UrAssIsSaaS

SaaS Eater

Acclaimed Answer

Why Joining that Series A is a Bad Idea

We see a million posts in the WR with younger AE's and SDRs evaluating a job opportunity at a Series A or Seed round startup.

I'm here to tell you why you should avoid that role like the plague if you have less than 5 years experience in the space.

(@braintank I hope Im not stepping on your toes here)

Joining a Series A or younger startup is the equivalent of walking into a kindergarten classroom after snack time and everyone just drank 3 cokes. No one knows what the fuck they are doing and everyone is bouncing off the walls.

At this stage its highly doubtful that the product has market fit. Shit, its normally just a thought still and is barely even MVP at this point.

The GTM strategy is undefined at best and they probably dont have ICP figured out yet.

Sales leadership has not been put in place, sales best practices are undefined, and the tech stack you need to be successful does not exist yet.

If you are an an SDR looking to become and AE or an less tenured AE coming from a larger company, how the fuck can you succeed in this situation. You are walking into a gunfight with a pool noodle. Don't let the founders and recruiters woo you with the promise of IPO, most startups fail.

Im not saying you should never take a role like this, if this is your end goal, great. Go get 5-10 years of really solid experience building out sales process and refining your craft before taking on a challenge like this. You will thank yourself for it in the long run.

🎈 Mentorship

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121 comment

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braintank

Politicker

31

Enterprise Account Executive

Series A founder before you're hired: we have product market fit and are being used at 50% of fortune 100

Series A founder after you've signed offer: Our product doesn't really work and no one is willing to pay for it. I let my buddy who is a janitor at Cisco have a free trial, so go make something happen! If it's not closed in 3 weeks we're fucked.

UrAssIsSaaS

Arsonist

7

SaaS Eater

This is so accurate its painful

Cafe.con.Leche

Executive

3

SDR

GD, I’m cry laughing right now 🥲😭🤣😭

quinoa

Contributor

1

order taker

Yuppppp.

justatopproducer

Politicker

1

VP OF SALES -US

Lol must be a hell of a janitor

Kenbee

Old School Bravo

1

Student

1000% accurate. I was lucky the company I joined was acquired after 1 year....but that was 1 hard year.

CoorsKing

WR Officer

14

Retired King of the Coors Knights

Well said. Add this to the list of posts I want pinned so we can stop seeing the same question over and over

UrAssIsSaaS

Arsonist

5

SaaS Eater

poweredbycaffeine

WR Lieutenant

13

☕️

I thrive in seed and Series A companies, but I’m also going to die young because of it. Choose your destiny wisely, children.

UrAssIsSaaS

Arsonist

2

SaaS Eater

You also have way more than 1 year of experience in this world.

poweredbycaffeine

WR Lieutenant

5

☕️

I should really write the medical implications of the early stage life style.

UrAssIsSaaS

Arsonist

2

SaaS Eater

You should

harebrained

Politicker

1

Enterprise Account Executive

My time in a Series A led to 15 extra lbs and the most drinking I've ever done at work

UrAssIsSaaS

Arsonist

1

SaaS Eater

Fun right?

emkayxx

Opinionated

0

Enterprise Account Executive

Haha well said.

JustGonnaSendIt

Politicker

10

Burn Towns, Get Money

I 100% agree with this.

However, many moons ago, with 1.5y of experience as a recruiter, I joined a Series A startup as their first BDR. I was woo'd by the founders and the dream of striking it rich on an IPO. The kool-aid tasted great.

It was hectic as fuck, but ultimately I think by hanging on and helping figure out how to create a real business, I have dramatically accelerated my experience level.

After 6 years, and being minted a Unicorn at Series F, I left because the PE money started driving the culture in a direction I was no longer compatible with.

If you can afford to get paid dog shit and are actually committed to learning, a Series A is a great crucible for sales experience, if they have good people and a good culture. Equity can be a nice bonus in the future, but it very rarely pays out.

If it's just bro-land, RUN from that bitch. Go work at a larger company, get some structure to your process, then come back at Series D or later when they've grown up.

UrAssIsSaaS

Arsonist

6

SaaS Eater

It takes a very special person to succeed in that environment, not saying people cant but its rare. Sounds like you are in that group, which is awesome.

