TennisandSales

Head Of Sales

Leaving Enterprise Sales

So if you have followed my drama ive been sharing you know I am leaving my current gig, to go BACK to the company I was at prior.

(this is a terrible idea for most ppl/ situations but i do feel like my circumstance is pretty unique but maybe thats another post)

This biggest change will be that I wont be selling large, complicated ENT deals anymore.

I will be focusing on shorter more Mid-market deals, and even free sign ups since the company has a super strong PLG motion.

The main reason for joining is because of the product, team, and the unique position I will have to develop as a sales person, but also more of a leader.

But I did have to do a TON of soul searching about will i be happy to no longer be in ENT sales.

We talk a lot about what it takes to get INTO ENT sales, but has anyone else LEFT enterprise to go back to mid market sales?

🚀 Career Goals

35 comments

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braintank

Politicker

Enterprise Account Executive

I'll be curious to see if anyone else has made the journey. I've thought about it during the months between enterprise deals...

ZVRK

Politicker

Enterprise Account Executive

Yes, those are the hardest… some of my deals took 12+ months to close, coming from a mid market role previously, this looked crazy.. so, I understand why you’d make a decision like that.

Sunbunny31

Politicker

Sr Sales Executive 🐰

No, but I'm interested in following your journey to see if you enjoy the transition. I'm like braintank - definitely considered it while going through enterprise procurement.

TennisandSales

Politicker

Head Of Sales

oh god procurement is the WORST part of sales. when all my deals were in procurement it was soooo draining. no fun at all

Sunbunny31

Politicker

Sr Sales Executive 🐰

Pretty sure most of my customers aren't fond of their own procurement processes either.

antiASKHOLE

Tycoon

Bravado's Resident Asshole

I'd like to think the WR Group Therapy has helped me with similar situations. I'm glad we could be the same for you.

poweredbycaffeine

WR Lieutenant

☕️

I just left the startup I joined post acquisition of my previous one…to join the company that acquired us. I left a senior leadership role to be an IC and holy shit am I happier. I can focus on building cool shit and not be blamed for something breaking that I didn’t own in the first place. The reduction in emotional output is the biggest benefit in my package…and I love the people I used to work with and most stayed post acquisition.

CuriousFox

WR Officer

🦊

Heh...package...

detectivegibbles

Politicker

Sales Director

I'm in the process of leaving to go back to previous company as well Tennis.

You could say my previous role was enterprise (med device) where deals could take anywhere from 2 months to 1-3 years depending on the facility.

My current role has been a nightmare since day 1. I've watched the managing director curse out vendors, berate employees, etc.

Keep us posted!

TennisandSales

Politicker

Head Of Sales

ughh yeah that sounds terrible!

FinanceEngineer

Politicker

Sr Director, sales and partnerships

I think you took the easy out. You could stay in ENT, but probably needed a new company either way.

TennisandSales

Politicker

Head Of Sales

ill push back on the "easy" part. it would have been SO much easier to stay when I am. comp plan is crazy good and the pressure is almost zero.

im stepping into a role where its just me and there will for sure be more pressure.

FinanceEngineer

Politicker

Sr Director, sales and partnerships

So you are giving up a role to take more or less money? That’s key here. It seems like everything else is kind of aligned

TennisandSales

Politicker

Head Of Sales

The OTE is slightly lower but the guaranteed is higher.

Diablo

Politicker

Sr. AE

I haven’t gone other way but I am sure you have weighted a lot of things before making this move. All the best and yes many more stories to come from you in te future 🎾

Pachacuti

Politicker

They call me Daddy, Sales Daddy

you gotta do you man - good luck in the new endeavor.

StringerBell

Politicker

Account Executive

Currently in ENT and wonder that sometimes. However, I've only been in ENT since July 2022 so basically the worst 8 months in the last while for tech.

Gyro25

Notorious Answer

Account Executive

I've been reading more about PLG sales/products. In essence, does a PLG-led strategy reduce the need for more outbound/inbound motions or is it mainly a strategy reserved for companies with high PMF? Curious to know.

TennisandSales

Politicker

Head Of Sales

The way i see it, it’s a shift based on how companies want to buy. They want to be more hands on without a bunch of hoops to jump through. They also want as little risk as possible. Why sign. $250k contract and risk it not working, when you can sign up for free or pay for a few users and scale it out. Then make the big commitment when your ready.

It CAN lead to a lower reliance on outbound if done correctly.

CuriousFox

WR Officer

🦊

Oof I cannot even imagine. I love the thrill of the hunt and the tactical strategy with ENT.

Justatitle

Big Shot

Account Executive

I hated the more upmarket deals, takes months, there's less of them, and losing one that your work on for 6-9 months is a gigantic kick in the nads. MM or lower for the rest of my selling career

RandyLahey

Politicker

Account Executive

Would love to hear your thoughts @TennisandSalesas to what the main driving factor was to leave ENT sales?

TennisandSales

Politicker

Head Of Sales

so the main driver really has nothing to do with ENT sales vs Midmarket sales.

my move is all about joining a company that has a product that is going to explode, that I am "passionate" about, and that has a role for me where I can continue to develop as a sales person.

there are pros and cons which i can get into but the actual sales cycle is not the MAIN driver for me.

RandyLahey

Politicker

Account Executive

I couldn’t be happy for you! Just like my boy Daniil, crush this new gig!

punishedlad

Tycoon

Business Development Team Lead

Been out of the WR the last few days (super busy), but I'm glad to see how this has been progressing for you.
Remind me, were you getting burned out on the ENT side of things?

TennisandSales

Politicker

Head Of Sales

not really, its more about the opportunity that im going into and what Ill be able to do there from a career advancement opportunity rather than wanting to stay or leave ENT sales

kittychachas

Valued Contributor

VP/Director of Sales

Was just thinking about this the other day. Ent sales is such a drag. Barely saw above my base last year but this year I’m on pace to clear my OTE.

It’s for sure a soul suck waiting with all the risk and uncertainty involved with these deals.

TennisandSales

Politicker

Head Of Sales

yep thats the downside for sure. but those PHAT checks are hard to forget about 😂

Project Manager - Disaster Recovery and Resilience

I left ENT sales back in 2015, after having done it for several years. Was in a sales capacity for a couple startups, that crashed and burned. Been recently interviewing for SMB/mid-market sales. Looks promising, haven't gotten the offer yet, but it looks promising.

ChickenWings

Opinionated

Tom Callahan's Son

Very happy in Mid Market vs ENT at my current company.

Many of the mid market opportunities we sell to generate more rev than ENT. Usage based

Groundskeep

Personal Narrative

Sales Development Representative

Dig deep while your on the tennis courts!!

Maximas

Tycoon

Senior Sales Executive

No tbh, FYI the way you're making your threads is really interesting even for the same topic, keep it up❤️

Juancallclose

Catalyst

Director

Congrats man. Good luck

Juancallclose

Catalyst

Director

We all chase that ent AE role and then when we get here we're like WTF is this?

TennisandSales

Politicker

Head Of Sales

hahaha well in to be fair, not all ENT roles are created equally.

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TennisandSales

Leaving Enterprise Sales

35 comments

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