Career advice for 30 y/o in software sales

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corgilady2011
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Career advice for 30 y/o in software sales

Post by corgilady2011 » Fri Apr 12, 2019 7:11 pm

Hi everyone, I need some advice and if you've been in my spot before - I'd love your insight.

I work in selling software-as-a-service at a mid-sized company that's in growth mode and have gotten some good opportunities selling to larger enterprise & have had a couple of really nice years. I'm 30, and this is my 6th year in sales. I can't help but feel a lot of loyalty to my current company given my success, and my desire to retire as early as possible as I'm able to guarantee a total 200K take home for at least another couple of years here.

My success seems to have caught the attention of another software company they reached out to me thinking I'm a fit for a couple of positions. I've been interviewing for the first one I was matched with and I'm feeling a bit intimidated and a bit out of my league as all of their job postings are indicating you should have 10+ years of quota carrying sales experience, and most of the people I've found on LinkedIn holding these roles easily have, in general, much more experience than that. I'm a bit torn at how to feel about the interview process.

I've gone into the first round of interviews just trying to be myself, and take the interview process as I typically handle a sales cycle with my clients. I've received outstanding feedback thus far and they've indicated they feel there's a lot of potential and I'm going into the last round of interviews in the next couple of weeks.

I'm really unsure how to feel given my loyalty to my current company that has treated me incredibly well and has given me a mountain of opportunity. On the other hand, I know that likely the best way to grow my career is to toss myself right out of my comfort zone, but it's also really risky as this has been my only sales role to date and I'm unsure of how I'd perform in other environments.

My husband has a fairly stable job with a large automotive manufacturer, but will be working on a contract basis until early next year.

At a high-level from discussions w/ the recruiter, the option would look like:

*Current role - $95K base, $225K OTE -- I took home $375K in an anomaly year, 250K in 2017 and on track to end a bit north of $200K this year. No stock. $4.5K added to 401K.
*Possible option - $135K base, $270K OTE, $270K RSU vested over 4 years. $5K added to 401K annually & an ESPP.
*Net worth - $800K including home equity/emergency fund, $600K without.

What would you do? what advice would you have as I evaluate?
Last edited by corgilady2011 on Sat Apr 13, 2019 2:28 pm, edited 4 times in total.

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cheese_breath
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Re: Career advise for 30 y/o in software sales

Post by cheese_breath » Fri Apr 12, 2019 7:47 pm

corgilady2011 wrote:
Fri Apr 12, 2019 7:11 pm

... I'm really unsure how to feel given my loyalty to my current company ...
Leave loyalty out of it. Your company treats you well because you make a lot of money for them. Have a bad year and see how loyal they are to you.
The surest way to know the future is when it becomes the past.

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RickBoglehead
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Re: Career advise for 30 y/o in software sales

Post by RickBoglehead » Fri Apr 12, 2019 8:23 pm

I advise you to ask for advice :wink:
Avid user of forums on variety of interests-financial, home brewing, F-150, PHEV, home repair, etc. Enjoy learning & passing on knowledge. It's PRINCIPAL, not PRINCIPLE. I ADVISE you to seek ADVICE.

Goal33
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Re: Career advice for 30 y/o in software sales

Post by Goal33 » Fri Apr 12, 2019 8:34 pm

“What have you done for me lately?”

You can make a lot of money more during a good year with [company name --admin LadyGeek] or other large SaaS providers.
A man with one watch always knows what time it is; a man with two watches is never sure.

HEDGEFUNDIE
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Re: Career advice for 30 y/o in software sales

Post by HEDGEFUNDIE » Fri Apr 12, 2019 8:35 pm

Do it. [company name --admin LadyGeek] is ubiquitous and you will gain credibility to work basically anywhere you want in tech afterwards.

random_walker_77
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Re: Career advice for 30 y/o in software sales

Post by random_walker_77 » Fri Apr 12, 2019 9:54 pm

I agree w/ the other responses. Go for it.
corgilady2011 wrote:
Fri Apr 12, 2019 7:11 pm
...and I'm feeling a bit intimidated and a bit out of my league as all of their job postings are indicating you should have 10+ years of quota carrying sales experience, and most of the people I've found on LinkedIn holding these roles easily have, in general, much more experience than that. I'm a bit torn at how to feel about the interview process.
Don't let that bother you, but don't go pointing that out either. Remember, they reached out to you. Your job now is to convince them that you'll be able to add value, and if you succeed, they'll make you an offer that'll convince you to join them. Besides, those requirements lists are usually just wish lists and most men know to treat it as such. Don't let it psych you out.

You might also find this article to be both interesting and relevant:
https://hbr.org/2014/08/why-women-dont- ... -qualified

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Re: Career advice for 30 y/o in software sales

Post by LadyGeek » Fri Apr 12, 2019 10:09 pm

This thread is now in the Personal Finance (Not Investing) forum (career guidance).
Wiki To some, the glass is half full. To others, the glass is half empty. To an engineer, it's twice the size it needs to be.

