Enterprise Sales: A Legitimate Career to Get Rich

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.

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.

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.


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. 


  1. EE says

    Graduated last year with a 3.0 Finance and could not get in as an analyst anywhere. Read on your blog that tech sales would be your recommended career path if you were starting today. I messaged a recruiter from Oracle that day and have been working here for a few months as an SDR.

    If anyone is looking to get in, I would recommend messaging the recruiters directly. They have quotas just like us, and will really push to get you the job.

  2. UK Sales says

    Thanks for doing this post.

    Couple of questions.

    With most software companies moving to the SAAS model. Do you think this will take away from the earning potential of selling perpetual lisences? I’ve witnessed some shady stuff, where clients are prompted to upgrade by clicking vs through their sales rep. Or you don’t recognise the revenue for retaining clients on the SAAS model.

    Any preference to established FTSE 100/Fort 100 Vs VC backed startup for earning potential?

    UK sales

    • TechSales says

      Probably not as long as the software needs to be re-bought every 2-3 years. SAAS is better for everyone…. Clients can choose who they want and pay for the service and companies can have recurring revenue (no need to release a new windows ever year)

      I would go big co in general. Startups often don’t have a ton of capital and a lot of the less funded ones are shit. A few cases where going to a startup is smart:

      1. Good product and you get equity (stock options I am very iffy on). You can make millions…even moreso because you help determine success.
      2. You’re a killer and want to close the big accounts (because you’re the first one in there). Good luck getting the Exxon account at any big co.
      3. The startup is heavily funded and has an incredible backing with good talent. There is a strong possibility to make more money.

      They use the startup excuse to pay you less than market. I am currently at a startup and looking to move because it’s all the startup problems with none of the benefits. And of course the promised stock options never came. I haven’t been here long but already looking to move because it is more downside than upside.

      Oh, and NEVER work for a Chinese or Indian owned company if you can help it. They pay shit compared to american cos. Learned that the hard way

    • Juggalo says

      “prompted to upgrade by clicking vs through their sales rep.”

      I’d guess this is probably on a company by company basis. For some, if its your account and the client renews/upgrades you may get commission regardless of the work put in. Some companies may not be this way, though.

  3. Aaron says

    Good post.

    Wish I had found this site earlier. I feel like I’ve wasted the past several years of my life in higher education. I am 26 now, and university hasn’t helped me much regarding social skills.

    Currently working on finding a job in IT, while constructing an affiliate site on the side. Might take the advice of becoming a ‘mild alcoholic’ in the hope of developing some much needed confidence.

  4. Saas says

    What are your thoughts on assessing if quotas are attainable when switching from one enterprise role to another at a new company? Quotas are usually inflated with internal forecasts expecting most reps to hit 60% of their quotas for the company to reach its revenue target. Curious to hear your thoughts.

    • TechSales says

      I always ask how many reps are at quota. Generally something like 1/3 killing it 1/3 around quota and 1/3 below it or something like that is what I like to see. Where it’s readily attainable if you are skilled and work hard.

      Any interview I’m going to grill the interviewer (more than they grill me usually) and then ask current/past reps how it is. Any red flags make me weary. Nothing like starting a new job and then realizing its shit.

      • TechSales says

        how many reps make quota, what the average tenure of the sales team is (many people with 1-2+ years is a good sign), how much the quota changes, average $$$, highest earner, etc.

        I like average tenure because it means they don’t churn and burn a lot. probably more common at higher end gigs where everyone is already experienced.

        SDR roles often have churn because it is an entry level role and lots of people just suck at it.

  5. Liquid Playboy says

    Thanks for this *awesome* post!

    I’m a 23 year old from Germany that wants to break into Enterprise Sales. The problem? My CV is terrible.

    1) 2013 I finished school in Germany (degree is equivalent to high school diploma) with terrible grades.
    2) 2013-2014 I had an 1-year internship in an insurrance company
    3) 2014-2017 I was working full-time online. Arbitrage on eBay, Affiliate Marketing, Consulting, Dropshipping, Freelancing… I tried everything. But. I’m currently not making meets ends and want to switch to something more stable.

    From 2014-2017 I also studied and worked here and there, but I always quit after a couple of weeks. I think I shouldn’t mention this in an interview.

    What are my strengths? Everyone tells me that I’m *incredible* charismatic (even total strangers and hot girls are telling me this), good-looking, very muscular, and have a great clothing style. I approach hot girls dead sober during the day time, so cold-calling would be nothing to me. I’m your typical Go-Lucky-Happy guy that everybody wants to be around and wants to be friends with.

