#245: B2B Outbound Best Practices: What’s Working Now with Cold Email and Paid Ads (with Alex Fine)

#245: Cold Email | Danielle Messler sits down with Alex Fine, co-founder of Understory, the agency behind some of the most effective outbound and paid strategies in B2B right now. Alex is leading the charge on a smarter approach to outbound called “Allbound”, a tightly integrated blend of outbound, paid media, and LinkedIn tactics that actually convert.

If you’re tired of cold emails that go nowhere or ad campaigns that burn cash without ROI, this one’s for you.

Danielle and Alex cover:

• Why most B2B outbound strategies fail and how Allbound fixes the disconnect between ads, email, and LinkedIn
• The cold email deliverability tactics that actually work in 2025 (including tools like Instantly, Smartlead, and Clay)
• Real-world examples of hyper-personalized, AI-powered outreach that book meetings with high-ACV prospects

Timestamps

• (00:00) - – Intro
  
• (03:11) - – What Is “Allbound”?
  
• (05:11) - – Cold Email Isn’t Dead (But It’s Evolved)
  
• (07:41) - – Tools to Improve Deliverability
  
• (09:56) - – Personalization That Actually Works
  
• (11:26) - – Real Example: Fraud Detection SaaS Cold Email Strategy
  
• (13:11) - – How to Keep Messaging Consistent Across Channels
  
• (15:11) - – Treating Each Channel Differently
  
• (18:19) - – Ads as a “Cheat Code” in B2B
  
• (20:49) - – Building Genuinely Personalized Emails at Scale
  
• (23:49) - – From Swiffer to SaaS
  
• (27:19) - – What Sales Teaches Marketers
  
• (36:04) - – Where to Find Alex + Upcoming Exit Five Event Plug

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Dave Gerhardt [00:00:00]:
You're listening to B2B Marketing with me, Dave Gerhardt.

Danielle Messler [00:00:17]:
Hey, Danielle from Exit Five here. Today I'm talking with Alex Fine, the co founder of Understory and honestly one of the smartest people I know when it comes to outbound and paid media. We talked about this concept he calls allbound, which is basically the smarter, more integrated way to run outbound, paid and LinkedIn without spamming people or wasting a ton of money. Alex breaks down what's actually working in cold email right now, why most ad accounts are set up wrong, and how to get way more targeted and personalized with your outreach without it taking a million hours. If you're a B2B marketer who wants your campaigns to actually convert and not just look good, you better make time to listen to this one today. Let's get into the episode. Awesome. Okay.

Danielle Messler [00:00:58]:
I am so excited to have you on the show, Alex. So this is Alex Fine. He is a friend who I've actually worked with in the past at the past companies. He's co founded agency Understory, has run ads for me and done a bunch of stuff. So we're excited to have you on today, Alex.

Alex Fine [00:01:14]:
Yeah, I'm super excited to be here. It's always good to connect with you.

Danielle Messler [00:01:17]:
Yeah, this is awesome. So I'm excited to jump into our convo today, but I want to talk about Understory because they drove such good results for us and you guys are just blowing up and I see you everywhere and you guys haven't been around that long, right? It's like not even two years yet.

Alex Fine [00:01:32]:
So funny enough, we started actually three years ago, but I would say two years ago, the business really picked up.

Danielle Messler [00:01:37]:
Yeah.

Alex Fine [00:01:38]:
And partially turned to you, by the way, going to these events like SaaS Open and Stuff like that. It actually got us into a really good place and we started to connect with the right people. The services got better and better and more robust. They became more productized and yeah, we honed in on what we were good at and we've grown to climb in the last two years. So that's why it seems like that.

Danielle Messler [00:01:55]:
Yeah, it's awesome. It's awesome to see. I love it. I love seeing good people with good products start to grow, which is cool.

Alex Fine [00:02:02]:
Appreciate it.

Danielle Messler [00:02:03]:
Yeah. So you have kind of a unique take, or maybe it's just one of those things that's always been. But you've named it called Allbound that you've talked about. So tell me about Allbound. What the hell is it? What does it mean? I see it on LinkedIn. Tell me more.

Alex Fine [00:02:19]:
So Allbound really isn't a new principle when you think about it? I mean, it's similar to lifecycle marketing, right? It's like, so finding your, your ICP wherever they exist. I think what's changed a lot is the way that each of these channels actually work. So, like, I'll use email as an example because everyone knows that cold email used to be a super hot button.

Danielle Messler [00:02:35]:
You could press and you could basically cold emails. Not dead?

Alex Fine [00:02:40]:
No, I don't think it's dead. That's why we make so much, you know, so many businesses that are working with us to generate results through cold email. And it's working like crazy. Like some of our clients, you know, they might have an ACV of $100,000. We might get them three or four leads in a day. So it's like, it definitely works. But what I'm saying is with Allbound in particular, it works a totally different way than it used to. And these tools, and I won't name drop any tools, last thing I want to do is bash anybody.