HornedToad
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Re: Career advice for 30 y/o in software sales

Post by HornedToad » Fri Apr 12, 2019 10:27 pm

Financially it's a no brainer.

Career-wise, it's also a step up in terms of company recognition and growth. Generally you learn the most, and grow and develop by stepping out of your comfort zone and trying something new. I think it's a great move.

Go to the last interview, do your best and be yourself and let what happens happen and then decide. They reached out to you for a reason and so far the feedback has been positive. Years of experience does not necessarily equal competence so be yourself.

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corgilady2011
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Re: Career advise for 30 y/o in software sales

Post by corgilady2011 » Sat Apr 13, 2019 12:12 pm

RickBoglehead wrote:
Fri Apr 12, 2019 8:23 pm
I advise you to ask for advice :wink:
Yes, thank you. I fixed it :oops:
HEDGEFUNDIE wrote:
Fri Apr 12, 2019 8:35 pm
Do it. (company) is ubiquitous and you will gain credibility to work basically anywhere you want in tech afterwards.
I have heard this before, but the job is sounding a bit too good to be true at the moment. While it will challenge me, I definitely think I can do the job. however I have a lot to sift through to make sure it really is as good as they are making it out to be. It appears the only positions that I'd be able to move up into if I received the role I'm currently interviewing for would be going into management. That's ultimately what I'd like to do in the longer term, but I think it's important to get a few more years of direct quota carrying experience under my belt first. My goal would be if I can be successful here, that I'd be able to find a managerial role after 3-5 years. This role would give me experience in indirectly managing/leading around 15-20 various resources to a common goal of selling into several large named accounts and ensuring their success. I do something similar today, just not really in that level-of-scale. I am mostly a one person does all, with pulling in a few resources (2 to 3) but that's mostly due to the limited resources my current organization has.
HornedToad wrote:
Fri Apr 12, 2019 10:27 pm
Financially it's a no brainer.

Career-wise, it's also a step up in terms of company recognition and growth. Generally you learn the most, and grow and develop by stepping out of your comfort zone and trying something new. I think it's a great move.

Go to the last interview, do your best and be yourself and let what happens happen and then decide. They reached out to you for a reason and so far the feedback has been positive. Years of experience does not necessarily equal competence so be yourself.
Yes, I think so too. I've noted above what my longer-term career goals are, and if it really is as good as it says it is, I think this could accelerate my career trajectory by several years. I actually have a very similar role in my current job, just not the same level of scale but I have started to feel a bit stuck from both a career & compensation standpoint and likely will not have an opportunity to further progress until the company grows to a point where they could better afford me to be out of a direct end-line sales role. I think I am probably around 5 to 7 years out from receiving managerial opportunity in my current role, although that is being a bit generous since they have historically hired externally for all managerial roles.
Last edited by corgilady2011 on Sat Apr 13, 2019 2:28 pm, edited 2 times in total.

HEDGEFUNDIE
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Re: Career advise for 30 y/o in software sales

Post by HEDGEFUNDIE » Sat Apr 13, 2019 1:22 pm

corgilady2011 wrote:
Sat Apr 13, 2019 12:12 pm
That's ultimately what I'd like to do in the longer term, but I think it's important to get a few more years of direct quota carrying experience under my belt first. My goal would be if I can be successful here, that I'd be able to find a managerial role after 3-5 years, either at SFDC or otherwise.
I have to echo what Random Walker alluded to above and ask you to consider: would a man say this?

Opportunities don’t come around every day. Wait until you’re “ready” and you may already be over the hill.

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cheese_breath
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Re: Career advise for 30 y/o in software sales

Post by cheese_breath » Sat Apr 13, 2019 1:31 pm

HEDGEFUNDIE wrote:
Sat Apr 13, 2019 1:22 pm
Opportunities don’t come around every day. Wait until you’re “ready” and you may already be over the hill.
+1
"Learning on the job" is probably what most of us do whenever we're promoted. I know I wasn't always 'ready' every time I was promoted, and I'm sure my superiors knew it too. But they had confidence to my ability to learn the job as I got into it.
The surest way to know the future is when it becomes the past.

Dottie57
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Re: Career advice for 30 y/o in software sales

Post by Dottie57 » Sat Apr 13, 2019 2:14 pm

Good luck at the next interview and job. Go for it!

stan1
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Re: Career advice for 30 y/o in software sales

Post by stan1 » Sat Apr 13, 2019 2:19 pm

You have your recommendation (and I agree with it) but you've posted too much personal information. I'd ask the moderator's help with redacting the company name.