    So… If you were in my feet, how would you try to land a career in Enterprise Sales? Keep in mind that I have a terrible CV, but *amazing* communication skills?

    • TechSales says

      that’s nothing… my buddy had 3 jobs in one year and still got an offer from a very reputable company. that was his 4th… that year… this was after switching over from engineering

      it’s all how you spin the story.

      i think i laid it out in the post but ==> apply online (works once in a while), contact sales recruiters until you get something, cold call managers

      that’s basically prospecting and if you do that well I can’t imagine it would take long at all to find something…

    • john says

      If you’re extremely good looking, its too easy for you to pull girls, make “friends” and get your foot in the door pretty much everywhere.

      Chances are you have a terrible personality. Try telling a shitty joke and flash your smile, guys will chuckle because they want perceived status by association and girls will giggle because they’ve been slippery since they saw you.

      Try cold calling. You’ll be shocked at how unreceptive people are through the phone without your good looks to back your voice.

      Other guys hate your looks. There will be a gang of jealous men scheming to pull you down everywhere you stay.

      Now to answer your question:

      Do door to door sales for a few months. Sell something targetted for women. Great work experience and CV builder. Give your contact info at households of potential employers (rich people).

      Get a job as a waiter at a restaurant close to the office of a company you want to work at. (Hospitality is based entirely on looks) Talk to the people in suits, make them like you, ask for the job when the time feels right. Easier to do with females. If no results, switch locations.

      • Wall Street Playboys says

        This guy is correct, doesn’t matter what random people in the internet think. If someone is actually smooth/charismatic or what have you… getting a job in sales would be easy. Anything besides success doesn’t count.

  6. J says

    Great post! You mention ‘Some guys start as Account Executives, but most start as SDRs.’ Who are the guys that get to start as AEs right away/ what do their background(s) tend to look like?

    • TechSales says

      sometimes you can switch industries into an ae role (situational)

      a lot of companies don’t have SDRs, so you would start as an entry level AE.

      maybe a personal connection (worked for my buddy)

      its really mostly situational or who you know.

  7. 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, and 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.


    -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


      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

  8. Banana says

    Thanks, love it.

    I’m a nerd, hated sales before and only loved to code apps and sites. But confirming what you’ve said: spending time with women, reading some books, and some ample suck-it-up time on the field greatly helped.

    Anyways: any Other websites/people/books you can personally recommend?

  9. CloudSales says

    Great overview here!

    Question for TechSales: I work in Account Management at Oracle. Get paid a % on module, services & user upsells into the install base along with closing contract renewals since we sell a SaaS product.

    My job is slightly different from guys on the direct side of the house who bring in net new business but I have a comparable quota to them.

    Would staying in Account Management pigeonhole me in the long term? Am I hurting my earning potential / marketability going forward?

    Would be great to hear your thoughts / feedback on this.

    Thanks for writing this post and thanks WSPs for all the gold you have dropped via this blog so far

  10. SaaSalesDude says

    Currently in enterprise sales as a manager. Went from SDR to SMB AE to SDR Manager. Curious on the author’s thoughts on staying in management (assuming they let me manage an AE team) or going back to an individual contributor role. Been in management for 2 years and my team has crushed it.

    • TechSales says

      no personal experience but I wouldn’t go to management unless I was managing a large group of AEs to move up to vp or something.

      i’ve heard you can get stuck at sdr manager and not be considered skilled enough to manage AEs and i’ve seen it happen.

      personally I would never be a SMB/SDR manager by choice

      all about where you want to go. If you want to be a enterprise AE is serves no function.

      its really up to you what you want to do.

      • SaaSalesDude says

        I guess it’s a gamble, then. I have good sales skills and have been told I can do either. Other executives have said that I could move to managing AEs without having done multiple years of ENT sales, but nothing is guaranteed. I’ll go on some interviews for AE positions and see how it goes.

        Only other problem can be golden handcuffs. I’m compensated very well since I manage a global team and I don’t know if most AE jobs (beyond the highest ENT AE roles) could match it.

  11. CloudSales says

    Thanks for this post, TechSales. Having gone through the Software Sales hiring process right out of college, I can attest that the information here is legit.

    Would be great to get your opinion / feedback on a question I have:

    I work in Account Management at Oracle. I sell into the Mid-market install base and get a % of all upsells (modules, users, services) and also get paid on the revenue that I bring in by negotiating renewal contracts since we sell a pure SaaS product.

