enterprise sales: a legitimate career to Get Rich 🤑 (2017)
all the practical details you need reagrding what a sales job looks like
Reading time: 22 minutes.
This is a guest post from frequent commenter “Tech Sales” who works in the industry and has already *made it* up the stack so to speak. Enterprise sales is one of the few careers we recommend in Efficiency and we thought it would make sense to do a cleaner overview of how to get into the space and luckily he was willing to do the post.
All of the words are his and we’ve made some basic organizational/formatting changes.
We’d like to thank him for his contributions and the Q&A section is now closed. If your question is redundant we didn’t approve them. Thanks!
WSPArchive: Note, this is an archive from a guest post that was in WSP. We had a reader recommend this one to us, so we thought we’d surface it. You know it’s a good one if a person remembers it so 7 years later
Executive Summary
< …. the headers … >
How To Make It In Enterprise Tech Sales
Next to Wall Street, Enterprise software is one of the best careers out there. The earning potential is extremely high, with the higher level VPs earning high 7 figures (search for the top earning tech sales people, they make over $5M in Google).
That was a few years ago, and is likely higher now… (2017)
The median for an enterprise account executive seems to be around 250k, with base salaries going to 100-150k and good years bringing your total earning up to $1M (or more).
The one funny thing about Enterprise software is that people do not hate it as much as Wall Street.
On Wall Street I don’t think anyone likes their jobs. In software, plenty of guys working at home 40-60 hours a week making a killing loving life.
No need to have “exit options”.
Where else would you exit to?
Plenty of people will stay in sales their entire careers and not hate their lives, unlike people in Wall Street who all want to leave.
See the founders of this blog for example. (WSPs note, as many of you know we left many years ago and we agree that around 95% of Wall Street professionals don’t like their jobs).
I’ve heard plenty say the job is super easy. However those were the guys who were good at it, a large amount drop out before they make any real money.
Where can I end up?
Assuming you start as an SDR... that should be much shorter than an analyst stint (1 year of your life. 6 Months if you’re a crafty hustler and 2+ if you let companies abuse you).
A lot stop at enterprise account executive.
If you get lucky you can have your established accounts and just do new demos and manage accounts working from home for 40 hours a week.
This position takes years to get to but with a six figure base and multiple six figure comp, most do not mind.
If you want to venture into leadership there is the VP of sales, CRO, and CEO in a lot of cases.
At the very top is founding your own company - see the Salesforce founder for example. His LinkedIn indicates he was a VP at Oracle before going off on his own.
Can I Do Sales?
The best sales guys I have met have a very high EQ with a level of social skills and the ability to hustle and grind.
If you’re your a nerdy guy who has Aspergers and can’t pick up the phone you will most likely have a hard time getting your first job, then subsequently fired if you do get your first job.
Feel free to give it a try however, it’s completely possible you will make it. To be honest the answer is I don’t know.
Even guys who I thought would kill it have given it up for greener pastures.
If you are a hustler and are good with girls (this is a dead giveaway, can you cold approach a girl and have decent results? You’d most likely be a good fit then).
The only real way to tell is try it for a few months.
You’ll know pretty quickly if this is something you can hack or not. Emphasis on the cold approaching part. If you can cold approach comfortably and do well, this would almost definitely be an excellent fit.
⚡️ Related Archive
Here is a related, extremely practical and detailed guide to making a lot of money.
WSPArchive: This is one of WSP’s greatest strengths - they have extremely practical guides with detailed numbers so you can literally compare and know what to expect on your journey.
Career Progression
The career progression typically goes:
SDR (6 months to 2 years)
Small Business Account Executive (1+ years)
Mid Market Account Executive (1+ Years)
Enterprise Account Executive
Enterprise Account executive is where everyone wants to be (along with the six figure BASE salaries and $1M earning potential).
Keep in mind this path is not set in stone… at all.
