What's the most money you've expensed selling an account? How did corporate take it?

I'll start with me.


I worked at a small start up a few years ago that sold loan processing software to banks. We needed a bank on the east coast for a client we had that needed to process over a million dollars in backlogged loans. Loans equal interest, so they really wanted to start processing these. They were sitting on a goldmine of revenue they couldn't tap into until they had a bank to underwrite the portfolio. So they sent me and one other person to this banking conference, gave me the company credit card and said, "Do whatever it takes, come back with a bank."


We flew all day, rented an SUV town car to drive us there & back, ended up becoming the title sponsor of the event, comp'd anyone who crossed our paths for a conversation, opened a tab at all the bars for everyone, bought turndown service for the hotel with our logo on it, had custom spirits made for us at their hotel distillery to give away at a mixer on the final night (300+ people), sponsored the golf tournament & spent a week out there. It was at the Ritz (no joke). We ended up getting 17 NDA's, 5 banks to review their financials & we came home with one bank contracted to underwrite the loans.


When checking out, I about had a heart attack. I asked the front desk guy if he could not itemize my bill and he said he wasn't able to. I called my boss to make sure the card would clear and she said it would. We ended up heading to the airport and on the flight home me and my buddy were both updating our resume's because we were sure we were going to get fired.


The next day we unloaded at the office, handed in our expense reports and then went home. They gave us the day off for travel. We come to work the day following and my boss comes into the sales floor and asks us to both come with her to the warehouse. The warehouse was on the way to the parking lot and it was the path you walked out every day, so I thought we were both canned.


She sits us down, looks at our expense reports and says, 'why did you both expense your boogie boards to your rooms?"...there was a moment of silence and we both said, 'we are happy to pay for that if that's a problem." They were $15 a person. She said she thought she could explain it to the board and that was the only question she had.


She let us go and the CEO gave us a few wry looks a couple times in the hall but never brought it up. We ended up spending over $40,000 on top of rooms & sponsorship in five days. But we came home with a bank.


/TheEnd

😂 Sales Humor
🏰 War Stories
🏙 Corporate Experiences
17
Biznasty
Opinionated
2
Lead Business Development Manager
This is the most amazing story I've ever read. I hope more people will share. 
FlintIronstag
Notorious Answer
1
Chief Marketing Officer
Thanks. It's funny now. It's still referenced at the three companies we all work for now. It was truly a legendary week in sales for us.
alecabral
Arsonist
2
Director - Digital Sales Transformation
Way more than I've spent, but you got the deal man so completely worth the bill I'm sure. The most I spent was 12K. Dinner for 10, including wine (that was the tough one to get cleared on by corporate), and a few approved gifts (under 100 U$ each) for the 10. I thought I'd spend more but honestly, these guys were ready to go home after dessert. Next day we got the PO.
FeedTheKids
Politicker
1
Solutions Consultant
As long as the deal closes - it's worth it! 
FlintIronstag
Notorious Answer
0
Chief Marketing Officer
True!
FlintIronstag
Notorious Answer
0
Chief Marketing Officer
Congrats! haha, that's great.
alecabral
Arsonist
0
Director - Digital Sales Transformation
Thanks! your story still is way better man, would have loved being there!
FlintIronstag
Notorious Answer
2
Chief Marketing Officer
oh man, we were lit. that's just the overview. by the time we left we were the epitome of America, capitalism, and everything these banking ceo's saw in themselves 40 years ago. their bff's. it was amazing.
FlintIronstag
Notorious Answer
0
Chief Marketing Officer
Next time
UrAssIsSaaS
Arsonist
2
SaaS Eater
This is what legends are made of. I cant hold a candle to 40k, but we were working a very important account to us, booked a meeting with them at 8am and said fuck it were doing this in person, not over the phone. Booked a same day ticket to vegas from SF, met with them for an hour and then flew home, in total was gone for like 6 hours but came home with the deal.

I think we spent like 2k on the flights, lunch, and transportation
FlintIronstag
Notorious Answer
1
Chief Marketing Officer
oh man! I've done the spontaneous bang-bang trips. Those are the best!
UrAssIsSaaS
Arsonist
0
SaaS Eater
Ya I love them, we can travel right now but looking forward to when we are able to again. 
FlintIronstag
Notorious Answer
1
Chief Marketing Officer
Yeah travel is kind of not happening right now. I hate virtual conferences. They’re just webinars renamed.
CuriousFox
WR Officer
1
🦊
Those were the days.
FlintIronstag
Notorious Answer
3
Chief Marketing Officer
now i have to ask to buy myself lunch :(
CuriousFox
WR Officer
1
🦊
Taco Bell my friend. That's the way.
FlintIronstag
Notorious Answer
2
Chief Marketing Officer
I don’t like pooping in the lobby at work.
CuriousFox
WR Officer
0
🦊
Understood.
FlintIronstag
Notorious Answer
0
Chief Marketing Officer
Chicken gorditas
LegacySoftware
Opinionated
1
Strategic Account Executive
Why I love small software companies with cash:


One account: ~$12K 

The big trip:
- Flew in the sales team, hotels, etc
- Trendy-taco shop catering
- Bougee steak dinner
- Houston Rockets floor seats

+ many follow-up dinners, many drinks, many gifts (I sent a box of chocolate covered strawberries to the head of accounting who merely held a discovery call with me... risky, but it worked)


Total sale: $350K ARR, $600K Services (does discounting the shit out of the implementation count? rate got brought down to like ~$140/hr)
FlintIronstag
Notorious Answer
0
Chief Marketing Officer
That’s awesome. Nice work.
TheNegotiator
Arsonist
1
VP of Sales
Never more than $500 on a single account. Hockey game and a nice dinner. Once expensed $400 for a dinner for 2 in Vegas. 2 employees, no clients. My VP was NOT happy. Most recently I’ve submitted 2x $7,000 reports. 3-weeks of company travel each time. So many air miles I can fly to Paris.
Blackwargreymon
Politicker
1
MDR
This is the most amazing story I've ever read. I hope more people will share. 
Clashingsoulsspell
Politicker
1
ISR
Way more than I've spent, but you got the deal man so completely worth the bill I'm sure.
FlintIronstag
Notorious Answer
0
Chief Marketing Officer
Whatever work! Go to Paris! Sorry about the VP being mad. Sometimes leadership has no ability to correlate expenses to revenue. It’s a shame.
MR.StretchISR
Politicker
0
ISR
This is the most amazing story I've ever read. I hope more people will share.
Mr.Floaty
Politicker
0
BDR
Territory obviously depends on how your customer base is, how spread out they are, areas that they are more concentrated in.
Cyberjarre
Politicker
0
BDR
Territory obviously depends on how your customer base is, how spread out they are, areas that they are more concentrated in.
6

Most money you’ve banked in a single year from selling?

Question
12
5

For those who sell AND do account management – best strategies/hacks for time management?

Question
10
24
Members only

Your Sales Career is Over! Money in the bank. Where you going?!

Discussion
41
Where?
81 people voted