    My job is different from a direct sales role where brand new business is closed. However, I carry a similar or higher annual quota.

    Do you think working in Account Management will hurt my marketability & future earning potential from moving into the Enterprise space?

    Shoutout to WSPs for all the gold they have dropped so far

    • TechSales says

      honestly have no clue from personal experience.

      i’ve seen other guys switch back and forth. there is customer success for the enterprise space AFAIK so it would probably give you a leg up there.

      if you want to move though just try to move now, no point in grinding it out here.

      only issue is you might have to convince the manager you can hunt for business and not just be friendly with current clients

  12. john says

    HAHAHA, I lost it at “underwater basket weaving”.

    Thoughts on focus enhancers (adderall, caffeine, coke) and sales?

    I find them good for pulling at parties/clubs, because the energy they give me makes it easier to focus on feeling good and projecting my own confidence and dominance.

    However, I find them detrimental for street cold approaching or dealing with new clients because they make it hard when having to switch attention to understand the client. Its difficult to reciprocate the many subtle cues of emotion displayed through shifts in voice tone, facial expression and body language when I’m too busy concentrating on a single channel of indication.

      • john says

        Damn. I want to work in your office.

        I’ve never tried.

        How does it compare to coke, addy, ritalin or modafinil?

      • TechSales says

        Adrafinil is the prodrug to modafinil. When it hits your liver the enzymes turn it to modafinil.

        I just have a little thingy with powder at my desk. It’s not illegal so I don’t really care. Honestly my manager wouldn’t care either if he knew.

  13. Lion says

    I currently been an SDR for the last 1.9 years due to the fact that my company didn’t have a clear career path for us.

    Not easy to jump from SDR to AE at another company as they’re looking for someone with closing experience. Best thing to do is lie and say you have closing experience to get in if necessary.

    It’s important the company you plan to work for has a clear career path for you to become an AE. Don’t want to spend next 4 years as an SDR cold calling. You’re pretty much done after that.

    • TechSales says

      might to just be best to lie and say you closed a few random deals as an SDR because the AEs were busy to get a new role

      “closing experience”

  14. JQ says

    Props to WSPs and TechSales for delivering from May (Is Starting a Company the Least)!

    Just started in ERP at an established company as a BDR. I know this may be too specific but which verticals would you recommend? From talking to a few folks they recommend manufacturing and wholesale distribution. But on the flip side, I also heard that the industry you work in as a BDR doesn’t have too much effect on your next options after the BDR program – all that really matters is that you’re a top performer.

  15. parakeetchief says

    I currently work at a software company in an account management role that I got right out of college. This was the only option other than working minimum wage at a restaurant and it kinda fell into my lap.

    Money is decent but I am not doing well with the role which is mainly helping accounts with problems and then trying to make sure to continue their subscription with the company. There is some sales involved but there is no cold calling, it is just trying to convince customers to stay with the company, very straightforward because:

    Happy? Stay with the company without doing much on your end, just send the contract.

    Unhappy? Leave the company and not much you can do.

    Do not like the role too much as a lot of it is putting out fires when customers aren’t happy and then hoping I get a good batch of accounts to work with. A lot of it dealing with baggage customers have left over when a sales rep did not deliver on a promise then having to be the person they vent to.

    What I want is more of a headhunter role such as an SDR but I wonder how difficult it will be with lackluster numbers in an account management role. Any idea?

  16. Silicon Valley Baller says

    Opinion on call volume (number of calls) vs quality of calls?

    My manager goes ballistic if any SDR makes less than 45 calls per day.

    I feel like I generate WAY more revenue when making 30 quality calls than 45 mediocre calls.
    By quality, I mean before dialing, thoroughly researching the prospect and their organization.


    Currently a new SDR at a well established SAAS company in Washington DC.

    It seems that San Fran > New York >>>>>>>>> DC


    My comp is….$30k base, $15k commission with OTE

    80% of the reps on my team don’t hit quota, and the 20% that do BARELY hit it while pushing as hard as they possibly can.
    (As a reader of this blog, I am of course in the 20%).

    • Silicon Valley Baller says

      Current plan of action:

      Get to Account Executive (AE)

      LEAVE….and go somewhere else where compensation is WAY higher

    • Lion says

      30k base with 15k commission sounds terrible to be honest. Especially if you live in Cali. Your total salary is someone’s base. I hope you get into an AE role fast so the next company you apply for you can at least lie and say you had a 60k base and OTE of 90k.

