TennisandSales

Head Of Sales

Acclaimed Answer

Im happy, but I might leave. Career Update

I shared a post about paying back a sign on bonus and a few ppl asked what the deal was, they thought i was happy. https://bravado.co/war-room/posts/paying-back-a-sign-on-bonus

So here is the update.

Ive been at my current company for 9 months. Im making the most money ive ever made. ill hit my OTE this year. Im pretty happy.

My boss kinda sucks, peep this post on that: https://bravado.co/war-room/posts/can-i-rant-real-quick-about-my-boss

The company I left to come here has been talking to me for the last few months. its a publicly traded company and their product is really really great and going to do crazy things in our industry. I left because they were going to stop selling the product for a year and focus on improving it. (crazy i know lots of details i could share but the big thing to know if that i left on good terms and the VP and I are friends)

SO they are going to start selling the product again but have no sales team. They have changed a bunch of things and want to hire ONE sales person to start. this person will be the "head of sales". this person will be an AE to start and will be in charge of determining the sales process and approach for the product. Then, when the time is right, hire a team.

THIS excites me SO much. they have done this in other divisions with great success.

the big thing is that my OTE will likely be lower at that company.

but i am just SO much more excited/passionate about them than what I am doing now.

I am concerned that in 2 years ill not be happy in my current spot and ill have missed out on this opportunity.

They have been trying to find the RIGHT person for 5 months and cant find the perfect fit.....besides me.

SOOOOO i am in a unbelievably privileged position to have to pick between two amazing opportunities (i know my life just sucks).

i am not looking to leave my current spot, but for this role, I might make the exception.

So thats my long post, what do you think?

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15

37 comments

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BourbonKing

Valued Contributor

5

VP of Sales

Nothing wrong with taking a small step backwards in order to take two steps forward (which is what it sounds like you'd be doing here). I assume that your OTE will increase once you start building your team and move into a pure leadership role. Unless there's more you're not sharing, I'd go for it--shit hot product, VP who's in your corner, opportunity to build a sales team the way you want...sounds awesome!

TennisandSales

Politicker

0

Head Of Sales

thanks! yeah it all does sound pretty great. i have a call today to hear about what the comp actually is.

i think im also concerned that if I leave, im leaving a spot where I COULD make a ton of money....or i might not

CuriousFox

WR Officer

4

🦊

Are you going to have a sales director salary? 🤔

Diablo

Politicker

2

Sr. AE

Great question 🙋‍♂️

TennisandSales

Politicker

0

Head Of Sales

great question. i was hoping to find that out today.....but I did not so the jury is still out on that.

antiASKHOLE

Tycoon

3

Bravado's Resident Asshole

You have valid points and concerns. What does your gut tell you to do? How does your wife feel about you going back? Those are two questions I would ask myself and base the decision on given the details.

TennisandSales

Politicker

2

Head Of Sales

great questions. Ultimately my wife wants me to do what I will find the most joy in doing.

my gut is telling me to leave and go back, because of how connected i am to the vision and how having that sense of belonging and connection is what kept me at a company for 5 years in the past.

SaasSlingin

Politicker

1

Sr AE

Curious how different of products are they? Which is more impactful? Which are u more passionate about?

TennisandSales

Politicker

0

Head Of Sales

GREAT question. So the product i sell now is higher ticket price, more impactful, but smaller market.

the old company has a larger market, smaller ticket price, a little less of a NEED to have (but still really important) but im a little more passionate about it than the current product haha

Diablo

Politicker

3

Sr. AE

First off congrats. It's a great move. I sense all the positive vibes in your post so I am assuming this is exactly what you want to do and have been waiting for. All the best !

TennisandSales

Politicker

1

Head Of Sales

thank you! i really am torn....and i think since im such a people pleaser, I know no matter what I do, someone will be upset and i really hate that haha

Tres

Politicker

2

Account Executive

It's a nice spot to be in! It sounds like it comes down to which is better for you at this point in life = higher salary, or management career path (which I think the second opp would be if you end up hiring an entire sales staff underneath you over time). People can make cases for both sides based on their own biases and preferences, personally I think I would lean towards option 2 (of rejoining your old company), but I wouldn't think either choice was bad.

TennisandSales

Politicker

0

Head Of Sales

Thanks! yeah i would be willing to take a hit to my OTE if my base would stay the same. but if the hit to OTE is TOO big then it will be a really hard choice haha

Kosta_Konfucius

Politicker

2

Sales Rep

That is awesome the spot you are currently in! Have you been in a leadership role or anything like the new opportunity?

