TheTrilogy profile picture
TheTrilogy profile picture

TheTrilogy

AE

Executive
Fire Starter
Contributor
+2

Calling all current and past pre-series A/Series A reps: should I make the move?

Hi sales savages, I was hoping you can help out here. I am currently working for a $100M+ ARR software company that is undoubtedly a market leader in the space. Things are going well, I am one of their top performers and have been making decent money here ($200K+).


A pretty interesting opportunity caught my mind - a new player in the space is rapidly growing and taking market share by providing considerably faster speed to value for the customers. They're only sat at 12 people right now and are focused on PLA (Product Led Growth) with their GTM function being spun up now.


They're looking for their first AE, with generous comp packages and stock options. I am tempted for several reasons:


  1. Stock Options: they're soon going to raise their series A and are being generous with the stock options
  2. Product Market Fit: I believe that their product solves an issue that many competitors don't currently, including us, which I believe disrupts the market
  3. They're growing at 12% per week, with some big hitters from major companies joining the board
  4. The opportunity to be the founding member of their GTM function, career opportunities, and influence
  5. Cashing out stock options in a few years
  6. Their base comp matches mine, it's just the OTE that I'm concerned about

Now, I heard enough about how hard it is to work at startups or series A companies. But I am curious if anyone can please advise on:


  1. Things to look out for, means to validate the opportunity
  2. What is a good % share for that stage of a startup?
  3. Outside of long hours, what else should I be aware of working for a company at this growth stage?

Thanks a lot for your advice and help!

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23 comments

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poweredbycaffeine
WR Lieutenant
5
☕️
1) Does the founding team have extensive success? Have they lead previous companies to acquisition or IPO? If a first timer, I’d tread VERY lightly and inspect the shit out of their skill set.

2) What’s their cash flow look like, and do they have VC money from funds that are currently spending money? If they are an A and haven’t raised in more than a year, they are likely dying on the vine.

3) Do you have the skills required or the desire to literally have ZERO guidance. Can you create a cadence, build pipelines from nothing, and expect no support? It takes a certain person to adapt to that environment, and you need to know yourself.
TheTrilogy
Executive
0
AE
Really appreciate your input, thank you.
ZVRK
Politicker
5
Enterprise Account Executive
I'd say it's a gamble, sort of a high-risk, high-returns type of situation you're in.

I'm currently with a bootstrapped startup-ish company, and here are some challenging circumstances I had to accept since I joined as AE #2 (first AE was the current CRO):

- A lot of pressure on sales. Sales is what makes or breaks the growth of the company, especially when it's beginning to grow rapidly, so there are a lot of eyes on sales, not least from the board.

- Processes and systems are still in the creation and testing phase. This can be frustrating if you're used to a well-tried process of selling with your current company.

- CEO-led sales. The CEO will be super involved in every major sales cycle. While this can be great and can maybe help you close some deals, sometimes it feels a bit too much.

Apart from these, the benefits are obvious as you've stated.

Happy to answer any specific questions you have. Just for context, I'm in the HR Tech Enterprise space, with a software company in the $5-10M ARR range.
TheTrilogy
Executive
0
AE
This was super helpful and insightful, thank you.
braintank
Politicker
4
Enterprise Account Executive
If things are going good why leave?
TheTrilogy
Executive
1
AE
Seems like a more exciting company, opportunity to be involved in something at the early stage, shape the GTM strategy, career opportunities. At this company I am now I am just a top rep, but one of many. And I don't want to/see myself in a leadership opportunity at this company in the future.
braintank
Politicker
3
Enterprise Account Executive
You also have the opportunity to make no money and be unemployed in 6 months...
CuriousFox
WR Officer
2
🦊
Folks seem to forget this part...
TheTrilogy
Executive
0
AE
Appreciate this 🙏
Sunbunny31
Politicker
4
Sr Sales Executive 🐰
Can you afford to take on this amount of risk?

If the worst was to happen and you end up without a job after 6-12 months, are you able to weather that and have the experience to find something new?
TheTrilogy
Executive
0
AE
I’d land on my feet pretty quickly, but youre right. Risk is high.
Diablo
Politicker
2
Sr. AE
You gave your answer yourself to braintank’s response. If I were you, I would still stick to my current company because the amount of added pressure I will have in a series could be tremendous. As ZV said, it’s a gamble so if you are lucky you will not regret but think both ways
startupminion
Executive
1
BDM
I was working at a pre seed startup and told they were going to raise in 4 months at the point of me joining. 4 months turned into 6, into 8, and guess what, after 1.5 years, they still have not raised and are no longer trying to raise and would like to continue bootstrapping instead. The cashing out of your stock options may never happen.

