55 Comments
Aug 3, 2021Liked by BowTied Bull

I followed this path to a point a few years ago.

Pissed away my twenty's in accounting & alcohol. Discovered WSP and decided to stop wasting my life away.

First: SDR role at a start-up in Paris

Second : SDR Role at FANG level company in Ireland

Third : SMB AE at High Growth Tech company selling all over Europe @90k

All in 2 years.

Then started programming to understand tech better and discovered I was so much better at tech than sales it wasn't even funny.

Fast forward 3 years and I'm an independent developer @140k

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Currently an SMB AE and a well known SaaS company. Education is in engineering, enjoy sales. Comp over the last 5 years has look like the following, all at the same company.

Year 1 (SDR): 55k

Year 2 (Associate AE): 82k

Year 3 (SMB AE): 122k

Year 4 (SMB AE): 220k

Current Year (SMB AE): 150k, on track for 270k.

With 5 years experience I get weekly emails for jobs that offer 200k plus equity at startups with full remote option.

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For anyone looking to get into tech sales, there is a website called RepVue (I am in no way affiliated and it's also a free resource) that gives you a breakdown of various sales organizations with scores that are aggregated anonymously based on ratings from reps that work there. It's like a Glassdoor type website but exclusively for salespeople.

You can see the percentage of reps that hit quota, average base salary, average OTE, top performer ceiling, inbound to outbound ratio, quality of training / enablement, product market fit and a whole bunch of other valuable pieces of information to help you make an informed decision.

Each organization is then given an overall rating and ranked relative to others. This puts a lot of the power back into the hands of sellers and gives you the insight to determine which sales organization is the best fit for you.

This is huge because if, according to RepVue, 70% or more of sellers at a certain company are hitting their quotas, the product market fit is solid, you get a good amount of inbound leads and the training is on point, then you know you have a 70% chance of making great money (as long as your experience aligns with the requirements for the role).

By the way, they have breakdowns by role too, so you can see SDR as well as AE data, and it's also broken down by market segment - SMB, Mid Market and Enterprise.

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My addendums:

1) Move to high-profile tech company if possible. Even SDR role is fine. Better for literally everything.

2) Territory is king. Sure, there are exceptions but generally you want to make sure your territory is good before you start. Even the best sales reps get burnt out if their accounts are shit.

Best combination is good fucking product + good fucking territory.

3) Degree etc. doesn't matter in sales. If no degree, get into SDR role at startup. Hop to enterprise by prospecting the hiring managers (treat it like booking a meeting) after 6m. After that, you just need the jump to AE - and then you're golden.

4) At least in my country, most sales reps have either somehow landed in the role or are lazy. You'll stand out if you go into the role on purpose + work hard.

5) Amount of social skills you learn is unfathomable.

6) Politics matter. A lot.

Ego of sales managers is through the roof as well (generally, everyone in sales has a high AF ego)

If someone wants to do sales in Europe, do this (if desperate):

1) Move to Dublin and get entry job at high-profile Tech company. Yeah it sucks, weather is shitty, girls are fat - but eating shit is part of it.

2) Stay 1-2yrs and try jump to AE.

3) Move back to home country and always be the guy from "XYZ company".

4) Get recruiting messages everyday for remote positions

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Spent close to five years in enterprise SaaS sales mostly at start-ups then Fortune 500 (started as an SDR -> AE). Don't do it unless you have no education or technical ability. You'll be stuck in a monotonous career you hate making a lot less than you would actually building the software or products you're selling. I've seen way too many career SDRs and AEs in their 30s with no skills and dismal future career prospects. Everyone thinks they're going to be the top rep when they start, but you never quite make your OTE and end up looking for a new job every 15 months or so.

Compensation is typically a 50-50 split between base and commission. SDRs start at $50-55K in high COL areas with an ~$100K OTE; AEs are usually at a $65K base. You might get 4 figures in commission in a good quarter. What you actually make in sales is a lot less than what you're told. The bigger problem is that it's difficult to get out of the field when you eventually burn out. You learn nothing tangible as a sales rep other than how to use a CRM. In retrospect, I'd skip the grind altogether and go into a technical role. You can (and should) learn sales on your own. No need to make a career out of it.

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This is rock solid.

I went the coder->technical sales route. Spent 10+ years as a developer and stumbled into sales engineering because I wanted to get more face time with people. Best accident I ever had.

Don’t be like me, make a plan and hit it without all the mucking about in stagnant coding positions (minimal upside earnings).

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Whatever you do don't go into mutual fund/annuity wholesaling. Made that mistake out of college and it set me back ~3y. Software sales is the way.

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Fantastic article - I followed the original WSP articles on Enterprise Sales and can confirm this is an awesome career path

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Thanks this post is a goldmine.

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What's your assessment of being an AE (field sales, yet now mostly remote work with online meetings) in a firm like FedEx/UPS?

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What is the best way to get ahold of the referenced E-book?

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Anything you would change or add for a 40 year old retiring from the military?

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This has been a fantastic read. But does anyone have any advice for someone who's been out of the workforce for a couple of years over the pandemic? Would be much appreciated.

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I've been in Corp FP&A at SaaS companies for the past 4 years. It's stable but low leverage with a really boring career trajectory unless you jump on to a rocketship at the right time. Been thinking about pivoting into Sales for a while now. Seems like the main (only) route is to get an SDR role and then move your way up. Does that check out? Should I just be scoping SDR gigs on LinkedIn and putting my name out there?

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Pure Sales role just seems to intimidating. Yes Sales is needed in everything. But a pure sales role of just cold calling and talking all the time, just sounds like hell. A Tech role in process design or customer experience or something in between (synthesizer) seems much more rewarding.

My default is introverted, the guys who absolutely smash these SDR type roles that I have met are more often you're typical extroverted types.

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