SportsSalesGuy

Enterprise Account Executive

How do you manage two full time sales jobs at once?

Thinking of going this route purely for maximizing income potential. Especially based off how 24' is looking with economy, job market, political landscape, wars, etc. (for those who follow Patrick Bet-David, know).

AE and maybe a BDR/SDR or Inside Rep position. Don't think I could do two AE roles at once.

MY ASK/QUESTION:

How the fuck do you do it?

I am trying to understand more so how you juggle meetings that you really cant miss and get 2x booked (i.e. Monday morning team calls with your boss at 9 AM) you cannot just not show to those or be on both calls at once.

I'm assuming you really have to stagger your start times for job 1 and then start job 2 and really manage calendars well but thats not news.

I know people have experience on this, I see it every so often, but it always seems to end poorly or seems very difficult and not worth it.

Cant wait to hear the feedback! and would love to hear some nightmare stories or funny stories as well.

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24 comments

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poweredbycaffeine

WR Lieutenant

10

☕️

You quit the one with a lower OTE and be a sensible human.

jefe

Arsonist

5

🍁

Yup. My first thought was "YOU DON'T"

SportsSalesGuy

Tycoon

4

Enterprise Account Executive

Lol this would be the move if applicable, yes

oldcloser

Arsonist

6

💀

I could see back to back inbound jobs that don’t duplicate hours. You could do that if you’ve got stamina. Otherwise, doubling up 2 OB jobs. You’re a 1/2 employee at each- at best.

HVACexpert

Politicker

2

sales engineer

Only so many hours in a day where outbound reaches your audience.

GDO

Politicker

2

BDM

haha, 2 real sales gigs seems like a nightmare

oldcloser

Arsonist

6

💀

No clue. @SalesPharaoh knows all.

SalesPharaoh

Big Shot

7

Senior Account Executive

Thank you for getting my attention to this post @oldcloser! let me contribute with my experience and lessons learned. @SportsSalesGuy take a look at my posts, you'll notice that many times I was incoherent, which reflected my mental state at the time there was a post I took down completely.
Anyways, I congratulate you to take the beaten path to wealth. Here are a couple of rules you should abide by to make yourself as successful as possible.
1st: there will always be a favorite job, that's fine even if it's the lesser paid one. It's the one you need to make sure they don't know shit of what you're doing between hours etc...it's also the job where they trust you to the extent on not to ask you questions on why you block times.
2nd: blocking your calendars is your best friend. under what title? not available has proved to be the most effective.
3rd: these two jobs have to be COMPLETELY different, you cannot do something close to similar. meaning you don't want to find yourself cold calling and saying the other company's name by mistake. So best, do AE work and Account Management, Partnership, something that is by nature doesn't put you out there as a function. Why? because the more you put yourself out there to more you risk to be exposed.
4th: Secrecy is your friend. Stick to yourself. You watch Pat Bet David so you know how important this is. Only your wife needs to know you do this, anyone else are on need to know basis if it will help you grow in any of the companies.
5th: you will always feel liberated because you have a "backup" that has proved that I'm more ballsy in my two jobs. This is a double edged sword it can pay off really well or backfire. So check yourself before you wreck yourself.
6th: You're gonna have to accept being an individual contributor and be comfortable with that if you want. Why? because you already doubled your income so why take more responsibility for 20% increase? It wouldn't help your goals.
7th: remind yourself why you do this? Most probably your doing it for money. no shame about that. embrace it. Some people are driven by careers other by money. you are the money guy who can juggle two jobs.
8th: You may want to stagger the start or basically cram the demos in a certain slot.
9th: Everyone really works for 4hours only. If you focus 4 hours you hit your targets.
10th: Be proactive. Always take the initiative with your managers in both jobs. Why? because that will reduce the risk of them requesting a meeting. The more you push for this the more they will feel you are doing more work than you are actually doing. That's just psychology.

Final: you and I know, that this is not sustainable unless you hit the jackpot on both. You don't know that yet. so have a target on which company you deep down want to bail out on. Meanwhile the income you got from have two jobs goes to your emergency fund. Things get stable the emergency fund is full. Reward yourself! you've earned it!
Again, id do this again.
Personal advices:
Wake up early in the morning you'll feel your day is WAAAAY longer.
Take care of your body
You can do this.
Most importantly set boundaries for both jobs (that should be a general rule)
Best of luck.

SportsSalesGuy

Tycoon

2

Enterprise Account Executive

Absolutely tremendous answer. Exactly what I was looking for!

Fenderbaum

Politicker

6

Retired Choirboy🪕

If it's temporary, go for it. Otherwise, save yourself some BS and stay with one job. Your loved ones will love you more if you have peace of mind.

Revenue_Rambo

Politicker

5

Director, Revenue Enablement

What’s worse than getting fired from a sales job?

Getting fired from 2.

Stick to the higher OTE. Put in an honest effort and focus on refining your skills. Stretching yourself thin like this will expose and amplify your flaws quickly.

SportsSalesGuy

Tycoon

3

Enterprise Account Executive

Great point

Pachacuti

Politicker

4

They call me Daddy, Sales Daddy

Very hard as a sales person who needs to be working 8-5. Its easier for those who aren't in customer-facing positions (software dev for example) to juggle multiple gigs.

SportsSalesGuy

Tycoon

4

Enterprise Account Executive

@SADNESSLieutenant think you have experience with this as well

CuriousFox

WR Officer

4

🦊

I think he got burned out

SportsSalesGuy

Tycoon

2

Enterprise Account Executive

Of sales or doing 2 jobs at once?

Sunbunny31

Politicker

3

Sr Sales Executive 🐰

Hard to know. Sadly haven't seen him for a while. But the two jobs were definitely a challenge. A few people have tried it. Nobody (at least on this platform) successful for more than a few months, at most.

Sunbunny31

Politicker

4

Sr Sales Executive 🐰

Find a job that pays you enough to do that one job. You have a life to live, which honestly doesn’t just mean being an income machine.

3

Retired Sales Professional

👍👍

wolfofmiami

Opinionated

2

🐺

It’s better to find like a inbound sales role at a small company that you just take like 50 calls a week and bank the 40k salary. Or finding a job that isn’t sales

SportsSalesGuy

Tycoon

2

Enterprise Account Executive

@wolfoftampa not sales, like what? any suggestions that could be easy transferable from sales experience?

wolfofmiami

Opinionated

2

🐺

A sales Manager role for a small team, sales enablement, part time customer service role idk you could be a photographer too there’s a lot of jobs lol

Diablo

Politicker

2

Sr. AE

I cannot think of doing 2. It will drive me nuts tbh.

HappyGilmore

Politicker

1

Account Executive

Not sure how 2 full-time jobs could work tangentially, but would hope there's a path where if you choose to work 2 jobs, one doesn't find out about the other.

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