Olly

Account Exec

Move from Corp to a Start-Up

Need your help, folks.

I work for a Corp as an entry-level AE after being an SDR, with not much of a promotion horizon, and the job is starting to bore me. Got an offer from a Start-Up to build their Sales Org from scratch. I lack experience, but they know me as we worked together, and trust I can do it. which means I'd be Head of Sales (most likely). They raised a nice seed, and the founder already sold his previous Start-Up. Needless to say, they won't match the salary and benefits Corp offers.

What would you do?

📈 Closing

☁️ Software Tech

🧢 Sales Management

56 comments

Sort by:

poweredbycaffeine

WR Lieutenant

☕️

Hell. Fucking. No.

You are going to be set up from failure from day one. You lack experience. They lack experience. They lack any real runway. You will be the scapegoat at the board for all commercial failure.

poweredbycaffeine

WR Lieutenant

☕️

Oh, I’m sharing that because I did just that. 5th employee. Took sales over from the CEO but I had 6 years under my belt. Without that I would have churned out in 6mo.

Olly

Catalyst

Account Exec

I replied before seeing this comment. Gotcha.

Olly

Catalyst

Account Exec

@poweredbycaffeine does it matter if I have experience as an SDR/AE who trained other SDRs, built sequences and Demo plays? It's not accurate to say I don't have any experience at all.

braintank

Politicker

Enterprise Account Executive

That is like 1% of the sales process

poweredbycaffeine

WR Lieutenant

☕️

Have you built a forecast, sales engagement plans, commercial agreements, customer journeys, hired sales teams, fired sales teams, built coaching and improvement plans, and the other 100 things I do every day as a VP?

CRAG112

Valued Contributor

Account Executive

^^^^^

Review some posts by Scott Leese. He's broken a lot of this down.

What caffeine is saying is only a very basic idea of what you will need to be able to do. Not to mention generate sales.

Olly

Catalyst

Account Exec

True. But as things get clearer, this turns out to be not a Head of Sales, but more of leading the SDR team + Semi-AE.

Olly

Catalyst

Account Exec

I have not, sir. But that's why I'm here - To learn from VP like you, @poweredbycaffeine . From a call today with the co-founder, I understand that this won't be a Head of Sales job, but more of establishing the SDR team, while doing some AE work.

poweredbycaffeine

WR Lieutenant

☕️

That context helps. Sounds like a lower risk.

Olly

Catalyst

Account Exec

Thanks - I didn't know that before today. And in that field, I am totally ready for building an SDR team, not to mention it shows progress. The risk is still out there (it is, after all, a start-up company).

Olly

Catalyst

Account Exec

Thanks. They have experience from the start-up they sold but I gotta say I feel I can do this for them, and it's either that, or rot in Corp until I find something else.

Sunbunny31

Politicker

Sr Sales Executive 🐰

OK, so clearly this is compelling because you feel you're stagnating where you are. Why is that? No room to move up?
Disclosure: if I were in your shoes considering where you are with your family so young and so many risks, I'd be VERY risk averse personally and would play it very safe. So I'm interested in seeing if there's a more conventional path for you where you are or with a more established company where you're not so likely to be set up for failure.

Olly

Catalyst

Account Exec

No room to move up, I don't get the Sales mentoring I hoped I'd get. The conventional path is staying at Corp, doing my (frequently boring) thing, and hoping to grow the pipeline in this economy. So there's always the chance of losing Corp job as well. For that matter, it's the same as a SU company.

Sunbunny31

Politicker

Sr Sales Executive 🐰

If you need mentoring, jumping into a start up as founding AE/head of sales is not going to get you what you need.
I'm sure it's very attractive and a very flattering offer - but take a step back and wonder why they'd want to pin everything on a brand new AE? You may be a fantastic rep, but you're very, very new. It's a huge risk.

Space_Ghost20

Valued Contributor

Account Executive

Caveat: except for the banks I've worked at, I have only ever worked for startups. Being a latecomer to the tech world has kind of restricted the list of willing employers for me.

