Why your outreach isn't working

I think the most popular conversation I’ve had with founders in October was that nobody is happy with the number of deals they have in their pipeline.

And cold outreach doesn’t work.

But here’s the thing.

Cold outreach always works, if you do it well.

The problem I’ve seen is that a lot of founders don’t want to go through the gruesome process of making it work well.

They immediately go to “how do I scale this.”

They write one email template, then send it to thousands.

They find a basic list on LI SalesNav and automate a drip campaign on Dripify.

They start with automation in mind instead of getting to the root of what prospecting is really about:

Finding companies that have the problem you solve.

Which requires a lot of thought and effort. At least at first.

In this newsletter I’ll go through the fundamentals of prospecting and outreach. I’ll also touch on what to avoid in the very early days.

Table of Contents

• The core fundamentals of prospecting

  • Targeting

  • Relevance

  • Timing

• Finding a problem

• Examples of messaging

• Coming back to automation

• Prospecting playbook

The core fundamentals of prospecting

There are really 3 things at play with prospecting and outreach:

1. Targeting

2. Relevance

3. Timing

Targeting are the people and companies you’re reaching out to.

Relevance is your messaging connecting to the problems they have.

Timing is about them having pain right now.

If any of these 3 things are off, then you won’t get a response. Or you’ll get a no. Or a fuck off.

And this is why prospecting and outreach is so hard - because it’s really easy to get one of these things wrong.

And when you try to automate everything, it’s hard to pinpoint which of these 3 needs to improve.

Let’s dive deeper into each of these.

Targeting

This is usually where most folks go wrong. Targeting isn’t easy. If you were able to find a list of prospects on LI Sales Nav using a couple default filters like employee range and industry, then you’re not really doing targeting.

The easy stuff is what all of the lazy sales reps out there are doing. And there are A LOT of lazy sales reps. Hundreds of thousands of them.

Which creates a lot of noise in the market. And impacts every single one of us who’s trying to prospect for business.

So what makes good targeting?

• It narrows your list down to something very specific, not something broad

• The targeting criteria tells you something about the problem they might be having

• The targeting criteria can be used in your messaging to help increase the relevance

The second bullet is really the most important one. What about this list of prospects signals they might have the problem you solve?

Just raised a Series A isn’t anything that signals a specific problem. And this is where a lot of early-stage founders go wrong. They target the easy stuff.

Now let’s pretend you’re selling a tool that helps with devops toil. What are things that happen at companies that could be a signal that this exists?

• Engineering team is growing fast

• Customer-facing team is growing fast

• Average tenure of devs is low (lots of recent hires, not a lot of Sr. devs)

• Lots of Jr devs in the org

• Hiring a lot on the infra or devops team

• Job responsibilities highlight dealing with issues

And there could be a lot more. With targeting, you want to be as specific as possible.

Relevance

Relevance happens when the prospect sees themselves in your outreach.

Most of the founders I’ve encountered make prospecting messaging very selfish.

“Hey prospect - I’m founder of this amazing startup. Our tool does X, Y, Z. We can give you unrealistic results. I’m important, so book time in my calendar. [founder_name]”

^they don’t actually say this, but this is how it comes across to prospects.

This advice is usually given by incubators and accelerators. Just start reaching out to a bunch of folks about your tech. Put it in front of as many people as possible. It’s really good, so they’ll be interested.

The problem with this approach is that the prospect can’t see themselves or their world in this. They don’t know if this tech is relevant to them. Because none of the messaging is about them.

So relevance happens when you make it clear about why you reached out (your targeting) and the pain that prospects typically have.

Timing

Timing is the last piece of the puzzle. It’ usually the hardest one to get right, unless there’s some sort of external factor that signals the problem is happening (maybe lots of open positions, hiring, firing, layoffs, regulatory changes, etc).

The reality is, prospects operate on their timeline, not yours. And there’s not a whole lot you can do about this.

A business juggles an increasing amount of risks and opportunities. These trickle down into strategic objectives, priorities, projects, tasks, etc.

Some of these are very urgent and impactful, and require a lot of resources. Some are less impactful.

Where you land in terms of priorities will dictate timing.

Are they feeling the pain now? Is the pain causing a problem? Is that problem impacting the business significantly? If yes, then you have a good shot at getting a response (assuming targeting and relevance are correct). If no, then it’s not going to lead anywhere.

Finding a problem

A lot of the bad advice founders get when it comes to prospecting really comes from the thousands of LI posts that are geared towards a Sales Development Rep (SDR).

