Amanda Zhu This hits.
The deal doesn’t really move forward. it keeps getting reshaped internally.
That day 34 moment is rare. You chose to understand instead of moving on.
I’ve been digging into that phase a lot lately, trying to keep that clarity after the call.
Curious how you approach it now?

When you are at an industry leading company, giving the customer time to try to implement other software and find the failure modes is one of the most perverse steps in Enterprise selling. My perspective has always been to transition to consulting mode, be there to help them and when they hit the brick wall you saw, be there to catch them and get them where they need to go.

I personally believe agreeing to a POC on day 2 significantly increased the deal length. Did you understand the success criteria and scope? What about their metrics and decisioning process? Is it normal for you to commit so many resources to that process without having an idea of what the next 90 days would entail?

Darren Jones yeah. Lack of commitment.

I’m extremely happy that you’ve documented how long this took and the steps you took to revive this.

1yr + is the new normal.

100%

If you hadn't run into the champion at a Happy Hour. Did you think you were going to have another crack getting into the account anytime soon based on the feedback they gave you? This is also incredibly valuable so thats for putting it out there

Trevor Lee No

never closed a deal this big (our biggest was around 800K) but I've definitely been through this workflow multiple times

Glad you won this huge deal Amanda. There are actually 5 defined steps to becoming an approved vendor at a big Bank. And then 10-12 steps to get a solution bought and installed. You cover quite a few of them in this post. And whether your sale can follow them rigidly or it becomes more ad hoc like the experience you shared.

I was interviewing for a marketing leadership role with a CEO for a compliance growth company and a big focus for them to scale was moving into enterprise. Obviously a big part of the role was how the ABM would a part of the growth strategy.

Wow! We should talk! That deal could have been done much faster and likely been much bigger. Happy to help.

I feel seen and heard!

As someone who’s been on the purchasing side of deals that worked out like this, I can’t help but wonder if the vendor just thinks we’ve lost our minds!

I don't know how true this is. But I wanna believe every moment of it

huge!! congrats on the deal. Curious if you think there were any internal/external signs between day 34 and 184 that could have revealed they were still facing the problem?

This is so true. Timing, right messaging, good team experience, and most importantly, a good champion who helps you get those other things right as well!

Hi Amanda Zhu — this is one of the most honest sales artifact I've read in a while. The day-34 detail is the whole post. One judgment call saved the deal; everything before and after was execution.

By conducting a post mortem, you didn't just get feedback you kept the relationship on life support.

As a RevOps person who work closely with Sales team day in and day out, supporting sales strategy with my analysis, these are the kinds of things we see and hear in our forecast calls! 👏

Amanda Zhu - very interesting post, 1: Great focus on understanding and aligning with your client- even when it’s not gone your way. 2: Having the grit and determination to uncover the real champion and value needed.

That's the reality. And reconnecting can happen in the most random of ways. Long sales cycles are a chore to get through but so rewarding at the end 👏

what a great post! I'd say your posts are in the top 0.1% here... they actually provide value.
I'd love to see how you do the account maps. Any way you can share your process or an abstract example?

Don't stop follow-up unless you get that hard stop conversation. In enterprise all kinds of things can stall a deal. So many times it's simply a re-org and the new person had no idea about a PoC because it went down the stack and never came back up. Follow-up, engage, don't get discouraged even after 99 calls of so!

I still find this over simplified

One of my most inspiring thread to read.

have an deal worth 600K$ and i think i need to flew to the place

hardcore

1 year?! That's insane

Thanks for sharing Amanda

I love this summary and good for you. Perseverance. Getting feedback. Reps cannot be afraid of rejection; it’s part of the job.

Wait Claude didn’t close the deal for you?

never get to see this behind-the-scenes detail, at this level. thank you for sharing it. so post-mortem is key

Curious. Are there standard phases to the process after that post mortem? Because that specific part of the pipeline may have saved the deal, but how did you integrate this use case for future deals?

As a b2b SaaS marketer this speaks to my soul, Amanda.

You could take it a step further, why did they self serve in the first place? Maybe saw one of your viral posts? Came across a Reddit comment? Heard about Recall from a colleague?

Sounds like every single EdTech deal 😅

Damir Bulic the real deal.

What were the learnings?

Amanda gr8 story, thank you for sharing the details. In my experience I also have revived dead/lost deals. Your examination of the milestones should be a guide for AEs on the gating, hills, troughs that happen in 7 figure deals

And if it was an outbound lead you could add up 40 calls 7 people 30 emails and 10 LinkedIn messages over 3–6 months just to get the right lead potentially ;)

Enterprise Sales require a rare combination of impatience and patience.