In any case, in this current market, a company like this will need at minimum 2 things from someone "building the sales org from scratch": a) wins they can personally deliver fairly quickly, and b) the ability to build and document a sales process that can be repeated by the reps they hire. I'm not going to say someone with relatively little experience can't do these things, but it certainly isn't going to be easy or simple. They probably don't have much in terms of marketing collateral, slide decks, a reliable tech stack, outreach sequences built out, demo structure, case studies, etc. If you're used to working at an established org, these are things that pre-existed in a repository for you when you were hired. You're going to be making a lot of this stuff on the fly now.

I would just advise you to be honest with yourself as to whether you think this is within your ability right now. And on top of that, if you're willing and able to fail. The severance package at these types of places when they lay people off is more like 1-4 weeks of pay, not the 3-6 months you often see at larger companies.

Revenue_Rambo

Politicker

Director, Revenue Enablement

💯

Olly

Catalyst

Account Exec

Thanks for the elaborate answer. Creating sequences, and demo structures are not strange to me. However, there's not even a Marketing team so it's pretty much a Swiss army knife guy (me).

I don't think there's a Yes or No answer here. I think it's if I'm willing to adopt the state of mind I'm going on an adventure while I still can, without jeopardising my family.

braintank

Politicker

Enterprise Account Executive

Creating sequences ≠ building a sales process

SoccerandSales

Big Shot

Account Executive

Clearly you want us to say yes because that is where you are leaning. To run your own sales org with minimal experience is setting yourself up for failure. Frankly, it looks like to me that this founder is trying to cheapen out on sales by taking you as opposed to someone with enough experience to do the job.

Olly

Catalyst

Account Exec

You absolutely nailed it - I have the same thought about the founder. Then again, we had one conversation and we didn't talk about Salary and I'm going to ask more than what I make today.

braintank

Politicker

Enterprise Account Executive

Nope

CuriousFox

WR Officer

🦊

What would this kind of experience matter if you are only able to claim it as 3 months on your resume? My point being you could get cut loose at any moment and not have the severance options that your current company may offer. I'd rethink this one.

Olly

Catalyst

Account Exec

Yeah - But what if the product is really good and they seeded a very respectful $ (given the economy). Might be a lot more than 3 months - But that's the risk I guess..

DataCorrupter

Politicker

Account Executive

I'd like to add something here that hasn't been touched on quite yet.

Let's say you take this opp and it goes south within 2 years.

If you get back into the market as an AE, I feel like you'll be radioactive to a hiring manager. You've gone SDR to AE to Head of Sales all within 5 years (guessing here) or so? That's literally crazy. And not in a cool, "you're a generational talent" sort of way. It signals that you think you've learned so much about sales in a short amount of time that you can do what your hiring manager does. I'm not trying to be a jerk (honestly), but it borders on unrealistic self-belief. Also, why would I, as a hiring manager, want to hire a guy who thinks he can do my job? Will he be second guessing me all the time, talking about how when he did the job he did this or that, or is he trying to replace me? I think you're getting the point here.

If you get back into the market as a head of sales you'll be in a weird and vicious cycle. As others have said, they're hiring you because you'll be cheaper than an experienced guy. If you get cut from this org, you'll be trying to find a similar job and will constantly be the head of sales at small companies with a super high failure rate. Maybe you get one that takes off, but as more VCs put money into the next funding rounds, they will look at your resume and wonder how you lucked into this situation. Then, they'll find an experienced replacement who they know can get them to the next level. My point is, you'll be a king (yes), but you might end up being king of a landfill.

A different suggestion: instead of going from a cush, public company where most everything is set up for you to succeed, to a seed/series A, where almost nothing is, I'd suggest you go to a late-stage (D to G) company and be an AE (and then sales leader) there. Take one step in a more sensible direction. You'll be surprised by how much one of these steps will help you grow personally. Plus, that's way more defensible on a resume, shows a logical progression.

Again, not trying to shit on you at all, but you should definitely think this one three/four steps ahead.

Olly

Catalyst

Account Exec

Thank you - That adds an interesting (and frustrating) perspective. But you're right. What if the title was Director of Business Development? Obviously, they'll bring someone above me, so I might as well not jump that high (referring to the scenarios you mentioned)

DataCorrupter

Politicker

Account Executive

That could work. It's explainable to the next hiring manager, more so than being head of sales. It just might be odd if you're only there for 6 months, which sounds like it's a not-unfathomable risk.
Like others have said, it's super clear you want to take it. I would caution you to think it out some more and really weigh the pros and cons. I don't mean that condescendingly, but the con of it (potentially) being a very short stint might actually outweigh any benefit you get from being Director of BD. Ultimately, up to you.

