Tag: Prospecting

In my last post I mentioned that I was going to spend 30 days working only five accounts. I quickly realized the first and obvious problem was that I had to figure out which five were worth my attention.

This seemed simple enough. I would start with my pool of accounts and then I would rank them. Decide what makes a company a good fit, give more weight to the factors that matter most, and let the best accounts rise to the top.

Simple.

Except that I immediately ran into a problem. The first run of the ranking surfaced the wrong companies.

Going into this, I assumed that the more evidence I could find of a problem my product could solve, the more valuable that account was to work. But when I looked at the accounts that rose to the top, I realized the system was rewarding something I hadn’t intended. One of the factors I was treating as evidence of opportunity was also really common among companies where there was less opportunity.

The problem wasn’t that these accounts were smaller. It was that I was giving them more weight than accounts where the same amount of work could lead to a much bigger opportunity. At the end of the day I am still in sales.

Once I understood that, I stopped trying to build one perfect score and started thinking about the order these decisions should happen in. If I were building this again, this is where I’d start.

Rules

1. Create your gates

These are the things that have to be true before an account is worth spending time on. Depending on what you’re selling, your gates will be different. To find mine, I made a list by asking myself, “What would make a company a hard no?”

Here are some examples:

• Company is outside your target market or geography.
• Company is too small or too large for your product.
• They don’t have the technical setup your product requires.
• There’s no actual use case for what you sell.
• They already use your company/product.

Structured funnel

2. Rank your remaining accounts

Once an account gets through those basic checks, ranking starts to become a lot more useful. Now you’ll be comparing companies that actually make sense.

Here are a few questions that could help you start structuring your funnel:

• How closely does it fit your ideal customer?
• What technology are they using?
• How are they currently solving the problem?
• How difficult would it be to replace what they already have?
• How valuable is the problem if you can solve it?

3. Understand what you don’t know

When you’re building your structural funnel, having a clear understanding of what you don’t know is just as important as having clarity on what you do know.

I’m working with limited tools, and unless you’re doing this at a company with unlimited resources, you’ll likely be limited to the tools you have available. Naturally, there was information I wanted to know about every company that I couldn’t get reliably across a few hundred accounts.

For some of it, I could find clues. Website traffic could tell me something about the potential size of an opportunity. The technology a company uses could tell me something about how difficult they might be to win. Recent hiring could tell me where they might be investing, and job postings could give me an idea of what problems or priorities they might have internally.

But those are still proxies. They can tell me where to look, but they aren’t necessarily reliable enough to make the decision for me.

As you’re building your funnel, each step is making a decision about which accounts deserve to move forward. If I’m going to use a piece of information to eliminate an account or move another one ahead of it, I need to know how much I can actually trust it.

One other thing I learned: the research should get more expensive as the list gets smaller. I don’t need to deeply research hundreds of companies. I need enough information to narrow the list, and then I can spend more time figuring out what’s actually happening at the accounts that survive.

From that, I’m left with a much smaller group of accounts that are actually worth paying attention to.

These aren’t the accounts that are most likely to buy. I don’t know that yet. I will say, these are the five accounts where the fit is strong enough, the opportunity is big enough, and there’s enough evidence to justify spending more time.

Rules → structured funnel → collected outcomes → learned ranking.

Next up: collected outcomes.

When I was a kid, we took a field trip to a water filtration plant. After lunch, a guide gave us a cut-open plastic bottle and had us build our own water filters out of gravel, sand, and charcoal.

When I was writing my last post, I was thinking about that field trip and building that filtration system. It maps surprisingly well to prospecting. I promise I’m not grasping at straws here. Hear me out. Finding the right companies and people at those companies is basically like building a filtration system.

The gravel

The gravel comes first because it catches all of the bigger stuff. In prospecting, those are the hard nos, the rules that immediately disqualify a potential prospect. Wrong size, wrong market, already a customer, whatever I’ve decided is a non-negotiable.

A hard no is a no. There’s no weighing it against anything else, and nothing further down the filter can undo it.

The sand

Once a company passes the obvious tests, I need to know whether it’s actually a good fit.

This is where the details matter. The economics. Who’s their customer? Are they currently using a product like the one I’m selling? And does what I actually sell make sense for their business?

I try not to think of fit as pass or fail. That’s what the gravel does. Mine works more like weighted tiers. Some fit factors are going to carry more weight than others, but enough smaller fit factors could potentially outweigh one larger one.

The charcoal

And then we get to the charcoal, which is to me the most interesting part of the system.

Gravel and sand filter by size. They physically trap whatever’s too big to pass through. Charcoal works differently. It filters by adsorption, smaller stuff actually sticks to its surface. This is my signal layer.

What’s happening at this company that gives me a reason to talk to them right now?

Maybe they’re hiring, maybe they’ve launched something new, maybe they’re expanding, maybe there’s a problem that’s visible from the outside. It could be job postings, customer complaints, changes happening within the business, or something else that gives me actual evidence of a problem or a reason why now.

The three questions

Boiled down, each layer is answering a different question:

Gravel — Can I sell to them? Hard eligibility.

