Space_Ghost20

Account Executive

Valued Contributor

Depth vs Breadth in Career Experience

I’ve got a little more than 8 years of sales experience, but it’s kind of spread out. 6 years were spent in financial services before I pivoted to the tech/software world where I spent one year as an SDR at an AI company, and then another year as an AE at a startup that sold background check and recruiting analytics software. For the last two months I’ve been an SMB AE selling expense tracking software. I want to leave, but I’m having a hard time fitting my experience into this market. I feel a bit too experienced for entry level roles (including my current one) but more advanced roles feel a bit out of reach too.

I fully acknowledge I could/should have been more strategic in my career decisions, but in my defense the jobs I took seemed like great spots at the time I took them (except my current job, that one I took out of desperation). I want to make sure I don’t fall into this trap again moving forward, so what’s my play here? Do I find a great line of software/tech and start back again as an SDR, or is there at all a market for people with a lot of experience, but in a lot of different things? Anyone else in a similar situation?

🚀 Career Goals

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18 comments

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Sunbunny31

Politicker

3

Sr Sales Executive 🐰

You've been an AE for only 2 mos. Why do you want to leave?

Space_Ghost20

Valued Contributor

2

Account Executive

I've been an AE for 14 months. Only 2 at my current job. I was laid off.

Reason I want to leave is this job is a poor fit for my skills, experience, and work preferences. There's no prospecting here, all day I'm just calling free trialers and getting them to upgrade to paid versions. Sometimes I'll have an actual demo, but very rarely. When I say SMB, I'm talking 90% self-employed people, or those with side hustles they are trying to monetize. Very rarely it's a mom and pop shop with a physical location.

Base pay is $50k OTE is $75k. I did the math, if I hit my historical rate of 110% of quota, I can hit $90k. There's no MM or Enterprise team here, the company doesn't even sell to those sized businesses. My last job my base was $75k, with an OTE of $150k, and yeah it was a startup so sometimes I did small deals to SMB, but I also sold to very large corps (like big 4 auto, and stuff like that). I'd like to think I could get back to that.

Sunbunny31

Politicker

4

Sr Sales Executive 🐰

Ah, excuse me, I completely misread your work history. So, I would recommend looking for a company where SMB is one tier in a list and get you the capability to move to MM and ultimately Enterprise if you want.
No shame in moving on in this case - but don't beat yourself up too much for being in this role. Needs must sometimes, and you gotta eat.
So yes, I do think you can get back to working with "real" businesses. This is but a bridge job to keep you going until you find the right thing.

CuriousFox

WR Officer

0

🦊

Don't stay somewhere if you are miserable. Protect your mentals bb. ❤

poweredbycaffeine

WR Lieutenant

3

☕️

What is stopping you from being successful in your current role or at your current company? Short stint aside, why jump when you’re not even ramped up and fully aware of whether or not you’ll do well?

Space_Ghost20

Valued Contributor

1

Account Executive

I'm fully ramped. Sales cycle is 3-5 days here. Occasionally you might have something stretch a week to 10 days.

My current OTE is $75k. Half my last OTE. I did the math and if I do 110% of quota (what I did at my last job) I'll hit $90k. I'd like to think I could get back to the level I was at without having to stick it out here.

poweredbycaffeine

WR Lieutenant

2

☕️

Then why not try to do that? Move up the ladder to MM or Enterprise and leverage that story to land a better fitting role.

Space_Ghost20

Valued Contributor

0

Account Executive

There is no MM or Enterprise team here. They don't sell to companies at that level. Moving up means management.
I strongly prefer to leave this company, but if you're telling that leaving after 2 months is a bad look and that I shouldn't do it, I suppose it gives me something to think about.

poweredbycaffeine

WR Lieutenant

2

☕️

Given all you’ve told us in this thread, along with the thread that I assume was about accepting this role, you’re going to have to build a very strong narrative to convince sales leaders to invest in you right now. Capital is being battled for within companies and training/onboarding sales talent is $5-10k on average. The time to payback is variable because you need to generate enough revenue to get your hiring back to black on the balance sheet—and that could take quite a bit of time.

