Resources for Buying and Selling Online Businesses

Turn Your Dead Email Lists Into Your Most Profitable Revenue Channel


Dean GinsbergDean Ginsberg is the Co-founder of Winback Pro, a brand that works with DTC brands to reactivate dormant email subscribers. Winback uses an AI-driven scoring, filtering, and deliverability stack to reactivate clients’ inactive emails and unlock thousands of dollars in incremental revenue from leads they’ve previously paid for.

Dean has over a decade of experience leading retention strategies for hyper-growth and enterprise companies, including Hello Fresh, Burger King, Teepublic, and Revel. He is also a Coinbase and Brave Health advisor and a WE ARE THE BOARD member. Before Winback, he was the Founder and CEO of Stacked Collective, a company that helped fast-growing companies build their first-party data strategies and transform their cross-channel marketing programs.

Here’s a glimpse of what you’ll learn:

  • [02:30] Dean Ginsberg shares his professional background
  • [04:19] The genesis of Winback Pro
  • [07:04] Building a successful email marketing program for dormant audiences
  • [10:16] Who is an ideal client for Winback Pro?
  • [11:20] Dean talks about email marketing strategies for ecommerce businesses
  • [16:11] The Winback Pro business model

In this episode…

Email marketing is a highly effective and versatile digital marketing strategy that enables businesses to connect directly with their customers, cultivate trust, and establish long-term relationships. However, executing successful email marketing campaigns requires expertise that many brands may not possess.

Whether you are a small business owner or a marketing professional, Dean Ginsberg, an experienced email marketer, affirms that email marketing can aid you in reaching your target audience and achieving your marketing objectives. While several businesses may have a clean, segmented email list with subscribers who have opted in to receive their messages, only a few of these subscribers may convert into paying customers. To address this issue, Ginsberg shares his journey of building an email marketing firm specializing in reactivating dormant emails through advanced filtering and deploying a proven playbook to avoid spam traps. This approach enables businesses to generate incremental revenue from their previously unengaged audiences.

In this episode of the Quiet Light Podcast, Pat Yates sits down with Dean Ginsberg, Co-founder of Winback Pro, to discuss how businesses can reactivate their dormant emails. Dean shares his professional background, the genesis of Winback Pro, building a successful email marketing program for dormant audiences, and email marketing strategies for ecommerce businesses.

Resources mentioned in this episode:

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Episode Transcript

Intro  0:07

Hey folks, it’s the Quiet Light Podcast where we share relentlessly honest insights, actionable tips, and entrepreneurial stories that will help founders identify and reach their goals.

Pat Yates  0:32

Hello, and welcome to the Quiet Light Podcast. Again, I’m Pat Yates. Today we have a great conversation if you like email marketing, and you really want to figure out how to juice that up, we’re going to talk to Dean Ginsberg with Winback Pro, and they concentrate on taking care, incremental value of your email, not just the actual email itself, they’re trying to revive your email list. So if you have 150,000 people, and only 20,000 of them done anything in the last year and a half, you have 130,000 leads, they want to try to find a button that will make these people work with that, they talk a little bit about the dead email, they have contingency based pricing, they have a lot of opportunity to be able to help you with an area that you’re probably not doing as well as you would really want to. So I’m excited to talk to Dean about this. And again, if you have questions about any of these vendors that we talked to, you can always give me an email to [email protected]. If you have questions about your business thinking about selling it, then obviously we’re here to help but that too. Today’s conversation should help you though, if you’re a direct ecommerce marketer and you’d like to concentrate on your email list, here may be a way for you to revive some of those people that may not be active. I think Dean’s got a lot of knowledge with So I’m anxious to talk to him. Let’s get right to it. Dean. Welcome to the Quiet Light Podcast today. I’m excited to have you here.

Dean Ginsberg  1:49

Great to be here. Thanks Pat.

Pat Yates  1:51

Yeah, it’s great. I know. We were just talking. You’re up in Brooklyn and New York. And are you like a sports fan up there? You Yankees Giants or Jets? What do we got?