Sand — Should I sell to them? Structural fit.

Charcoal — Why should I talk to them now? Observable signal.

By the time a company makes it all the way through the three layers, I don’t just have a company that fits my ICP. I have a company that passes my hard rules, that I actually know is a fit, and I actually have a reason to reach out to.

If you don’t know what I’m talking about, read: The List Is the Problem, Not the Message

If you spend any time in the sales communities on Reddit, you start to notice the same questions repeating. Usually from someone who is new to sales.

They have a list of a few hundred companies, a quota, and a sequence they are supposed to fill. And in one form or another, they’re asking: “who am I actually supposed to reach out to? What am I doing wrong? Pretty sure I’m getting put on a PIP –what do I do?”

The answers they get are often overwhelming. Send more. Personalize everything. Follow up 15 times. Most of the advice is about the message and the volume and very little talks about the actual list.

A little bit about me:

I’ve worked in sales since I was 16 and can tell you that right now is the hardest it’s ever to been to actually sell something.

Why?

Inboxes are fuller, everyone has access to AI and messages all sound the same. So what do we do?

The reframe

Most of us, when outbound isn’t working, assume the problem is what we’re saying. So we rewrite the subject line, refine the body and add another follow-up. But the harder truth is that a lot of the people and companies in the sequence never belonged there in the first place. No message can fix a list of the wrong people.

Hear me out. Because there’s a number that makes this concrete. At any given moment, only about one to two percent of a market is actively looking to buy. That holds across nearly every kind of B2B selling.

Sit with that for a second. If only one or two accounts out of a hundred are ready to buy this quarter, then the list of companies your new boss just gave you is all noise. That means your job isn’t to reach everyone who could buy. It’s to find the few companies and people who fit and have a reason to move now.

That leads to three simple questions to ask before anyone goes into a cadence.

Question one: does the business actually have the problem?

Most descriptions of an ideal customer are really just a description of who a rep wants to talk to. “Marketing leaders at software companies with 50 to 500 employees” is not a real target. It is a demographic. It says nothing about whether that company actually struggles with the thing you fix.

The better test is almost too simple: can you look at a company and say, in a sentence, why they specifically have the problem you solve? If you can’t, they do not belong on the list. Not because they are the wrong size or industry, but because you have no evidence of the pain.

Two things save you a lot of time here. First, don’t trust the filters in your prospecting tool. A company can match every box — right industry, right size, right region — and still have no real use for what you sell. Pull up their site or their product for a minute and check if what your selling would actually fit into how they already work. Second, be honest about which accounts deserve your best hours. There’s pressure to chase only the big logos, but a middle logo deals that closes this month is often what keeps your numbers alive while large deal drags across two quarters. Keep those smaller accounts nurtured with a lighter touch rather than overlooking them.

Question two: can this person buy, or open a door to someone who can?

The first question gets you the right company. This one gets you the right person inside it.

New reps often stress over whether to reach out to the decision-maker or to someone lower down. The honest answer is that it depends on your goal, but it’s rarely only the decision-maker who makes a decision. I like to split my outreach between C-Suite and someone closer to the actual work – who really feels the problem. They’ll make the case for you in rooms you’ll never be invited into.

The one person to skip is the one with no authority and no path to it. A pleasant conversation that leads nowhere is still nowhere. So the test is straightforward: this person passes if they can buy, or if they can credibly carry you toward someone who can.

Question three: is there a reason to reach out right now?

This is the question that most reps skip, and it’s the one that fixes reaching too wide.

Fit tells you a company is a good match. Timing tells you they are a good match today. The strongest outreach almost always points to something happening in the prospect’s world right now. If your message could have been written a month ago, it’s already stale.

So what counts as a reason to move now? A few of the clearest signals, strongest first:

• A decision-maker changes jobs or gets promoted. This is the single strongest one — people rethink what they buy soon after stepping into a new role.
• The company recently raised funding. ( Yes, everyone knows this one)
• They are hiring for roles that point to the work you support.
• They use a tool yours works alongside, or they are swapping tools in that stack.
• They engaged with content, attended an event, or asked publicly about the exact problem you solve.
• They left a critical review of a competitor, on the weakness you happen to be better at.

You do not need all of these. You need one, and it needs to be current.

The whole thing on a sticky note

Before anyone goes into a cadence, they should clear all three: the business has the problem, the person can buy or open a door, and there is a reason to reach out now.

And for everyone who does not clear all three, the answer is not “delete.” It is usually “wait.” A good-fit account with the right person but no trigger yet doesn’t get a sequence; it gets patience, and your attention the moment something changes. Most sales are made on the follow-up, when a good fit finally meets a real need.

It feels backward, but the reps with the steadiest pipeline are usually sending less, not more. A smaller list of the right people, reached at the right moment, beats a giant list of the wrong ones every time.

Why I wanted to write this down

I’m writing this down for the person on Reddit with three thousand accounts and no idea where to start. When I began, no one handed me a simple way to decide who was worth the effort.

Qualify hard. Be patient with the rest. And put your best hours into the few who have actually earned them.