    • UK Sales says

      In an SDR role you’re at the top of the funnel. No one cares about you. If you churn and burn it doesn’t matter.They find a replacent. Your job is to fill up the top of the funnel, find the leads and pass them on. This is important to remember.

      It’s likely your company is Accountant led. The cold numbers guys that see for every 50-100 calls each sdr makes the company generates 3 leads, from those 3 leads 1 sale is made at $x profit. You’re a small voice in a large company arguing against this.

      That’s why when you’re in am SDR role you’ve got 2 jobs.

      1) make sales, earn your commission (do this early morning)

      After you’ve made money

      2) Manipulate your call stats so on a data point it looks like you’re doing your job.just don’t get caught. Leave long winded voice messages to dead leads, call internal numbers, get passed around. Don’t spend more than an hour doing this, you just do this to keep your manager off your back and to keep his manager off of his back.

      • TechSales says

        hate to say it but I am guilty of making unnecessary calls (usually to IT decision makers who I know never, ever answer) to make managers happy after hitting my quota for that period.

  17. says

    Literally could not agree more. Started my own Tech Recruitment Agency and have seen first hand how guys in their early 20’s are making more money than most. So many of them work from home and are doing an ‘easy sell’. I highly recommend this career to anyone. PS recruitment in Tech companies isn’t half bad either ;). WSPs gives the best career advice on the net

  18. Anonymous says

    I did technology sales for six years spanning startups to FTSE100.

    I’d have potentially blown my brains out if handed a firearm, in the last several years.

    This career pays well, but is mind-numbing for anyone creative.

    I went into digital marketing and content design and am much happier – and able to work anywhere in the world.

  19. says

    Reading this post made me think we might work at the same company!

    “However those were the guys who were good at it, a large amount drop out before they make any real money.” – In my sales sector, guys 2-3 years in find themselves being the last 10-20% left of their sales school classes

    “Enterprise Account executive is where everyone wants to be (along with the six figure BASE salaries and 1M earning potential).” – Alot of the sales advisors in my company have framed pictures of the biggest checks they ever recieved (Biggest I saw was 875K)

    “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” – They’ll also drop you in 4-6 months if you can’t produce anything.

    Went to one of your target schools, know at least 6 folks that went to oracle. Cali oracle (Santa Monica) folks are getting 50K base.

    I’m currently working in tech sales (company splits up technical salesmen and client salesmen) and my base is higher while my commission is lower than say, an AE. I’m quota’d but the most I’ll be making is maybe 125% of base. Will take a magnifier to AEs at the company because of this post, thanks. Going to figure out if I should stay in tech sales or pivot to general client sales.

    • TechSales says

      I have my ups and downs but I’m relatively consistent.

      agreed companies will drop you eventually if you cant produce.

      • says

        nothing beats working from home when you dont need to be in the office though. alot of time to work on *side* projects. Plus for my company (idk about yours) most sales guys are gone 50% of the time travelling to client offices so there’s no need for “appearances” (look like you’re working hard, coming early, leaving late) just getting OTE is the key

  20. hunter says

    I am currently a Software Engineer and am thinking about breaking into sales, by SDR, I assume you mean sales development representative. I am assuming that when you first start as an SDR, you will be making inside sales calls where you make calls from the office or your house. How much travel is involved, I don’t know how to drive a car, not sure if you need to drive to suburb or something to meet the clients in time as a sales person. I guess my question is to ask you to kinda break down the day to day schedule of a Software Sales person.

    • TechSales says

      sdr just call and prospect all day. if you’re already a Software Engineer you might be able to go straight to AE or SE.

      • hunter says

        Sorry, could you say what AE and SE stands for. Like Account Executive and Sales Executive? I saw a lot of job postings for sales engineers. What are those? Thank you.

      • TechSales says

        sales engineer is like 60/40 70/30 base/comm

        you don’t really have a quota and you support the team in giving demos and helping with technical stuff. your job is a lot more secure. a lot less risk but your possible upside is nowhere near an account executive

        ae = account executive. basically a sales rep.

  21. 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.

  22. albert says

    what cities are these high paying technology sales job/career located mostly, could you do sales for a company like oracle or google, SAPS without having to move to an expensive city like New York city or San Francisco, says that if you live in a major city that is not as heavily focused on tech like Philadelphia ? Thanks for doing this.

    • a says

      The bigger the city the more tech opportunities. Simple as that.