“You have to book the meeting.”

The reality is, you don’t.

Anything that pushes your product to someone, without relevance, and asks for a time commitment is rarely going to work. Even if you try to scale it up.

The reason this advice is given is that SDRs are compensated on booking meetings. That’s their sole job. Get a meeting on calendar for their Account Executive.

Their performance is measured on their ability to book meetings. They get assigned a meeting quota.

So logically, if you ask for more meetings, you’ll get more meetings, right?

But you’re not an SDR. You’re a founder.

A meeting gives you nothing if there’s no opportunity for you to close a deal.

And there are no opportunities unless you’ve found a painful problem to solve.

So when you’re doing prospecting and outreach, especially on LinkedIn, you should be qualifying for pain.

That’s it.

If they don’t have pain, you don’t book the meeting. You avoided a waste of time for you and the prospect.

Examples of messaging

Here’s a sample rough message that we can break down:

“Hey Jane - looks like you’re hiring another developer in Pakistan. How has Joe been able to manage their commits as a fractional CTO with an 8-hour time difference from the team?

A lot of founders struggle with getting verbal reports from the team that doesn’t really match the output.

I’m building a tool that gives you visibility into what’s been committed and how it impacts your dev velocity.

Worth exploring?”

Breakdown:

Looks like you’re hiring another developer in Pakistan. Hiring is the trigger, and it’s stacked with two qualification/fit criteria. Another signals that there are multiple, and Pakistan is the location of the outsourced team.

How has Joe been able to manage their commits as a fractional CTO with an 8-hour time difference from the team? This question opens up the possibility of pain, and again stacks on different qualification criteria. Joe is a fractional CTO, 8-hour difference references the outsourced team.

A lot of founders struggle with getting verbal reports from outsourced teams that don't really match the output. This is an example key message detailing the pain prospects feel, given the context of the observation. Another mention of outsourced teams (qualifier).

I’m building a tool on Github that gives you visibility into what’s been committed and how it impacts your dev velocity. This is a key value point of the tool. Also mentions Github as another qualifier.

Worth exploring? Easy low-commitment yes/no ask to wrap it up.

Here’s another example:

“Hey Joe - saw you have a CRO in Austin, a CMO in London, and you’re based in Copenhagen. You’ve also brought on a fractional CTO in Barcelona.

A lot of CEOs struggle with gaining alignment on key priorities with their executive teams, especially when they’re fractional or remote. This often leads to frustrated execs not agreeing on execution, which really slows down growth.

Does this match what you see?”

saw you have a CRO in Austin, a CMO in London, and you’re based in Copenhagen. You’ve also brought on a fractional CTO in Barcelona. This shows a distributed exec team, and a fractional role. Part of your targeting and creates relevance. You’re talking specifically to the prospect here.

A lot of CEOs struggle with gaining alignment on key priorities with their executive teams, especially when they’re fractional or remote. This often leads to frustrated execs not agreeing on execution, which really slows down growth. Struggle and frustrated are pain words, creating an emotional connection for the prospect. Gaining alignment on key priorities is a common problem that many executive teams face. Fractional and remote highlights that it’s more difficult specifically for them, which matches the targeting. slows down growth is the negative impact on the business.

Does this match what you see? Easy yes/no question that validates pain.

These aren’t perfect examples, but they show the work involved in connecting targeting, relevance, and timing together.

Coming back to automation

Automation either amplifies good or amplifies suck.

It does not help you find good.

So if you write a single template, and send it to 1000 people, you’ve really created one message.

If you copy paste a template in your LI DM to 20+ contacts. You’ve only really written one thing.

If you created one broad list, then automated connects on Dripify, you’ve taken one action.

When you’re in the process of figuring out what good looks like, you need repetition. You need fast iteration. You need to gauge responses, or lack of responses, and adjust.

You need to get better at messaging. At shortening it. At making it more specific.

You need to practice articulating the pain. You need to practice connecting your research to potential problems.

And the more you do it, the better you get.

So if you want to figure this out as fast as possible, skip the automation. It is WAY too easy to just slack off. Put it on auto-pilot. Hope you get some results.

But hope is not a strategy in sales. Taking action will help you move faster.

So put in the reps. Get better at figuring out targeting and messaging. You’ll stand out more in your outreach, and you’ll get closer to figuring out what you can or should automate.

But never start with automation.

Prospecting playbook

I’m in the process of writing a prospecting playbook specifically for founders. If you’re interested in getting early access to what’s currently available, just reply to this email and LMK - I’ll send you the link.

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.