Dollar

Enterprise AE

Need advice : Go to a Big Company (Google/SFDC) or early stage startup [8+ years of Experience]

Hi Folks,

Looking for some advice here. I've worked in a couple of startups, seen them grow 200%, have been a successful Enterprise AE (200% achievement multiple years), led teams for a short while.

I'm at crossroads where I have multiple opportunities:

Go to a a smaller startup, less than $10M ARR right now, great team, management, product & PMF. Go in as Head of sales, built the global sales team and help them get into Enterprise. I def see this company reaching $50M ARR in 3-4 years.
Go to a big player like Salesforce/Google as Strat AE, learn how to sell multi-million dollar products, multiple products in one deal and grow my skills. Something I've never done or seen anyone closely do.

Both the paths are exciting, areas where I'll learn a lot. I'm contemplating whether I follow a traditional growth path to go in a bigger organisation, grow their, hone my skills and see where my future takes me ; OR, go to a smaller startup, go through the grind, learn building global teams on the job and gain that experience over the next few years.

In case it helps, I'm 29 years old, 9 years of selling experience, and all the opportunities above pay the same.

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23

36 comments

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ten7

WR Lieutenant

13

Enterprise AE

Dollar, I just went through pretty much the same thing. Start-up role vs. opp to work at DocuSign.

3 things weighed heavily on my decision: being able to sell in the way/style I wanted, flexibility with my work/family schedule and income potential.

I ended up picking the start-up. They were open enough with me to let me talk to all their sales team members BUT also their CSM team (gave me good insight into client base, potential, what clients were saying about using the tool, actual sales cycle timelines, etc.).

I got to see their SF dashboards to see what pipeline and churn were really like. Spoke with the VP about where I was in my life and my priorities and expectations around work/life balance, family obligations, etc. and that outlined that I needed flexibility in my work schedule and support with certain tools for my style of selling.

They said they wanted me and proved it by giving me everything I asked for (and then some). I felt valued right from the start.

I think if you set those expectations (how you want to sell, your strategies/style of work, availability, your vision for the team + culture, etc.) upfront, the start-up could be a great experience especially since it sounds like you'll be at the helm of driving the sales team and strategy forward.

At the Big Corp I was considering (great ppl, product and benefits) my feeling was that there was a lot more red tape, "colour within the lines" kind of approach with a slower style of selling compared to what I was used to. I felt personally I would get bored fast.

When it comes to benefits (I read some ppl mention well if you want to settle down/ have kids then big corp. is better) and I don't necessarily agree.

I'm a new parent and I can say that the start-up has great benefits and support for families. I think it all depends on the culture of the start-up vs. Big Corp. If you're thinking about this in the future, why not ask these questions to both teams to see what they offer so you have that info beforehand.

In the end -- I'd suggest considering these two questions:

1. Which role actually gets your excited? You want to make sure that you're waking up and looking forward to the work you're doing.

2. What feels right in your gut? Your gut will never steer you in the wrong direction.

Make your decision and then don't look back.

Sorry for the novel but hope some of this helps!

Good luck :)

Dollar

Executive

3

Enterprise AE

This is super helpful Ten7.

I went the same way. I've spoken to every senior level exec at the startup, their board members & current angel investors.
I know everything about their net ARR, net profit, money in bank and gameplan for series A raise. I've also spoken to one of their VC prospect who is pushing hard for a Series A here.

Thats why, I'm super confident on their revenue numbers and just how they are running the business.

I think the reason even why this startup is a contender in my head is because based off of every research/digging up/questioning I could do, I feel they are definitely the right mix of Exec team + Industry + Market tailwinds + Product/Vision + Current revenue ops.
I feel that strong combination is rare to come by.

ten7

WR Lieutenant

0

Enterprise AE

Awesome stuff Dollar, sounds like you've done your homework! Love the thoroughness approach...definitely share here when you make your decision :)

Good luck!

AustinOG

Executive

0

Acvount Executive

Sounds like you did lots of research but you never mentioned equity. You don’t make your money going to a start up. You make your money when you exit, but founders aren’t always good about spreading the wealth.

PartnerGuy

Good Citizen

6

VP Channel Sales

I honestly think it's where you are in life. Corporates come with huge pressure but far more easily manageable and can be quite comfortable if you're reasonably decent.

If you want to take a gamble at making serious money, make a name for yourself in a much higher 'titled' role then for sure go for the start up as I assume there's also stock options?

If you're about to settle down, have kids, get married etc I'd say a big corp.
If you're pretty chilled and up for losing a couple of years to work and build a team from the ground up for sure go for the start up.

