Sabrinathsaleswitch

AE

Roast My Boss (nah, we don't want EOY deals)

It's end of year, we have a prospect ready to sign. It's a large deal that was committed and has already had about 3-4 redline rounds.

In the final 24 hours, my boss decides he’s holding strong on a contract term - that’s never been conveyed or taught as a dealbreaker in my time here - and with thin reasoning to support it. Basically “vibes” (although I wonder if he benefits somehow to have it come in later or gets a bonus on this contract term).

The prospect has been explicit that they cannot and will not cave on this term. They've explicitly said it will open a can of worms and basically...we'll lose the deal. Beyond that, it’ll have larger repercussions for our company as well – our reputation within this segment, and existing entities affiliated with this prospective company.

Did I mention my boss has no sales experience?

I am livid. Others in sales and mid-management disagree with the decision but have no power. And my boss is on PTO through the EOY like he gives no shits.

Anyone hiring who WANTS a rep who will close whale deals? LOL

#funnynotfunny #peanutsforchristmas

😂 Sales Humor

19

27 comments

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Sunbunny31

Arsonist

9

Sr Sales Executive 🐰

Wait, hold up.
He's drawn a line in the sand and noped out on an open contract?
Is there anybody (ahem, like a CEO) above him who might just gaf?

jefe

Arsonist

8

🍁

^^^

This guy is a fuckwit

Sabrinathsaleswitch

Good Citizen

5

AE

Haha love this

Sunbunny31

Arsonist

2

Sr Sales Executive 🐰

He’s very eloquent. Also accurate.

oldcloser

Arsonist

6

💀

yep - lose the deal or bring in a C resident? Option B all day.

Sunbunny31

Arsonist

6

Sr Sales Executive 🐰

“I’m guessing it’s ok with you that we lost $$$ with this deal because that is going to happen”

Sunbunny31

Arsonist

3

Sr Sales Executive 🐰

I’ve totally pulled this card even in friendly orgs. Amazing how much attention you can get when there’s significant money on the line.

Sabrinathsaleswitch

Good Citizen

7

AE

Oh I spelled it out in a group Slack what the trade offs were. And the long-term ramifications that will hurt OTHER deals and investments we have out there.
The middle manager was going to suggest he consult the CEO but chickened out on putting themselves on the line too. It's like I'm watching bombs go off around us and everyone is chill AF

Sunbunny31

Arsonist

2

Sr Sales Executive 🐰

Who’s your boss’s boss? And why is s/he not all over this?

Sabrinathsaleswitch

Good Citizen

0

AE

CEO. Not sure he's aware. And I don't think my boss has consulted him. Just full on rogue.

Sabrinathsaleswitch

Good Citizen

6

AE

Yup. One that was 1+ year in the making and super strategic. We're gonna have a "come to jesus" call in the new year, but the prospect has already been explicitly clear and started using fighting words last Friday. Make it make sense. Everyone's too nervous to escalate to CEO and go above him.

oldcloser

Arsonist

6

💀

Career making potential moment.

sketchysales

Politicker

1

Sales Manager

What do you have to lose by escalating it? Other than pissing off your boss?

Sabrinathsaleswitch

Good Citizen

0

AE

That's it really. I'm considering it but EOY has passed sadly...unless there's some giant plot I'm unaware of and he's "saving" us somehow, but I doubt it. Rationale seemed thin and more fear-based.

DollHairs

Good Citizen

2

Owner

seems like a good idea to "escalate"

Justatitle

Big Shot

7

Account Executive

uhm, dog, slack your CEO and say, "Hi, this deal has been committed and I assume forecasted to you as closing, we are held up due to this and my boss is on PTO and unreachable, I want to maintain a good image at this org and am asking if this term can be agreeable so that we can close this before EOY."

poweredbycaffeine

WR Lieutenant

3

☕️

Fake his signature?

Kosta_Konfucius

Politicker

2

ERP Sales

Brutal!!

Diablo

Politicker

2

Sr. AE

get your boss's boss or your will be smacked.

Pachacuti

Politicker

2

They call me Daddy, Sales Daddy

Is it your manager or the company attorney? Theres a big difference. If it’s just your manager - screw him. If it’s the company attorney - screw him too, but it should be taken seriously.

If you are just working with your boss, you need to rope in Legal and your boss’s boss. Get more eyes on it asap.

Armageddon

Opinionated

2

Enterprise Account Executive

I'd escalate to CEO

Filth

Tycoon

1

Live Filthy or Die Clean

Jump above that douche's level up to the boss or the board and go full whistle blower. No need to worry about employment b/c you don't want to work for any person OR any organization that backs a person that isn't about growing the company's revenue and your bank account. Full send.

MRK47

Tycoon

1

Head of Growth

As others have said. And if nothing else than for self-preservation, you need to escalate and ensure higher ups are aware. When the deal goes south, the CEO will find out and want to know why…..middle manager starts pointing fingers without you in the room.

But before escalating, try to gauge if the term in question really creates exposure to the business or if precedents have been set before where this term or similar were conceded. You don’t want to escalate to CEO (or other leaders impacted by this deal) to be told your middle manager is right to stand firm (bad look for you). Either way, escalating will damage relationships with your boss so make a judgment call of the risk vs reward in doing so. If there is a chance one side may concede the term but would push the deal into 2025, then gain agreement now that it can be factored into your 2024 numbers. And remember when clearly showing the $ impact of losing the deal, you calculate / show LTV.

Sabrinathsaleswitch

Good Citizen

1

AE

This is great advice. While we're firmly in 2025 and EOY has passed, we actually have a conversation on prepping for different scenarios for another negotiation call (pushed by me) so it's going to open a door internally to a conversation that I believe will help me determine if I should be escalating to C-Level or not. There's not much precedence for this term as it's 1) newer so not many historical deals to call out and 2) a lever that hasn't gotten pushback up until now.

braintank

Politicker

1

Enterprise Account Executive

Lots of great advice here.

As someone who has run into similar situations recently avoid slack and email.

Set a 15 minute meeting with relevant parties. Explain the situation objectively (chatgpt can be helpful for this). Ask for guidance then go on mute.

Goes back to one of my mantras: "never lose alone". If the deal is going south you need to bring everyone you can onboard to either:

1) save the deal
2) cover your ass, so if the deal falls apart no one can say you didn't "leave it all on the field"

Sabrinathsaleswitch

Good Citizen

1

AE

Thank you! This is literally happening now.

braintank

Politicker

0

Enterprise Account Executive

Glad we could help!

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