Dean Ginsberg  2:00

I grew up a big sports fan. And it’s dropped off since then. But I was a Big Giants and Yankees fan.

Pat Yates  2:07

That’s probably kind of required there. Right? The Jets had to be a little bit better for you to be able to do that anyway.

Dean Ginsberg  2:11

Yeah, totally. I mean, I go to any football game. Yeah.

Pat Yates  2:14

I know. I know. You have a business that we’re going to talk about email and how people can utilize that channel. But I always love for my listeners to hear a little bit more about your background. And you know, where you started in business, maybe your schooling, things like that. Tell us all about it. We’re anxious to hear.

Dean Ginsberg  2:30

Yeah, I have a crazy background. So I think, oh my god, I could go back pretty far. My first business I started when I was 14. I grew up in New York City. And I used to throw dance parties for high school kids in lofts that I found on Craigslist, are insane. So I built that up, we actually ended up building it to like having five major events across the city every year. And then we donate half the money to charity. So that was kind of my first foray into the business world, which is a little illegal, a lot of fun. But kind of a school of hard knocks there. And then when I was in college, I started a coach bus transportation service to bring college students home for school break. And that was like when I started building, like really selling tickets online, got me into ecommerce. But the first tickets were sold, like I printed it from Microsoft Word and I signed each ticket and then sold them and like the quad. Yeah, and then I started a summer storage service for college students. And that’s really where I got, I learned, I kind of saw the impact of UX and conversion rate optimization. It was like the first storefront I built on Shopify. And I mean, what’s hilarious is like I spent about $30,000 money that I made from the previous businesses and don’t think that company out. And if I had just taken that $30,000 and bought Shopify stock in 2010, I would be in a much different place in my life.

Pat Yates  4:05

You would be in a Chapter at this point, you wouldn’t have to worry about it. That’s a great point. Yeah. So what other things, you had to have something that you really enjoyed about email before you started what would that have been what gave you the itch?

Dean Ginsberg  4:19

I ended up being the first hire at a company called Daybreaker. And Daybreaker throws morning dance parties around the world. And when I was on that team, just in the course of two years, we expanded to 28 cities it was all Bootstrap. One of the founders was the founder of General Assembly. And my actual title was founder’s apprentice to Matthew Brymer, who was one of the founders of GA and I got to be like, get kind of integrated into the GA team. I got to be into it. We did a lot of sponsorships. So I worked a lot with like Nike, Samsung, the NFL and I was at a pretty young age called in as a contributor to these, like very advanced marketing teams, and Daybreaker was built with no paid marketing. So it’s only email, word of mouth and the events became pretty viral — a lot of press. And in a short period of time, we built up a pretty sizable email list and the whole company was built around email. So getting good at marketing for that was about getting like, good about a branding, getting good about events, but really about like, what does it mean to build community through email. And in the process of doing that, I was kind of looking at some of these, like bigger companies, and their email program and what was possible and the way they thought about it, and I was like, we’re doing stuff that they’re not doing, and we’re moving faster than they’re moving. So I ended up building a consulting firm that did digital transformations for mostly private equity companies. So the PE firm would acquire a brand, or usually a legacy brand, and then bring us in as the execution partner to revamp their whole ecommerce infrastructure. And my job was particularly around conversion rate optimization, and email, omni-channel and data infrastructure. And over time, I was just like, I’d love the data infrastructure and the email side. So I ended up building a different Consulting Group just focused on that. So yeah, Winback is like, a very long time coming of actually starting brand side, very broad, narrowing in and then narrowing and again and again.

Pat Yates  6:33

It’s really funny, when you look at Winback Pro, something struck me when I hit the first page, it says, join the waitlist. You talked about something that makes you think that there is some incredible results, which I’m sure they are. So I want to dive into that a little bit. So you did all the background stuff and you went to Winback Pro. And email is not the easiest thing for a lot of people to pull off. And some people think it’s an old-school model of being able to market but clearly not tell us about the philosophy behind Winback. You don’t have to get into details yet. But what made you decide this is the pain point that a lot of people have that I can fix?