The majority of people dont though haha.

OldSaaSRep

Old School Bravo

3

Sr Enterprise Rep

Agreed. You have to wear multiple hats and thrive in an environment with no structure. Deals are won because of creativity, not by adhering to a process. If you're good at this level you can impact the future by establishing processes that work etc but it's certainly not for everyone.

lehman

Good Citizen

1

BDR

What does a series A environment offer in terms of development that a larger organisation lacks? Apologies if it’s a stupid question

UrAssIsSaaS

Arsonist

7

SaaS Eater

Series A and younger will have very little structure, process, training, and playbook in place. Larger orgs will have a lot of this ironed out already.

So in theory a Series A or younger will give you more freedom to develop but if you dont know what youre doing, its going to be hard to develop this right skills and know where to go. This is the role your manager should play in helping you develop but in these very young companies, you wont get that guidance.

I would argue that larger more defined orgs will offer more development than a small startup.

JustGonnaSendIt

Politicker

5

Burn Towns, Get Money

Exactly this. Series A is the wild west. Very little oversight, very little structure, and what little oversight and structure exists is constantly changing it's shape and goals.

So, someone who lacks experience will really struggle unless they either have external mentorship or do a great deal of self-education about the challenges being faced.

There is also the rare founding team that has done this before and has a recipe for success. But typically they also have a coterie of people they'll drag in to Series A because they already know them, making it tough to organically find these opportunities.

I had the benefit of both external mentorship and a personal interest in what it takes to build a successful tech company, so I stuck with it.

There were times I was on top of the world that something I did worked. Many times, I felt incredibly defeated and the goal posts were constantly moved by our Founders.

There was a period of time in the middle of this experience where I was about to jump off the ship of being in sales all together, because I thought I was useless. But somehow we pulled thru and I now feel like a I have a huge edge on some folks that have never had that experience.

Net-net it's a very high risk / high reward game, where you often lose. I consider myself incredibly lucky.

Series A is the career equivalent of playing Roulette. Lots of ways for it go to wrong and very few ways for it to go right. But when it goes right... OH BABY do you win financially and psychologically.

It's much better in the vast majority of cases to get good fundamental skills from a larger, more mature, more structured organization. THEN you can take those skills into the Startup market if you wish and attempt to strike gold.

UrAssIsSaaS

Arsonist

5

SaaS Eater

Outside mentorship is so key if you are going to take this on without the requisite skillet.

Also these are awesome insights, sometimes I forget that there is real value in the WR.

bandabanda

Tycoon

5

Senior AE Mid Market

“Many times I felt defeated and the goal posts were constantly moved by our founders.”

Damn, so much truth in this. I’m at a series A today and have yet to hit quota, I’m the top performer. I often think “how the hell am I going to move up if I can’t say I can carry quota.” At the same time, my performance can speak for itself. I consider myself extremely lucky too though…I’ve developed a great relationship with my manager and there’s lots of trust there.

I flip flop every day between leaving because I see the cracks forming and wanting to stick it out for the next series round. It’s such a wild ride 😆

Lioness

Good Citizen

2

Sr Field Enterprise Account Executive

You'll develop patience or you'll develop high blood pressure.

Larger companies have inefficiencies too, but inexperienced startups make and cling to mind-bogglingly bad decisions. This isn't just inexperience; It's poor judgment.

Don't make the mistake I did in thinking I'd be the voice of reason; It's like trying to teach a cat to bark.

JustGonnaSendIt

Politicker

1

Burn Towns, Get Money

Good callout. Patience and perspective are key in any selling role.

There's always drama, both internal to your company and external with customers or the market.

You have to be consistent, persistent, and disciplined. And none of those are possible if you're emotionally running around making snap decisions.

The other thing about being in Series A that you have to consider is that it's the first of many critical learning cycles for the business. The recipe for success is not figured out.

So don't let missing quota bother you if you're the top performer. What you're doing is making an impact that is bigger than just hitting a number. Each success brings you closer to the right model, and each miss is a learning opportunity.

braintank

Politicker

7

Enterprise Account Executive

100%

braintank

Politicker

8

Enterprise Account Executive

shameless self promotion: https://bravado.co/war-room/posts/somewhat-comprehensive-guide-to-avoiding-a-toxic-startup/comments/180929

UrAssIsSaaS

Arsonist

4

SaaS Eater

No shame in this - promote that fucker. Its a great piece!

bandabanda

Tycoon

1

Senior AE Mid Market

Thanks for this!

