Why Outbound Still Wins in the Age of AI

Introduction

Jeremy Schiff:

Welcome to Cold to Closed, the show about what actually happens between a cold touch and a closed deal.

I'm Jeremy Schiff, CEO of Salesbot, and I talk to the people building real pipeline today: founders, revenue leaders, and go-to-market operators.

Today I'm joined by Kevin Warner, Founder and CEO of Leadium, an outbound sales leader who's helped teams build predictable pipeline through structured systems.

Kevin has worked across multiple companies and seen firsthand what separates outbound teams that scale from those that stall.

Kevin, great to have you here today.

Kevin Warner:

Always a pleasure. Great to speak with you again.

Jeremy Schiff:

Likewise. Obviously you and I know each other pretty well, but for the audience, can you give us a little background on who you are, your journey, and what you're focused on today?

Kevin Warner:

Absolutely.

I'm the Founder and CEO of Leadium. We started the company back in 2015, so we're over a decade into helping businesses build outbound sales programs.

Before that, I worked across a number of technology companies in customer success, business development, sales development, and product roles.

One of the things I learned early in my career was that no matter how good a product is, it doesn't matter if nobody can sell it.

One of the first companies I worked for raised over $30 million and eventually made its way to the public markets. It also never generated meaningful revenue.

That experience taught me a lesson I'll never forget: sales is the foundation of every successful company.

Around 2014 and 2015, sales development was really becoming its own discipline. Outreach was emerging. SalesLoft was growing. Apollo was just finding its footing. DiscoverOrg and ZoomInfo were evolving rapidly.

That felt like the perfect time to build something around outbound, and that's what eventually became Leadium.

What Has Actually Changed in Outbound?

Jeremy Schiff:

You've been helping companies build outbound programs for more than ten years.

What have you seen change the most over the last few years?

Kevin Warner:

It's funny because everyone lives inside this bubble where every week there's a new tool, a new AI platform, or a new promise that technology is going to solve all of your problems.

Technology has absolutely improved.

It's helping teams execute faster. It's helping teams measure more accurately.

But outbound is still rooted in fundamentals.

Can you place a cold call?

Can you send a personalized email?

Can you build a real relationship on LinkedIn?

Those things still matter.

What I see today is a lot of companies trying to automate away the human elements of selling.

They're trying to send ten thousand emails and hope AI somehow creates relevance.

But the teams winning today are still the teams putting real people into the process.

They're still making calls.

They're still writing thoughtful emails.

They're still building relationships.

Technology helps facilitate those activities, but it doesn't replace them.

Jeremy Schiff:

I completely agree.

It feels like a lot of organizations are generating more activity than ever before, but not necessarily creating more meaningful conversations.

Kevin Warner:

Exactly.

One example I use all the time is real estate.

People ask why we still need real estate agents when Zillow exists.

Couldn't Zillow just add a buy-now button?

Technically, yes.

But people still want guidance.

They want someone to help them understand what they don't know.

Sales works the same way.

Technology can make salespeople more efficient.

It can make them more informed.

But it can't replace the human aspect of helping someone make a decision.

That's why I think fully automating sales is a losing strategy.

The Most Important Ingredient in Outbound

Jeremy Schiff:

When you look at outbound programs that are succeeding today, what's driving the biggest impact?

People talk about targeting, data quality, messaging, AI, personalization. Where do you think the biggest opportunities are?

Kevin Warner:

All of those things matter.

Great data matters.

Great messaging matters.

Technology matters.

But the one thing that's still most important, and the thing most companies don't have enough of, is knowledge of your product and your market.

Founders often think they understand their value proposition because they built the product.

But if you haven't spent enough time talking to customers, you don't actually know what value they care about most.

You might think Feature A is why customers buy.

Meanwhile customers are buying because of Feature C.

The same thing happens in product development.

Companies build functionality they think users want, only to discover later that nobody uses it.

Sales works exactly the same way.

You have to understand how your market views your solution.

You have to understand what problems matter.

You have to understand what motivates people to buy.

Without that knowledge, all the technology in the world won't save you.