Alex Fine [00:03:03]:
But there's these tools out there that used to work in the old way of Allbound that no longer work. So now it's become a very complex task to do Allbound efficiently and effectively. And you have to use all of these different tools that don't necessarily integrate with the existing tech stack you used to use. Right? So you have tools like, like I said, I won't name drop them, but the ones that integrate directly with your CRM, where they help you push data into other places, those don't have deliverability functions. And deliverability is the name of the game right now. If you can't deliver into the primary inbox, no one ever sees your message. So you can't actually generate any leads because if you're in spam, no one knows who the heck you are. No one knows what your email about because they never see your email.

Alex Fine [00:03:39]:
So you have to use tools like instantly here.

Danielle Messler [00:03:40]:
Yeah, you can name drop tools. That's totally fine. I think people we know, our audience, like, loves to find new tools that give them an edge. So, like, feel free to name drop.

Alex Fine [00:03:48]:
I'll talk about the good ones for sure.

Danielle Messler [00:03:50]:
Yeah. And I want to kind of hone in on what you said about like deliverability being the name of the game right now, especially with cold. Cause I feel like every day I see a meme on LinkedIn of like, you know, the bad cold emails you get. I am particularly vicious with marking spam so what would you say about deliverability? Like, what do people get wrong in this new kind of day and age? And how can you improve that for better results?

Alex Fine [00:04:16]:
Yeah, I mean, so like the fundamentals, right, of landing the primary inbox, don't use links, don't use images, things like that, things that can be picked up by a spam filter and determine this could potentially be harmful, this could potentially be phishing, this could potentially be something like that. Even when you add open tracking or click tracking to an email, something like that, what it does essentially is just throws a pixel into the email. That pixel is read the same way as a link. It can be used to steal your information, something like that. So that's, you know, red flag number one. Don't put anything that can be determined as a link that could potentially be used for harmful stuff or phishing, anything like that. That's problem number one. But to the way that all these spam filters work, it's getting more and more complex and it changes on a daily basis.

Alex Fine [00:04:54]:
But think about it like this. You've got companies like Google, right? Everyone uses Suite for the most part in the startup world as their email client, right? Then you've got the bigger companies that are using Outlook. Both companies are playing very heavily in AI. If they're using AI and they're serving products to the world with their AI, why would they not be internally to, to identify spam? So they are. The issue is, is every spam filter acts in a different way. So Microsoft spam filter might act completely differently than Gmail spam filter, right? So you have to figure out ways to get around those spam filters. And sometimes it's the length of the copy, it's the specific words you're using, it's the amount of HTML that you're using or not using a different stuff. So, so being able to get around that and navigate through the deliverability traps that exist everywhere is key number one.

Alex Fine [00:05:38]:
So for us, for example, we use tools like Instantly and Smart Lead, which have all of the functionality available for you to get through those spam filters. So whether that's ESP matching, sending Outlook emails to Outlook inboxes, Gmail emails to Gmail inboxes, things like that can make a big difference. The volume of emails that you send and the reason for the volume of the emails that you send being important. If you're sending 10 emails from one inbox and you just said you like to mark people as spam, so let's say I send to 10 people, 9 of 10 don't mark me as spam. But one does, right? Or maybe if I'm only sending 10 emails from that domain in a day and I get two spam complaints in a day or something like that, then Gmail is going to say, okay, you get two out of 10. 20% of the people that you reached out to just marked you as spam. You might be a spammer. So what you do is you diversify your email infrastructure so you send across multiple different inboxes, and by doing that, you diversify your risk as well.

Alex Fine [00:06:28]:
So if you have one inbox gets crushed from deliverability because two people marked you as spam, but then you have another one that no one marked you as spam because your ICP is honed in on, your targeting is great, your messaging is great. People are actually appreciating getting your emails. You're in a much better place. But you need to diversify your infrastructure across multiple different clients as well as multiple different inboxes and domains.

Danielle Messler [00:06:47]:
Yeah, so something you said is interesting about, like, getting around the spam filter. So what would you see as a difference between, like, a genuine cold email that is actually genuine, genuinely written, relevant, helpful, and the ones that like, actually are spam? I said I'm vicious, but, like, if it's a really good cold email and it's, you know, I can tell it's an actual person on the other end. The ones I'm like, vicious with are like, when it's clearly copying and pasted from like different parts of my LinkedIn, like, you can tell it was a mass send, it's not relevant. Or they're like jerks when following up. And they're like, well, I guess, like, keeping your job isn't of interest to you. I'm like, I know you're stupid, little psychologist Ghax. Like, yeah, those are funny.

Alex Fine [00:07:29]:
No, I mean, the key really, I mean, you know us, we're huge Clay users. We're Clay power users. We're Clay Enterprise Partner. Clay is. Clay is our baby. We love it. But everything that we do is in Clay, and that's how we really avoid that ever happening. So our segmentation targeting is on point.

Alex Fine [00:07:44]:
You know, it's like we use all different types of triggers. We can do social signals, we can do really whatever you can think of. And we build triggers around that. We'll do custom scrapes to find out exactly who's within our ICP and find messaging that's actually relevant to them. So we can do things like identify whether or not a company is growing. If company's growing, they might need more resources for X, Y and Z. Whatever it is, it depends on the customer that we're working with. But it's really about making sure that you're reaching out to the right people at the right time and you're sending the right message.