CuriousFox

WR Officer

7

🦊

Dude. This needs to be pinned. 👏👏👏

UrAssIsSaaS

Arsonist

4

SaaS Eater

Appreciate you

TennisandSales

Politicker

7

Head Of Sales

Yep you nailed it.

If you are new, you HAVE To evaluate your manager. your direct manager will be SO critical in your development.

If you are reporting to founders or first time sales leaders. yikes.

do some MAJOR vetting

carbonara

Executive

1

Account Executive

Just joined a Seed / Series A and it’ll be first time sales leader coming from FAANG. However, very strong founding team and team across the board.

Tough but this is a great post!

OldSaaSRep

Old School Bravo

0

Sr Enterprise Rep

One suggestion, don't worry about instilling process right away. Figure out how to sell it, bring in rev, then put a proven system in place. What works at FAANG likely won't work right away so stay flexible and adjust quickly.

carbonara

Executive

2

Account Executive

Good point, just trying to get things into pipeline at the moment as we sell it, and bring in revenue!

OldSaaSRep

Old School Bravo

1

Sr Enterprise Rep

Good Luck. I learned the hard way.

UrAssIsSaaS

Arsonist

1

SaaS Eater

Ya this is great advice. If youre joining as the first sales leader, just focus on figuring out how to acquire customers, once you have a decent idea there you can begin to see patterns and iron our processes from there.

OldSaaSRep

Old School Bravo

0

Sr Enterprise Rep

Exactly! And acquiring customers doesn't always equate to revenue. The first few customers may be testing the product for you. Focus on users, gaining feedback, the value to the customer (often very different than was intended). Make them very happy customers then use that as a springboard to the market.

UrAssIsSaaS

Arsonist

2

SaaS Eater

Ya totally. If the product is that young youre probably going to have to give it away to your first 10 or so customers just so you can start to get feedback.

If you have a good product team, what youre selling should look vastly different 6 months later and start to look like something that there is an actual market for.

peachykeen

Politicker

5

sae e-commerce

Sorry savages, I indeed asked this question not too long ago. Everyone was very helpful, as was this. Despite having been in sales for a long while, I honestly don’t have much (any) experience in how tech companies work, what’s good and what isn’t. Soooo #learningcurve

UrAssIsSaaS

Arsonist

6

SaaS Eater

No apologies needed. This gets talked about constantly in here so I figure if we can get it all into one place as a resource for everyone, were all better off.

And I dont have to copy and paste the same response 100x

bandabanda

Tycoon

2

Senior AE Mid Market

Really wish there was a way to pin the best posts about certain topics. You'd have a few in there for sure @UrAssIsSaaS (your guide from last year was awesome).

People can use the search bar and spend a few minutes searching but still miss it unfortunately. And then we roast them for posting about something that's been said 100x

UrAssIsSaaS

Arsonist

2

SaaS Eater

Appreciate it. I know this has been requested quite a few times. Every other forum I have ever used has sections and stickies, why the WR doesnt is beyond me.

Jbeans

Opinionated

1

Director of Sales

lol yep it’s a tough crowd.

ChunkyButters

Tycoon

5

AE

Great post!

From personal experience this is spot on.

I was hired as an SDR and within 1 year of joining the org, we went through a massive layoff and I was the only sales rep left. I was promoted to an "AE" role, but not doing any outbound. The Board of Directors had us pause all outbound until the product was fixed (hint: took about a year).

I gained great experience learning about a business, start ups, operations, and working with the team. I took it as an opportunity to join sales trainings, read, and explore different ideas about a sales process. This actually gave me the opportunity to develop our sales process from what I thought would be successful...from my long 2 years of sales experience.

We hired a VP of Sales, and what I developed was actually a good foundation for him. He took it and applied his experience to make it a more defined process.

We started to actually see some traction, I was getting closing experience, and deals were filling the pipeline. Then...COVID...and more layoffs and I was on my own again.