Dean Ginsberg  7:04

Yeah. So when I was running, my previous firm was called Stacked. And I was oftentimes brought in, at the sea level or by the board to revamp the lifecycle program. And then on a day to day, I’m working with the retention team. And pretty consistently, I’d run into this conversation where the CEO or the board is like, we need a revenue bomb. Why don’t we just email everybody on the list? Which, if you’re on the retention side, you’re just like, please don’t do that. There’s this thing called deliverability. And it will mess up our whole program. And also like, stay out of my sandbox, right? And so I was often the liaison in those conversations to advocate for the retention team, while also showing the company that you can drive lift without performing bad practices that are eventually going to hurt the program. Sure. And but really, when I looked at it, I was like, to be honest, like, I just keep saying this thing like best practices, we should do this. And I’m like one of the most advanced people in the space like parsing crazy rates. And to be honest, when it comes to like deliverability. I was more like echoing sound bites than I deeply understood the first principles of what it meant to like, what was the best strategy for the doorman audience, right. And that was where this all kind of came about, I went through this like six months, putting my head down, and really thinking about what would it look like to build a program specifically around doorman audiences, that would both win them back at a higher rate, but also reduce the risk and their targeting. So that when you’re having the business conversation with the C suite, and the board, it’s not just a, we follow best practices. And this is what we’re told to do. It’s like we deeply understand this topic, we understand where to take risks, and where not to take risks. And because of that, we can drive actual lift across the program while improving deliverability. So it was really just a process of like, narrowing, narrowing, narrowing, and recognizing that this is not a nice space. This is, for some brands, it’s 80% of their list is considered dormant. And these emails just sit there. And I’ve always been a big advocate for doing something with what you already have, as opposed to paying money to get new things. So yeah, we built this program. To be honest, when I started, I didn’t know if it would work. And pretty quickly the results started coming through and it’s been pretty amazing.

Pat Yates  9:33

I would imagine it is because as an ecomm entrepreneur myself, you know, you look at your mailing list as one thing, it’s an ability to have a touch point. And you can monetize from you can look at the monetization from a top-level but sometimes you don’t see those dead emails that are around for three or four years that you know and sometimes you walk past that because if you get good results against what the normal metrics are, you may not think anything of it but there’s so many things out there that you can gain. Tell us a little bit about I know that you had how you work, there were four real steps. And I’ll mention them because I may not be an order evaluation, filtering playbook and incremental revenue. So tell us a little bit if you’re coming in and someone’s evaluating with you what the criteria is, they have to be a certain size, is there a certain amount of email addresses you need?

Dean Ginsberg  10:16

Yeah, we’ve been sort of playing around with that, as this company is pretty young. So now we’re pretty clear. Like, if the company is doing over $20 million in ecommerce revenue, they’re likely going to be a good fit. But one of the things we do even before we sign is we run an estimate of how much list we can generate for the program. And then we make a decision if that’s going to be worth our time. And if it’s worth the brand’s time, sure, because we charge just a percentage of the incremental revenue that we generate from the dormant audience. So we take on the risk of can we drive revenue here? And so it’s up to us to do that upfront work to figure out if this is going to be worth everybody’s time?

Pat Yates  11:00

So in that process, tell us a little bit of how it would work I mean, you don’t have to give any trade secrets. But if someone comes in and has you analyze that, you say, yes, let’s go, is there another platform, let’s say they’re using MailChimp, or Klavio or something like that? How do you end up working it from the point after you analyze it to where you’re actually getting in there and doing the work?

