Currently interviewing - help choosing a new sales job

So I've been on the job hunt for about a month now. I'm currently a media consultant (AE) for a large media company - where in short I sell radio and digital advertising to businesses. I've been at this company for almost 5 years now, and although it's definitely been challenging (started off building a book of business from 0, then basically felt like I had to start all over after the pandemic hit) I've really grown as a sales professional and on pace to have my best year ever. I'm on a really good roll right now, and have some really nice things in my pipeline. And although it's definitely hard walking away from something I've put my blood, sweat and tears into for years that's starting to really pay off - there are a lot of things with the company that have happened that've rubbed me the wrong way and there's a lot of difficulties with campaigns post-sale that just makes my day-to-day incredibly frustrating.


With that, I've already been interviewing with some different companies - but the ones that I'm furthest down the interviewing process with and seem the most promising are all pretty different.


One is with a SaaS company that my buddy works at, and he loves his job there. From who I've interviewed with it seems like a cool culture and the company has been growing pretty strong. I originally did a whole interview loop for a mid-market AE role, but since I don't have prior SaaS experience they gave it to someone who did - but they really liked me so now I'm interviewing for an Emerging-market AE role. It's an "expansion" AE role so i really wouldn't be calling on new clients, but rather have a client list of businesses already using their software to some degree and then trying to upsell them. To start it's $60k base / $120k OTE, uncapped commissions, and you get a pretty good equity package (i believe around $35-45k in stock) and stock buying options which i find really cool. 100% remote. Good product-market fit. Majority of reps are hitting their quotas.


Another opportunity is with a sports media company that makes custom content that gets pushed on a bunch of different channels/shows/etc. that they have. Essentially what you sell is custom videos/content with well-known athletes and celebrities for big brands that then get pushed out all over the internet on different social media platforms/channels/etc. to help with their marketing/advertising. Since I come from a media/advertising background I feel like I wouldn't be completely starting over with something brand new, and being able to do things with big athletes and brands is exciting. Definitely a bigger sell where the minimum deal is around $250k-$500k+. Was told it'd be at least $100k base / $200k OTE (uncapped commission) to start. Predominantly remote.


The third job is with a huge international insurance company, where the main thing i'd be selling is trade credit insurance to businesses (it's risk mitigation; basically if you're a business that has this you're insured to have your invoices paid even if a customer doesn't pay it because of bankruptcy, insolvency, etc.). My territory would be the NY tri-state area. The manager i've been interviewing with was straight up and said that this would be the hardest sale of my life, and it's definitely a grind for the first few years building your book of business from 0. However, people can make a lot of money here. The top rep in the territory made over $1M, and by year 3 if I'm good i was told i'd be making $250k+. Starts off with a $100-120k base + commission on new business (not renewals); and then when you build your book of business up enough you get put onto the "senior" comp, plan which is 100% commission (but higher commission rate, get paid on renewals, much more lucrative). I've met with the regional VP of the NE (who'd be my manager) and a couple existing agents there who all seem pretty cool, and the money seems great (really the main reason why i barked up this tree in the first place); but I feel like insurance sales might be a bit mundane and idk if I want to go and grind my face off again. This would be an in-office/hybrid role (office is in Manhattan).


Obviously - these roles are all very different. I'd love to get anyone's advice who've been in similar situations; as well as input from anyone who's working in any of these industries. Yes I want to make BANK - but i don't want to go somewhere that i'll regret 6 months down the line and be miserable.


Any and all advice/feedback is appreciated! And anyone that's been in any of these industries for a while and could shed some light on the money, personal development, longevity, etc. would be awesome. Thank you fellow savages.



📬 WR Feedback
🤝 Interviewing/Offer
🎯 Career Development
9
E_Money
Big Shot
4
💰
I would choose between the first two. Internal referrals from friends are always reliable because, if they are good friends, they would tell you if it was actually shitty. Plus working with friends is always fun. 

And in my experience there is a lot of opportunity for growth in SaaS as well. 

The second job sounds most similar to what you're currently doing like @Pachacuti said. 
Skerp22
Catalyst
2
Account Executive, Expansion
Appreciate the feedback, and yea a referral from a friend is huge. And it’s in SaaS, which seems to be the hot thing in sales these days. The only thing is that the pay is lower than what I would’ve wanted. Obviously if/when I get an offer I can ask for more, but starting that much farther down kinda blows. But you’re right a out the other gig, def is very interesting
E_Money
Big Shot
2
💰
You could always pull out the "I would honestly rather work here, but I have another offer that is much higher so if you could come up to X that would make the decision easier for me." Worst they can say is no and then it's just up to you. But in my experience making decisions based on money can lead to shitty job situations. 
CuriousFox
WR Officer
3
🦊
Take a deep breath and go for it! Tell fear to fuck off. ❤🦊
Skerp22
Catalyst
2
Account Executive, Expansion
The legend himself! 🦊 Appreciate the advice. Do you have any thoughts on choosing which path?
CuriousFox
WR Officer
1
🦊
Yes. I give the same advice to everyone. Do what's best for you and your family. Only you can decide that. ❤
Sunbunny31
Politicker
3
Sr Sales Executive 🐰
Just reading your comments, you sound the most enthusiastic about the second opportunity.  
Pachacuti
Politicker
2
They call me Daddy, Sales Daddy
You will never know if you'll regret the opportunity until you take it. 

That said, the 2nd seems like a close match to what you're doing now so it will allow you the shortest ramp to success.  

What personally interests you the most and inspires you?  I know I can't sell something I don't believe in.  What do you most believe in?
Skerp22
Catalyst
2
Account Executive, Expansion
Thanks ! This is great feedback. So i’ve come to learn and see the value in what all of these jobs sell - but as far as interests go the media one is big. Great content and videos is huge, plus being able to sell a product incorporating famous athletes and musicians seems really cool
FoodForSales
Politicker
2
AE
I'm not in SaaS, but from what I read here it seems to be "the thing".   But that base seems low, especially if you are in the NY area.  

The other two seem more promising, but Insurance has always bored me and if I had to sell it I think I would just kill myself.
Skerp22
Catalyst
1
Account Executive, Expansion
Yea SaaS def seems to be all the rave now. I agree the base/ote for that one is low. It is for the “emerging” market which is for smaller businesses but still.

And for insurance that’s what i’ve had in the back of my mind as well - I actually do see the benefit of this particular insurance but i just feel like insurance sales as a while can be, for lack or a better word, “dry” (PS - any insurance savages that say otherwise let me know)
ClutchDeluxe
Valued Contributor
0
asking people for money
Congrats on the offers!

One of my best friends is in trade credit and because it's really specialised, he's doing super well now. It's uber corporatey (if that's your thing)
Cyberjarre
Politicker
0
BDR
"Too busy" usually indicates that they aren't sold on the value of your product...other than the rare cases where a place cannot take on any more new business like you mentioned, what business doesn't want to make more money or have more customers?
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