Why Outbound Is a Learning Process

Kevin Warner:

A lot of earlier-stage companies simply don't know enough about their market yet.

Other companies understand their market but don't understand outbound.

They don't know their conversion rates.

They don't know which segments perform best.

They don't know which messaging resonates.

Outbound isn't something you launch and immediately master.

It's an acquisition channel.

Just like paid advertising or SEO, every market behaves differently.

Every segment converts differently.

You have to run campaigns.

You have to collect data.

You have to learn.

You have to optimize.

And that process takes time.

Months, not days.

Jeremy Schiff:

That's a really important point.

A lot of people want immediate answers.

Kevin Warner:

Exactly.

People ask, "Will this outbound program work?"

The honest answer is that you won't know until you start learning from the market.

And it's not enough to measure meetings.

You have to measure what happens after the meeting.

A segment might produce lots of appointments.

But if none of those opportunities close, was it actually a successful segment?

That's where the analytics become important.

What Does Good Data Actually Mean?

Jeremy Schiff:

Let's talk about data.

Everyone says they need better data.

But better data means different things to different people.

For some teams it's coverage.

For others it's accuracy.

For others it's buyer signals or company insights.

How do you think about that?

Kevin Warner:

The more specific your data is, the more valuable it becomes.

If I know exactly which market converts.

If I know exactly which signals matter.

If I know exactly which message works.

Now I can start building something predictable.

The challenge is that level of sophistication costs money.

And companies often buy premium data before they've established the fundamentals.

That's where things go wrong.

If results don't happen immediately, people start pointing fingers.

Is the SDR the problem?

Is the data the problem?

Is the messaging the problem?

Nobody knows.

Because the foundation was never built.

Focus First, Then Scale

Kevin Warner:

One exercise we do all the time is very simple.

If I told you that today you only get one hundred calls, who are you calling?

Most companies can target twenty industries.

Five personas.

Ten different use cases.

But you only have one hundred calls.

Who gets them?

Draw a line in the sand.

Start there.

Learn from those conversations.

Then improve.

The biggest mistake companies make is trying to do everything at once.

Focus creates clarity.

Clarity creates results.

When Should Companies Invest More in Data?

Jeremy Schiff:

How do you think about the economics of all this?

When is it worth paying more for better data?

Kevin Warner:

That's one of the hardest questions in outbound.

A lot of organizations focus entirely on appointments.

But appointments aren't the goal.

Revenue is the goal.

A bad meeting wastes everyone's time.

I'd rather have fewer meetings with a higher close rate than a calendar full of unqualified opportunities.

So when we evaluate outbound programs, we look beyond meetings.

We look at revenue outcomes.

We look at conversion rates.

We look at pipeline quality.

Those are the metrics that matter.

The answer to whether premium data is worth it depends on how mature the organization is.

A company that understands its funnel can often justify spending more.

An early-stage company might not be there yet.

Building an Outbound Engine

Kevin Warner:

People often think outbound is just data and SDRs.

It's much more than that.

You need strategy.

You need leadership.

You need messaging.

You need technology.

You need training.

You need analytics.

You need data.

You need execution.

All of those pieces have to work together.

If one part breaks, the entire system becomes less effective.

That's why outbound is so difficult.

And it's also why great outbound programs become competitive advantages.

Final Thoughts

Jeremy Schiff:

One thing I keep hearing throughout this conversation is that technology matters, but only when it's built on top of strong fundamentals.

Kevin Warner:

Exactly.

Technology should amplify what already works.

It shouldn't replace it.

The companies that win are the ones that understand their market, understand their customers, and use technology to make great salespeople even better.

Closing

Jeremy Schiff:

Kevin, thanks so much for joining me today.

I feel like we could keep going for another hour.

Kevin Warner:

Likewise. Always enjoy these conversations.

Jeremy Schiff:

That's a wrap for this episode of Cold to Closed.

Big thanks to Kevin Warner, Founder and CEO of Leadium, for sharing what's actually driving outbound performance today.

If you got value from this conversation, share it with your team and follow along for more conversations with founders, revenue leaders, and go-to-market operators.

We'll see you on the next episode.