Jewcan_Sam81

Account Executive

Valued Contributor

What is the biggest deal disaster you had in 2021 and what did you learn from it?

So we talk a lot about our glorious victories and the dollar bills we're getting in our pockets from them. But, and it may sound stupid, I find a lot of good thoughts and vibes when a deal falls to shit and I dust myself off to secure a big victory.

My question is: what is the biggest deal mess, disaster, explosion, implosion, etc. that you had in 2021 and, if you're inclined, what did you learn from it that made you an even bigger savage? I'll start:

I had this deal cycle going, really choice SaaS system spanning across four different departments (Ops, Finance, WD, Manufacturing), poised for a six figure deal easy. Everything was cruising, my SP and my overlays were aligned, just needed to get that implementation partner involved for us to drive this home.

Turns out the dude I usually work with at this partner quit, and this new a-hole took over all sales from him. And to say this guy was one of the biggest dealkillers I have ever seen is an understatement. Blustering, pontificating, demeaning, superiority complex, the works. He sounded chill and fine on the pre-meeting strategy call. A bit of an ass but that happens sometimes, I've worked with this partner many times, so I wasn't too worried. But then the call starts, and 7 people from my company from 5 different departments could do nothing but sit back and watch as this guy took an RPG launcher and blew the deal to smithereens in the span of 20 minutes after 4 months of work.

The lesson: While there is very little I could've done, the main thing I learned is to get insight on the people you work with from others that might've worked with this guy. Had I asked around the sales org I'd have been told to avoid this guy at all costs because he'd already killed two other deals that quarter alone.

Who's got some juicy story and a possible life lesson to give the WR some commiseration time?

🏰 War Stories

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1nbatopshotfan

Politicker

4

Sales

Didn’t proof a proposal that I sent and it included a very cheap option. The client picked that option at 7k instead of the 30k option that would be a better fit. Have had to slowly sell additional usage to get to the 30k at a discounted commission rate. Dumb, lazy and I’m paying for it.

At least it wasn’t a monster deal.

CuriousFox

WR Officer

4

🦊

I've had endless internal issues which I've thankfully been able to hide from my clients.

Diablo

Politicker

2

Sr. AE

Happened to me as well. I send the quote and this guy ended up resigning the same evening. Followed up with CEO, other team members who never gave a shit till date.

MCP

Valued Contributor

2

Sales Director

Mine was a personal one. I took a job I knew wasn’t right just for the money. I planned on staying for 6 months & then jumping, but they tossed me after just 4. I learned to be patient and wait for the right one, but the wife was pressuring me to just get working again.

buckets1

Politicker

1

AE

Had a current client on our minimum plan saying they wanted to expand company wide over the next couple years. My (low level) contact invites 5 or 6 director and VP levels to the demo so I invite my VP to gain executive alignment. Next thing I know my low level contact is reaching out directly to my VP to request she runs a demo herself due to her experience working with our larger clients. Like uh what? Who makes a request for a VP to demo software? Lol.
Anyway...about 20 people get invited to this next demo that I run and my VP attends. Turns out I really should have done better discovery because we learn during the demo from a C-level that the real purpose for the demo was to gain executive buy-in on using their minimum plan, which they already purchased for a measly $5k. What a waste of time for everyone involved.
Moral of the story: run better discovery especially when your contact is a hella novice buyer.

DungeonsNDemos

Big Shot

1

Rolling 20's all day

Oof this one hurt to read. Sorry to hear. Good learning opportunity though

Sunbunny31

Politicker

0

Sr Sales Executive 🐰

Moral of the story: trust no one. ;)

HeStoleMyTwix

Valued Contributor

1

AE

Got completely ghosted on a $130k arr deal after 7 meetings and a proposal.

The number of hours I've spent wondering if the dude was a psychopath farming me for a quote are ungodly

DungeonsNDemos

Big Shot

0

Rolling 20's all day

Mine would be not 100% vetting a new partner signup. They came to us to use our product for a specific niche. Then right when they signed up asked me if they are able to sell anywhere else (outside territory).
I said yes, BUT - has to be approved for any pricing and outreach.

Well. The next day I get an angry call from my Boss saying my new partner is cannibalizing our customers because they started just blindly shooting out cheaper pricing to people we already sold to..
Really fucked up my week there and had to very carefully disarm the situation.

I learned my lesson there.

Cabbie

Good Citizen

0

AE (Account Executive)

Had the worst meeting of my (admittedly relatively fresh) career to date literally yesterday.

I've had a great few months for deals & my progression in my company, so been riding high and feeling a bit invincible.

Managed to book a meeting with a large company in an industry I know like the back of my hand (because I worked in it), and the meeting's with all the senior leaders & decision makers.

Went in extremely confident (arrogant's probably a better word), and because of it didn't prep as much as I should have.

Designed my value prop for someone much further down the pecking order than who was actually in the room - despite knowing exactly who'd be there ahead of time and the fact that they'd probably want a higher-order conversation.

Got too technical, too quickly; managed to confuse the entire panel and absolutely bombed the meeting.

Barely managed to scrape through to a second meeting including some lower stakeholders, essentially for damage control.

Lesson: gotta remember to think about who's in the meeting, and the fact that they may only be aware of the symptoms of the problem you can solve - not the specific processes that got them to that place.

Also: "don't get cocky, kid".

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