Episode 490: From Cold Outreach to Warm Revenue: Building Scalable, Human-Centered Email That Closes Deals

Adam Rosen 00:00
When you do it at its best, what is the outcome? When you look at social and sales, at their best, they’re about the human component. They’re about relationship building. They’re about adding value.

Bob Woods 00:15
Welcome to the Making Sales Social Podcast, featuring top voices in sales, marketing, and business. Join Brynne Tillman, Stan Robinson Jr., and me, Bob Woods, as we bring you the best tips and strategies our guests are teaching and using so you can leverage them for your own virtual and social selling. Welcome to the show.

Brynne Tillman 00:38
Welcome back to Making Sales Social. I am your host, Brynne Tillman, and I am very privileged to be talking with Adam Rosen today. Adam is a world-traveling entrepreneur who sold his first tech startup in 2019 and has since built multiple successful ventures. He is the co-founder and CEO of an email outreach company where he helps startups, unicorns, and Fortune 500 companies drive revenue through high-performing outbound and newsletter-based email systems.

Email has been Adam’s growth engine from the start. It helped him raise capital, land enterprise clients like Amazon, Apple, Goldman Sachs, and Disney, scale platforms to over 100,000 users, and exit businesses at strong multiples. Beyond tech, he has also led multi-million-dollar real estate developments and acquired and exited media properties, all while building a lifestyle that allows him to work from anywhere in the world. That’s a lot. Adam, welcome to the show.

Adam Rosen 01:44
Brynne, thank you for having me. How cool.

Brynne Tillman 01:47
I love the idea of working from anywhere in the world. I hope you’re taking advantage of that.

Adam Rosen 01:52
I’m trying to. I’m in Hawaii right now, so there are worse places to be.

Brynne Tillman 01:56
That is on my bucket list. I haven’t been yet, so that’s awesome. Before we jump into your email genius, we ask all of our guests the same first question: What does making sales social mean to you? My tongue isn’t working today—apologies. What does making sales social mean to you?

Adam Rosen 02:16
I like to look at everything through the lens of: When you do it at its best, what is the outcome? When you look at social and sales, at their best, they’re about the human component. They’re about relationship building. They’re about adding value.

No matter how you generate sales or what business you’re in, the more you can make it feel social, like a real relationship, and value-driven—because at the end of the day, that’s what sales is—the more you’re going to win in sales.

Brynne Tillman 02:56
I love that. Let’s see if we can bridge that to email throughout our conversation today. You’ve built and exited companies in diverse markets. What patterns show up every time a business scales successfully?

Adam Rosen 03:13
First, it’s getting to product-market fit. The more businesses you start and the deeper you are in the entrepreneurial world, the more you realize how difficult it is to truly achieve product-market fit. But for anyone who wants a successful exit, that’s the foundation.

Once you have product-market fit, that’s when you focus on building scalable systems. Without scalable systems, you won’t have as successful an exit. When you combine true product-market fit with strong systems that allow you to scale, that’s when building—and eventually selling—the business becomes really exciting.

Brynne Tillman 03:59
That’s great. I love that. Now, how does email play a part in growing a sellable business?

Adam Rosen 04:09
For me, it’s been everything. As you mentioned, with my first tech startup, cold email is how we got our main investor. It’s how we found the company that bought my startup. It’s how we got Bank of America, Amazon, Apple, Goldman Sachs, and Disney as customers. It’s how we got the majority of our 100,000 users to sign up for our platform—through cold email.

Fast forward to today, about half of our 170-plus customers have come from cold email. That’s why we run an email agency. It’s been the biggest driver of our business growth, and it can be for anyone listening.

Brynne Tillman 04:58
I have a lot of down-the-rabbit-hole questions around this. When you say cold email, are we talking about buying lists? Where are these emails coming from?

Adam Rosen 05:11
There are many sources for getting lists, but the simplest way to define cold email is this: It’s reaching out to someone who didn’t necessarily opt in to receive emails from you. They may or may not know you, but they fit a specific target audience you want to reach for a particular call to action—whether that’s a 15-minute call, a webinar, or visiting a landing page.