WildBill
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Re: Career advice for 30 y/o in software sales

Post by WildBill » Sat Apr 13, 2019 2:51 pm

Howdy

Interesting post. I have been on several different sides of your situation. Here are some thoughts

What is your ultimate goal or ideal career path? The reason for this question is that as a direct contributor enterprise sales is a position where the upside is potentially almost unlimited, as long as the company you are working for is reasonable. Is your current organization that way, and do you have an opportunity to really drive increased sales? If so, why move?

For example, in a previous life I was a VP with several sales organizations reporting to me. We had a number of experienced reps who earned gobs of money, way more than me or most of the other company executives. Some (jealous) guys in other disciplines, or the occasional clueless HR type would discuss cutting commissions, or “equalization” or some such nonsense. Always nipped it in the bud because those few guys were driving a disproportionate level of sales. Revenue is the lifeblood of any business and the guys that are driving it are precious.

Another thought - if you want to advance into a management track, it maybe possible at your existing company, especially if they know a competitor is sniffing at you. You do not use that interest as a lever to extort something: you use it as an opportunity to have a frank discussion at your current company, if you chose to do so. This needs to be handled with finesse, but if you are good at sales you will also understand how to finesse it.

You should ask yourself these questions as you have a lot invested in your current employer and that may be the place you want to be. Only you can answer that. Your thoughts re these questions should inform you on whether going to a larger competition with a potentially wider range of opportunities is how you want to proceed.

Keep selling

W B
"Through chances various, through all vicissitudes, we make our way." Virgil, The Aeneid

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Re: Career advice for 30 y/o in software sales

Post by LadyGeek » Sat Apr 13, 2019 3:57 pm

stan1 wrote:
Sat Apr 13, 2019 2:19 pm
You have your recommendation (and I agree with it) but you've posted too much personal information. I'd ask the moderator's help with redacting the company name.
The OP has requested our help. I've redacted the company name from several posts.

(The OP has redacted the company name from her own posts.)
Wiki To some, the glass is half full. To others, the glass is half empty. To an engineer, it's twice the size it needs to be.

Trader Joe
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Re: Career advice for 30 y/o in software sales

Post by Trader Joe » Sat Apr 13, 2019 4:25 pm

corgilady2011 wrote:
Fri Apr 12, 2019 7:11 pm
Hi everyone, I need some advice and if you've been in my spot before - I'd love your insight.

I work in selling software-as-a-service at a mid-sized company that's in growth mode and have gotten some good opportunities selling to larger enterprise & have had a couple of really nice years. I'm 30, and this is my 6th year in sales. I can't help but feel a lot of loyalty to my current company given my success, and my desire to retire as early as possible as I'm able to guarantee a total 200K take home for at least another couple of years here.

My success seems to have caught the attention of another software company they reached out to me thinking I'm a fit for a couple of positions. I've been interviewing for the first one I was matched with and I'm feeling a bit intimidated and a bit out of my league as all of their job postings are indicating you should have 10+ years of quota carrying sales experience, and most of the people I've found on LinkedIn holding these roles easily have, in general, much more experience than that. I'm a bit torn at how to feel about the interview process.

I've gone into the first round of interviews just trying to be myself, and take the interview process as I typically handle a sales cycle with my clients. I've received outstanding feedback thus far and they've indicated they feel there's a lot of potential and I'm going into the last round of interviews in the next couple of weeks.

I'm really unsure how to feel given my loyalty to my current company that has treated me incredibly well and has given me a mountain of opportunity. On the other hand, I know that likely the best way to grow my career is to toss myself right out of my comfort zone, but it's also really risky as this has been my only sales role to date and I'm unsure of how I'd perform in other environments.

My husband has a fairly stable job with a large automotive manufacturer, but will be working on a contract basis until early next year.

At a high-level from discussions w/ the recruiter, the option would look like:

*Current role - $95K base, $225K OTE -- I took home $375K in an anomaly year, 250K in 2017 and on track to end a bit north of $200K this year. No stock. $4.5K added to 401K.
*Possible option - $135K base, $270K OTE, $270K RSU vested over 4 years. $5K added to 401K annually & an ESPP.
*Net worth - $800K including home equity/emergency fund, $600K without.

What would you do? what advice would you have as I evaluate?
Welcome to the forum. I would take the possible option, if that position is offered. Your current base salary is too small. Always seek better upside (commission).

Also, working at different organizations will only help your experience at your age. SaaS is a great space. Good luck.

vrr106
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Re: Career advice for 30 y/o in software sales

Post by vrr106 » Mon Apr 15, 2019 2:43 pm

I think you also need to factor the relative stability of each company, both in the short and long term. If you're in a mid-sized company that has been growing but will see a deceleration in growth, chances are you see less accerelators and lower OTE. OTOH if double digit growth is expected to continue, you can reap great rewards. With a larger company, you could have the potential of RSUs which over a long term can be very lucrative if you stick around. So when you figure out what you want to do, think about the prospects of the company as well.

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