      I’m sure Philadelphia has opportunities just not as many as NYC or San Fran. Cities like Austin are good because they are not too expensive.

      If you’re open to opportunities you might be able to progress faster too. If you’re at the only tech company in Nowhere KS you’re kind of out of luck.

      In NYC you can know a few recruiters and be on a phone interview within 24 hours if you want a new job.

  23. D-Train says

    I’m 29 yrs old work in tier 3 Wall Street making $110K in NYC. Made a lot of bad decisions career wise, but luckily found this blog. I have an easy job with lots of downtime and will probably max out at $200K, but no more than that.

    After reading Efficiency it’s clear I should move to sales. At my current company, I put out fires, diagnose issues, and will occasionally go to a bank to give “demos”, but I am not a salesman, more of a customer relations/ tech contact. If I have experience dealing with angry traders, some client entertainment experience, and give “demos” now, would I be able to spin that and go directly into an “AE” role?

    My compensation will probably hit $125K this year at my job, but I don’t like finance and understand the power of learning sales and how that will help many aspects of my life. Would I be crazy to move to a junior sales role where my comp might be 70/30? I know it’s a gamble, but it seems worth it. There’s no undo switch so i’d hate to hate my job and be making $25K less.

  24. Student sales says

    I’m a college student who’s taken wallstreetplayboys advice and made sure to get sales experience with my POS student jobs since junior year of high school.(Clothing/knik knaks and Watersports) but finally got a good job selling timeshares. Im not a natural by any means but between learning game and learning sales the improvements are drastic.

    I have two questions:
    -For TECHSALES: If I follow the path to get into banking,and after a while decide I want to switch over to software sales would it be difficult? Would my experience selling timeshares before completing my degree be helpful for getting my foot in the door?

    -For WALL STREET PLAYBOYS: Will bringing up prior sales experience on my resume help with landing a front office job on wall street?

  25. HarmonicPinch says

    I’m 25, working in IT for the past 2 years at an international bank in NYC as a software engineer. Make like 80k and it’s super chill 9-5.

    I have a good holistic knowledge of technology and also can obviously develop. Would assume that puts me above the average SDE bro. I played sports in college and am pretty personable, although some days slightly autistic. Think there’s a good path to spin that background into a solid AE or some sort of more technical sales role that’s above base level (and pay)?

    • EE says

      I would say most sales managers are more concerned about your personality and selling potential. All technical training will be covered extensively the first week on the job.

      It all depends on how you spin your background. Door to door sales is a great bonus on your resume. I did lawn care for my neighbors in high school. I spun that as knocking door to door since I was 14 years old.

      There’s also no real way to double check that. So, theoretically, you could just put that on your resume and no one would question you

    • TechSales says

      if you are in NYC I would call up a recruiting firm and see what they can do.

      the one I recommend starts with a b and end with etts. they place a ton of tech people.

      try to angle as an SE is probably the best way in if they won’t give you a job as an AE.

    • ohaithere says

      >> I have a good holistic knowledge of technology and also can obviously develop. Would assume that puts me above the average SDE bro.

      Nah fam. If you’re actually an above average SWE, you would easily clear 200k-300k total comp within your first 3-5 years out of school. 80k is extremely low for total compensation a good SWE in NYC.

  26. AspiringTechSalesKillah says

    This guide is fantastic. Currently have two years experience as an SE and about 9 months in a B2B sales role in an unrelated industry. Brought in enough business so far this year where I’ve proven I can sell, so planning to make the shift back into tech as and SDR or AE by the end of the year.

    I’ve had a number of interviews for SDR roles over the past year. Having technical background can be helpful, but I can tell from my interviews that they really grill me about my desire to switch to a purely sales role. For anyone with more of a tech background who wants to switch, I would make sure you can handle objection questions such as “with such a strong tech background, why sales now?” etc. These tech firms are really looking for a competitive attitude, and the ability to think on your feet.

    This guide is great given the timing.Picked up some great pointers, so thanks!

  27. Engineering Student says

    Love the guest posts. Would be very interested in one on quantitative finance assuming you know someone who would fit the bill.

  28. Jeremy says

    Your blog helped inspire me to quit my corporate finance career making $200k/yr in July 2016 and start a real estate related business. I am 36 years old and knew that my future income potential would be limited to <$500k/yr in my career.

    My first year of this new business generated $340k of net profit. Now that business is fully scaled up in one area I am projecting $1M net in second year and am making plans to expand to a second area. This will consume 3 days per week of my time.

