SMB to Enterprise sales?

I have worked with small businesses for my first 4 years in sales. Started out in commercial insurance. Now working in SMB tech sales.

Any advice on breaking into enterprise sales?

I have always been customer facing, managing the sales cycle from cold call to close myself. Enterprise sales is a whole different beast.

Would it make sense to dip back into an enterprise SDR role? Or do you have any strong advice for breaking into the enterprise world?

☁️ Software Tech

7 comments

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CoorsKing

WR Officer

Retired King of the Coors Knights

Talk to whoever leads your enterprise sales team at your company and ask them what are some characteristics they look for in hires, what makes their best reps successful, and advice.

Then, pick one of the reps and have them mentor you. Work on any gaps between your current skill set and what you learn from the above.

Enterprise is very strategic and very much a relationship based sell.

braintank

Politicker

Enterprise Account Executive

Coors advice is spot on. Ask, shadow, learn.

It took me about a decade to move from SDR-> SMB -> Mid -> Enterprise. The keys were consistency, continuous improvement, and communication.

I was consistently a top performer, so my name was brought up when promotions were available and I had the numbers to back it up.

I went out of my way to become a product and domain expert as I moved up. This helps b/c as @CoorsKing said, ENT is more strategic. You have to be able to adapt from selling based on features to selling based on business outcomes and/or risk reductions. Thinking less like a rep and more like a CFO.

Lastly communication. I was never shy to "order what I want". Meaning, I told my managers that I wanted a promotion and asked what I'd need to do to get there. No one can read your mind.

Finally -- under NO circumstance -- should you demote yourself back to SDR. You're shooting yourself in the foot by doing that.

Sunbunny31

Politicker

Sr Sales Executive 🐰

Agreed on all fronts. It's a step by step process, and you prove yourself along the way.

bandabanda

Tycoon

Senior AE Mid Market

Brain dropping the fire yet again. Keeping this one for myself too, thank you sir

Diablo

Politicker

Sr. AE

These are the best advices I would say. Start nurturing yourself as much as possible - might want to explore Midmarket if your skill sets don't fit enterprise level. Doesn't make sense to even think about getting into an SDR role

Pachacuti

Politicker

They call me Daddy, Sales Daddy

Do you have a ceiling on the accounts you can call on? If not, swing for the bigger account if you have the bandwidth. If you do have a ceiling, call on the largest you can.
There is no special sauce to “enterprise” account, they just take (much) longer to close.

TennisandSales

Politicker

Head Of Sales

Enterprise sales is like getting into Saas no one will let you do it unless you have done it before.

So if you have an Enterprise team at your current gig that is the best place to try and break into it.

But you also have to decide if you will like ENT sales. The longer sales cycles the multiple meetings, selling internally and navigating all the bullshit is not always fun.

Some people will be much happier in a more fast paced environment. and thats cool! Lots of money to be made there.

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