How to manage pipeline like an elite seller

Founders let deals happen to them.

Elite sellers make deals happen.

The difference is in the nuance, mindset, and follow-ups.

Most founders I’ve worked with eventually flip a switch. They go from learning the basic tactics, to closing a handful of deals, to actually working their pipeline.

Once they make that jump to working pipeline, revenue really starts to grow. 5, 6, 7, 8 deals closed per month. Big chunks of MRR coming in.

You can’t get there unless you get the basics right (like discovery, questioning techniques, demo structures, meeting management, and follow-up frameworks). It all starts there.

But once you have a good working knowledge of these, moving to proactive selling will really help you get more deals to close.

Let’s dive into pipeline management:

Table of Contents

• How to organize your pipeline

• Sorting and scanning through your pipeline

• Working the Pipeline

  • How long to wait in between touchpoints

  • Pre-mortems and deal plans

• Isn’t this salesy?

How to organize your pipeline

Everyone conceptually knows about deals and stages. That’s the easy stuff.

For the best organization of stages, name them in past tense, and stuff that you do in every sales cycle. For SaaS, I have:

0. Identified (basically a meeting booked but not held)

1. Qualified (meeting completed, have the pain we can solve, understanding of path to power, buying relatively soon)

2. Demos Completed (We’re done showing software, everyone who needed to see it saw it

3. Proposal Sent (we’re done reviewing implementation, pricing, packages, etc)

4. Contract Sent (we’ve finished all the random procurement stuff and negotiations and a final contract is out for signature)

5. Closed Won

Sometimes I’ll add a stage in there for Verbal Received (maybe between proposal and contract). But keep the stages simple so when you look at your pipeline, you know exactly where it sits.

When you’re looking at your pipeline to figure out what to work, always start at the end and work backwards. The stuff that’s approaching close should be worked first - get those deals across the finish line.

Then move stuff that’s sitting in the middle.

Then focus stuff at the front.

Sorting and scanning through your pipeline

In your CRM or whatever dashboard you use for managing deals, you want to see a few things:

• Deal amount

• Expected close date (hopefully you’re getting this as part of your Reaching a Decision discovery from the FOUNDER framework)

• Last activity date

• Next steps

• Pain/Objectives/Negative Consequences/Driving Events

• Any identified risk

• Likelihood to close

So you’re going to have probably 3 reports/boards you’ll work off of. One for early pipe, one for mid pipe, one for late pipe.

You’ll be sorting it by expected close date first. What is coming up now. Focus on those deals first.

Then what has the highest amount with a high likelihood to close. Often I see founders stuff their pipeline with large enterprise deals that will never close, spend way too much time on them, and neglect the stuff that will actually close now.

So expected time, amount, likelihood to close.

Working the Pipeline

Assuming that you’re not at the “I have no deals in my pipeline and no customers” phase where 100% of your time should be spent on pipeline generation, the general rule of 3rds applies to pipeline management.

1/3rd of your time moving bottom of the pipeline to close, 1/3rd of your time moving early-mid pipeline forward, 1/3rd of your time adding new deals to the pipeline.

If you don’t have enough pipeline, then focus a bit more on adding more deals. But try not to drop to less than 1/3rd of your time prospecting for new business if you have good pipeline - it can dry up really fast.

With all of your deals in your pipeline, you are moving them towards next steps. You’re doing this either through meetings/calls, or follow-up emails/LI DMs/Cold calls.

Every deal in your pipeline should be worked minimum weekly. If you have 35 deals in pipe, 7 of those deals are worked each day. Will take about 20-30 minutes of your time.

What you’re doing here is sending summary emails from calls, then holding the prospect professionally accountable to what they said they would do.

A good signal that deals are live is when the volume of back and forth emails go up. If you constantly follow-up with no response, there’s trouble there. You need to go figure it out. Talk to different stakeholders in 1:1 threads, ping people on LI, give them a good ol’-fashioned call. But when there’s no activity, there’s no deal.

As you get closer to winning a deal, the activity will pick up significantly to finalize the details of a deal. ← This is where I see a lot of founders fail. They get the verbal, they send a proposal/contract, they back off. This is where buyer doubt hits the strongest, right at signature. If you’re not hearing from them, finding and handling objections, etc, you’ll lose a lot of deals you could have won right at the finish line.

How long to wait in between touchpoints

I get this question a lot, and a lot of founders have head trash around being too pushy/salesy. So they end up running a “wait and see” approach. They let deals happen to them, instead of making deals happen.

General rule of thumb, make the deal happen as fast as possible. You need momentum. The longer in between interactions, the slower the momentum, the harder it is to close the deal.

If someone books an intro call, they’re qualified, want a demo. Do it next day, not next week. Follow-up with your meeting summary (summarize FOUNDER discovery framework + clear next steps) right away. If they need to take action, ask them when they’ll do it, and with who. Suggest the shortest possible timeframe. Then hold them accountable to doing it when they said they would (set a reminder in Superhuman or Kondo to reach out on a specific date).

If you have multiple stakeholders in a deal, then 1:1 sidebar with everyone. 3 stakeholders = 3 touchpoints on the deal per week. That’s enough to cut through inertia.

Don’t ever let a deal go without an interaction within a week. If they push you out several months/quarters, that’s not a live deal. They’re not buying right now. Close lost that deal, get it out of your pipeline, do a nurture (ping them every 30 days with something relevant). Your pipeline should only have stuff that you’re working to close.

Pre-mortems and deal plans

The best sellers I worked with didn’t just do post-mortems. They did pre-mortems.

Average sellers go and look at deals they lost, and wonder what could I have done differently.

Elite sellers look at the deals they have now, they look at their FOUNDER notes, at any identified risks, and they come up with the next 3 things they could do.

They do scenarios for how each call will end - if yes, this is what you do. If maybe, this is what you do. If no, this is what you do. They map that stuff out. They map out scenarios with procurement pushback vs not. They map out scenarios where execs are bought in vs not. It is really hard to figure out how to run a deal when all you’re doing is reacting.

When I ask founders what the next step is, most of the time they can really only answer what the next meeting is (if they have one). They can’t really walk me through how they’re going to get the deal to close. They can’t tell me their next 5 follow-up emails they’re sending. Because they haven’t really thought it through.

Pre-mortems and deal plans will significantly boost your win rate.

Because you won’t wait for deals to happen to you. You’ll be proactive about it.

Isn’t this salesy?

“But Dan, doesn’t this seem pushy or salesy?”

Excuse me, but aren’t you trying to sell them? Aren’t you trying to close a deal? WTF are you doing here?

If you’ve uncovered a major pain for them, they feel like you understand them, and they agreed the solution would solve that pain, then you move them to commercial agreement. If they move through that, they outline the next steps, then you hold them accountable to what they said they would do. What’s pushy or salesy about this? You want it to happen, they want it to happen. It’s just project-managing timelines at this point.

You’ll never be able to force someone to buy, so get the idea out of your head that you’re salesy. That’s losing you more deals than you realize.

“But Dan, what if I do this and they say no?”

GREAT! Get that deal out of your pipeline, stop wasting time with folks who won’t buy. The best answer in sales is yes. The second best answer is no. No response? That’s hell. That’s an energy suck. Get that shit out of your pipeline.

Do things that move people towards yes or no. That’s the job.

Do this well, and you’ll become a pro at managing your pipeline. Don’t put any thought to this, and the pipeline will manage you, and you’ll dread doing sales.

Let me know what you think of the newsletter! Always want to cover topics that you care about.

For more practical early-stage sales tips, connect with me on LinkedIn.

If you’re looking for more hands-on help implementing your first sales process, reach out for coaching packages.