Alex Fine [00:08:11]:
So, yeah, I know a lot of these people, but you've got the people out there that are like, I don't care. I'm just going to send 2 million emails a month, hope something sticks. Even if I have a 0.1% reply rate, if I send that many emails, surely I'll get some leads. And you're blowing everyone up. You're causing the problem. So we don't do that. We're very. I like to say it's all the time.

Alex Fine [00:08:27]:
I posted on LinkedIn all the time, but we are not a volume agency. We're very targeted, specific. And it's because so many people complain about this stuff and rightfully so. My inbox looks insane, so. Yeah, I totally hear you.

Danielle Messler [00:08:38]:
Yeah. In my last position, just. And even in this one, just having, like, head of something in your title is the worst. I'm like, I just, I want to change it to something that no one wants to sell to because the targeting can just be so bad. But no, that was our experience with you guys too. And I think that I posted something recently and like, we joke of like, you know, cold emails, dead and blah, blah, blah. And it's like, no, just like the shittiest version of it dies quickly because someone figures out it could work and ruins it.

Alex Fine [00:09:07]:
Yep. Yeah, exactly. It's a spray and pray stuff that's. I mean, it's been the problem since email started as a. As a channel. Right. There's always been the spray and prayers and they're not going anywhere. And it's becoming more and more sophisticated and people are just finding ways to send more and more emails.

Alex Fine [00:09:21]:
So, yeah, got to get around it.

Danielle Messler [00:09:23]:
Email is just one piece of what you're talking about, right? Yep. This Allbound concept. So what else? Like, how does it work? What else is in there? How does it work together and why is it, you know, something to look at in 2025?

Alex Fine [00:09:33]:
Yeah. So at the end of the day, the goal is for you to be able to identify the entire buyer journey, everything that happens in the cycle that influences step one, step two, step three, and then get someone to actually convert on your service or product. So when we say Allbound, typically what you do, like, for example, you've worked with Us on the paid media side. So, you know, we'll run ads. So for example, we might have a LinkedIn ad going, a branded search ad going on Google, an outbound campaign doing LinkedIn outreach, all simultaneously, all in a cohesive way. So the way it might work and this, this is a real example that we've, we've seen with many, many clients and we've also seen happen many, many times within each client. We might send an email to somebody. That email gets logged the next spot, right? Attached to a contact record, a work email, a personal email, wherever we sent it, right? So if we send that email that gets logged into HubSpot, next thing is they might see a LinkedIn ad.

Alex Fine [00:10:21]:
They might be served an ad specific to their job title in an ABM campaign, something like that. They click on the ad, maybe they even fill out a form, but they don't actually convert into a meeting, anything like that. There's some sort of drop off somewhere. Then what they end up doing maybe a day later is they get a second email because they never responded to the first one or two or three days later and they say, oh, I actually just saw an ad. I never followed up with that company. I saw the first email was actually really interesting. They go and search your company on Google, they search it with a branded search ad, they click that, they convert, they fill out a form, they book a demo, something like that. That entire journey is now tracked in like a HubSpot.

Alex Fine [00:10:55]:
And you can see every single little thing that influenced one another directly in chronological order. So you can see the timelines for when these events happened, what steps were taken and how it all looks. That's all about in a nutshell. The key is being able to do all of these different channels effectively. Like I said, email, same as it used to be. You have to figure out all these integrations. You have to stitch things together. You have to get creative in terms of deliverability, in terms of the sequencing tools, everything.

Alex Fine [00:11:20]:
You have to make sure also you have some sort of identifier. So if you're using a personal email or a work email, you need to be able to have that information within HubSpot, otherwise it's not going to tie to the same contact, right? So you have to get really creative in the way you do that. And most of that work is done with clay for the enrichment piece to make sure you have that unique identifier, whether it's contact id, work email or personal email, whatever it is, to map all of that stuff back to that individual or that company. So I spoke really fast at you, but that's Allbound in.

Danielle Messler [00:11:48]:
No, it's great. And I think something important you said is the consistency between channels. And can you tell a little bit more about that of like how you kind of tell the same story through the email, the served LinkedIn ad, maybe the LinkedIn message, the other things that you're doing and how does that play into the effectiveness of this strategy?

Alex Fine [00:12:10]:
Yeah, so you actually didn't get a chance to work with us in this way. But we work in pods, so we have specialists on every single channel. No one that's running outbound campaigns in understory is running paid social ads or paid search ads, and no one that's running paid social is running paid search. They're all unique skills. So it does become hard to keep that cohesive message when you have multiple different people working on multiple different campaigns. It's not in a silo because we work in pods, but it's all about collaboration. So everyone's working together to align on the messaging before anything actually gets pushed live. So we make sure that the campaigns are cohesive, timelines are cohesive.

Alex Fine [00:12:42]:
When you're serving an ad, when you're sending an email, when you're sending a LinkedIn message, things like that. You also have to treat every channel differently with email. You know, you want to keep your message short, punchy, concise, provocative and relevant. But you also are able to tell a little bit more about what your product actually is or what your product does. Right. You don't want to be hard selling people, but you are able to give people some context. LinkedIn. I mean, you have a good following on LinkedIn.

