Deal Lab Breakdowns Issue # 01

Deal Lab Breakdowns is a weekly newsletter breaking down GTM campaigns, strategies, and the thinking behind how we run outbound at The Deal Lab.

We’ve been doing creative outbound since 2023, and I’ve personally been earning my living in outbound since 2018.

Most teams don’t lose because they lack tools. They lose because they don’t have a strategy that produces signal, improves over time, and compounds into a system.

The goal here is to make the thinking legible.

This issue is about using RSS feeds and podcasts as outbound triggers to break into high-value enterprise accounts that normally ignore cold outreach.

This play was built for enterprise IT execs.

This market has a few defining constraints:

When you’re selling into a market like that, brute force gets you nowhere.

You have to earn attention.

This client was six months into an annual contract with an outsourced BDR team, paying $40K per month.

At that point, they had essentially no wins to show for it. They’d paid six figures for activity.

We came in on a $5K/month month-to-month deal and ran a four-month pilot.

The first three months looked like most outbound pilots: some activity, some learning, but nothing that felt like traction.

In month four, we tried this RSS + podcast trigger play.

That was the inflection point.

We started getting intros quickly, the motion became repeatable, and we ended up retaining them for over a year.

This campaign wasn’t about “podcast personalization.”

It was about using the podcast as pre-earned context and starting the conversation where the buyer already is.

If someone goes on a podcast, they’re putting their name and thinking into the world.

They want it to travel.

They want people to notice.

They want to feel like it landed.

So when you reference something they said, it doesn’t feel like cold outreach.

It feels like: someone heard me.

That is a fundamentally different posture than: here’s another person asking for 30 minutes.

Most outbound asks the buyer to do the work.

Understand you. Understand why they should care. Understand why now. Take a meeting.

This play reverses that.

The message feels like payoff for something they already did.

They already invested time in the conversation.

You’re showing them it mattered.

Enterprise IT is not a “book meeting and close in 10 days” market.

In this world:

So the goal isn’t always conversion.

Sometimes the goal is: earn goodwill, get introduced, get routed correctly, get permission to stay in touch.

That’s why this worked. The client didn’t need more noise. They needed meaningful dealflow.

In this market, you can’t burn your list.

If you only have 800 targets, blasting them with generic outreach is the fastest way to ruin the channel for yourself.

This play is built for precision and relationship-building, not volume.

The format stayed consistent. The inputs changed.

HealthsystemCIO is one example, but we ran this across multiple podcast ecosystems. The goal was to turn fresh podcast appearances into outbound triggers without relying on manual effort every time.

1) Find podcasts that consistently feature your buyers

We used GPT and manual research to find podcasts where the guests were literally the people we wanted.

2) Use Clay to monitor RSS feeds

We tuned into RSS feeds so every new episode became a trigger.

New episode equals a real reason to reach out while it’s fresh.

3) Scrape the show notes page

When a post dropped, we scraped the show notes page to capture:

That one point became the anchor for credibility.

4) Enrich the guest

We enriched them for LinkedIn, email, and company data so we could map them into a usable dataset.

5) Use Ocean.io to generate lookalike accounts

Once you have one guest, you have a starting point.

We used Ocean.io to generate lookalike companies similar to the guest’s org. That gave us more accounts where the same narrative would land.

6) Waterfall contact data

We ran a waterfall across multiple providers depending on what we needed, including tools like Prospeo, IcyPeas, BetterContact, and others.

7) Auto-write the message and auto-enroll prospects

This is what made the system scalable.

We used Clay + GPT to generate the first-draft message using:

Then we automatically enrolled those prospects into Smartlead campaigns so the outreach shipped without manual copy-pasting.

If we ran this today, we’d also run a parallel version on LinkedIn using Heyreach.

Not because LinkedIn is “better,” but because in enterprise IT, some buyers are simply more responsive there.

The podcast context works the same way, and multi-channel follow-up would likely lift total conversions without adding much extra work.

The message always did the same thing:

We didn’t ask for a demo.

We asked for 15 minutes of questions.

That mattered because it made the outreach feel real.

The buyer could tell this wasn’t templated “personalization.” It was a continuation of a conversation they already cared about.

Source episode:

https://healthsystemcio.com/2025/11/13/memorial-hermanns-okafor-says-extracting-the-value-of-it-investments-requires-a-greater-investment-in-training/

Subject: your podcast

Hey {first_name} - saw your HealthsystemCIO episode about extracting value from IT investments.

The point about adoption and training being 3x the tooling cost was sharp.

If I called with 15 mins of questions on how you think about value realization inside IT teams, would you take it?

Thanks - Kellen

Most outbound fails because it asks a buyer to start from zero.

Zero context. Zero relationship. Zero reason to care.

This play works because it starts from something already real.

The buyer already published what they care about. Your outreach just continues it.

And the CTA matches the moment.

It’s not “here’s my pitch.”

It’s “can I ask you something relevant about the thing you already chose to talk about?”

That’s why you get intros.

If you try this play and it works, I’d love to hear about it.

If it doesn’t, I’d love to hear that too. The failure cases are usually the most useful.

And if you want a breakdown of a specific campaign, channel, or target market, send it over. I’ll add it to the queue.

Kellen
The Deal Lab