    I am going to spend the remaining 2 days per week with family, focus on improving my health and expand my knowledge base.

    Thank you guys, keep it up.

  29. Anonymous says

    I do market research consulting for commercial tech, interested in this route in the future given my current role forces me to learn about a wide range of SaaS, IaaS, and PaaS.

    I’m also considering getting a deeper understanding of the technical aspects and going the SA route.

    Thanks for this post.

  30. Student_Canada says

    Amazing post. I have been looking for something to outline the path to Enterprise Sales and this is perfect. Entered final year at University and this post has solidified my drive to get into the industry. Cold messaged several Account Executives at major firms and start ups and response rate was high.

    I have no background in tech and recently interested in tech sales. Experience includes a few internships for major bank (not investment banking) and several years as a waiter/server. Planning on getting out of the financial services industry and hoping to land a role as an SDR and work my way up in < 1 year. I do not see many postings online yet for SDR roles. Will be looking for full time roles to start in ~8 months and have started to reach out to Account Executives now. Not sure what the recruitment timeline looks like for sales, but hopefully I am on track. LinkedIn is a great tool.

    First comment on the blog. Have been following since entering University 4 years ago. You guys have had a major impact on my last 4 years. Recently finished Efficiency and will re-read. Great post and hope there will be more to follow on the topic of Enterprise Sales.

    Keep up the great work.

  31. evader says

    A lot of this post is wrong. Tech and Silicon Valley are not friendly at all to salesmen-at Facebook for example, the salespeople make pennies of what the engineers do. Of course that’s just one example, but you’re coming off as someone who doesn’t understand much about Silicon Valley. Bringing up Oracle is a really bad example because Oracle isn’t doing jack today. The main companies are FB, Google, Amazon, Apple, etc. and almost none of them care about salesmen. Plus, the Salesforce founder, Mark Benioff? Dude was a great VP at Oracle, but not in Sales: the guy knew everything about engineering. It’s not like your views are totally off, but increasingly, companies are more Engineering driven, and in Silicon Valley, the “salesman-only” professions get nothing. Believe me, I know the importance of sales-don’t get the wrong idea from this comment. Everyone should know how to sell to excel at life. But sales without tech expertise, or “salesman-only” people, get nothing in Silicon Valley. I love a lot about your blog, but as someone who knows the ins and outs on tech, this post has got problems. You guys are men who can take constructive criticism, so try and learn a bit more about tech-most of your other views on life are spot on.

    • Wall Street Playboys says

      We’re in a good mood, we didn’t even write the post, and anyone who reads this will realize you missed the point entirely. So we’ll let it stand.

      Talking about fb/amzn/goog on an enterprise sales post? Come on Man. Especially when you know we use fb/goog all day everyday for ads… again. Come on.

    • CloudSales says

      Have you sold technology in a B2B setting before? If you haven’t, you are not qualified to say if this post is right or wrong. I have been in the industry for 2 years and this post is pretty accurate based on my experience.

      Don’t have any experience selling at Facebook so not going to comment on that example.
      Oracle is still a major player in the enterprise tech space – pretty much all the fortune 2000 have Oracle products in some capacity. They control a lot of the back office technology systems for these companies.

      You are listing companies that are mostly B2C – this entire post is about selling technology to other businesses. You seem to be missing the point.

      You cannot sell to the enterprise without a well-oiled sales team. Why? Because your prospects can lose their job if they buy the wrong solution – your job is to convince them that your offering is the best fit and build comfort.

      Not trying to downplay engineering here – but enterprise tech deals are not typically won because of product features because most competing products in the market have very similar features and functionalities. These deals are won because the salesperson is able to differentiate their offering and win the deal.

      Google Cloud and Amazon Web Services both have very well paid and large sales teams to give you an example.

    • techsales says

      The better sales team will (usually) win. And in the case of millions of dollars on the line the skillet is inherently valuable — so will always be in demand in competitive b2b situations.

      If you pay less the sales team will then jump ship asap to your competitor and then you are SOL.

      The dude calling on existing advertising accounts at Google of course is not going to be nearly as lucrative — its pretty ez. Anyone can do that.

      But cold calling a CIO of a F500, or leveraging your personal network, to then carefully show them what they care about over months or years and delicately close the deal. That’s what you are paid the big money for.

  32. Playing Catch Up says


    What do you think about someone working in sales in their 20s, going for an MBA at some point, and then trying to break into Wall Street since they did not have the resume for it out of college?

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