Alex Fine [00:13:05]:
I have a pretty good following on LinkedIn. Can imagine someone like Dave, but my inbox is blown up every single day on LinkedIn. I probably get no exaggeration, at least 10 random messages a day trying to sell me something on LinkedIn. Right. So you have to have some sort of really relevant punchy message that's not selling you at all. Never hard sell on LinkedIn. LinkedIn is a totally different channel. LinkedIn is designed to be very conversational, right?

Danielle Messler [00:13:32]:
Yeah. No one likes a pitch slap.

Alex Fine [00:13:34]:
No one wants a P. And if you have a message that's longer than two lines in the first time you ever send someone a message, you're instantly getting deleted. I'm not even reading it. I'm not reading past the second line. I'm closing that out, right?

Danielle Messler [00:13:45]:
Yeah.

Alex Fine [00:13:45]:
And most people are fighting with this at the same time. So it's like really, how can you cut through the noise? Send something that's punchy, send something that's just thought provoking and you know, just a genuine question. Start a conversation. And then any person that's good at selling knows once you have that initial in, you can weave your way through, start the conversation, move into a sales cycle, get people interested and yeah, you have to treat every channel differently. So it's really about creating a cohesive message that you can use across multiple, multiple different channels, but framing it in a way that's unique to each individual channel.

Danielle Messler [00:14:14]:
Yeah, I, we have Smarter network. Cass Bober, she's like a landing page expert and one of the tips that she's always stood out too. And it's, it's one of those things where it's like, I see how it happens as a marketer when you have like a million things going on is that the actual like ad that runs to the landing page, the messages aren't in sync. So obviously I'm going to click out of it. Cause I'm like, if I click on one thing, expecting it, but then I'm driven to this other link and I think obviously the more variables you add in, the more likely that is to happen because you're trying to get things done. So I think the pods is, is really smart and something that like even marketers can learn from here.

Alex Fine [00:14:53]:
Totally. It's the only way to have quality control. If you know, if you're not working together in tandem and everyone's working in a silo, you are going to have that disjointed messaging. So you have to work in a pod.

Danielle Messler [00:15:02]:
Yeah. So what are you seeing work in B2B right now specifically, like where would you invest? Obviously it's different.

Alex Fine [00:15:10]:
It depends on the vertical. Yeah. Within B2B. So like in B2B services we see ads work a lot better if you're. This is where the spam stuff by the way becomes a problem. B2B services, because services can be so all encompassing and you can sell to such a mass market, you have people that are sending millions and millions and millions of emails on behalf of their service. So I'll be honest, it does work. It's one of those games though where you send so many emails and then surely something's going to stick.

Alex Fine [00:15:35]:
That's it works. But for companies like that highly recommend ads, it depends on the services that you're actually in. Everything is bespoke. I mean it's not a one size fits all approach. You know, you have to have a bespoke account plan based on your icp, your value proposition, things like that. So I don't want to say one thing works particularly well for one segment. With B2B SaaS, we crush it with ads. But at the same time, like I said, we have some clients if we're able to get really granular on the icp, find relevance.

Alex Fine [00:16:01]:
I can use an example here. Email can crush it.

Danielle Messler [00:16:03]:
Yeah.

Alex Fine [00:16:04]:
And then LinkedIn in terms of efficiency, I mean, if you're really good at copywriting, you and I both know someone who's excellent at copywriting, and that stuff converts extremely well. Especially if you have a Strong presence on LinkedIn or using the right profiles, it can make a massive difference, I would say, in terms of efficiency, LinkedIn outreach is huge. Tools like Areach can make a massive difference in your ability to generate pipeline. The issue you run into with LinkedIn is a volume game or it's not a volume game. Right. You can only send maybe 20 messages in a day, something like that, to keep your account from being at risk of being blocked or banned. So with that said, it's very efficient, but you can't send a lot of volume. So you need to be extremely targeted.

Alex Fine [00:16:42]:
Email is super efficient. You just have to do it the right way. You have to be able to personalize and stay relevant and have a very tight list. And then ads. Oh, my God, ads are a cheat code. So you've seen that firsthand.

Danielle Messler [00:16:54]:
Yeah.

Alex Fine [00:16:54]:
I'll give you an example of email, because email is one of those things everyone says outbounds, that's all over LinkedIn. Yeah, we have the data in front of us every day. We get slack notifications every day that just disprove that. But anyways, we see it all the time. So, like, I'll give you an example. And this is one of my favorite clients, actually an old friend of ours too, but they sell a product. It is a SaaS company that helps you fight return fraud. So people who are basically weaponizing return fraud on telegram groups or subreddits, like these little niche communities where people are just doing bad stuff so they stop bad actors, they catch this stuff and then they use that as their messaging, right? It's like, hey, we found your company, your exact name, in a return fraud group where they're weaponizing return fraud and just committing fraud on you guys, right? And we say we have screenshots because we do.