I love this!! That's what enterprise is. If you're able to measure the numbers of emails during the process your brain is going to explode 😅

In my opinion, enterprise sales comes from trust. Even if they ghosted you, then if the pain becomes apparent and they trust your services then they will come. Btw nice to hear this Amanda!

Absolutely, I actually heard people say that if they don't sign in a week or two, it means they don't have the need. Insane!

linkedin becoming more and more slop.

This, a million times, this. Thanks mapping this out.

I thought it was an Anthropic invoice.

This. I saw a recent post on LI recommending that C-level and sales leaders share all the emails in connection with a purchase they made internally just to show their reps the seemingly random walk of a sale.

That's exactly what I needed! Thanks for the reminder and kudos for the HUGE deal

I thought day 258 would be the worst, then got to day 301.

Amanda Zhu Between day 34 post-mortem and the day 184 random investor run-in, I hope your team wasn't dragging the deal's close date out quarter-by-quarter, over and over. This is the type of prediction that can and should be productized now. Congrats on the win!

What went wrong
Noted

Day 34 is where most reps write the obituary, Amanda Zhu. You wrote the autopsy report. That's the difference.

But here's what bugs me about this story: 369 days, three account maps, two champions, and a commercial model that shifted.

Love how detailed this is. The "hard no" post-mortem is underrated. That single honest call has bailed me out of dead deals more times than I can count.

taking notes on your exact enterprise flow! thanks for the sharing🙂

This is refreshing

Timing (first 3-12 months of a newly promoted stakeholder), stressing out that costs of non-action are higher than fear/stress/costs of CHANGE is more important than pain points. Was in a champion role - took me 9 months to sell it internally.

Congrats on the deal Amanda Zhu and thanks for sharing the journey. Every enterprise deal is a snowflake. There are a ton of patterns. But identifying which one is active is hard work. Well done. I am curious, what was the reason for the deal dying in the initial month?

Amanda Zhu what went wrong went wrong in the first 34 days?

When I was selling Red Hat I ran into a HUGE casino company in Vegas. They had bought $5M in Automation SaaS, but had never installed it or used it & they were up for renewal in 6 months!! They came to a training I was doing to learn how to use it. SMH 🤦‍♀️

Amanda Zhu Love this timeline... but you forgot the part where this deal quietly gave you your first of many gray hairs somewhere around day 184.

And by day 369, the contract’s signed and you’ve aged just

Love this Amanda Zhu 💖

Spent a big part of my career selling into the enterprise. The day 34 call is everything. Most people skip it because the deal is dead and it’s painful.

So marketing got credit for that, right?

Persistence is often the only difference between a hard no and a $1.3M win. Treating a dead deal as a discovery session rather than an exit interview is what built the bridge to that eventual signature.

Yep! Very typical long and complex cycle.

You complete me 🫶

This is so reassuring to see. I’d read a book of these stories.

Everyone in this comment thread: let’s write a book together.

Jen Allen-Knuth didnt you say you could get these done in 2 weeks if you just asked?

Matt she did but only if you text procurement on day two, duh

You use stripe for million dollar invoices?

you could just ask Claude to overcome all the objections and close the deal at day 33

30 days for price negotiations. Wow.

There is nothing simple about enterprise level sales- or purchasing

That's why enterprise sales is like a Marathon Amanda Zhu! You have to think & prepare for long term though sometimes people may check your sprinting abilities as well along the way 😊

Couldn't agree more, Amanda. The 'plug-and-play' narrative for Enterprise AI is a myth. Real transformation happens in the unglamorous layers: data governance, integration with legacy stacks, and aligning AI outputs with actual business logic.

This is what a durable relationship looks like. Enterprise deals are not linear.

If you sell into large organizations, prepare to be surprised by what eventually closes... 12, 24, even 36 months later.

Amanda Zhu great perspective. Kudos to you and the team for your persistence. Enterprise sales are tough, and this example highlights the effort it takes. There were many gates you could have quit.

this proves that there's no one single playbook when it comes to enterprise closing

Kudos to your team for being tenacious until it got signed. Most teams give up.

Amanda Zhu Day 34 post-mortem is the whole story. Most people walk away from a dead deal and move on. The one call that kept this alive wasn't a sales tactic it was just genuine curiosity about what went wrong. That's what got them back in the room 150 days later.

That's a great Sandler sales tactic. 😎

Congrats on getting it done. Day 34 is the whole game.

Most reps treat a hard no like a breakup. Delete the deal, move on, never look back. But that's exactly when you finally get the truth, because nobody's protecting anything anymore.