Dean Ginsberg  11:20

So we were up in live within 10 business days of the kickoff call, we build all the flows, we do all the creative, we build them all inside of bear ESP. We also set up a custom dashboard that measures incremental lift by pulling from their ecommerce platform and from their ESP. And then we have a number of deliverability tools that we set up and the team manages. So the first thing that we do with a brand is we run a deliverability audit. Like what is the baseline structure of the account? Are there things that can be cleaned up, even before we start targeting this riskier audience? Right, we build out all the copy and then all the copy that we leverage. We’ve tested this across all these different brands, and we’re constantly optimizing the general templates and then customizing it for the brand itself. Then we set all of that up and there ESP. We start to pulse users through. And we make adjustments and test as we’re as we’re going to improve the results. So the like, to be honest, it’s pretty heavy lift in terms of onboarding, like we’re not really a product, and we’re not really an agency or like a product lead service. But we’re really taking on the brunt of it, so that the team can focus on their active audiences. And then we’re only charging a percentage of the lift that we generate, if we’re successful.

Pat Yates  12:41

That’s amazing. So it doesn’t really matter what system they’re sending it out of you come in and you look at those, and is it just straight marketing? Is it that you guys have a philosophy of how you send these out? And what the marketing says, Is it tied to a discount? What usually moves the needle for people to be able to have some success with you?

Dean Ginsberg  12:57

Yeah, there’s two parts to it. One is you have to figure out which are the safe emails, and which ones are the toxic ones. Right. So when people are looking at a dormant audience, they’re typically taking a binary approach, right user has not engaged with email and X amount of days, do not email them, except for like Black Friday, and then they expand the audience definition. Right. And that is really a kind of the worst of both worlds, you’re like building up risk in the list. And then you’re actually just hitting them, you’re making a like sudden movement to hit them more rapidly, which signals to the inbox provider a number of red flags. So the first piece is when we’re building out an individual risk score for all of the emails in that audience, we’re saying, these emails are risky, these emails are less risky, these emails are good. Right? Then we’re filtering out the bad emails using a different range of filters, depending on the score. And I go into detail on that, because that’s really the critical factor. Right? It’s, if you can identify who is safe and who is not safe to email, you can expand your targetable segment significantly. And just expanding your targetable segment with content that is specifically tailored to that segment, you can drive lift. When you combine that with this, the templates that we know drive higher engagement, you’re also signaling to the inbox rather that these are emails that people want to receive. Right. So if the inbox providers like these are emails that people want to receive, not only do you get into the promotions, tab and spam, but there’s instances where you get into the primaries tab, and that’s where you see engagement really spike. And as long as your content structure and retargeting are such that you’re not getting high spam rates, and you’re staying well below their thresholds, then you’re actually driving a very positive program both for deliverability and for performance. So it’s really this two-pronged approach like, are we emailing people who are safe? Are we expanding the target-able audience in a safe way? And then are the emails that we’re driving, not only driving engagement and conversions, but are they signaling to the ISP that we are performing safe and like best practices when targeting this audience, and that begins a snowball effect. Right. And so the results are not like a one trick kind of like polls, it’s these two elements that play off of each other, and then the team that is constantly looking at data not just available in the ESP, but in our deliverability monitoring suite, to figure out, okay, this content is performing for this, this inbox provider, but not for this other one, we need to adjust the segments to kind of single out this one inbox rather than try different copy. So it’s very much like an active approach.

Pat Yates  14:12

And it also seems like, obviously, it’s an ongoing process that if people do this, it may not be one that changes that it might be two or three emails, it means that comment, is it something that happens quickly, or it has to happen over time?

Dean Ginsberg  16:11

It has happened over time. So the way that we do it is we build outflows, typically, the flows are like five to seven emails, and we’re building out flows for different sub-segments. But then once we can get somebody to engage, then we know, at a certain threshold that this person is not only a real email, meaning like they are not a spam trap, they’re not going to get flagged, but they’re back on the hook. And they can now be pulled back into the evergreen email program of the brand. Right. So the wind backflow itself actually drives lift, but the bigger impact is that it drives reengagement, and then once your users reengaged, we now know that we can pull them back into our regular cycle, expand our target audience without expanding our risk definitions.

Pat Yates  16:58

Okay, so are there things that verticals that work better for you? I mean, are the business services, ecomm services are there? Does it crossover? Are there things that are just super successful in your funnel?

