The War Room

[Poll] How did you break into your biggest deal, ever?

Sales Army,

I've got a hypothesis I need your help with: How do the BIGGEST deals actually get done? Think back to the biggest deal you've ever closed in your career, ever.

How did you break into the account? How long did it take to close? Any cool moments??

How did you break into the biggest deal of your sales career?
Attached poll
*Voting in this poll no longer yields commission.
πŸ”Ž Prospecting
WR Officer
Head of Growth
A little bit of a few of these options, honestly... I had a partner who was working closely with a company. The company had a small amount of spend with us, but nothing big. I worked with the partner to explain why they needed to increase their spend ~50x. It was a fairly quick sales cycle and painless.
VP Sales
Met at trade shows and conferences.Β 

Took 17 months.Β 

Kept interacting with Β same prospect at least 10 conferences over 12-month period. He was the CIO of the largest University system in the US.Β 

Finally agreed to talk outside the conference. Flew out several times, met and pitched various stakeholders, they ONLY did business this large in person and when the RFP was out 9 months later, I knew we had an inside track to win. Signed a five year paid up front deal that was 8x my quota that year. Β My quota was $600k. Β At a small company, commission was extrmely high, especially when the kickers over quota kicked in. Β 

2016 was a very good year mainly because this deal closed in September, got married in October, bought our forever home after that and then welcome first of two kids a year later.Β 

That one deal change my entire trajectory in sales and personal life. Β 

That’s why I love large deals. Β Take forever to work on, have to stay persistent when you believe you can help, do the grunt work and it pays off.

Replicated at smaller scale at the fourth largest system a year later and then took my first Director role at a larger company and the rest is history!Β 

Even sold the same CIO different software at the next company but it was small deal in comparison but was more of a two call close. Β 

Account Executive
Previous user jumped to a prospect company and got a warm intro from my VP
Valued Contributor
Corp Account Exec
Bottle of whiskey
WR Officer
My first deal in tech sales. Did a multi-thread email to a C-suite/VP/Director from F500. The deal took >8 months. The Director didn't respond to my email but the CXO/VP did (both were on vacation when I received the reply).
WR Officer
Senior Account Executive
Cold email. Two years later I closed a $2.8M deal. Straight up stole it from the incumbent of 20 years.Β 
@sahilΒ why don't you introduce multiple box checking?Β 
Former CIO I was doing biz with bought an equity stake in a new venture. Brought me the biz and we closed 1 year worth of quota within 2 months.
[Thread] What's the biggest deal you've ever sold?
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