Alex Fine [00:17:39]:
And people are like, oh my God, send the screenshot over. What's happening? We've been noticing an uptick in return fraud or returns that show up. And then people send the box with a rock in the, in the box. So, so they say send it, we send it, Boom, there's the end. It's like, thank you so much. You just helped me figure out exactly where the source of this is coming from. How do you guys help us prevent it? You know, stuff like that works extremely well on the outbound side. And you're actually doing a major service for these, these companies, they're super happy because not only did you identify a problem through whatever web scraping you're doing, but you give us a solution to fix it too.

Alex Fine [00:18:09]:
So it's action oriented problem solving. So that makes a huge difference for clients like that. And like I said, they have a high ACV and they're booking anywhere from four to seven leads a week on average. But recently it's been more like three or four a day.

Danielle Messler [00:18:20]:
Yeah, well, because you're. I think the important thing is, is like you're actually offering them, like you said, value. Like, hey, you guys showed up here, you might want to check this out, flag this. And especially if that's actually corresponding to what they're seeing. So that's just like really great targeting and that's what I mean.

Alex Fine [00:18:39]:
Yeah, exactly.

Danielle Messler [00:18:40]:
Yeah. Personalization. Not in the sense of like, oh, your first name is in the subject line and we know that you're the head of risk at whatever B2B, your B2C E commerce company. And it's so generic. And that's something I want to talk about is actual personalization and how you guys go about doing that. And obviously it's different from client to client and ICP to icp, but is there like a, a framework or process you follow to get genuine personalization that goes beyond like first name, job title, the college you went to, and the mascot?

Alex Fine [00:19:14]:
Yep, totally. And it comes from very, very deep research and it's agentic research. It's not like us going and researching every single individual prospect. Right. It's like we build these workflows that can identify whatever is relevant to that individual Persona based on their job title, based on research we've done on their company, things like that. To find those variables, like, I'll use the example of the same company because I have permission to use them. So I'll use them as.

Danielle Messler [00:19:35]:
No, it's a good example. It's interesting.

Alex Fine [00:19:36]:
Yeah. And it's one of those things too. When we first took them on, I knew we'd be able to generate leads for them, but I didn't know the velocity in which we'd be able to generate leads for them. And I've been very, very pleasantly surprised because like I said, they're also old friends. So you know, I'm thinking the whole time like, I don't want to lose my friend if this doesn't work out for them. And I know this is a tough issue to crack into, but no, we've been very pleasantly surprised. But what we're doing for them in terms of personalization, so what we'll do is they sell to e commerce retailers, right? So think big companies, like big, big companies like I can't name drop their companies, but name brands that you know and love, right?

Danielle Messler [00:20:07]:
Yeah.

Alex Fine [00:20:08]:
If you're sending emails to these people, what you can do is you can identify, you know, what an average sale price might be based on the items on their website, based on what's at the top of the page, based on what's their sponsoring, things like that. So let's say I'll use the, the reference of pickleball paddles, right? Pickleball paddle, I don't know, bucks, 200 bucks on average. Let's say based on the research that you've done, you think they probably sell 100,000 pickleball paddles a year, something like that. Out of those, we know about 2% of those are returned based on fraudulent returns or something like that. Someone says use it for a month and they say, I don't want this anymore. I'm going to return and get all my money back. Right. Totally against the return policies, but they're going to do it anyways.

Alex Fine [00:20:48]:
This company is going to have excellent customer service. They're going to take care of them. So what we do is we say, okay, looks like your primary product that you're selling is this. Looks like you sell on average about a hundred thousand of them. If 2% of those are being returned fraud fraudulently, you're missing out on X number of dollars annually in return fraud. That's the level of personalization that we'll do. By the way, here's how I calculated that number. Let me know if I'm off something like that.

Alex Fine [00:21:13]:
The reason I'm reaching out is because we've been seeing company or telegram groups weaponizing your return policies and committing fraud against you guys. Not sure if you've seen this internally, if you've seen a spike recently. By the way, more than happy to send a screenshot of the exact color green group. We found this in something like that. And then people are like, oh my. Well, your numbers Sometimes, like, your numbers are great. How did. I can't believe you calculated this.

Alex Fine [00:21:34]:
And sometimes they say you're actually way off. But I appreciate you letting us know about the Telegram group. You sent us a screenshot. They review it. They're like, oh, my God, you weren't kidding. This is crazy. And then they're like, can we book you guys? Help us solve this problem. So that's the level of personalization that we'll actually end up doing for clients like that.

Danielle Messler [00:21:48]:
Yeah. And you're using. So you said you use, like, agentic. That's a new word, isn't it? Agentic research.

Alex Fine [00:21:54]:
Yeah, it's a fancy one. I hope I'm saying it right, but.

Danielle Messler [00:21:58]:
I've never said it before.

Alex Fine [00:21:59]:
So it's basically what we do is we build AI agents in clay and we just have them run. We have multiple different steps in every single clay table that we do. So, like, find this, find this, find, find this. Once you found that, extrapolate the information from this one, this one, this one, and come up with this formula. So something like that. And we do it. Like I said, it's totally bespoke, depending on the client that we're working with. But in that case, like, that's the method that we're using, and it's working so well because people are like.