Dean Ginsberg  17:10

So, we’re just focused on ecommerce brands. And that’s not to say that this strategy wouldn’t work in other verticals. But we’ve just found that we have a sweet spot on ecommerce. So when we’re sort of building out our scoring algorithm, when we’re building out our segments, where we’re building out our copy structure, all of that has been tested and proven across ecommerce brands. And so that’s what we’re really structured and focused on. Even within ecommerce, there’s many different types of brands, both in terms of how large they are, but also industries subscription versus one-time purchase, large average order values versus small average order values. We’re finding success pretty much across all those verticals. But we’re still testing and seeing if there’s an opportunity to narrow down even further.

Pat Yates  18:05

That’s a great way to go about it. And especially if it’s all ecommerce are there, I mean, you have some customers I saw in there, and I’ll throw a few out HelloFresh and Burger King, I was sort of surprised to see, like the Burger King. That’s incredibly interesting to me how they use lists like that to be able to do it, because you would think most is app-driven or digital. Are there examples of things that you could talk about them and give away trade secrets of things that have worked out in the past?

Dean Ginsberg  18:29

No, well, so to clarify on HelloFresh and Burger King, those were both clients of Stacked Collectives, my previous business on the website, that’s more referencing, like, these are companies that I’ve helped grow personally. But for Winback, we’re working with like, true classic, we’ve worked with rich wallets thesis. We work with Puma. We work with a number of like, very fast-growing ecommerce brands, and they’ve been passed around in those circles. And it’s really just been word of mouth. And in terms of like, the strategy is actually pretty consistent across all the brands, their copy may adjust the different tests that are running a very standard playbook of tests. And then the results from those tests actually dictate like, what direction do we go in?

Pat Yates  19:18

So when customers come in and work with you, or how do they get, I know they get feedback inside their system. Do you all do reporting that shows this lift and things like this and different segments of it? How do they get feedback other than just seeing the numbers come in?

Dean Ginsberg  19:32

So two pieces. One is like we measure lift against the whole the audience. So we take the audience and right before the first email send, we split out for some brands, it’s 50/50, some brands, it’s 90/10. But a portion of that audience is going we’re not going to email and then we measure the revenue generated by the control group, against the revenue generated by the target audience that we’re isolating just the impact of program, instead of, oh, they saw a Facebook ad they referred by our friend they had a random thought in the shower right so many things can drive a purchase for particularly the Stormont audience. measuring it against a holdout allows us to just isolate what is the impact of our program versus not running our program. We break that down for the brands not just in terms of what incremental revenue we drove. But also what is the percentage of the discounts that they use between the target and the holdout. What is the profit margin lift that we saw using a Cox report? So we really have this, like, these ethos in the company of build for business owners, and business owners don’t just want to see this is how much revenue you drove me, but this is how much profit you led, right? And then all the tests that we’re running are not just optimized for how can we grow revenue? It’s how can we drive whatever metric is most important to the brand? And for some, that’s like, we want to do very low offers, we want to just focus on profit margin. Right. Okay. Well, now we’re going to run a bunch of tests. And we’re going to see how these tests impacted both our profit margin and our discount amount relative to a holdout audience. So yeah, I mean, we spend a lot of time on analytics, because ultimately, if you’re not measuring it, it’s not really happening.

Pat Yates  21:22

Yeah, that’s definitely a good point, I see that everything is success-based. I mean, obviously, they can come in and talk to you during the evaluation process about what the cost is, and everything like that. They have all that laid out before they get the campaign running, correct?

Dean Ginsberg  21:35

Yeah, yeah. So part of it is we do an estimated list. And there’s sort of a high, medium-low, it’s a pretty — usually a wide range. But the way that we build that list is we look at what is the performance on that revenue per email basis across all the brands that we’re working with? And we cluster those by, who is this program performing like Astonishingly, well, for who is it performing, like pretty good, but not great, and who’s kind of in the middle. And so those numbers that we’re pulling for those estimates, we don’t know which type of brand they are until we start running the program, but we know they’re going to fall into one of those clusters. So they have a pretty good idea of the revenue that we’re going to drive. And we also have a good idea of the revenue we can drive and if it’s worth our time to focus on them or another brand.

