Making the jump from startup to established org

Hi all, I'm looking for some advice on thinking longer term about my career.


TLDR; my sales experience is in Series A SaaS companies. I wonder if making the move to a larger org is worth it or even possible given my experience so far.


Some background

Got into sales about 5 years ago after being a data analyst for a a couple years. I had joined a startup (10th hire) as an analyst and started randomly going on sales calls as a technical resource. I really enjoyed it, so I made the change and became the first sales hire. As you can imagine it was a s**t show for a while until I figured out how ppl bought things. Was at that company for about 4 years - we did a series A, 6/7x the company to about $3m ARR - before some poor (imo) strategic decisions meant the company went into a nose dive. I tried to get growth going again but was unsuccessful.


Joined another Series A company as an early sales hire back in June. Another sales rep and a head of sales also joined at a similar time. Sold a few deals early on but there's been loads of messaging changes, product changes, new verticals etc. Things have been pretty slow the last few months - for me and the whole team.


In neither case I've had no sales training, other awesome sellers to learn from or loads of repeatable at bats. Everything I've learned about sales so far has been trial and error/reading/webinars etc.


I guess I've got two questions:

  • Is this normal for a sales hire at a series A company? Real patchy deal flow, total hustle for every scrap?
  • If I did want to go into a larger org, would I be taken seriously given I don't have like "5+ years of demostrable quota outperformance and presidents club"? Like at my first company there were no formal quotas - it was just that we needed to grow by $X each year and that was it.


I'm confident I can succeed at a larger org, just want to get a perspective of what my experience looks like from folks already in those orgs if possible.


Thanks for reading what seems like my life story. Appreciate any thoughts.




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9
Kosta_Konfucius
Politicker
5
Sales Rep
I have seen many people make the transition, I would do some wordsmithing to talk about your success especially if there wasn’t any quotas. Have listed out the revenue generated, typical deal, and rank to offset no quotas

In my experience the larger companies typically pay less than the Series A and Bs. Just want to let you know that part too
jefe
Arsonist
3
🍁
All of what Kosta said, especially the wordsmithing and salary/comp realities.
It'll probably be good for you to get some more formal sales training and be able to absorb from top performers.
saastaastic123
Good Citizen
2
Sr. Account Executive
Thank you! Have noticed that the salaries seem a bit lower at larger orgs
Sunbunny31
Politicker
4
Sr Sales Executive 🐰
You trade higher salaries + risk for lower salaries + great benefits.
CuriousFox
WR Officer
0
🦊
Great benefits AND flexibility.
Sunbunny31
Politicker
3
Sr Sales Executive 🐰
As Kosta said, list out what you did accomplish -x % growth year over year or increased revenue from $200k to $10m - you get the idea. Come up with great ways to showcase your skills and highlight your accomplishments.
oldcloser
Arsonist
2
💀
And don’t drool in interviews.
ThatNewAE
Big Shot
2
Account Executive - Mid enterprise
Oldcloser is in a savage(r) mood! 😂
GDO
Politicker
0
BDM
Yeah just boast your accomplishments.
oldcloser
Arsonist
1
💀
They’ll only know what you tell them. Otherwise, 5 years with data before that? Seems right to me for a step up.
Diablo
Politicker
0
Sr. AE
Why now, make your resume relevant. Show what they want to see - numbers, numbers, numbers as ultimately that’s what you will be responsible for :)
Justatitle
Big Shot
0
Account Executive
It is a lot easier transition to go from startup to established than established to start up.
Built-in storyline of wanting stability and not having shit change every 5 minutes. Brand recognition, financial stability etc...
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