Dollar

Executive

1

Enterprise AE

Yeah, there are def some good stock options. We are looking at 0.5% of the stock pool. What do you think of that?

Feds_Watchin

Politicker

3

AE

I got in the game late. First gig in sales was a BDR at age 26. Late stage startup. Got some equity worked my tail off. Made it outside as the Federal Sales Manager. 6 months later, Chapter 11 bankruptcy. In totality it was 14 months from IPO to chapter 11. Next stop was a Series A company that lets just say, lacked direction. I built their channel program and they thought I did such a good job they brought me back inside to improve lead gen. My quality of life was terrible. 3rd and final startup was an utter mess with founders having no clue how to scale a sales org. I found myself completely burnt out in my early 30s with this nonsense. I’m done chasing equity but I’m not working at FAMGA or Oracle. I found a place that sells somewhat dull software but I can convey the value prop and the people around me are tolerable for the size of the company. I think maturity will aid in hopping back into the startup pool but I don’t miss it one bit.

Lioness

Good Citizen

0

Sr Field Enterprise Account Executive

There's beauty in the simplicity of prioritizing basics like "can I sell this?" and "are the people tolerable?" You can still make good money and your living doesn't take over your life.

beerisforclosers

Politicker

2

Account Manager

It sounds like you've done the startup game for a bit. I would say no harm in trying a bigger company. Personally, I love it. There's a lot to be said for name recognition in sales, and the benefits are hard to beat. Plus something so satisfying about closing the bigger strategic ops with companies everyone you know is familiar with.

That being said, I intend to leverage titles and experiences here to jump to a startup after I build more of a brand and network.

Lots to learn and achieve either way! Good luck with your journey!

aiko

Politicker

0

Sr. Account Executive

I'm on the same boat!

LordBusiness

Politicker

1

Chief Revenue Officer

I guess it depends on what blows your hair back, and what you want log term. If you see yourself as a leader of humans, who enjoys putting together the puzzle of process and people to drive growth, the option A seems solid. If you see yourself as a lifetime individual contributer, with more “work life balance” to compliment the pay check and full control of your own destiny then option B. Either way, congrats for building a filler foundation to your career!

Dollar

Executive

0

Enterprise AE

Thanks for your perspective here.
I thought the same way and I definitely feel that being at a startup gives me a better "kick" right now. I also feel I have a higher risk appetite to do something like this today than in 5 years from now.

I think what I'm experiencing is FOMO of what if I never work in a big place and truly get to hone my craft? The experience of closing multi-million dollar deals, running true Strategic deals.

LordBusiness

Politicker

3

Chief Revenue Officer

For what its I've never worked at a "big shop" and have never regretted it. I took my role at my current company when they were doing $6 million in revenue a year in 2016 - this year we are on pace to do $90 million in revenue. I've helped my team find big 7 figures deals, with multiple influencers and champions. Sounds like your already leaning so I'd say go with your gut. You are correct on the timing, it doesn't get easier to make moves when your an old man like me with a family of 4 and two off to college in the next few years.

PartnerGuy

Good Citizen

3

VP Channel Sales

I've done both and for sure there are pros and cons to both. Without doubt I learnt the most at smaller companies and that's got my to a high position at an earlier age which I'd never have been able to at a bigger place.

What I'd definitely say is that LordBusiness is right, it's much harder to make a move when you've got more responsibilities, but also you've got 20-30 odd years to work if you're 29, there's plenty of time to do bigger places so don't worry about FOMO. Do what will give you the bigger kick now and get you that experience and take the higher risks while you can.

Dollar

Executive

1

Enterprise AE

Oh wow! That sounds great!
Tbh, I think thats what'll give me a bigger kick, actually building something with my own blood & sweat.

I think a part of me also feels that I'm not ready for it. (You know the devil voice in your head)

SalesPharaoh

Big Shot

1

Senior Account Executive

It really depends on you and what you see ij that startup. Are you going to have stocks in this? Is there room to be a partner of that startup? Or get more stocks? What are the compensations between both?

Dollar

Executive

0

Enterprise AE

Comp on a base/variable level is same frankly. (20k diff in OTE)
Obviously the startup has a big chunk of stock options. I can see them getting a 4-6X valuation during their Series A raise from where they are now.