So, I decided to find a new role. I had a fair amount of time and good experience from my last gig, but limited ACTUAL CLOSING / SELLING experience. Which, made finding a new gig harder.

I ended up in a great spot, and love where I work. Slanging deals without issue and have really developed faster in my current environment. We're not a startup, but a small PE backed SaaS firm. More defined processes, leadership, and training.

The experience I gained in the Series A was incredible, but it definitely created other challenges when looking for traditional AE roles.

UrAssIsSaaS

Arsonist

2

SaaS Eater

Appreciate you sharing! definitely good learnings all over the place. Tough to learn if you're not put in a spot to sell tho.

ChunkyButters

Tycoon

1

AE

Exactly.

I gained an incredible amount of non-sales experience. Which...is great...for when I decide not to be a seller.

I joined to have a meaningful impact and not be just sales person #420. Which, I got out of the experience.

Finding a middle ground was important to me when I got my current role. 100 person company, great product / market fit, but not large enough where I get lost in the numbers.

alphasales

Politicker

4

Sales Manager

Can confirm, drank from the cool-aid. Joined a seed round start-up thinking I was hot shit.

No process, no tooling, no ICP, no product-market fit. These companies take advantage of cheap capital. Don't think these founders intentionally want to fuck salespeople around they're just often very inexperienced.

You need to have a fucking strong track record of building well-oiled easy to execute go-to-market strategies.

UrAssIsSaaS

Arsonist

1

SaaS Eater

Bingo

Gyro25

Notorious Answer

3

Account Executive

My first sales gig was a series A in HR automation like literally every other fucking company in the country.

Surprise surprise, our budget was ass, no product market fit and we went bankrupt. Lmao, I did learn al lot though, I learned to stay the F away from series A startups that have no direction or a good product. A hard lesson, but a lesson nonetheless.

UrAssIsSaaS

Arsonist

2

SaaS Eater

Not everyone has to go through this!

Gyro25

Notorious Answer

1

Account Executive

Lol definitely not, but I was out of college, broke, and naive, and didn't even know what a funding round was. Definitely learned quite a lot though.

thatsaleswoman

Member

3

Enterprise Account Executive

PIN THIS PIN THIS PIN THIS 👏🏼👏🏼

UrAssIsSaaS

Arsonist

1

SaaS Eater

appreciate it!

bandabanda

Tycoon

3

Senior AE Mid Market

You forgot to add they leadership will constantly say “we just hired this new developer/product manager/sales leader and they’re going to fix everything.” 🤦‍♂️

So accurate I’m crying (we finished our series A last year). I lost it at the kindergarten analogy. The CEO’s motivation is literally “I want to make tons of money.” Which isn’t bad, albeit. But very little vision and ACTUAL leadership happening. Doesn’t seem to care about customers at all honestly. Product team is all over the place.

God bless you for this.

UrAssIsSaaS

Arsonist

2

SaaS Eater

Yup this is why most startups fail. If you can find the right spot its an awesome experience, if not you're fucked.

Cafe.con.Leche

Executive

2

SDR

So, what about startups that are commission only? Asking “for a friend” 😬

braintank

Politicker

3

Enterprise Account Executive

the worst of both worlds ;)

UrAssIsSaaS

Arsonist

1

SaaS Eater

Ive already given you my thoughts on this haha

Justatitle

Big Shot

2

Account Executive

Yeah, series A is highly risky but can be incredibly rewarding. but know what you are getting into. I went into a bootstrapped company and it was in fact the worst decision I ever made. I've only been in series B or further since.

UrAssIsSaaS

Arsonist

2

SaaS Eater

Lol ya boot strapped is everything I outlined on steroids. I love the hectic environment but even that's a pass for me.

Justatitle

Big Shot

0

Account Executive

The CEO had built out the product and refused to give up equity to VCs for money, we went out to dinner when he was visiting and he stiffed the waiter on a tip, it was that moment that I started looking elsewhere

UrAssIsSaaS

Arsonist

1

SaaS Eater

Jesus ya if that's not the reddest of flags. What's he really in this for lol

DungeonsNDemos

Big Shot

2

Rolling 20's all day

@UrAssIsSaaS What color pool noodle do you recommend?

