*facepalm* How 1 subject line destroyed a Q3 deal.

I shot myself in the foot right at the finish line...

TL;DR: after 2 1/2 months, I sent an email with a subject line referring to a comment that my champion made to me explaining why he thinks we might be able to get a deal over the line before September ends, and it had the opposite desired outcome...



After investing a lot of time into each stage of the sales process and building a strong rapport with my champion, I made a silly mistake that could potentially cost me a deal. At the very least, it halted progress before the end of Q3.๐Ÿ˜…


My champion is all-in on how our solution solves his problems. I'm in the Fin-tech space.


Here's a brief backstory:

Our journey started with a representative from Company X, let's call him 'Rep A'. We explored their current reporting tools and identified several limitations they were facing with their budgeting and planning processes. An initial interest was shown in our product's KPI and budgeting features, along with the potential for operational data integration in the future.


In our second meeting, we delved deeper into Company X's primary business challenge - an unstructured budget and financial planning process. This issue was causing them difficulties in aligning teams and documenting ROI for capital expenses. Furthermore, they lacked a functional tool for revenue forecasting. Rep A was seeking a system that could delegate GL-level tasks to the team, allowing him and the CFO to focus on strategic decisions. Our product's features were presented as solutions to these challenges.



Later, we introduced the CFO and decision-maker in the process. Company X's team was developing an annual operating plan, which included various forecasts and plans. The CFO expressed concerns about their existing budget process and heavy reliance on Excel. However, the idea of using our product for budget collaboration and automated calculations was well received.



Towards the end of our journey, we discussed pricing options and proposed a special discounted package for EOQ.


Rep A was sold, but the CFO was hesitant to pull the trigger.


I got on the phone as soon as I got an email asking for us to set up another demo with the COO to start discussing operational use cases.


This was going to prolong the process and quite frankly, make the whole idea about changing way more daunting. Rep A agreed with me on the phone that the CFO was biting off more than they could chew.


We discussed some ideas that ultimately led to him believing all the CFO needed was a push to execute in some way. I brainstormed with my manager and sent over an email to the CFO with my champion cc'd that acknowledged the hesitation, reminded of the most pressing problems/challenges that they expressed, the special pricing (which was considerable), and a course of action โ€“ executing the agreement while concurrently demonstrating additional operational use cases to the COO.


I made a mistake by using a private comedic phrase from my champion as the subject line. Looking back, it wasn't clever or beneficial at all. Instead, it made my champion uncomfortable and might have compromised our trust.


The response I got back in a direct email to myself and manager was:


"Pushing too hard using my language, advising against that going forward."


Ouch.

Never again will I make that mistake. Thanks for coming to my Ted Talk.

Has anyone else done something similar before?

Has anyone still been able to recover?

๐Ÿฐ War Stories
โ˜๏ธ Software Tech
๐Ÿ˜ณ Ethics
18
braintank
Politicker
7
Enterprise Account Executive
What was the phrase?!?!?
CuriousFox
WR Officer
1
๐ŸฆŠ
๐Ÿ‘€๐Ÿฟ
BigOstrichEnergy
Valued Contributor
1
Full Cycle AE
Haha, I canโ€™t give the details behind the phrase as it relates to sensitive information, but the phrase itself was โ€˜Weathering the floodโ€™.
AnchorPoint
Politicker
0
Business Coach
glad I am not alone.. cant believe I read that
BigOstrichEnergy
Valued Contributor
0
Full Cycle AE
Didnโ€™t realize I created a cliffhanger anyone would care about ๐Ÿคฆ๐Ÿฝโ€โ™‚๏ธ
jefe
Arsonist
4
๐Ÿ
Hope it only delays and doesn't kill the whole thing.
Lesson in being careful and avoiding being too clever.
BigOstrichEnergy
Valued Contributor
1
Full Cycle AE
๐Ÿคž๐Ÿพ hope so.
Diablo
Politicker
2
Sr. AE
Good thing is you learnt from your mistake. There are always expectations at both ends so I am sure they knew youโ€™d try hard to close EOQ but it might have been a bit harsh I am sure
Take your prospect for a drink ๐Ÿฅƒ
BigOstrichEnergy
Valued Contributor
1
Full Cycle AE
Yeah I think youโ€™re right. Would love to buy him a drink, but we are in n opposite ends of the country. ๐Ÿ˜…
Phillip_J_Fry
Opinionated
2
Director of Revenue
Oof. At least the deal is still alive, so you've got that going for you, even if it's not in quarter.
If it makes you feel any better, a manager of mine forwarded an email chain from employee A to employee B, where employee A had been talking mad shit about employee B.

Later stage deal and it derailed the whole project.
BigOstrichEnergy
Valued Contributor
0
Full Cycle AE
Ooouch that sounds like a huge gut punch. ๐Ÿซ 
Sunbunny31
Politicker
2
Sr Sales Executive ๐Ÿฐ
You're not dead yet. Just humbly tell rep A you appreciate the coaching and will be happy to take direction. And then do so.
Best of luck. I want to see the next chapter!
BigOstrichEnergy
Valued Contributor
0
Full Cycle AE
I appreciate the advice! I definitely fell on the sword in hopes we can move on.
Pachacuti
Politicker
2
They call me Daddy, Sales Daddy
Happens even to the best of us. Easy to be impatient, hard to wait it out. Especially when mngt is breathing down your neck.

Good luck trying to win it back!
oldcloser
Arsonist
2
๐Ÿ’€
You committed no crime- seriously Iโ€™ve gone so much further over the edge. Not that you need it but youโ€™ve got my permission to let yourself off the hook. Flip side? You will need to eat the necessary pile of turds with Rep A. Not a deal killer. Youโ€™re gonna live
ZachBlide
Opinionated
1
AE
Ok you pushed a bit too hard. I wouldnโ€™t beat yourself up about it. I think every salesperson has done that at least a couple of times - helps you learn where the line is. But doesnโ€™t sound like a biggy. I would be surprised if that actually put the deal at risk
pirate
Big Shot
1
๐Ÿฆœโ˜ ๏ธ Account Executive
Look you never know. Could have been a melter with someone else. Sales is risky sometimes
Justatitle
Big Shot
1
Account Executive
All I really want to know now is the line that was used
BigOstrichEnergy
Valued Contributor
0
Full Cycle AE
I shared in another comment. The phrase I used came from something my champion shared with me as an inside joke in private. The phrase was โ€˜Weathering the Floodโ€™. I used that as my subject line to the CFO with my champion ccโ€™d.
CRAG112
Valued Contributor
1
Account Executive
Professionalism at all times my friend. No matter what. Whether at the golf course, the strip club, or Fed ex.
FormerStartupJobHopper
Tycoon
1
AE
I don't understand the issue. Your champion sounds prissy
SgtAE
WR Officer
1
AE
EMEA and APAC reps when AMER team keeps using NFL and Baseball references in their meetings.
DrChaos
Good Citizen
1
Outbound AE
You know, irony and jokes generally are not well understood when written. I haven't lose deals like that. But I had bad experience in my life when writing a joke which was totally misunderstood. So, jokes only on meetings :)
BigOstrichEnergy
Valued Contributor
1
Full Cycle AE
Great advice. I appreciate it.
GDO
Politicker
0
BDM
I really don't get what's wrong with doing this?
Beans
Big Shot
0
Enterprise Account Executive
But what was SAID
3

Best subject line for an email when a prospect is ghosting you?

Question
11
4

End of Quarter finish line

Advice
5
8

First Name in subject line of email?

Question
9
Should you add a recipients first name in an email subject line?
45% yes
26% no
29% doesnt really matterโ€ฆ
147 people voted