapon of elite sales people is to survey the end users and give that feedback directly to the execs. You'd be surprised how much disconnect there is internally at large companies.

9) Sell with a mindset of crawl, walk, run. It's far more common in enterprise sales to land and expand than to close a massive deal all upfront. Make it clear to the buyer what comes first, and what's more long term.

10) The easiest thing to do is nothing. A willingness to change over longer sales cycles becomes paramount. Don't just think about ways to make the buyer's business better, make sure you're explaining how not changing is risky. What's the opportunity cost of doing things the old way?

11) Politics are real at big companies. Make sure you're speaking to people that shape the power dynamics. Don't ever forget that any purchase can be a power move within a company.
Mid-Market AE
How big is the jump. What do you consider SMB and what do you consider Enterprise?ย @Canyouseemyscreen?ย 
Account Executive
We're looking at going from 5-30 people sales teams to 100+ people sales teams.ย 
Mid-Market AE
Cool, I sell to a middle ground between that range. The major things I've seen are 1) drive of company. You're hitting a point where people can be middle management and are pretty apathetic to change 2) champions are more key here 3) more formalized buying process 4) if you self source, being a bit more targeted with outreach - your first thought is to break through noise of other sales people.

With smaller teams, they probably have some growth ambitions so they're more eager to make a name for themselves. As they grow is more about not messing up.ย 

Depending on what you sell, your actual DM is going to be further up the chain or need to get approval up the chain. They're also going to be a bit more removed from the pain points you solve.ย  So getting some champions is key

The buying process is going to be more formalized, approvals will need to happen and you'll have to loop more and more stakeholders in along the way and bring them up to speed. Video's are really good for that kind of stuff.ย 

For self sourcing,ย  don't get away from what's worked for you in the past. But, understand that you can likely do better research and target a bit more effectively. Also, you're selling into a lot of noise. So you need to stand out in their inbox, VM, etc.ย 
Director of Sales
Enterprise checks are way better BUT the work is more difficult. I chose the unpopular route of "job hopping" 3 jobs in 3 years but I was early 20s when I took my first AE role with a 100k base / 200k OTE. Beauty is that once you have quality ENT experience you are golden. ENT is selling to an organization, not an individual. You often have to build relationships in multiple groups and at different levels.ย 
Assistant to the Account Executive
I went from 5k deals and 2 weeks sales cycles to 1mill deals and 18 month cycles. Honestly I struggled at first because I wasn't getting quick wins. With SMB if I got 1 close a week I was struggling lol now I am in enterprise and getting 1 meeting a week is insanely good.ย 

My biggest recommendation is learn and learn. If you are the first enterprise AE there then reach out to people and learn from them. Whether that be a colleague who has enterprise experience or if you are reaching out on LinkedIn. Just learn. AND learn patience.ย 

I struggled with enterprise at first but now I really enjoy it. I am building relationships and partnerships. Learn to listen. My favorite part is knowing that the customer doesn't go right off the bat asking about pricing...that doesn't happen for a while in enterprise and I love that because I get to build a ton of value first.ย 

Best of luck to you! It's a grind but definitely a different grind.ย 
Enterprise AE Comp - SaaS Sales
SMB/MM AE --> Enterprise AE Transition?
Which SMB AE role would you take?