SalesPharaoh

Big Shot

0

Senior Account Executive

Well it's up to you there was a post over how to value your startup and if yours checks out then go ahead

Salespreuner

Big Shot

0

Regional Sales Director

@SalesPharaoh : very right questions put forward. Yes these will help decide quickly and move on with either

SalesPharaoh

Big Shot

0

Senior Account Executive

Thank you for your feedback @VKN_Salespreuner going into a startup can be tricky for anyone because it may have high growth numbers and suddenly collapse later on. We all want to be in the right boat before it becomes a ship.

Salespreuner

Big Shot

0

Regional Sales Director

Absolutely 💯 agreed 🔥🙏

Patrick_Bateman

Fire Starter

1

Senior Sales Consultant

Startup all day every day if you want any shot of making real FU money. It’s only possible with equity/stock options. Corporate is the way to go if you aren’t a swing for the fences guy and just want to be “well off” which is just death by averageness. Go with the startup and don’t live with regret. Short the VIX

CuriousFox

WR Officer

1

🦊

Speaking from experience, yes the red tape SUCKS. However there are many more benefits to a big corporation. What did you choose?

softwarebro

Politicker

0

Sales Director

Is management your long term goal?

Dollar

Executive

0

Enterprise AE

Yes, I'd say so. Long term, I do want to run global businesses. My goal is that in another 10 years, I should be at a C-level running global teams, preferably 3 digital million dollar businesses.
I'm someone who puts a lot of effort to try and achieve this goal.

softwarebro

Politicker

6

Sales Director

If your goal is to run and operate a $1 billion + global sales organization then I would suggest learning the enterprise business from salesforce. I took a sales leadership role at a start up several years ago- honestly one of the best jobs I’ve ever had. I had a blast I learned a lot but all in all that experience did not translate well into highly structured enterprise leadership. Just a warning start up a sales / sales leadership is an absolute grind.

CaneWolf

Politicker

0

Call me what you want, just sign the damn contract

You and I have similar career lengths but in very different places.

I've done two start-ups and two more established organizations with several hundred or thousands of people. I fucking hated the start-ups. Established companies are definitely more my thing. I've seen the same from a lot of my peers who have done the start-up move post more established companies.

I think, for the most part, sellers tend to prefer one bucket or the other. It sounds like a) you like the start-up life b) you have an opportunity to significantly grow your wealth and portfolio.

I think you pull the trigger on the start-up as Head of Sales. If it bombs out, there is plenty of time to go to the larger organizations.

betweenworldandme

Good Citizen

0

Enterprise Account Executive

I think this question really boils down to the risk appetite of the individual. How do you as an individual view opportunities? If you're at your core, generally risk averse, then deep down you're always gravitating towards option 2. But if you truly enjoy a higher risk reward situation then the startup scenario (option 1) will always give you the kick to build something under you. I believe you'll have great career paths in either direction, no question about it considering your work experience. What you should consider is where you are falling with respect to craving/wanting stability in the next few years. Hope this helps!

cinnamonrolex

Good Citizen

0

Inside Sales Representative

I started my Sales career at at a start up and can't picture myself at the big corp I had an offer from a couple years ago. I'm clearly biased and not near as experienced so take this with a grain of salt if you must. But you can't beat stock options, the opportunity to help take a company IPO, and the huge opportunity to grow at start ups. Yes, it's stressful, messy, and chaotic at times, but I can only picture myself working at startups from here on out.

Chep

WR Officer

0

Bitcoin Adoption Specialist

I'd take option 1. So much more personalized at a startup vs an enterprise where you're just a number

saygrace

Valued Contributor

0

Sales Executive

Start up for sure. Congrats on being this far ahead in your career path for such a young age.

thegrinch

Politicker

0

SDR

Based off reading the comments, it sounds like you've already made up your mind. It sounds like the start up opportunity is calling your name and that's where you want to be

Justatitle

Big Shot

0

Account Executive

I think this depends ultimately on what you want. Do you want to build out a strategy for a team and lead them and have the opportunity to be a ground floor leader or do you want to be a cog in the machine at a google/sfdc type deal. Personally will take the startup over the established company every day of the week

aiko

Politicker

0

Sr. Account Executive

I think there is value in working at Salesforce. Docusign, not so much.

I had a friend go through the interview process at Docusign after leaving a startup and they don't offer any flexibility. They also cold call soooo much. Not sure if you're into that.

Salesforce on the other hand, they have a strong leadership team where you will get promoted if you perform. SF has more strategic deals as well.

If you've always worked at a startup, maybe now might be the time to try a larger company? If you hate it, there are always more startups :).

redrabbit

Opinionated

0

Account Executive

Would love to hear how this panned out

anothersalesgiy

Good Citizen

0

Enterprise Account Executive

Second this - how’d it go dollar?

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