Some guys start as Account Executives, but most start as SDRs.
You can do this in 1-2 years probably if you are a killer and start as an SDR at a very early stage startup. Then get extremely lucky and given enterprise accounts to close because they need someone that minute… and by chance you’re the most senior SDR.
WSPArchive: This sort of advice is very useful, don’t glance over it. If you are good at what you do, it makes a lot of sense to position yourself in situations that are likely to HAVE to give you more responsibility (by necessity). A fast-growing startup with potential is the best place to be if you’re starting your career.
Comment: Startups
The Anti-Villain says
Working at a startup in sales takes a whole different level of hustle, ESPECIALLY if you’re one of the co-founders.
Often times you’re going into an environment with:
very little structure
barely a wisp of a sales process
only a general idea of who your real target market is. (This isn’t necessarily the case for the ones that get millions in funding)
Startup sales, from my experience, is way harder than sales at an established company.
But:
You usually get much better commissions
You get much more freedom in your actions
It’s easier to leverage for equity
If you already know you have the sales chops, hustle, and experience needed to be a top salesperson then startup sales can pay off big time for you.
The ability to sell is a gift that’ll keep on giving.
You’ll never be out of a job, and you’ll have a serious advantage with any businesses that you start.
TechSales says
sure.
but you also have no real sales process and you end up building one
product often has bugs
no market awareness
little support
often lack of $$$ (we need fundng)if the upsides outweigh the downsides it can be worth it
Comment: How to play the start up
💬 Brett says:
This is scary accurate. I started at a medium size “start-up” and was an SDR for 2 months before moving to inside sales for another 2 months and I became an AE in 4 total.
PLAY THE POLITICS. If you’re at a small company, find the small/midmarket manager that will eventually become your boss. Hang out with him, get beer with him and go to lunch.
When you interview initially, set the expectation that you are not coming here to be an SDR forever – you want to become an AE as fast as possible.
When a position on the team I am now on opened up, upper-management did not want me to interview. Because of my relationship with the manager he was able to give me a shot and I blew up the interview.
Like this article says, this isn’t a 100-hour a week job BUT if you hope to be promoted quickly, put in the time and log the hours to learn what it is you’re actually selling (I would say the vast majority of the SDRs at my company have no idea what our product does outside of the basic value prop in their pitch). The important people at other departments should know who you are and take a genuine interest in how everything functions together.
I’m 22 years old, I make more money than all of my friends, but also remember… once you become an AE that isn’t the end of the journey, just a stepping stone towards a very comfortable life. Don’t be the guy that buys the nice car, watch, etc. out of the gate.
Been reading this website since I was in college and man it’s fun to see how everything comes together.
For most it will take 3 years on the very low side.
For those talented/lucky to 5 for those who are engaged.
Longer even if you let companies use you (a lot of companies will keep you as an SDR as long as they can, 2-3 years in some cases.
The best solution here is to leave to a better company as an AE after 1 year max. Different geography if there are not a lot of options.
Compensation and Roles
Keep in mind these are rough numbers, and you might see different numbers in different places.
The advice given is for those who want to become an enterprise AE, or higher as fast as reasonable.
SDR — $45-110k
All In.
HIGHLY dependent on geography and market you sell to.
A small business rep might make 45k in Kansas for example, while an enterprise SDR might make 110k in NYC.
You’re setting appointments for the account executives. 100+ calls a day reading from a script.
Probably equivalent to being an analyst minus the 100 hour weeks… More like 40-50.
My SDR role was in at 8 AM out at 4:30 sharp with an hour lunch break.
What to Do?
Get promoted from this role as fast as possible. There is not a lot of money to be made unless you get a few % on the backend and somehow originate a million+ dollar deal.
I would say it is almost worse to start at Oracle than a startup. Oracle makes you stay in an SDR role for 1.5+ years. I’ve seen it done in 6m at a startup, and even faster.