UrAssIsSaaS

Arsonist

2

SaaS Eater

I think pink tends to set a solid tone

DungeonsNDemos

Big Shot

2

Rolling 20's all day

Save that one for Wednesdays

emkayxx

Opinionated

2

Enterprise Account Executive

For anyone looking for other side of this, I joined a Series A company three years ago. I had no SaaS experience and only 4+ years of Telco sales experience. At the time, they were doing $2M in revenue - today we're a $40M company. I've gone from doing $50k deals to $200k+ deals and have gained the experience of seeing a company go from 50 employees to 500. It has single handedly changed the direction of my career.

If you're looking to join a Series A company, here is what I'd vet:

1. Vet the product and market fit
- how many current logos are friends and family vs true outbound/inbound deals closed
- what is the pain of the problem being solved
- is the product a nice to have vs need to have
- what is status quo vs what the world could like for the prospect evaluating the software

2. Leadership
- vet the shit out of the calls with the VP sales and CEO, CTO etc. ..a ton of the success at a Series A company comes down to the overall direction of the leaderhsip team and where they take the company. Are these smart people? What have they done in previous role?
- then ask yourself, do you see yourself getting along and working for these people for the next 3+ years?

3. Culture
- speak with other folks in the organization and see where they came from - are they top performers or meh?

4. Once you check the boxes of 1-3, still know that this is going to be a gamble.

NOTE: One thing I love about Series A is that as a sales professional, you can help shape the GTM strategy. You're going to have a ton more at bats than a typical Series C+ company and so you although your win-rate will probably be lower, the business won't say no to deals coming through the door. This could translate to good $.

carbonara

Executive

0

Account Executive

Great comment, thx for sharing! How has your commission structure changed over the growth period?

OldSaaSRep

Old School Bravo

0

Sr Enterprise Rep

Great points. I'd add dig deep into the funding. Who's funded, how much is remaining, burn rate, growth expectations, expected next round of funding and most importantly, HOW MUCH DID THEY GIVE AWAY TO THE INVESTORS!! Nothing worse than receiving shares and finding out years later they are worth shit because the company is completely diluted. This is so common with first-time founders. The VC's will take everything if the founders don't know better.

emkayxx

Opinionated

0

Enterprise Account Executive

Looking back, I think there was room for it to have been much better earlier on in the Series A-B range. It was pretty standard though, I think we were paying out 9% for the first 0-70% 11% at 70-110% and 12.5% at 110%+. There were also some big pay hitting certain thresholds at 120%+. We are Series C+ now and these numbers have only gotten better. With how crazy the market is right now for sales talent, they knew they needed to get much more aggressive.

emkayxx

Opinionated

0

Enterprise Account Executive

Great add on man, I can't believe I didn't think to include that. Vetting investor history is a must.

UrAssIsSaaS

Arsonist

2

SaaS Eater

Really appreciate the contrarian look at this. All really good input that I 100% agree with.

The motivation behind the post wasn't to say that joining a Series A is a no go across the board. I work for a series A now and its been one of the best experiences Ive had in my career thus far.

The gist was more that not everyone is cut out for a Series A, especially if you dont know what you're doing yet. The questions you outlined are so freaking important to understand before you join. I placed a huge emphasis on all of those things before joining where I am now and Im way better for it.

Wish I could nail this to the top so people could more easily see both sides of this conversation.

OldSaaSRep

Old School Bravo

1

Sr Enterprise Rep

I by no means meant to paint a negative view of joining a series A company. I 100% agree that it's definitely not for everyone. It can be an extremely rewarding and fulfilling experience.

SADNESSLieutenant

Politicker

2

Officer of ♥️

not me joining a series a and establishing all sales proccesses, ICP, tech stack, target market, and GTM/ABM strategy as a 2nd yr SDR - check out my recent posts on how its going lmfao

carbonara

Executive

0

Account Executive

Would love to connect with you! In a similar boat - if you’re open to it.

SADNESSLieutenant

Politicker

1

Officer of ♥️

and how would we connect?

UrAssIsSaaS

Arsonist

2

SaaS Eater

You trying to say a DM feature would be useful?

SADNESSLieutenant

Politicker

0

Officer of ♥️

A DM feature would be nice, that way I can slide into all the pretty girls dms with unsolicited 'hey beautiful' 's

Pachacuti

Politicker

1

They call me Daddy, Sales Daddy

Good advice overall.

