Comprehensive Guide for Moving to a Startup

Badger Gang,


UrAss is back to drop some knowledge on making the move from a massive sales org to a startup.


I see some form of this question all the time in here "Im thinking about moving from my company and going to a startup, what should I expect". If this is something you find yourself asking, follow along.


For context, I am moving from a pretty well known public company with about 2000 sales people. I was managing a mid market team of 12 and we sold a SaaS product. I moved to a 70 person company with a 10 person sales team and am now the director of sales. Ill give you the 5 things that have stood out to me most in making this change.


1) Pressure makes diamonds - in a massive org you really only matter to yourself, your goals, your paycheck etc. You only have minimal impact on the business.


In the startup world you MATTER. The revenue you close can make or break the company (especially really early stage startups - dont get me started on how we define a startup, different convo). You have real implications on the success of the business. I love this pressure and thrive knowing the impact I can make, BUT not everyone is cut out that way. If you dont want that pressure, dont move to a startup.


2) Expect to train yourself - I have had your run of the mill onboarding and training experience in my first week but the only way I will succeed in leading this team is by getting my hands dirty, figuring out the process on my own and asking those that are winning. The process isnt fully baked and wont be spoon fed to me. Which leads me to my next thought...


3) Have your own process or be ready to build - massive orgs know what it takes to win, as an AE or manager you are purely there to execute the plan that is laid out. If you do, you close a ton and make a bunch of money. At a startup there is no process yet, its your job to define it.


I tend to believe there are 2 types of salespeople in this world, those that create the process and want to figure out how to win, and those that are fantastic at executing the plan that others have laid out. Both are great, just different and if you are the latter you will struggle at a startup.


4) Get comfortable with no one knowing you - One major (dis)advantage of a massive firm is that your prospects know you, you dont need to educate them on who you are and what you do. You just need to show them why you are better than what they currently do.


At a startup no one knows who the fuck you are and what you do yet, so be ready to break down that wall and educate your prospects.


5) Fast paced is an understatement - Everything moves quick, you need something done and its turned around in like 24 hours. Product and engineering actually listen to you and build what you ask for, and it happens quickly. If you are frustrated with red tape and bullshit slowing you down, startup life might be for you.


If you're still with me, I appreciate you. Hope this helps anyone thinking about making the jump.

๐ŸŽˆ Mentorship
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๐Ÿ›ฉ Onboarding
50
DungeonsNDemos
Big Shot
7
Rolling 20's all day
This is some solid advice! Hopefully we can get a few less posts per day now on "what should I know going to xyz startup???".
I would emphasize knowing yourself and how you operate so can go to a company with structure that best aligns to you.ย 
UrAssIsSaaS
Arsonist
3
SaaS Eater
Appreciate it! Thats the goal, but lord knows the search bar is tough to navigate and once this is off the new tab no one will see it lol
DungeonsNDemos
Big Shot
2
Rolling 20's all day
lol true. You can only stop the tide for so long
bandabanda
Tycoon
1
Senior AE Mid Market
Seriously, the search bar is rough. I know they are working on it.ย 

This post needs to go in a Bravado public swipe file.ย 
UrAssIsSaaS
Arsonist
2
SaaS Eater
Shout it from the rooftops lol
InQ5WeTrust
Arsonist
7
No marketing, mayo isn't an MQL
Envious of you being part of a 12 person team. The largest I've had so far is 6.

Your points are all 100% on point.ย 

Especially process and being able to live without name brand recognition/resources. Sales people I've seen fail have come from large firms and haven't known what to do.ย 

New Head of Sales ex-Gartner - 'We should have a conference with all the Heads of X'ย 


Me - 'Sir this is a startup Wendy's we have pork and beans, wet wipes and a dream'ย ย 
UrAssIsSaaS
Arsonist
2
SaaS Eater
Lol so true!ย 

Being part of a larger sales teams is fun for sure, leading them though can be a challenge. Largest team I have managed was 16 and that was a handful haha.ย 
dwightyouignorantsale
Politicker
4
Account Executive
This is really awesome advice. In your experience at startups, when it comes to creating a sales process, is that something that you (or one of the early reps) creates and everyone follows that blueprint? Or is it truly sales rep by sales rep based and each person does their own thing?
UrAssIsSaaS
Arsonist
4
SaaS Eater
So we just took this team from 2 reps to 5. Initially it was rep by rep but thats not scalable so my job is to identify what each rep does well and build a process around that and then roll it out to the rest of the org and anyone else that starts.ย 
dwightyouignorantsale
Politicker
1
Account Executive
Iโ€™m sure thatโ€™s not an easy job, but probably very rewarding when you find something that works. Very cool, thanks for sharing!
UrAssIsSaaS
Arsonist
3
SaaS Eater
If it was easy it wouldnt be worth it! Building shit is what I enjoy, which is why I took this role.
CuriousFox
WR Officer
4
Senior Account Executive
Thank you for taking the time to write this lovely advice. I keep going back and forth with myself if I want to try this again.ย 
UrAssIsSaaS
Arsonist
2
SaaS Eater
Im here for the people.ย 

