Hi Reader,

How is your team winning complex deals before they “close?” Interesting question, right?

Revenue predictability isn't optional at any stage, it's your basic survival. It will be very hard to scale until you have it. If your pipeline looks promising, and your team is working hard, yet deals that start hot go cold, cycles stretch, and buyers who seemed enthusiastic suddenly go quiet, keep reading.

Here's what stings, most of that delay isn't the buyer's fault. It's happening because of how deals are being positioned and managed from the very first conversation.

Last month I partnered with ZoomInfo for a live deep-dive into this exact problem. Five frameworks. Here's the best of what we covered.

1. Your First Conversation Sets the Entire Tone and Most Teams Are Wasting It

With outbound, you're in control. You can research the company, use AI to understand the people, use ZoomInfo to map the org chart, and reach out to five, six, seven people simultaneously, building relationships across the buying team from day one.

With inbound, you're often stuck with one person, and that one person can block you from getting positioned properly.

Fix it before the first call. Find the other people who should be involved, then send a pre-call email, "I've spent quite a bit of time researching your company, and I'm curious if any of these people [name them] would like to be on the call with us."

All they can say is no. But if you bring a compelling insight in that email, they just might say yes.

Whether inbound or outbound, buyers don't want to hear what you think. They want to hear what other companies like them are doing. Instead of "Here's what I suggest," try, "Let me tell you what some other companies like yours are doing and how they've been successful." That's inside knowledge they can't get anywhere else. You're the only one who can bring it.

And never, ever, leave a call without a scheduled next step. A next action the customer agrees to, with a date.

2. Stop Adding Time to Your Own Deal Cycle

I know that's hard to hear. But it's true.

Go through every customer touchpoint and ask, what are we doing here, and is it excellent? Are you making customers wait days for a quote? Leaving gaps with no value added? Failing to schedule the next action before you leave the call? Buyers are already thinking, "If it's like this now, what's it going to be like after we buy?"

Keep the buying team engaged between touchpoints. A relevant article with a simple note, "Read this and thought of you," goes a long way.

Don't assume the team will keep their boss informed. They won't, they're busy. A short note like "Great to meet you at the show. I wanted to let you know I met with Ben and Susan, just keeping you in the loop" keeps the right people engaged without overwhelming them.

Never stop asking who else is going to be involved in making this decision. Who's whispering in their ears? Who at the top can squash this initiative? Who can pull their team's attention to a different priority, which is often why you're getting ghosted?

Build relationships with people who can become coaches, people who are on your side, want you to win, and will give you accurate information about what's really happening inside the account.

3. Lone Wolf Selling Is Not a Thing Anymore

It was the '90s. It doesn't work. So, stop it.

If you're selling to companies 100 to 1,000 times your size, they want to see a solid team behind you. Build a strategy with your team before you approach top accounts. Who are you going to approach? Who from your team is best suited to approach them? What's important to them?

You might need to position a senior leader from your team with someone senior on their team while your sales team talks with leaders at other levels. Maybe your customer success team needs to get in early and explain what the experience looks like after they buy. This lets buyers know that onboarding will be excellent and that you'll stay with them.

Every day, ask yourself, what does my buyer need, and how can I help them hit their goal? If you don't know what result they're trying to get and how it impacts their business, the seller who does will win.

4. Position and Prepare CEOs and Senior Leaders

You ask the CEO to be on the meeting and the CEO comes in and hijacks the conversation. Or tries to close too early. It happens all the time.

That’s not positioning. You're not trying to close. The CEO is there to help give the buyer confidence and mitigate risk.

Bring in a senior executive when they're bringing in theirs, or when you need to differentiate and build their confidence is important. But whoever you bring in has to be thoroughly prepared. They need to know their role on the call, which questions you want them to ask, and what you want them to say. The salesperson still runs the call. There may be times that it does take a CEO or senior exec to close a deal but that should be carefully planned and orchestrated.

So, the lead seller should write out a sales call plan and prep the team in advance. Maybe even practice!!

5. Prevent late stage Stalls and “No decision” outcomes

Seven things you can do right now to prevent late-stage stalls and boost your win rate

1. Involve the right people from the beginning. Use ZoomInfo, LinkedIn, and every tool at your disposal to figure out who the people are and what they care about.

2. Add valuable insight. Especially what you know about what your other customers are doing. You don't have to drop names. Try, "Another manufacturing company like you, around $100M in sales, is doing this."

3. Instill confidence, in them, not in you. Help them feel confident in their ability to make a great decision together.

4. Map the process. Walk them through what's going to happen, engineering, legal, procurement, and about how long each step takes. You've done this many times. They haven't.

5. Agree on the timeline together. They agree, you agree, everyone knows what it looks like.

6. Always agree to a next step. Every single call. A next action the customer agrees to, with a date. Don't be the seller chasing people for their next meeting.

7. Be willing to walk away gracefully. "I don't think this is the best solution for you right now" builds more trust and more future business than pushing a deal that isn't ready.

The Real Shift

The best sales teams aren't just selling better. They're thinking differently about how buyers make decisions. They care about outcomes for the buyer.

Your ultimate job in a long sales cycle isn't to close the deal. It's to guide the buying team so they gain confidence in their ability to make a great decision together. Not confidence in you. Confidence in themselves.

That's how you win complex deals.

👉 Watch the full webinar replay with ZoomInfo ​

Or if any of this hits close to home for your team, reply to this email and let's talk.

To your sales success,

Alice

P.S. If this newsletter got you thinking about what's actually working in complex B2B sales right now, I want to personally invite you to join me on April 28 at 12 p.m. Eastern for something I've been looking forward to for a while.

I'm sitting down with positioning strategist Andy Cunningham and Adam Miller, CEO of ELEVATE, for a live conversation called Sell More Stuff, The New Chemistry of B2B Selling. No fluff. No product pitches. Just a real, C-suite-to-C-suite conversation about why so many deals are stalling and what revenue leaders can do about it right now.

It's free. It's live. And it's one hour that could genuinely change how you're thinking about growth.

👉 Save your seat here, Sell More Stuff, The New Chemistry of B2B Selling​

See you there, April 28!
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