Cold email is called “cold” because they don’t necessarily know you. As for sourcing lists, there are more options today than there were five or ten years ago.

Brynne Tillman 05:50
Let’s say I have this cold list. They don’t know me. I’m opting out of emails all day long. What are people doing wrong in the emails I delete versus the ones I actually read?

Adam Rosen 06:11
There are two sides to this. First is the technical side—infrastructure. Email has changed a lot, especially in recent years. Landing in the inbox is harder than ever. Many people struggle because they don’t have the right infrastructure in place.

Assuming the technical side is handled, the biggest mistake is not focusing on value. It has to be about what’s in it for them.

In a cold email, you’re not trying to close a $500,000 deal. You’re selling 10 minutes of your time. That’s it. So you need to:

• Fully understand your ideal customer profile 
• Identify the problems they’re facing 
• Articulate how you solve that problem 
• Show social proof 
• Make it simple and easy to digest 

Founders often overload emails with information. I see emails that are three paragraphs long. If your own mother wouldn’t read it, a stranger won’t either.

In three to four sentences, you should clearly state the problem you solve, why it’s relevant, your social proof, and a simple call to action.

Brynne Tillman 08:22
Is that for the first email, or do you warm them up with value first?

Adam Rosen 08:27
You can warm them up, but with cold email, it can be transactional. You can say, “Here’s a problem we solve. Here’s our solution. Want to chat?”

You can add value, and I typically do that more on the newsletter side. But people are actively looking for solutions to problems. I have 27 things on my plate I’d love solved yesterday. If the right solution showed up in my inbox, I’d be happy.

You’re not necessarily a nuisance. You might be exactly what they’re hoping to find—if you position it correctly.

Brynne Tillman 09:11
On LinkedIn, we say never ask for a call until you’ve earned the right through value. Email feels different. Often when I see an email asking for a call in the first touch, I think, “Why would I want a call with you?” What’s missing there?

Adam Rosen 10:21
There’s no one approach that works for everyone. In our Slack, we have two channels: one for glowing replies and one for negative replies. The same exact email can get both within minutes.

Some people prefer a value-first, nurturing approach. Others just want to know what problem you solve and whether it’s relevant.

There’s no magic bullet. The key is positioning it in a way that resonates with the right audience.

Brynne Tillman 11:38
I get emails daily saying they found errors on my website and asking if I want a report. How would you fix that email?

Adam Rosen 11:59
If it’s legitimate and truly personalized, that’s one thing. But most of the time, it’s fake personalization sent at scale.

If someone said, “Brynne, I noticed these three specific issues on your site that may be limiting conversions,” that’s helpful. But vague claims like “I found errors—want a report?” are usually bait.

If it’s real, make it genuinely personalized. If not, don’t do fake personalization. It’s obvious.

Brynne Tillman 13:02
I love that answer. When we talk about emails, are we including newsletters and mass emails, or just individual outreach?

Adam Rosen 13:15
Both. And with today’s tools, you can personalize at scale. Things that used to take two hours per email can now be done across thousands while still feeling customized.

For example, if someone posts a job that signals they might need your solution, you can automatically send a relevant, personalized email triggered by that event.

But lazy tactics—like fake referrals or gimmicks—are outdated. They worked in 2017. Now, they just insult people’s intelligence.

Brynne Tillman 14:53
AI has definitely improved personalization, but engineered empathy can feel obvious. When you’re building the full package—cold email, newsletters, inbound—how do you align marketing and sales? Is it all calendar booking? Drip campaigns? What does that look like?

Adam Rosen 15:59
It could be everything from cold outbound booking meetings directly through Calendly, so the sales team just has to show up, to deep CRM integrations. In the second half of 2025, we’ve gone much deeper with CRM integrations, especially with larger companies that have thousands and thousands of contacts in their CRM.

They’re investing heavily in advertising, but their sales teams weren’t doing a good job of reaching out to those prospects once they entered the CRM. So we build systems within the CRM to ensure consistent, high-quality touchpoints. If you’re investing money to generate leads but not following up properly, that’s wasted investment. So the answer is: all of the above.