Ya its a tough one, I personally love it. Ive worked in large orgs, small orgs in large orgs and now true startups and Im a big fan of the freedom and speed of the smaller stuff.ย 
mitts2
Politicker
3
Account Executive
Great post and super relevant. If I could add a bonus point in favor of startups, I would say:

Creativity within the bounds of reason: Startups offer so much more flexibility and creativity for your sellers and those that take advantage of that freedom can make a killing. In many cases, Startups do not have as stringent of approval processes which means your sellers can be super flexible in terms of negotiation, proposals, pricing, etc. That said, that creativity needs to be within reason and within logistics of the broader business model.ย 

I was around the 150th person at my company. We have since grown to around 400+ so I have seen some of that shift from startup to larger org first hand. Don't take for granted that ability to get creative during the selling process.
UrAssIsSaaS
Arsonist
4
SaaS Eater
ya totally agree with this. Every logo and dollar in means more so you can get creative in how that is earned.ย 
bandabanda
Tycoon
3
Senior AE Mid Market
Solid advice and 100% affirm these points. I've worked at 1 large company and 2 start-ups so far.

I'll add to number 5 - if you love collaborating with other departments to see things come together, you might thrive in a startup. I love working with Marketing, Product, and CS to see the whole customer buying journey and onboarding come together. In a massive company, you're a cog in the engine. At a startup, you get to learn all parts of the engine and build it into a well-oiled machine (hopefully).ย 

Braintank was inspired by you and wrote this post to go hand in hand. 2 must reads for people asking about this!


https://bravado.co/war-room/posts/somewhat-comprehensive-guide-to-avoiding-a-toxic-startup
Sunbunny31
Politicker
2
Sr Sales Executive
Fantastic post.ย  ย That's very well laid out.ย  ย I think you covered exactly what the differences are and the expectations very well.
UrAssIsSaaS
Arsonist
2
SaaS Eater
Appreciate it! That was the goal.ย 
FamilyTruckster
Politicker
2
Exec Director, Major Accounts
Great write up @UrAssIsSaaS. Wish we could sticky something like this.ย 
UrAssIsSaaS
Arsonist
2
SaaS Eater
Appreciate it, agreed. Or I should figure out how to write headlines that show up when people search lol
Mjollnir
Politicker
2
Account Executive
yo this might be an advise I would actually look for in a few weeks time so thanks in advance!
UrAssIsSaaS
Arsonist
2
SaaS Eater
Thats what its here for so glad it was helpful!ย 
SaaSsy
Politicker
1
AE
Love that I just happened to see this as Iโ€™m weighing a decision about this right now! Thanks for sharing and great advice about self-awareness for finding the right fit.ย 
UrAssIsSaaS
Arsonist
1
SaaS Eater
Glad you thought it was useful!ย ย 
RahRahBooty
Opinionated
1
Business Development
Great post and very accurate. I left an org with over 5,000 sales people to be sales person #1 at my current company. Itโ€™s a lot of work, and itโ€™s definitely not for everyone. I love it though.
UrAssIsSaaS
Arsonist
2
SaaS Eater
Ya it takes a certain type of sales person to go be AE #1 at a company. If you can nail it though, super rewarding. Good on you!ย 
RahRahBooty
Opinionated
0
Business Development
It has been VERY challenging, thats for sure lol.ย 
SuperSaasMan
Executive
1
Enterprise Account Executive
I've worked for two different start-up Saas companies over the last 5 years and this couldnt be more accurate!
NeverSatisfied
1
Head of Sales
I wrote the following quote down as I start exploring positions outside my current role:ย 

"I tend to believe there are 2 types of salespeople in this world, those that create the process and want to figure out how to win, and those that are fantastic at executing the plan that others have laid out. Both are great, just different and if you are the latter you will struggle at a startup."ย 

As someone newer to direct sales experience, I currently lead sales at a startup and resonate with the quote above.ย  I know I would excel in a role where I am executing the plan that others have laid out as I am having a TON of trouble selling a product from scratch with no oversight..ย  and I am not ashamed! Thanks for the fantastic quote
UrAssIsSaaS
Arsonist
1
SaaS Eater
Im only 6 months late getting back to this but hope you have sorted out some of those challenges and are getting it dialed in!ย 
CharmingSalesGal
Politicker
0
Account Executive
This is phenomenal. For someone who's currently an AE at a start up, looking to grow professionally with the company, this gives me hope that what I'm doing and the hard work I'm putting in now will pay off in due time. Thank you, @UrAssIsSaaS!
UrAssIsSaaS
Arsonist
2
SaaS Eater
Without trying to send like Gary V, keep grinding! Itll pay off
socialselling
0
Sales Enablement
Ooh, this is super solid advice, thanks!
PleaseAdvise
Opinionated
0
Account Executive
Good stuff! Thanks for sharing
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