Being a founding team member was one of the things that lured me into the role, but I soon realised that it’s not that great. Founding team member = work as hard as the founders, while still having to defer to founder(s) and getting just a fraction of the equity they have.
oldcloser
Arsonist
1
💀
I'm a glutton for startup punishment. But knowing that means I know every eyeball is on me for results. Nobody will give a flying fart about the cool new process you stitched together or the dazzling thing you said or did that made a conversation happen. You have to be able to operate without attaboys. Do a gut check there.

Next, you'l have to constantly merchandise your efforts to a group of people who just generally don't get it. They won't look. But if you don't communicate they'll wonder. If they wonder, they'll ask. If they ask, they'll want to have input. It will be worthless. You'll have to listen.

I'd suggest a really honest personality evaluation of those to whom you'll report. Sales has enough daily misery that you don't need personality conflict or panic on top of it. I'd determine their real tolerance for sales cycle. Dig deep here. If they tell you its 6-months, make sure they actually believe it. If they don't, you're miserable at 90 days guaranteed.

So, if you like the idea of building shit autonomously with a revenue gun to your head and all of the glory that may or may not materialize somewhere down the road. Startups are cool.
ChumpChange
Politicker
1
Channel Manager
Definitely a high-risk / high-reward decision. Series A signals to me that nothing is built out and they've been somewhat stumbling into their progress. I suppose the question to ask is what is their expectation in 3/6/12 months and what type of control do you have over the GTM function?
Maximas
Tycoon
0
Senior Sales Executive
Just don't risk your current position at least for now ,but just keep it your mind as a plan B,for example if the promotion cycle -or anything similar-didn't go well as expected at your current company you may think of giving it a shot in that case to get to the other one...
Justatitle
Big Shot
0
Account Executive
It seems like the series A is on the early adopter size and usually it’s really hard to break into the mid-market enterprise echelon of clients because there’s features or functionality that will take months to years to build and they are always strapped for resources. That said not sure what TAM is but you being the first AE will likely have a 3-4 month leash to see if it works and if not then it’s see you later. If they’re open to sharing ask when they intend to go for series B so you know how much pressure you will be under
Pachacuti
Politicker
0
They call me Daddy, Sales Daddy
High risk / high reward scenario. It isn’t the opportunity you need to evaluate, it’s the potential downside. If they go out of business in 6 months (or let you go) what’s next for you?
buckeyenation
Acclaimed Answer
0
AE
Sounds like they want to hire you as a rain maker. Careful. Sales person is worth nothing without lead support behind them.

I am a 2x founder and we always reps too early.

100m arr = well oiled machine. Series a startup = dumpster fire.

And regarding your options - google Amt. alternative minimum tax. If you leave the company early after vesting but before liquidity event, you are stuck with big tax bill if you exercise options.

There is no such thing as a get rich quick scheme.
TheTrilogy
Executive
0
AE
I’m incredibly grateful for your comment. Thank you.
TheTrilogy
Executive
0
AE
This was my first post here and I’m so grateful to everyone for commenting and providing your perspectives and inputs. Some things I simply wasn’t aware of, some I didn’t consider hard enough. Thank you all.

To those interested: I decided that I’ll stay with my current company for now and likely won’t move into non established GTM functions for at least a 2-3 years. Your comments made me reevaluate my character and my financial goals, and I’ve realised that it’s a much wiser choice to stick to large companies while things are going well.

Appreciate you all, thank you!
CRAG112
Valued Contributor
0
Account Executive
What did they raise for seed and what did they raise for series A?

remember. The success of sales will be fully on you if you take this role. Whatever you do now to get 200k a year, if you are willing and able to do 3x to 5x that daily to be successful, guaranteed you can be.

you’ll also have to be a master of managing up, kissing butt, not getting someone to hate you, etc.

hard to say for sure, but this role could be as dangerous as someone’s first VP sales role at a similar company.
CRAG112
Valued Contributor
0
Account Executive
I think this is definitely what people mean by gambling on yourself.

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