However, starting at Oracle is a great resume booster, so do what you want.
There is not a lot to do except learn how to use the phone and position yourself to move into an AE role at your current company.
When I started I spent 1 day training, the next day I was on my phone and set up my first appointment. Don’t feel bad about leaving as you are probably adding value day 1.
Most jobs take 1 year to be beneficial to the company, a good SDR will do it on DAY 2. You’re already generating revenue.
After 6 months you can start looking for new AE jobs at another company unless your current employer brings you up to speed.
DO NOT GET TRAPPED HERE
Plenty of companies will hire you as an SDR and just leave you there. If they do that look to lateral to an AE position after a year to another company.
It’s not worth it to take the time to look for the perfect SDR job.
Everyday spent looking for a job is a day you can be grinding putting in your time trying to get promoted.
If you’re not long out of college think of this as grad school. Eat ramen and have roommates for a bit.
SMB AE — 100k-120k (Estimate) and Mid Market AE — 120k-150k (Estimate)
What to Do?
These jobs are much better, but still a stepping stone if you’re the kind who wants to make it to the enterprise.
Additionally, you will start doing demos and do a lot less cold calling.
Minimum duration of 1 year.
It’s possible to go from SMB AE to enterprise AE, but you generally need 3-5 years of experience. So you’re paying your dues until you can get to the big leagues.
The most common route is probably:
SMB 1-2 years
MM 1-3 years
Enterprise however many
Put up solid numbers until you can get promoted. No reason to leave unless you get pigeonholed or you cannot be promoted any more.
Enjoy the higher salary and ability to live a decent life.
Enterprise — 200k-300k. Up to Millions with accelerators.
The big leagues.
Same as before, but now you’re selling to companies with thousands of employees. After you make it here no need to sell to SMB or mid market ever again.
Same as the other Account Executive Roles. Ideally you do little cold calling, as there are not that many fortune 100 or even 1000 companies to call.
If you add in a few reps and few SDRS, that’s less than a few hundred companies per person, much less than a highly productive SDR can contact in one day.
Many stay here.
150k base
250k OTE working from home a lot earning up to 1M.
Not too bad…. at all. (Wall Street guys might disagree…. seven figures or bust?).
Note: Some companies go SDR ==> Inside Sales == > Outside Sales. The timeline and pay is similar to SDR ==> SMB/MM AE == > Enterprise AE.
VP on Up
Can’t really comment here as I’m not an expert.
The general consensus is that you make more than most reps, but less than the best.
Which is how it should be, and why many stay selling to the enterprise indefinitely.
However it is less selling, and a lot more managing and training.
If you want to chill on the grind, this is a good place to go.
If you are one of those “I gotta be at the top” types. Working your way up and shifting over to enterprise leadership at a big company as soon as possible might be a good route.
Flirting with the idea of starting your own company of course, or figure out some way to get a good chunk of equity as a sales centric founder or even as a rep.
Keep in mind you are NOT an “idea person” as a cofounder. Without deals, the nerds have nothing to make.
How Do I Get a Job?
The best way is by far…
👀 Keep reading with a 7-day free trial
WSPArchive: The rest of this content is paid. You can subscribe with a 7-day trial to see it.
If you’re serious about getting a career in sales - you should be happy to trade a few dollars for this information and all the future ones to come. If you aren’t serious - then you shouldn’t be wasting your time reading this.
🍷 Premium
We also offer a premium subscription, that gives you:
Access to archives posted more than 7 days ago. Any post over 7 days gets locked. (including this one)
Access to original content, including the well-acclaimed:
Our 40 best takeaways from 2023 (year in review)
The Channel Playbook (13 pages of actionable marketing advice regarding channels)
ROI. $6 a month for advice that can help you thousands is a trade we’d take any day.
Keep reading with a 7-day free trial
Subscribe to Wall Street Playboys Archive to keep reading this post and get 7 days of free access to the full post archives.