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In Need of Advice on Large, Enterprise-Sized Opportunity (2.5 M ARR)

So I'm on a SMB team at my company and somehow stumbled across a massive opportunity and am trying to do everything I can to bring this puppy in. The buying signs are there and the sales cycle is going well. We have a somewhat commoditized SaaS product (job postings, TA resources, etc.) and are able to operate on monthly contracts (I only get comped on first month MRR anyways). It's looking like a decision will be made this month, as our sales cycles are pretty short.


Where my true worries lie is my managers ability to help me sell. I've only been at the company for 2 months, so my product knowledge is not super high, and am in need of support for things like demo'ing. This deal would be the largest, non-enterprise deal ever, but my manager and I are selling it with the resources of a SMB sales team, meaning that we really don't have relevant marketing material/ case studies to share. My manager lacks selling skills and I really don't even want to bring him into the conversation in fear of them somehow botching it. Do I dare attempt to go over his head to rope in one of my directors or VPs to help bring this in? Anyone have experience selling deals of this size and have any pieces of advice that come to mind?

πŸ“ˆ Closing
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15
Ch
ChunkyButters
Politicker
+5
AE
Any enterprise size deal like this should have MULTIPLE leaders from your team engaged. If your manager doesn't want to pull in a VP, he's a shit manager.

My advice:
- Ultra-prep for every meeting.Β 
- Play quarterback - what do you want your manager doing, what do you want your VP doing, what do you want your SC doing, and so on...
- OVER PREP
- Multi thread (update DMs on their end who weren't in the call)
- Recap emails sent to individuals post meeting
- Layout typical evaluation steps and guide your prospect through the buying cycle
- Figure out every way this deal can go wrong and prep for it. Then be ready when something you didn't think of pops up
- Bring in your VP, CEO, Mom, Corporate Bro, and anyone else into meetings WHEN APPROPRIATE
- Ask for help and guidance from any other successful rep you know. Go over every step of your deal and look for where you missed.

If this is as big a deal as it sounds like, you should not be limited to the SMB resources. 2.5M ARR is not a joke and resources should not be allocated based on your team, but the deal size.

Shit, I sell 25-50K deals and my CRO, CEO, and even Chairman are willing to talk to prospects when appropriate and IF it delivers value.
Gottapumpthosenumbers
Opinionated
+2
Strategic Growth
This is an excellent post!^
Ch
ChunkyButters
Politicker
+5
AE
Thanks, now I just have to remember to apply my own advice every now and again!
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BillyHoyle
Tycoon
+11
Senior Account Executive
This is perfect and exactly what I was looking for. Thank you a ton for this.
Ch
ChunkyButters
Politicker
+5
AE
As 34 pointed out, you could also pass it to a more experienced rep if you feel you're taking on too much water. Better yet, both of you double team it and work out a commission split.Β 

Obviously being uncomfortable is how we grow and learn, so don't just give it up. But, if you think bring in your top closer from the enterprise team will increase your win likelihood, its not a bad move (especially if your manager is fucking it up). You're still taking initiative on the deal, showing leadership you know when to ask for help, and when the deal is won you'll still look like a hero.

I've got my fingers crossed for you. Will be looking out for an update on this one.

Remember: Think of any and every way that your deal can go sideways and prepare for that.
- EX. Prospect goes dark - Why? Not enough value? Didn't uncover the true pain? Didn't uncover the real business pain? Couldn't relate pain back to value? Prospect decided they want to buy from a bigger/smaller shop?Β 

Before every meeting have a desired outcome, and then prepare in every way for how you get there.

The more you work these deals the faster and easier the prep work is, but the first one is going to be a time suck and feel like a lot of work.
Show 2 more replies
LordOfWar
Politicker
+7
Director
All of this is great advice.