As a side note, just want to say that if you take it I hope it goes exceedingly well and you prove me and others totally wrong. I really mean it. If you take it, go kick some ass.

Olly

Catalyst

Account Exec

I'll have you to know, that your input completely changed my perspective, and it makes so much sense. I'm gonna go with the AE title. If this will be a short sting, the AE title will help me get on track a lot faster.

Thank you!

DataCorrupter

Politicker

Account Executive

I'm honestly happy to have helped.

If you don't mind, come back and check-in and let everyone know how it goes.

Diablo

Politicker

Sr. AE

Looks like you really want to give it a try.

Olly

Catalyst

Account Exec

I do. They were very impressed with me when we worked together, and it seems like this is a great opp for me to move up and gain major experience with building teams.

braintank

Politicker

Enterprise Account Executive

Or get burnt out and fired in <1 year

Olly

Catalyst

Account Exec

Yep. Or make an exit and earn some dollars. That's the risk right

dwarfygoat

Territory Lead

My main concerns would be A) your lack of experience, not necessarily your ability to learn and execute. It takes a lot to build up things from scratch and experience will definitely help to move fast and confidently. B) seed round is very early. The mix of both supports @poweredbycaffeine's scenario of unpredictably chaotic outcomes.

Kosta_Konfucius

Politicker

Sales Rep

You are young, so you can fall on your face. But what would happen if this falls on your face with 3 months, are you financially going to be ok?
Its going to be a lot of work and a low chance of success.

Olly

Catalyst

Account Exec

If I'll tell you I'll be OK - Would you suggest taking the job?

ScorpionZD

Executive

Enterprise SDR

From what it sounds, no

Justatitle

Big Shot

Account Executive

it is a no from me if I was you.

thesearentleads

Member

Account Executive

Doyouhave15minutes

Executive

Account Executive

Way too often a founder who does not have a working sales process hires a VP of Sales to "figure it out" and they typically end up in the same spot after the blame is placed on the VP for not meeting high-growth expectations set by the board. I understand the market is tough but I would say no.

ConwayStern

Member

The responsible part of me (read: Lilliputian) says no. You have 2 kids and a partner, so unless your partner is a private equity VP or something you may find yourself out on your ass in 3-6 months without a paddle. I know the stress I've experienced looking for a job when it was just ME to look after, couldn't imagine having a family to support as well.

That being said, I've just recently done something similar. Joined a startup that my good friend / college buddy launched a couple years ago. I'll just highlight the key differences:

- I'm single

- Have enough savings / fall back plan to not really worry about getting axed if I can't hack it

- I'm an extremely big risk-taker

- Given our relationship and understanding of how we work, I have a little more latitude in terms of fucking up. Can't count on the same for you

- My title, to start, is "Renaissance AE," which makes a lot more sense considering my work experience

The first 3 months I was basically an SDR and didn't have much responsibility past that. Together we're building the sales org but it's not delegated entirely to me, we fill in the gaps for each other when necessary.

We've had conversations about where the role can go but are not shy about being realistic, i.e. if I can't keep up I'm out. That's something I'm 100% comfortable with and understood going into it.

To the point that other commenters brought up regarding finding employment afterwards, it won't look all that crazy to go from SDR -> SMB/Commercial AE within a couple of years, which on paper is what it looks like now.

Olly

Catalyst

Account Exec

Thanks so much for writing this. Today I sat with the co-founder and turns out it's not going to be the Head of Sales for me, but more similar to what you were doing ("The first 3 months I was basically an SDR and didn't have much responsibility past that. Together we're building the sales org but it's not delegated entirely to me").

I've been a BDM, an SDR, and now an AE for a total of 6 years. So doing a jump to a Start Up where I'll be an SDR team lead or Director of Sales Development (just a title, to demonstrate progress) will contribute to my future. What do you think?

It sounds like I'll be doing what you did in the beginning. What would you call yourself? What was your title?