Brynne Tillman 16:46
I love this. We have a lot of clients with very large email lists that aren’t converting. What are they doing wrong, and what should they be doing in 2026 to optimize that list?

Adam Rosen 17:00
First, they’re not emailing them consistently.

Brynne Tillman 17:04
Even if they’re sending a weekly newsletter?

Adam Rosen 17:08
Number one is frequency. Number two is quality. Number three is personalization.

It’s not just, “At the beginning of every month, are you interested in talking now?” It’s about building a real system with consistent, high-quality touchpoints. Emails should be short, clear, and personalized so they don’t feel like just another generic message in the inbox.

Brynne Tillman 17:40
Give us an example of what that might look like.

Adam Rosen 17:43
One of our clients is one of the largest real estate development firms in the country. They’re spending a lot on paid ads and generating significant interest. But their sales team wasn’t emailing leads more than once or twice—70% of leads received no more than two emails. The quality was low, and personalization was poor.

For example, they have developments in Texas, Alabama, and Florida. A lead interested in Texas should receive different messaging than one interested in Florida. If someone says they’re looking to build a cottage for their family and grandkids, that should be reflected in the outreach. If another says they want a summer home, that should be included.

It’s about using the relevant information prospects provide, following up consistently—because we all know how important follow-up is in sales—and making the message feel handwritten. It should feel human. It should feel social.

Brynne Tillman 18:57
One of the biggest traps I see is weak follow-up messages like, “Circling back” or “Just checking in.” What subject lines actually get people to open a follow-up?

Adam Rosen 19:16
It depends, but a simple one that works well is just: “Hi, [First Name].” For example, “Hi, Mary.”

Then in the body: “Are you still interested in the Texas property?” Keep it value-driven, short, and to the point, with a clear call to action. There needs to be a direct question.

Brynne Tillman 19:49
That’s great. As we wrap up, what’s one question I should have asked you but didn’t?

Adam Rosen 20:04
I’m a sales lover. In all my companies, I still run sales. It’s the role I’m most hesitant to hire for. I also love sales data—I track everything: close rates, lead sources, time to close, all of it.

One of the biggest problems I see in startups is struggling with sales, especially when it comes to evaluating lead sources. People often assume that meetings from cold email are low quality and unlikely to close.

But once someone says, “I want to chat with Brynne to learn more,” they are a warm lead. They are just as valuable as a referral or inbound website lead.

In fact, cold outbound can produce higher-quality leads because it’s intentional. I might target companies with 100 to 250 employees, sales or marketing leaders, B2B organizations, and so on. Compare that to someone randomly booking through your website—they might be a perfect fit, or they might not have the budget.

With outbound, you control the targeting. So the real shift is this: stop looking at cold leads as cold. Once they book a meeting, they’re a real opportunity.

Brynne Tillman 22:12
I’m sure there are listeners thinking, “Adam, this is great. I haven’t thought about my email list this way.” Who should reach out to you, and how?

Adam Rosen 22:31
We work with solo founders at an early stage and offer pricing options for them. We also work with large companies like the UFC and Allstate, where we operate at a much bigger scale. And we have everything in between.

If you’re interested in using email to grow your business, email me at adam@eocworks.com. Whether it’s sharing tips or exploring ways to work together, I’m always happy to help people who are taking the initiative to learn and grow—like the listeners of your podcast.

Brynne Tillman 23:08
I love that. Thank you so much for being here. Next time, we’ll dive deeper into newsletters—I know that’s a topic many people are interested in. For now, thank you for your insights. And for all our listeners, when you’re out and about, don’t forget to make your sales social.

Bob Woods 23:28
Thanks for watching. Join us again for more special guests with marketing, sales training, and social selling strategies that will set you apart. Hit the subscribe button to get the latest episodes of the Making Sales Social Podcast. Give this video a thumbs up and comment below with what you’d like to hear next. You can also listen on Apple Podcasts, Spotify, Amazon Music, and other platforms. Visit our website, socialsaleslink.com, for more information.