If you’re making this move it better be for the perfect company, selling a product you can bring immediate strategic value to, and you need to oboe your why, your when, and your how. Why should they hire you, when are you going to generate value, and how are you going to do it?

Space_Ghost20

Valued Contributor

1

Account Executive

So far, I haven't been putting this job on my resume. As far as prospective employers know, I've not been working since being laid off. Obviously, that's not going to cut it much longer.

If my goal is to be back to where I was six months ago (compensation-wise, job duties, etc.), will that task be easier now, or after spending 2+ years selling $500 software subscriptions (as opposed to $50k ones)? Not that it matters now, but would it have been better if I had taken a non-sales temp job instead of this one?

poweredbycaffeine

WR Lieutenant

2

☕️

I can’t be sure, but keeping yourself in sales is good. However, my last hit shout the why what and how…build a strong narrative and get yourself where you need and want to be.

TennisandSales

Politicker

3

Head Of Sales

YO are we twins?

I was in financial services for 5 years.
then became an SDR to get into tech, it was in digital marketing there for 6 months
Got an SMB AE role in a niche market. There for 8 months.
got a SMB AE role in Digital marketing

Then got an ENT AE role in that niche market (thats where I am now)

Left that role after 2 years
got another ent AE role in the same industry. Left there after 1 year.
Going back to the company I left.

......man thats insane when I type it out.

MY ADVICE:
do NOT go back to being an SDR! you dont need to do that.

Do you like any of the industries you have worked for enough to want to invest in that market? that was my decision and its payed off BIG time.

Expense management is a big market and lots of players. You could find some good opportunities there.

Why do you want to leave this new gig?

Space_Ghost20

Valued Contributor

2

Account Executive

I liked AI, I could see myself working in that field again. The recruiting/hiring solutions job, was interesting but not really that exciting to me.

Anyway, I want to leave this job for two reasons: a) the pay is not that good (still sticks in my crawl that I took a $25 cut in base, and $75k cut in OTE) and b) aside from the title, I don't really see this job as adding anything for me. There's no outbound prospecting, it's not a complex sale very transactional, average deal size is $500-1500 ACV. I very much see it as a step back. There's no MM or Enterprise team here, so growth is pretty much limited to going AE > team lead > sales manager > sales director. That's not really want I want to do quite yet.

Diablo

Politicker

2

Sr. AE

Damn that’s bad. I am sure you had to pick this up at a lower base/ote to keep the cash rolling in but it’s never late. If you aren’t happy, you got to move. Did you already shortlist the category in software you want to work in?There are a lot of SMB that caters to org with higher headcounts that could help you drive better ARR.
Just curious if you company doesn’t have any plans to make the product for broader and bigger companies ?

Space_Ghost20

Valued Contributor

1

Account Executive

This company is a "startup" (their description) that's been in business for almost 25 years. My guess is if they haven't figured out how to sell to higher level companies by now, they never will.

To be honest I have not really narrowed down what category of software I want to sell in. I know I don't want to sell to government or education (incidentally is fine, but not exclusively), but otherwise I don't really know. That's really why I posted: to know whether it's better to be narrowly focused, or is a broad spectrum of experience still ok.

Sunbunny31

Politicker

0

Sr Sales Executive 🐰

Broad spectrum still exists. Also specialization within larger companies, so if something doesn’t appeal in a vertical, there are others to choose from. I’d definitely pay attention to the advice given by pbc - there’s a lot of great experience there to back up the recommendation.

Space_Ghost20

Valued Contributor

1

Account Executive

Yeah his advice was veryhelpful, even if not what I was hoping to hear.

It's one of those situations where I made my bed, and now I might have to lie in it.

Maximas

Tycoon

1

Senior Sales Executive

Not have been in the same situation before, but I would definitely search for a better opportunity with a higher payout even for tasking a SDR role for having a +8 years of sales experience if I were you!

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