Pat Yates  22:21

Yeah, I think that people have to understand that sometimes you just don’t in emails, one of those that I see a lot of people say, you know what, already have a list, people will be engaged, eventually, they’re gonna buy, and they just leave that thing dormant and get the results. I mean, is there a period of time that you’d have to sign a contract for a period of time to be able to start getting traction? Or do you guys go ad hoc over a period of time? How’s that structured?

Dean Ginsberg  22:43

So we do ad hoc. So yeah, there’s a 14-day out clause. Contracts are month to month, there’s a setup cost, which includes the deliverability audit, and then everything’s on performance after that. So that’s how it’s currently structured, there’s a chance that could change in the future. But right now, we’re focused on like, if we’re not driving lift, we don’t want your money.

Pat Yates  23:07

Yeah, I mean, that’s a great way to look at it. Because people know that, I mean, if you’re confident in what you do, and you’re charging a monthly fee, and then it’s a small transaction fee, that says a little bit, but with you putting all the money on that. So again, we’re with Dean Ginsberg with Dean, what other things would you want him to know about Winback? I hope everyone reach out? I mean, there are other things we haven’t talked about.

Dean Ginsberg  23:26

No, I mean, the program’s pretty straightforward. It’s like, you’re not doing anything with this audience. If you are, by definition, that’s not successful. We only charge a percentage of lift outside of the onboarding cost, which includes this deliverability audit, which I think every brand should do, because of some of the things we uncovered in that process. And so really, we structure it to be a no-brainer. And it’s just a question of if it’s the right fit, and we’re incentivized to tell you, if it’s going to be worth your time. So, we’re not going to waste anybody’s time, we’re not going to waste our time, we’re pretty ruthless with who we bring into the program and who we say, let’s circle back into the later date. But yeah, I mean, there’s for example, we were about to release a bunch of case studies. On average, we’re generating over $100,000 in incremental revenue for the brands that we’re working with within two to three months. That’s free money. That’s free money with a five you’re getting a 5x ROI on realized revenue. If you got that from a paid channel, you’d be ecstatic. So if it works for a brand it is we really built it to be a no-brainer and to be a big help to their program. And yeah, we’re just we’re growing slowly, steadily. We’re improving every day and yeah, man says a lot to build.

Pat Yates  24:56

Yeah, but I love what you’re doing. I think, you know, especially when people are doing stuff that success space, it just says I put my money where my mouth is a lot of people, we get a lot of noise out there about agencies and stuff that want big fees. And then they take a percentage or they don’t take a percentage because a big fee. And it’s great to see that you guys are out there doing anything. So if people wanted to reach out to you, Dean and talk about, how do they get in touch with you?

Dean Ginsberg  25:17

Yeah, I’m pretty active on LinkedIn. So just find me on LinkedIn Dean Ginsberg, search Winback. Also you they can go to our website, We’re actually in the process of building like revamping our new website. So depending on when this comes out, we might have the new site up. But yeah, if you sign up to the intake form, I’ll shoot you an email.

Pat Yates  25:17

That’s incredible. And plus, haven’t you see join the waitlist on there says a lot about your services. That means people are having to get in there pretty quickly to be able to work with you. I’d encourage everyone to reach out to Talk to Dean and those guys over there and see if they can help you with their email. Dean. I appreciate you being in the Quiet Light Podcast. Hey, buddy. It’s been awesome.

Dean Ginsberg  25:55

Yeah, thanks Pat, this has been great.

Outro  25:59

Today’s podcast was produced by Rise25 and the Quiet Light content team. If you have a suggestion for a future podcast, subject or guest, email us a [email protected]. Be sure to follow us on YouTube, Facebook, LinkedIn, Twitter and Instagram, and subscribe to the show wherever you get your podcasts. Thanks for listening. We’ll see you next week.

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