Alex Fine [00:22:26]:
Like I said, they're either. Your numbers are actually pretty close. I'm impressed that you're able to calculate that. Please send the Telegram group. Let us know how you can help. Or they say, your numbers are way off. But we're interested regardless because this is a problem that we're seeing, you know, something like that. But the fact that we were able to, one, find these companies in some sort of fraud groups or something like that to show that we're trying to do the research to actually calculate the amount of money that they could be saving if they can fix this problem, something like that.

Alex Fine [00:22:52]:
They just appreciate the level of research that actually went into that, whether it's us doing it or not. They're like, wow, whatever you did is very sophisticated, and you're actually solving a genuine problem that needs to be solved immediately, like, yesterday. So, yeah, that's what's working for us.

Danielle Messler [00:23:05]:
Yeah. That's the difference between. Hey, Danielle, saw you went to Northeastern. Go Huskies.

Alex Fine [00:23:11]:
Yeah.

Danielle Messler [00:23:11]:
You're also head of marketing. Do you care about SEO and.

Alex Fine [00:23:16]:
No, I don't give a shit about SEO. I just work in marketing, you know?

Danielle Messler [00:23:20]:
Yeah, exactly.

Alex Fine [00:23:21]:
Yeah, it's. Yeah.

Danielle Messler [00:23:24]:
So I think let's shift to ads. For a second because we've worked together and specifically LinkedIn ads. What are you seeing people making mistakes with right now? Like blowing money on when you get a new client? What do you look at? What can marketers avoid?

Alex Fine [00:23:41]:
To be honest with you, Ali is the right guy, as you know, to talk about the ads. But yeah, I mean, we see accounts set up completely improperly almost every single time we audit them and from well known agencies and stuff like that, people will come to us and say, hey, I've been working with X, Y and Z and we're not getting results. We got results for the first week and then they completely died off and we never saw results again. And we're not sure what's happening, but we're spending 60k a month on our paid media spend and we're not getting anything back for it. Can you take a look and just let us know if we're, if we're doing anything wrong? We'll dive into these accounts, we'll audit them, it'll be clear as day what's actually happening. And then from there you can make a ton of optimizations, but there's just settings that people are using wrong. Like I said, Ali is really the person to ask. I don't want to speak, speak about ads and say things that I don't know all the answers to.

Alex Fine [00:24:23]:
My understanding is more high level than Ali's for sure. Ali manages our paid media team. But yeah, we see ad accounts completely improperly set up all the time when we audit them across paid search too. It's not only paid social.

Danielle Messler [00:24:35]:
Yeah, that's scary. Especially if you have someone in there who you assume has expertise setting it up and then you realize it's all set up wrong. What I mean, okay, I'll ask Ali this next time we chat. Um, so something cool. I want to talk about like your background a little bit. You obviously. Well, we've talked a little bit about you starting as, you know, a personal trainer and helping set up meal plans for the moms in your high school group. But then you went on as like an account executive.

Danielle Messler [00:25:03]:
Right. So let's talk a little bit about your experience there, like working with marketing. Tell me about that.

Alex Fine [00:25:10]:
Well, I have a very unique background for where I am today. It's like very untraditional. For sure. So I started off working at Procter and Gamble selling soap, tampons, toothpaste, you name it. Like funny things, right? The retailers. Yeah, Selling to Walmart, to Target, and I was like 23 years old selling these $100 million, contracts, the biggest retailers in the world.

Danielle Messler [00:25:30]:
Yeah.

Alex Fine [00:25:30]:
And thinking that was completely normal. And then it took a step back and I realized, oh, my God, this is like just a masterful marketing company. They're like, they're a product company. Right. They sell everything. They sell, really everything you can ever think of. Everything that's in your house is probably a P and G product.

Danielle Messler [00:25:44]:
Yeah. Have you ever seen one of those charts where it's like every product you ever known and then it's down to like three companies that make all of it?

Alex Fine [00:25:51]:
P and G, Johnson and Johnson. Like, yeah, totally. That's how World works. But they're a master in marketing. That's what they do. So I saw all the ways that they, you know, created shelf schematics, the way that they advertised everything like that. And it got me really fascinated with marketing because at the end of the day, I was building marketing plans. So I was in charge of the home care business at Target in my last role.

Alex Fine [00:26:11]:
So I was building shelf schematics at Target for Swiffer. So, like, if you were walking into the Swiffer aisle at a Target and you see Swiffer Dusters, Swiffer, Wetchat, Green Swiffer, they're all designed in a very unique way. The whole point is to play with your shopper psychology. Right. It's like, okay, the first thing you're going to see is like what you recognize as Swiffer. The green Swiffer. That's what everyone knows. They think the green Swiffer.

Alex Fine [00:26:33]:
So that's the very first thing that you're going to see on the outside of the aisle. Right.

Danielle Messler [00:26:36]:
I can picture it so clearly in my head right now.

Alex Fine [00:26:39]:
Yeah, exactly. You know it like the back of your hand. Exactly. That's the way it works. But you see the green and then from there you go in, then you see the purple, you see the Swiffer wet jet, then you see the Swiffer Duster as you go further and they're color blocked.