ConwayStern

Member

Good to hear you're having these discussions. My official title is still AE, however it being a startup that almost doesn't matter. Behind the scenes I'm building the sales process, doing rev ops, marketing (in the form of events/conferences, we have a head of growth/marketing who is great but is starting to get spread a little thin), cadences and whatever else needs to be done.

When we get to the point that we're looking to bring on more people, that's when we'll start to really looking at if it makes sense to transition over to more of a departmental leader vs. IC vs. player-coach. Best thing you can do here is just go with the flow.

Olly

Catalyst

Account Exec

That's literally, word-for-word, what they described to me today.

Pachacuti

Politicker

They call me Daddy, Sales Daddy

If you’re young and have no kids, wife, etc. then I would consider it. It’s very high risk-high reward.

But all you’re getting is a title here. And don’t think for a minute they won’t hire someone with 5min more experience than you to be your boss when they can afford it.

They are hiring you because (1) they know you, and (2) you are what they can afford. That’s it.

Also, do you LOVE what the start up sells? If you don’t have founder level passion, it may not be a good fit. They will want a lot more from you than the corporate job.

Olly

Catalyst

Account Exec

Thanks, that's a great answer. Married with two toddlers.
The thing is, I don't know yet what will be the salary. What if it will be more than what I make now?

Pachacuti

Politicker

They call me Daddy, Sales Daddy

Again - high risk high reward. Other than title, which anyone with eyes will be able to see you don’t have the experience to support, what are you getting?

CPTAmerica

Opinionated

President/CRO

Are you comfortable living on the base pay they are offering? Are you ok with the risk of failing and losing your job in 6-12 months? Are you getting equity in the startup? Do you have a spouse or dependents at home that count on your paycheck?
If you answered yes to the first few and no to the last, it's a no brainer to me. If the answers are mixed you have some more thought to put into it.
“If somebody offers you an amazing opportunity but you are not sure you can do it, say yes – then learn how to do it later!”
― Richard Branson

Olly

Catalyst

Account Exec

So the thing is, I don't know the base yet. But I'm going to ask for more I make today. I will be getting equity as well.

But, I will have to work my ass off to compensate for the lack of experience in building a Sales team and strategy.

Revenue_Rambo

Politicker

Director, Revenue Enablement

How much of a bump in pay do you expect?
10%? 20%?

The title and opportunity sound great, but that extra cash is going to cost you something that you won’t get…. TIME.

Be prepared to give up work life balance. Are you able to put in 14 hr days? Take calls at all hours of day and night because your prospects are in a dozen different time zones? Hold weekend sessions with the ownership team?

You maybe confident in your abilities but the grind will take its toll. If you come out the other side professionally successful, what will you have sacrificed with the family?

CPTAmerica

Opinionated

President/CRO

Obviously you need details before making your decision. You need to find out what the pay is, how much equity (and vesting schedule), what will your budget be, what do they expect from you in the first year.
Of course it's hard work but you're gaining tremendous experience that others may never have.

Maximas

Tycoon

Senior Sales Executive

You can go for it, since I can see you love it and very enthusiastic about it ,but not like to be the head of sales directly,it's kinda early for you to hold that title till acquiring the required experience, otherwise they might hold you responsible for any possible failure!

Olly

Catalyst

Account Exec

@Maximas you nailed it. That's exactly what I have in mind after talking to the co-founder today. Maybe a title that would be less compelling, and that won't hurt my future hiring.

Maximas

Tycoon

Senior Sales Executive

Go for it,good luck my man!

ScorpionZD

Executive

Enterprise SDR

Red Flag

ThatNewAE

Big Shot

Account Executive - Mid enterprise

I am doing something of the same sort - and I am glad I landed here to read the comments. Now I am in two minds lol.

Bravado is a community of trusted sales professionals endorsed by their customers.

Products

The War Room Jobs Salary Guide Tech Sales U

Company

About Us How It Works Blog Bug Bounty

Contact

Press Careers

If you are hired as a contract sales rep by a Bravado customer, we may ask you to prove access to the employee email account provided to you by that customer. This data will be shared with customers to track your sales productivity; customers can use this data to confirm you meet the minimum activity requirements to pay out your ramp stipend and commission.

Olly

Move from Corp to a Start-Up

56 comments

Related posts

Who do you want Corp to roast in an interview?

Sahil Im looking for an Update on this deal....

When To Move On