Prospect borderline trolling us towards the very last step of confusing buying process before signature, suggestions?

So this is going to be a doozy but I will try to make it as concise as I can.


I have this big deal ($75k+) that can greatly impact my quarter and we started talking to the prospect in February. They are these two older Midwestern guys.


February


  • CSM and I get on meeting with prospect
  • Say they are interested in expanding which would double their spend with us
  • Say they need pricing ASAP for budget meeting in following week
  • Budget meeting happens and no idea if they are getting approval


March


  • We have call to get better idea of decision-making process
  • They say other directors will need to see a demo
  • Share all the pains and timeline and all of that
  • Say that they will likely need many calls
  • Say they have meeting with finance to see if they can get approval for pricing
  • Renewal is in September
  • We propose an upgrade and earlier start to our best package
  • The above is their incentive to renew early and sign


April


  • We strategize a way to have a "coaching call" with them where they can coach us on what the directors want to see on a demo
  • They flood me and the SC with questions
  • We schedule that call with their Directors to show them the demo
  • We were confused on whether we need that call with the Directors to move forward or if we can move forward already so we schedule the call with other Directors
  • They slip out towards the end of meeting that they got the approval from finance which left us confused
  • We try to get another call with them as previous bullet point was said in final minute of meeting and then they had to bounce


May


  • Say they have approval from finance to move forward
  • Schedule an "enablement" with all their Directors
  • CSM steps in and says "let's finalize our expansion first so it makes sense"
  • They get on a meeting with me, my Manager, and CSM to confirm that they can move forward
  • Talk to us in-depth about decision-making process
  • Say they need legal to review and can then send it to their CIO for signature
  • Said once it goes to CIO it is a done deal as CIO trusts legal to do the vetting


Then the legal review happens and it is short.


Barely a redline process, they just want us to remove auto-renew language and we do that. Then they say its all good and send the Docusign. We might get this in during May as opposed to waiting until September!


I follow up, call the two Directors, right to voicemail.


My Manager gets in and follows up to ask them if they received the Docusign, crickets.


CSM follows up about enablement and asks about the Docusign, crickets.


MEANWHILE, the Directors reach out to us for Support questions around their current account and making things efficient there WITHOUT addressing the DOCUSIGN THAT IS OUT. This happened yesterday.


WTF kind of Game is being played here.


What do I do?

๐Ÿฐ War Stories
๐Ÿ‘‘ Sales Strategy
โ˜๏ธ Software Tech
9
Filth
Tycoon
7
Live Filthy or Die Clean
Breathe, go outside and scream and cry into the void, take a shot, smoke a bowl then calm again and call those directors reaching out and set a meet and explain what is going on and get their take.

its a cluster but you have to start with whoever you can actually get a hold of. If it's bad news only time to get it is ASAP and if it's good news you'll want to understand where you should be acting so it's not you that screws a deal - we can't stop dumb buyers from being dumb in the buying process unfortunately.

It sucks, vent it out, rage hard, then go be a pro and make it happen anyways. Be willing to get on calls, virtual meets, or go see them in person to make sure they know you are real if you have to jump to new decision makers.
jefe
Arsonist
4
๐Ÿ
This sums it up.
BitcoinAddict
Executive
3
AE
My quarter has been crap so far and generating pipe, despite my best efforts and that of my SDR, which can close this quarter has been tough.

But yeah, taking that advice.
Sunbunny31
Arsonist
4
Sr Sales Executive ๐Ÿฐ
It kind of sounds like those directors think it's a done deal, while it just hasn't been signed yet. Sometimes an innocent "hey guys, I'd love to get you started, but we don't have a signed contract yet. Not sure what's up. Maybe it got stuck in Docusign?"
Breathe, you haven't been told no yet, and it just sounds like there's a delay.
Best of luck landing this. :)
CuriousFox
WR Officer
3
๐ŸฆŠ
Filth this needs to be pinned on gawd.
Notmyrealname
Politicker
3
AE
I've had this happen to me before. Deal was never in trouble, just nobody signing the doc, nightmare for forecasting. Took quite a bit of follow up but got their in the end. They told us our deal was tied to one of their deals that had similarly stalled, but I was told by our champion that their deal was already signed and they 100% needed us on board. CTO might have been swamped, maybe they were hoping for a panic discount. I wouldn't sweat too much when you're manager is involved. Saves an awkward forecasting call but will probably work out before September ๐Ÿ˜œ
Gasty
Notable Contributor
3
War Room Community Manager
They're reaching out with questions after all this back and forth, isn't that a good sign? Keep following up on getting that signed. It'll happen, trust the process. They've not said no yet. Just think of a way to create urgency, it's been dragging for months but ensure that you don't scare them away. Breathe and give them a breather too.

They might have been occupied or even so, the document might've gone to spam. Just follow up. Best of luck!!
poweredbycaffeine
WR Lieutenant
1
โ˜•๏ธ
Got a home address?
Revenue_Rambo
Politicker
0
Bad MFer
Kosta_Konfucius
Politicker
0
ERP Sales
Itโ€™s almost like they are just trying to mess with us
13

How do you all handle a situation where a prospect has a contract approved and is ready for signature, but one of their family members just passed away? Want to be extremely sensitive to the situation...feel there's never a "right" time to reach out and never want to be salesy...

Question
20
19
Members only

Tomorrow is a very special and an important day in my life. Getting ready for the introductory call with the Salesforce recruiter. Thank you all for all the advice and guidance so far. The first step in what could be a long journey.

Advice
23
13

Iโ€™m in the cloud contact center technology space, having a hell of a time getting a second interview, and I think itโ€™s because I am getting stuck. Instead, they do not like my response to the following question โ€œwhat are your goals with this new role.โ€ Any guidance would be appreciated.

Question
21