If you think you and your manager are not enough then ask their boss (VP, CEO, w/e) to audit your pitch. They might add some good points and you'll likely find a natural way to suggest adding the pull of a senior person to your meeting.Β 

I bring in my CEO sometimes as it helps lend weight to the deal and makes the prospect feel like we really care, especially when I talk up how the CEO is always busy but took a special interest in this project (even if he isn't/didn't).Β 

Just make sure anyone without full knowledge of the details has their talking points pre-written (by you!) and does not go on tangents. Most CEOs/senior management loooooove to talk.
JuicyKlay
Politicker
+9
AM
Sounds like you have a really cool C suite!
CorpBroette
Opinionated
+3
New Business Account Executive
This is exactly what I'd be looking to do.Β  Great post!

I've even prepared

- emails from my boss and VP to my customer
- questions for them to ask on a call
- questions I don't want them to ask on a call (and why).
- pricing (what we're asking for/list - what we want - the walkaway) - so many superhero's trying to just give as much away to get it done in my business.

Essentially - give them work but also prepare and be explicit about what you don't want them to do.
CoorsKing
WR Officer
+11
King of the Coors Knights
Bring whoever you need in, but keep your manager in the loop and on constant coms so they do not feel completely left out. I routinely do this, my manager is not great but my VP is the definition of a savage.Β 

Shit, I have had my CEO step in on a cycle before.Β 
Chep
WR Officer
+10
Business Development Team Lead
Good luck. I don't have the experience necessary to give any good advice, but after reading your story I hope you pull it in fellow sales savage
34fifty
Valued Contributor
+5
Team Lead
Remember that you would be competing against the enterprise teams of your competitors who would have access to the resources that you would not have. The safer bet would be to take the credit for passing the lead on. But if you do decide to go for it, all the best. Bring in the money!!
BillyHoyle
Tycoon
+11
Senior Account Executive
Fortunately, it's not a competitive situation. It's more of a price justification situation. Most of the companies we work with use us and 2-3 of our competitors at the same time.
BillyHoyle
Tycoon
+11
Senior Account Executive
Also, I'm in sales... I've never taken a safe bet in my life. I'm more of a 6-leg parlay kind of guy! lol
Show 4 more replies
SaaSsy
Politicker
+3
Sales Executive
That's a tough situation and I definitely understand you wanting the support since you're so new. Personally, I would go to a VP, but try to openly communicate that to your manager (don't ask, have a reason why you want to learn, etc). If he is a decent leader, he'll understand that if you win this deal, it makes him look good and it's good for the company overall! Unfortunately egos can cause drama, but hopefully this works for you. Good luck!
GlenRoss
Politicker
+6
Account Executive
Bringing in a director or VP is a great move imo. Not only for you but it adds a lot of credibility to your team and the resources you are showing you are willing to dedicate to the customer. Don’t let your manager ruin it and don’t pass it on to another rep but def get help
braintank
Politicker
+6
Enterprise Account Executive
Mentor told me: "never lose alone". You'll kick yourself if you try to do it alone and fail. Bring others on board to help, it increases your chances of winning, will learn a ton, and even if you lose you'll be able to look yourself in the mirror and know you left it all on the field.
nomdeguerre
Valued Contributor
+5
VP of Channel Partner Sales
If your manager is not helping get the appropriate resources and I get your hesitation of going over his head, here are a couple of suggestion for getting the resources:
1. if you haven't already tell your manager that you think the two of you need support from the broader team including your leadership.
2. if that doesn't work propose to him that you ask your leadership for a deal review, so leadership can validate that you have everything covered.
3. if that doesn't work either I would bring up the deal in any weekly sales call where leadership is present (hopefully you have a call like that).
4. if that still doesn't work, you should tell your manager that you believe the two of you need help from leadership, then go over his head.

Like many people have said this deal needs the support of your broader org and leadership, don't waste it.

Just my two cents.
goose
Politicker
+11
Sales Executive
Prepare for 'no decision'.
ChiefGreef45
Catalyst
+5
Account Executive
Nice lay out @ChunkyButters. @BillyHoyleΒ Best of luck on this, definitely want to hear updates on how it's going!
Dman1b
Fire Starter
Azure Specialist
Kiss this one goodbye! I only said that for the commission point......
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