AE @ Gong | Closed Won 🦙 | 5x President's Club

Creating raving fans @ Gong. Founder of Closed Won. Dad to Monty 🐾 

Brian LaManna

Most painful (lost) deals I remember.

-One that had a DocuSign out for signature around March 15th, 2020. The team took a few extra days to look it over... COVID hit... and they never ended up signing.

-6 month evaluation, decided they were going to move to us from a larger competitor, and then not realizing they had an auto-renewal. I take fault for not pressing harder on this.

-21 month deal cycle that continued to push quarter after quarter for a variety of excuses, despite promising interest. Nothing as painful as a super long deal cycle with twists and turns. Eventually turned it Closed Lost.

-Running a successful evaluation with someone who told me "I am the decision maker and signer on this" ... when it came to sign, someone else blocked it from happening. Lesson learned... if someone blurts out "I am the decision maker" .... they are most definitely not the decision maker 🤣


Quickly learned to never celebrate a deal until it's signed.

Time really does kill deals sometimes.


P.S. Redesigned the website around Closed Won Club at https://closedwon.xyz/ ... how do we like it?

AE @ Gong | Closed Won 🦙 | 7x President’s Club

Mike Groeneveld

GTM Advisor | Extreme Ownership | Servant Leader | Angel Investor | VP of Global Sales at Everstage

Vice President of Global Sales

Everstage can help you unlock the power of incentives and turn your sales teams into a revenue-generating weapon. Sales commissions automation saves time, motivates your payees, achieves high-accuracy commissions and wins more deals. Hyper-growth companies like Chargebee, Postman, Nitro, Thought Machine and Sosafe trust Everstage to automate their commissions process.

Learn more about Everstage here - www.everstage.com

A prospect asked for a proposal. The rep sent it same day. The $60k deal disappeared overnight.

I still remember the rep’s face the next morning. Pure human emotions: not angry or dramatic. Just that quiet drop, like, “I really thought we had it.”

And honestly, I get why they rushed.

The demo went well. The prospect was engaged. Asked smart questions. Nodded at the right moments. Said the magic line: “Send me a proposal.”

That line hits a rep’s brain like dopamine. You feel the deal tightening up. You feel the quarter getting easier. You want to be fast, helpful, on it.

But in B2B, “send the proposal” often doesn’t mean “we’re close.” It often means, “I need something to forward.”

And when you send it too early, three things happen.

First, the proposal gets judged by people you’ve never met. Finance, procurement, IT, a VP. They see a number and a scope with zero context. That’s not evaluation. That’s a drive-by.

Second, price lands before alignment does. If you haven’t sanity-checked budget range and what they’re actually buying, the proposal creates sticker shock. Sticker shock creates ghosting.

Third, you confuse interest with authority. The person who loved the demo might not be the person who can defend the spend internally. The proposal becomes their way to work without committing to a decision.

This is the part reps don’t get taught early enough: Your job isn’t to be the most available vendor. Your job is to be a premium partner.

And premium partners don’t rush documents. They slow the moment down and clarify reality.

So now, when someone asks for a proposal, don’t say “sure” and sprint.

Ask one calm question first: "Happy to send it. Do you have a few minutes to review it together?"

That one question changes many things.

Because the space in B2B SaaS is tight. Competition is everywhere. You need to understand their feedback on your pricing. Explain how it's unique vs. your competitors. Get mutual alignment on how it will provide ROI for your customer. 

The reps who win long-term are the ones who can feel that trigger and still choose patience.

Not because they’re slow. Because they’re serious.

SVP of Global Sales @ Everstage | Scaling B2B SaaS from 0-$100M | Extreme Ownership | Angel Investor

Your forecast accuracy tells me more about your culture than your pipeline.

When a rep gives you a number, they aren't just looking at a CRM. They're making a choice: Do I tell the truth, or do I tell the manager what they want to hear so I can get off the call?

The Three Forecast Lies:

1. The Safe Number:

The team always beats their number, but only at the last second. They aren't being disciplined, they're sandbagging. They've learned that being wrong hurts more than being honest helps. They're protecting themselves, not the business.

2. The Comfort Story:

Every deal is "in a good place." No concrete facts, just vague stories. This happens when the culture treats bad news like a personal failure. If honesty creates tension, people will start bringing you comfort instead of reality.

3. The Punished Risk:

You ask why you didn't hear about a slip sooner. The answer is simple: Early risk gets punished. If you give a rep "heat" for a deal slipping in week three, they will wait until week twelve to tell you next time.

How to Get the Truth?

Forecasting doesn't get better with a new template. It gets better when you change the environment:

- Reward early truth:

If someone flags a deal slipping in week two and they get heat for it, next time they'll wait until week eight. That's human nature. People avoid pain.

- Stop tying the number to the person:

Reps lie when they feel like a miss makes them look incompetent. When the number becomes identity, reality disappears.

- Ask questions that pull out the real risk:

What has to happen next for this to close on time? What are we waiting on that we can't control? If this slips, what will the reason be?