UrAssIsSaaS

Arsonist

2

SaaS Eater

appreciate it.

Diablo

Politicker

1

Sr. AE

Nailed it

Jbeans

Opinionated

1

Director of Sales

We work with a ton of start ups. All of this is true! Great intentions but def not a lot of processes in place. Constantly moving goal posts, delays, Always waiting on next round of funding. Love the enthusiasm and have been privy to some very cool designs / concepts but sadly not a lot make it to market! At this stage in my life /career? I’d be very hesitant to join one due to the high risk factor!!

UrAssIsSaaS

Arsonist

1

SaaS Eater

Ya I dont think all of the founders out there have ill intent, they just dont know who they are, what they are doing, and how to do it correctly yet so its really hard for someone with very little experience to walk into that situation and succeed.

quinoa

Contributor

1

order taker

Something I'm still trying to figure out after years. Continue down startup land or find a really good established company with solid product market fit. Processes, playbooks, ICPs, personas, go-to-market all dialled in. Plenty of people making 200K+ as AEs in these. (lots here in the WR looks like.)

UrAssIsSaaS

Arsonist

2

SaaS Eater

Ton of stability and earning potential here. Maybe not the crazy upside but a lot of other perks living in this world.

meetalk

Good Citizen

1

Account Executive

I did exactly what you have said not to do, and it turned out to be exactly as you said. I wish I read this a year ago. I feel like they’re close to a turning point, but I feel burned. And I have 6 years of experience and am pretty damn good but it’s a cluster and didn’t make any where near OTE. Now trying to leave is tough and looks bad on my resume. The reward is not worth the risk.

UrAssIsSaaS

Arsonist

1

SaaS Eater

Curious what # you were on the sales team and if this was series A or not?

Mickjames

Member

1

Enterprise Account Executive

Oh dude. I just learned that the hard way. Thank heavens I got out and aligned with my dream organization

UrAssIsSaaS

Arsonist

2

SaaS Eater

Win some and lose some, glad youre in a good spot now!

OldSaaSRep

Old School Bravo

1

Sr Enterprise Rep

Spot on assessment of a Series A company. The only way I'd join another series A is as VP Sales with a ton of options and full autonomy over sales. This is not the place to learn sales, it's a place to waste a ton of time basically gathering market research on the product and what it's missing.

Evan4k

1

Account Executive

I've worked for a few Series B-D Level Orgs and must admit that they've been the greatest accelerants to my career growth.

While it can sometimes feel like fighting a fire with a water gun, if you have the stones and willingness to make executive decisions and own the process you'll, at the very least, have a great story to tell at your next spot.

Would definitely agree that having a fair amount of experience and your own processes in place is fairly intrinsic to success even in these later stage environments.

UrAssIsSaaS

Arsonist

2

SaaS Eater

Ya my point isnt that no one should join a series A. I joined one 6 months ago and its been amazing. But I also had spent the prior 6 years building out a sales or at a publicly traded company that gave me the experience I needed to succeed in doing the same for a series A.

I think its also important to note that series B-D is VASTLY different than A.

We raised B about 3 months ago and our company is entirely different than when I joined just after raising A.

SpicySpitter

Opinionated

1

SDR Overseer

I went into one with that experience and it was a shit show so 100% agree don’t do it without any experience. Disaster waiting to happen

UrAssIsSaaS

Arsonist

2

SaaS Eater

Ya sometimes. experience isnt enough to save you if the company is doomed from the start.

SADNESSLieutenant

Politicker

1

Officer of ♥️

https://bravado.co/war-room/posts/should-u-quit-die-negotiate-or-find-a-better-job/comments/227675

ChiefGreef45

Catalyst

1

Account Executive

Thanks for sharing this! Seems like I'm in the same boat joining a preseed company as their first salesperson. Totally agree that if I did this 2-3 years ago, I'd be totally screwed.

Not to say that it's now a cake walk (it's not), but good to hear I'm not the only one dealing with a day to day like this

UrAssIsSaaS

Arsonist

1

SaaS Eater

Definitely not! and I dont want everyone to think you cant join a young company, it just takes someone that has done it before to be successful!

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