Danielle Messler [00:26:50]:
The yellow.

Alex Fine [00:26:51]:
Yeah. You know exactly where to find them. Right. And then you even have like the way that you're pricing things so you'll have the most expensive products that you want people to sell. Not necessarily the most expensive, the most high velocity moving products at eye level. You're short, so maybe not your eye level, but like.

Danielle Messler [00:27:05]:
Not my eye level.

Alex Fine [00:27:06]:
Yeah, for most people's eye level. Right.

Danielle Messler [00:27:08]:
I have to get someone to reach the Swiffer, the green Swiffer from the shelf.

Alex Fine [00:27:13]:
But it's like you get there and you See like what they call, so they have like a base tier, a mid tier, some, some of the categories they have like a mid to high tier and then they have like the really high tier products, right? So what you're going to see is like that middle, high tier, mostly at eye level. So you're trained. Like the very first thing you're going to see is that. And then what you do is as you go lower, you have the slightly cheaper products on the bottom shelf you have the cheapest and at the top you have the highest. But what it does is it trains your shopper psychology to say, okay, this one's pretty expensive, I want that one. But I don't want to spend that much money. I don't want to get the cheap one because I don't want to cheap out. I want good quality.

Alex Fine [00:27:44]:
So I'm going to get something in the middle and you end up getting pretty much high level. So I was doing that for two years in my last role at P and G. And I just thought about the fact that like marketing is really just understanding human beings. That's all it is. And I became fascinated with it. And I went into sales in tech. I was selling tax technology software, which is boring as hell, but it's super important. Passion, proof, you know, everyone needs it.

Alex Fine [00:28:07]:
And I learned really a lot about technology and you know, how to sell technology and how buyer psychology works in tech. And then from there I was like, okay, I love marketing. I built all of these skills and sales over the last seven years. Why don't we blend these two things and Ali and I, so I think you know this about us. But Ali and I were like best friends in high school. We've known each other 15 years. We were roommates in college. Like Ali is like family.

Alex Fine [00:28:30]:
Like we've been.

Danielle Messler [00:28:31]:
I love it.

Alex Fine [00:28:32]:
Yeah, we've been, we've been super close for literally 15 years. So we tried to start a little agency when we were both working at jobs. Ali was at Metadata, I was at P and G. And we were like, okay, let's start an agency and see where it goes. But we were both working full time jobs couldn't actually make anything work. If you don't actually commit, nothing ever happens. Building a business is the hardest thing I've ever done in my life, but the most rewarding. But it requires a ton of time and commitment.

Alex Fine [00:28:53]:
So having a side hustle just never worked out. So we went and did our own things for another, call it two years working jobs. And then the opportunity arose for us to Try again and commit full time. I closed a really big deal at my previous company. I had this big commission check. So I had the Runway. Ali had a good situation and we just figured it was a perfect time to start. We have the freedom right now to actually start.

Alex Fine [00:29:13]:
Take a pay cut temporarily and see what we can do. Here we are. That's the story.

Danielle Messler [00:29:17]:
I love it. Yeah, I love it.

Alex Fine [00:29:18]:
So I'm selling soap too.

Danielle Messler [00:29:21]:
Yeah, I love it. I love that you said, you know, you sold tax software. I feel like everyone has to sell something like boring but essential. It's like the biggest challenge. But if you can learn in that environment the skills you pick up. Like my first job marketing in Tech and SaaS. I was at ProfitWell and we were selling like retention software and like pricing software to help you optimize your pricing and making that like sexy and desirable.

Alex Fine [00:29:52]:
Yeah.

Danielle Messler [00:29:52]:
Is a big challenge.

Alex Fine [00:29:54]:
It's a totally different style of selling. Right. It's a gift to selling the value of it versus the sexiness of it. With tax technology in particular, it's like, it's almost fear based. It's like this is what's going to happen if you get your taxes wrong and the IRS comes for you because you know, you're dealing with companies like Facebook, like Google, these massive companies. You get a. There's a tax there, it's going to cost you hundreds of millions of dollars. Right? Yeah.

Danielle Messler [00:30:14]:
Not to mention the bad press.

Alex Fine [00:30:15]:
Exactly. So you're. Most companies come inbound in tax technology, but the biggest deals are the ones that come outbound. So like, I can't tell you the name of this company, but there was a gigantic company that does. They do 7 million transactions in Malaysia alone. And they were very interested in Malaysia. That was the catalyst because Malaysia had this new e invoicing mandate where they were basically saying like, hey, we don't know how the heck we're going to solve this problem with Malaysia in particular. By the way, we have problems in 14 other countries as well.

Alex Fine [00:30:42]:
Can you please help us? And it was like, okay, Malaysia is the catalyst. Let's solve Malaysia first and then from Malaysia we'll expand. And that ended up being that deal that allowed me to basically have the freedom and that came through outbound. I met, I sent them a message about Malaysia. They were like, oh my God, we have this problem in Malaysia. And I was like, well, I think everyone's going to have this problem in Malaysia. So I figured you guys reached out to them, built the contacts there and expanded the shit out of it. But it's like, it's not even necessarily about making it sexy.