Accuracy is a result of trust. 

When your team feels safe enough to be honest, your forecast becomes boring. And in sales leadership, boring is a compliment.

Have you ever closed a deal without pitching your product, just by solving the buyer's anxiety?

I watched a rep do this on a $160K deal and it was the cleanest example of buyer psychology I've seen in a while.

The champion liked the product. You could tell. He was engaged. He was nodding. He was asking the right questions.

But there was hesitation sitting right behind his eyes.

If you've been in enough calls, you know the moment I'm talking about. The buyer is present, but their mind is somewhere else. Their replies get slightly slower. Their confidence drops half a notch. You can feel them thinking.

Most reps respond by talking more. More features. More proof. More ROI.

She did the opposite. She paused and said, "What's bothering you?"

In a direct way. Like, I can see you like this, so what's the real issue.

And he finally said it. "Honestly, I'm new here. If I push this through and it doesn't work, I'm the person who's going to wear it."

Then he listed the real landmines.

- My boss will ask why this was the priority.
- Security will slow it down and I'll look like I didn't do my homework.
- Finance will ask what we compared against.
- And if adoption stalls, it becomes 'my project' that failed.

Once he said that, her job got easier.

Because she stopped selling to his curiosity and started selling to his risk.

She gave him a short internal note he could forward without rewriting. She mapped what the first 30 days would look like so he wasn't walking in with vague promises. She answered the "what if this goes wrong" questions before anyone else could.

That's what moved the deal forward. He could take it upstairs without feeling exposed.

If you're a rep, this is the habit to build.

Before you pitch, slow down and read the human in front of you. Try to understand what pressure they're under and what they're going to get challenged on internally.

Ask questions that make the real worry show up:

- What's the first pushback you're going to get?
- Who's the hardest person to convince?
- What would make this a bad decision in their eyes?

Then listen like it matters, because it does.

When buyers feel heard, they stop performing. When they stop performing, you get the real problem. And when you solve the real problem, the product conversation becomes the easy part.

That's partnership.

You're not trying to win a call. You're helping them win the room they have to walk into after the call ends.

The Sales quarters I feel happy about have no noise, shouting, or fireworks.

I learned that over the years.

Early on, when you’re leading a team, you chase the dopamine. The late-night war room. The last-week scramble. The comeback story. The moment you hit the number and everyone feels like a genius.

It feels like leadership.

But after you’ve done this long enough, you realize something uncomfortable: If your quarter needs drama to win, you’re borrowing from the next one.

The quiet quarters are harder. Because when things look “fine,” that’s when teams get lazy.

- You skip the prospecting block because you’re technically covered.
- You push the deal review because the notes look clean.
- You respond a day late because it doesn’t feel urgent.
- You stop staying close to customers because renewal is months away.

So the discipline became the whole game for us.

Forecast hygiene. Fast responses. No fantasy commits. Coaching when it’s calm, not when it’s on fire.

And then you hit a quarter where nothing heroic happens.

No miracle deal. No last-minute save. No fireworks.

You still close the quarter well.

And you feel happy for a different reason: Because you didn’t need adrenaline to be good.

How many follow-ups in sales is a good amount of follow-ups?

This is the most debatable question in B2B. Everyone wants a clean rule. Two follow-ups. Three follow-ups. Five touches. Ten days.

I don’t think the answer lives in a number. I think you as a rep already know the answer, because you were in the conversation.

After a demo, when you’re waiting on a buyer to respond, your job is not to “follow up the right number of times.”

Your job is to adapt to what you already saw.

There are buyers who are genuinely serious, but their company is a mess. They are in back-to-back internal meetings. They are dealing with security, finance, politics, or a fire drill.

With those buyers, even one follow-up works, because they will answer like an adult.

They will say something specific.

"Give me five days" or "I’m traveling until Thursday" or "We need security sign-off, I’ll come back after that" or "I need to align with my VP, can we reconnect next week?”

Serious buyers give timelines. Even when they are delayed.

Then there is the other kind.

The buyer who is “interested” but vague. The buyer who replies with soft words and zero commitments.

"Let’s circle back", or "Send me the deck", or "We’re evaluating".

You can feel it when it happens. The energy is different. The conversation is slippery. No one is owning the next step. Sometimes they’re shopping. Sometimes they’re using you to benchmark competitors. Sometimes they’re convincing themselves they are doing diligence.

And the more you chase that buyer, the worse your posture gets.

So if you want a practical way to think about follow-ups, use this instead of a number:

Ask yourself one question after the demo: Did this buyer behave like someone who can give a real yes or a real no?

If the answer is yes, one or two follow-ups are enough. They’ll tell you what’s going on and they’ll give you a timeline.

If the answer is no, do not turn yourself into a reminder system. Close the loop fast.

A rep who was in the room is the best person to decide what to do next.

Because follow-ups are not a math problem. They’re a read of the buyer in front of you.

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