TennisandSales

Politicker

0

Head Of Sales

yeah, I have been a manager of a small team before. and ive always been involved in training and developing others, but most of the time those responsibilities are not in my job description.

Sunbunny31

Politicker

2

Sr Sales Executive 🐰

You sound so excited about this opportunity, I am very happy for you! Even if it’s a lower OTE, if it’s a livable opportunity, I’d tell you to listen to your gut.

Of course, the bargaining chip to lure you away is replacing the salary you’re walking away from. ;)

TennisandSales

Politicker

1

Head Of Sales

Thanks!!! And yeah the more i think about it the more the base needs to AT LEAST stay the same

Sunbunny31

Politicker

1

Sr Sales Executive 🐰

Exactly! Honestly, that’s what the boomerang effect is for - you keep moving up. They’re trying to take you from a role you like. They should be able to increase your comp. Isn’t that part of why you left in the first place? Also there’s that issue of the signing bonus. Honestly, they need to make sure you are taken care of.

TennisandSales

Politicker

1

Head Of Sales

yes it is part of why i left before! (nice memory!) an i think the same thing. they should take care of me if they want me.....after my last meeting i had....i didnt get the vibe that they will be willing to do that, i didnt get any comp numbers like I thought i was going too, so that is annoying and the saga continues i guess.

Sunbunny31

Politicker

1

Sr Sales Executive 🐰

I'm sorry to hear that, but worst case, you stay where you are, which you like.

And don't let your former company take advantage of you. Maybe they think they have you hooked and can lowball.

TennisandSales

Politicker

1

Head Of Sales

yeah that is a good point. im in no hurry to leave so if its not going to be right, its a no go.

And i am for sure trying to make sure i dont get taken advantage of haha

Sunbunny31

Politicker

1

Sr Sales Executive 🐰

When will you have an update on this?

TennisandSales

Politicker

1

Head Of Sales

i have a small update i could share!

Sunbunny31

Politicker

0

Sr Sales Executive 🐰

Please do! Looking forward to seeing it.

SaasSlingin

Politicker

1

Sr AE

Now I know what you were talking about when you mentioned you were in the thick of big ol decision to make

TennisandSales

Politicker

0

Head Of Sales

hahah!! yep!

BlueJays2591

Politicker

1

Federal Business Dev Director

Head of sales is a great position if you want to go into management. Could lead to a lot more money down the road

TennisandSales

Politicker

1

Head Of Sales

Yeah it’s true. I’ve always been a “get it now!” Kinda of person but the long game is a good thing too

BlueJays2591

Politicker

1

Federal Business Dev Director

Do you want to go into management at some point?

TennisandSales

Politicker

1

Head Of Sales

yes i do. ive been a sales manager before, turned down a director of sales role in the past because it wasnt the right fit, but I do see my self going into leadership at SOME point

BlueJays2591

Politicker

0

Federal Business Dev Director

Well, seems like your timeline moved up a bit lol. Management has some nice perks (equity if your company has it)

TennisandSales

Politicker

0

Head Of Sales

Haha yeah potentially! Haha they are a public company so i would get some nice stock benefits

WhoDey

Opinionated

1

VP of Sales

I'd much rather work for a leader I admire and respect.

TennisandSales

Politicker

0

Head Of Sales

me too! But then on the flip side I feel like the more I work with him, the more I can kinda manage his stupid shit haha. id rather not, but its not the worst thing if im making good money.

Jaytea

Catalyst

1

N/A

I say yes, if ur young seems like the financials are good since it’s a publicly traded company. If u believe in the company u will be a lot richer since u have equity. Go for it as LONG as they are financially stable with a good ARR. I’ve joined a couple startups and ARR matters.

TennisandSales

Politicker

0

Head Of Sales

yeah I get what your saying. The publicly traded company will be better off financially, but I would make more at this current job. such a hard thing to work through, when i just dont want to make a mistake ether way.

ConwayStern

Member

0

AE

i am a big risk taker and firm believer that the right team can find success (almost) anywhere. sounds like you’ve found that team, plus an opportunity to BUILD ONTO SAID TEAM?? i’m getting excited just typing this out.

ain’t no shame in taking a little haircut if you have convictions that it will grow back ferociously. don’t let life pass you by!

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