Alex Fine [00:31:07]:
It's about providing the value that they're going to have peace of mind. They're going to be able to sleep at night knowing they're covered in Malaysia and 14 other countries.

Danielle Messler [00:31:14]:
Yeah. Again, smart targeting because it's like relevant. You knew they were struggling with it. You knew there was probably a pretty good chance that they needed to figure this out sooner rather than later and was at the right time.

Alex Fine [00:31:25]:
Totally. And the company was at. Was first to market with a solution for the Malaysian E invoicing mandate. So it's like, okay, no one else has it. Let's talk, you know?

Danielle Messler [00:31:32]:
Yeah. So when you started kind of, what do you think the top skills from sales are that marketers should learn? Because I feel like you have a really good mix of both and having that sales experience and then also going deep into like learning marketing. And I think it's something especially in B2B. Like, I would like to learn more sales skills because I'm like a content gal. So what are the things that you, you found most valuable?

Alex Fine [00:31:56]:
Persona based pain. It's like understanding exactly what affects that individual person. Not the company, the individual person. At the end of the day, human beings are selfish. They care about themselves first. It's just the way that people are. Right. And it's like whether you love it or hate it, that's the reality.

Alex Fine [00:32:10]:
So you have to understand how to relate to that individual person. What's keeping that person up at night if that person, like, for example, use tax technology. If the director of tax at a giant corporation says, oh my God, I might be in the news personally if I get this wrong, it's like, solve for that problem, you know, and then be very specific with your messaging, with your targeting. If you're doing ABM campaigns, it's even easier. But there's a ton of stuff you can do to just make sure they're relevant to that exact Persona versus generalizing a message across a company. Hey, Google looks like you might struggle with this. It's like, no, hey, danielle@exit5 looks like you might struggle with this. In particular, I'm sure this is affecting the way you sleep at night.

Alex Fine [00:32:47]:
And then you're like, actually, yeah, it is. So let's talk. You know. So I think that's the key that a lot of marketers, marketers try to blanket things. They're like, okay, I'm going to create this generalized campaign that I think is going to be really efficient for me, but it's like, you have to constantly be testing, you have to constantly be segmenting, and you have to be able to listen, to hear people, understand people, and actively listen to people. I'm talking a lot on this because it's a podcast, but it's like, if you get in a sales call with me, I do. Fireflies tells me I do about 20% of the talking in a call. You know, it's like, the point is you want to hear people understand their pain, understand what keeps them up at night, solve for that.

Danielle Messler [00:33:20]:
Yeah, that's a good point. Especially the, like, 20% talking. Actually, the newsletter that just went out today, it was about B2B copy, and one of the tips was like, you need to listen way more than you think you do. Let them talk. Find those pain points, those key phrases, and that's your gold.

Alex Fine [00:33:36]:
Totally. I got in trouble so many times growing up, and people would tell. My teachers would always tell me, you have two ears and one mouth, so you should listen more and talk less. And I just never forgot it. It stuck with me forever.

Danielle Messler [00:33:47]:
But I love that. I feel like they tell that to every little kid that has some form of add, too.

Alex Fine [00:33:53]:
The ADHD was out of control. It would never shut up.

Danielle Messler [00:33:55]:
So, same. Except I was more of the daydreamy kind. No, but this was super awesome. Where can people find you? Obviously on LinkedIn. Alex. Fine. Exactly how it sounds. You guys are at understory.

Danielle Messler [00:34:08]:
And, yeah, you're also going to be a guest on our upcoming event on B2B emails in the cold and outbound section. So I'm super excited about that.

Alex Fine [00:34:17]:
Yep. Yeah, the best place to find me is definitely LinkedIn. I don't have any other socials. I don't exist anywhere. And yeah, LinkedIn, hopefully YouTube in the near future, but for now, just LinkedIn.

Danielle Messler [00:34:28]:
Awesome. Well, we'll keep an eye out for LinkedIn. And thanks for stopping by and sharing your knowledge.

Alex Fine [00:34:33]:
Thanks for having me.

Dave Gerhardt [00:34:38]:
Hey, thanks for listening to this podcast. If you like this episode. You know what? I'm not even gonna ask you to subscribe and leave a review, because I don't really care about that. I have something better for. For you. So we've built the number one private community for B2B marketers at Exit Five. And you can go and check that out. Instead of leaving a rating or review, go check it out right now on our website, exitfive.com our mission at Exit Five is to help you grow your career in B2B marketing.

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And there's no better place to do that than with us at Exit Five. There's nearly 5,000 members now in our community. People are in there posting every day asking questions about things like like marketing, planning, ideas, inspiration, asking questions and getting feedback from your peers. Building your own network of marketers who are doing the same thing you are so you can have a peer group or maybe just venting about your boss when you need to get in there and get something off your chest. It's 100% free to join for seven days, so you can go and check it out risk free and then there's a small annual fee to pay if you want to become a member for the year. Go check it out. Learn more exitfive.com and I will see you over there in the community.

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