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!
How to Make It In Enterprise Software 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… 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 as 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.
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.
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 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 6 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.
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 — 200-300k. 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. Again, I’m really not the best person to ask here… so look elsewhere. The advice in this section is purely speculation.
How Do I Get a Job?
The best way is by far internal referral. If you have a family friend, neighbor, relative, friend’s dad. Literally ask them for a job. If they are a manger they might be able to hire you, if they are a rep they can recommend you to their manager and you might get an interview. Alternatively ask someone in software sales. Maybe I’M not hiring, but I probably have a friend who needs good people, and I’d be doing 2 people a favor. People in the industry often know others in the industry naturally.
Otherwise apply online for SDR jobs until you get something. It might take a few interviews for you to land something. Once you get it feel free to take it if you want, grind it out for a year or so and move to AE. Cold calling also works. Might be kind of weird in other professions, but if you can cold call and pitch a manager you can probably pitch a prospect just fine. Plus it puts you ahead of 100 other candidates…. Otherwise messaging on LinkedIn also works I’m assuming (never tested).
Target School List for Oracle Class Of Program: If you’re wanting to get into Oracle right out of school I suggest going to one of these schools: “Baylor Berkeley Boston College Cal Poly Cornell Duke Georgetown Stanford SMU Texas A & M UCLA U Mass U Michigan UCSB UNC USC UT Austin UVa U Wisconsin Indiana Penn State THE Ohio State Wake Forest Va Consortium HBCU*” That was copied word-for-word from a response from an Oracle Sales Manager when I was gunning for software sales at the end of college. So do what you want with that information. I think a 3.2 is also preferred… If you want this I also suggest getting in contact with an Oracle Sales manager via LinkedIn or another method, they might be able to help you cut the line and get you an interview.
Enterprise software sales is perfect for the low to mid 20’s hard worker who does not know what to do. You can realistically reach enterprise in a few years (before 30). One of the realistic (albeit VERY hard) to make a million dollars a year before 30. If anyone asks you the often dreaded “What do you do?” — “I sell enterprise software”.
Probably the best answer ever. The person probably knows you make a lot of money, but has no clue if that is 100k or 1M. Emphases on them knowing you are probably well off, but not knowing if you are actually rich or not. It seems like everyone knows of someone making a killing in software sales.
What to do (in a few words): Get a job as an SDR, grind to an AE position, make it to enterprise AE. Congratulations, you’re in one of the best reasonable-to-attain jobs on this planet. Feel free to celebrate.
ON GETTING THE JOB TO ANSWER YOUR QUESTIONS
1. When you’re Interviewing for a job, here’s what they look for on your resume:
A college degree. It is possible without a college degree, however this is highly recommended. You might be able to be a rep with no degree, however getting into management will be very hard. You’re on your own if you decide to go without it or not. I’m assuming if you’re reading this blog you decided to go to college…Underwater basketweaving from Local Community College is fine. One of my managers went to a for profit school…. it just gets you in the door. After you’re in you’re in.
Sales experience. Even door to door or retail count. The rationale is that it makes you much less of a risk to hire if you have already been successful in some sales environment. If given a choice a manager will choose someone with 1 or 2 years selling pots and pans door to door successfully over a decent candidate from a good school. Mr. Pots and Pans honestly has a better chance at making it because of his proven record. However the new grad still has a decent shot.
Easiest way by far is from an internal referral. Even a rep giving your resume to a manager will very often get you an immediate interview. I’ve gotten friends in with zero experience from the inside and they skipped the entire interview process at a start up, all because the sales manager WAS HR at that point. We had no candidates lined up, so it was literally: He sounds like he can sell, He’s hired!. Literally no one else to compete with. Usually sales hires for sales. HR does a god awful job deciding who would make a good sales person.
If breaking into Investment Banking was a 10 on the difficulty scale, software would probably be between 4 and 6 depending on factors. Challenging, but doable for most college graduates. Apply to a ton of entry level roles. Go to networking events. It took me a few interviews until I was finally hired. No harm in starting at a start up. It might actually push your career forward at lightning speed. Oracle makes you stay at the basic level for 2 years, it took me 6 months at a start up.
2. When you meet or email someone. Talk about your ability to hustle and how you work really hard. Talk about your good social skills. Tell a story about how you were in a frat in college and partied a bit and everyone loved you. You thought you might be good at sales. Talk about the sports you played in college and how you are super competitive. If you’re a nerd, talk about how no one realizes it but that academics at a top tier institution are ruthlessly competitive and you are extremely competitive in that aspect and how you hate losing. I’m not sure if this is true but it would most likely work.
3. When you get an interview focus on… Focus on not being nervous. If you were in a sport emphasize your competitiveness. If you didn’t play sports on college emphasize how hard you work. Talk about how money is a good motivator for you (important). You want a big house, fast cars, and your girlfriend likes to spend cash like crazy. Even if you don’t it will help you get the job. (Sales Manager is thinking: “This guy is going to work his ass off”)
Act confident and a bit of aggressiveness helps. Talk about how you are good with women if you think the sales manager is young and might be comfortable on the topic. A lot of sales managers know that the two are extremely similar and this will put you in a positive light. Watch out though, it is possible this can backfire if you have a female manager or some sort of weird SJW manager.
4. If you still have trouble… Get a sales job in business to business. Paychex, ADP, anything really. Show some success and you will have an easier time getting interviews. Try contacting sales recruiters. If they can place you they will for a quick 5k+ (their commission from the client). Honestly even if you are a complete dweeb eventually a hiring manager will give you a shot for you to prove yourself at one of the second tier companies. If you can’t sell (Ie get fired more than a few times from sales jobs for not performing) that’s a bigger problem and not something I can help you with. It might be time to find a new career.
5. How to improve sales skills…. Go out and chase women, pick up a mild alcoholic habit and hang out at bars. Learn to like people. As much as this blog tells you to hate average people, you’re most likely going to sell to average people and that attitude will NOT make you friends. So at least fake liking them. There are a ton of books out there on this topic. To start: fanatical prospecting, challenger sale, and so many more. Oh, and before anyone asks. I have NEVER been drug tested for a business to business sales job.
6. Other Random Thoughts: Even for guys that are good, you are going to have huge ups and downs. Even the top producers have them. Some days making money is so easy is a joke, some days you will feel like you are trying to walk through an endless desert trying to sell. It also depends on the company/market fit. If you have a ton of hot leads waiting it can be as easy as a few phone calls. Sometimes you’ll be given a list of random people and it is very difficult.
It’s best to be friendly with your co-workers. There are usually enough leads and territories to go around. Your job is to create opportunity, and very rarely is there a “limited” area to prospect. Of course it is a work environment so don’t trust anyone too much, but be friendly if you can.
The reasoning? If one of your “buddies” leaves to go to Oracle/SAP, a hot new startup, becomes a manager/VP at a top company, or you need a job in a year you can give them a call. The best path to a good job is through a referral. There’s less throwing you under the boss. Managers will be on your ass if you don’t produce, but if you do you can pretty much do what you want.
On recruiters: I love sales recruiters. Many people hate them and find them really annoying, however I really don’t mind them. They’re one in-mail away from hooking you up with jobs extremely quickly. Just remember that they get paid to place you, so be sure to vet the jobs they show you. Never harm in seeing what jobs they have at that moment that might pay a multiple of what you are currently making
Wall Street Playboys Note: It is important to recognize all the Careers outlined in our book are 100% fine. We never worked in Enterprise sales and that is why we brought in a Guest poster. If you are currently an M&A investment banker or working at Facebook in tech… there is no reason to switch.