Numbers and Narratives

Achieving Relevancy and Trust in Marketing - w/ Drew Price

Sean Collins and Ibby Syed

Hey everyone - this week, we had an incredible conversation with Drew Price. We dove deep into career growth, the importance of personalization in marketing, and how to build trust with your customers. 

Drew shared insights on creating personalized weekly digests for Grammarly users, tackling the challenges of starting and scaling teams, and the vital role of leadership buy-in. Plus, he revealed his upcoming Maven course and inspiring newsletter on Substack. Don't miss this episode—it's packed with practical advice for lifecycle and retention marketers! Check it out now!

Drew: https://www.linkedin.com/in/drew-price-9081849/
Drew's Newsletter: https://scalingcrm.substack.com/


Speaker 1:

Hi, I'm Ibi Syed, I'm Sean Collins and this is Numbers and Narratives.

Speaker 2:

All right, Drew.

Speaker 3:

what did we talk about today, in the length of a so today we talked about the zero to one motion from a few angles. One is what should your focus points be, or deliverables be your output? Two should be what's the next steps on how to create more leverage for yourself, whether it's by hiring an agency, building out a team. And then three would be we got into KPIs what really matters, both objectively but also qualitatively.

Speaker 1:

All right, so I think the best place to start is Drew. Do you want to introduce yourself? Go over a bit of your background and then we'll jump in.

Speaker 3:

Sure, yeah, thanks guys for having me. So I'm Drew Price. I am a lifecycle and retention marketing advisor. I used to lead at programs lead programs at places like Grammarly that's kind of the biggest case study as well as agency side and publishing side as well. So about 18 years of experience in the email channel that's the deepest level of experience. But I was also Grammarly's first head of product marketing, did some brand identity work there in the early days, and so I can kind of flex into that stuff. But happy to talk about bottom of the funnel and you know whatever direction you guys want to go in.

Speaker 2:

As always, you know, drew is being a humble, humble person. Drew is one of the smartest people in the lifecycle and retention space. If you aren't already following him on LinkedIn, you know I know normally the CTA is at the end of the show, but follow Drew Price on LinkedIn, subscribe to his newsletter called Scaling CRM and just listen to everything he has to say, because he is wildly smart at how to do things for a company at scale, how to build a program to get a company to scale and how to build a team. Thank you, sean, appreciate that.

Speaker 1:

Yeah, links are in the show notes, but yeah, no, seconded. I didn't actually follow Drew until pretty recently and looking through all the things, it's all gold. I think it'd be fun to start off by asking where would you start? Like, what are most lifecycle teams doing wrong or not doing at all?

Speaker 3:

When you get into the validation phase and the build out phase whether it's zero to one or you're a little bit further along what oftentimes happens is people will build one journey at a time, one flow at a time, and usually focus on activation first and then kind of get into engagement and retention and then maybe, like a year or two later, get into win back or paid user retention and value realization and some, like things, get stacked as must haves versus nice to haves and my push and I actually teach this in a zero to one course is to diversify your investments from the get-go.

Speaker 3:

So what is a foundational layer for activation, engagement, retention, paid user retention, sentiment etc. This can be contextual to your unique business and offering, but define four or five or six lanes and make investments in all of those lanes across a longitudinal spectrum again, rather than just focusing on onboarding and activation or first purchase only. The point there is your opportunity cost right. The whole thing with lifecycle and bottom of the funnel really I guess everywhere in the funnel, but especially bottom of the funnel, is you're getting paid dividends when you invest in automation and you stand up programs and you start to hit baseline results. So you're going to have really, really huge gaps if you're only doing it one phase at a time.

Speaker 2:

I mean, I guess, from a just a time and effort perspective, right, like you're still sort of going down a checklist and saying like I'm going to knock this flow out. I'm going to knock this flow out, but it's rather than like trying to spend time testing and optimizing and really honed in on just one stage of the user journey, you're saying like, hey, make a change across the board so that it's a consistent experience. You're addressing all the parts of your funnel and then you'll see where the biggest gaps are as you look at those performances, and then you kind of go back and so it's. It's almost like rebuilding your full lifecycle approach completely, as opposed to optimizing one, one layer of the funnel, then going to the next one and that that's necessarily easy.

Speaker 3:

But that extra hustle at the get go in the build stage could really reap dividends for you and you'll just have increase. Your learnings will be 10x, your revenue potentially could be 10x, even if it's indirect revenue. But what happens a lot of times is lifecycle marketers go from build mode to maintenance mode and that's going to happen. If you just focus on activation for a few quarters you're going to go into maintenance mode, suffering just in the activation world and trying to make investments in the other worlds. It's going to be harder Oftentimes. You'll try to hire your way out of that situation. So I'm saying go into concepting and creative execution and production and implementation yeah, more broadly, before you enter that maintenance and optimization stage.

Speaker 2:

I wish we had had this conversation a year and a half ago, because I feel like you are speaking directly at me.

Speaker 3:

It's an aspirational vision, but I'd rather push people in that direction.

Speaker 2:

Why do you think that is such a common approach for teams? Or, I guess, like quagmire for teams?

Speaker 3:

This gets into something I'm passionate about, which is from a mentorship standpoint, but also from an education standpoint. The scope is massive for lifecycle people. So that's one of the issues is you're handling between day-to-day operations strategy. It's a very technical role, but it's also very creative and it's sometimes very reactive. You become a services function with a company Like there's just so many plates to spin and there's not a lot of blocking and tackling that we can do to advocate for ourselves. A lot of times these are things that need to be done and you have limited budget. So I'm just saying short answer is scope is just so massive that we end up getting kind of stuck in the weeds no matter what we do.

Speaker 2:

Yeah, I, I that one, especially you, saying there's there's so many plates to spin, but these are things that need to be done. Like that is certainly a problem I have felt, you know, at a bunch of jobs where you know you want to say like, hey, I need you to like back off a little bit so I can focus and knock this stuff out and like, well, so are we not going to do this thing? Like right, well, that you're right, that message does have to go out. We do have to fix this problem, we do have to do these things, and so it is really hard to kind of advocate for yourself out of this laundry list of tasks.

Speaker 2:

And yeah, I think you know one thing we talk about a lot is I think a lot of marketers and a lot of teams get stuck in sort of this checklist mentality where it's just running down a to-do list every day and it's not re-examining why you're doing anything or is there a smarter way to do this or a better way.

Speaker 2:

It's just sort of like I have to write a blog, I have to post two things on LinkedIn, I have to send out a weekly newsletter, and so it's less about. Well, why do you need to send out a weekly newsletter. Oh, your subscribers are going to like not open next week's because you didn't get one out this week. Is your business going to crash? Like, do you have to? What if you just made a better product and it was a bi-weekly newsletter?

Speaker 2:

And so I do think that there's something there of of we don't do a great job of looking up from the checklist sometimes and re-examining it, and I like that. Your, your focus here is really like okay, don't don't just get so mired in that idea of like the onboarding, the activation flow, but like remember that it's a journey and a whole experience and if you onboard someone successfully and the rest of the comms are a different design style, a different voice, have different messaging and offering, like it's not going to work anymore and it's going to fall off after they exit that onboarding flow or whatever, and so kind of doing global updates. I like that.

Speaker 1:

Yeah, going off of John's question, one of the things that I was pretty interested in is you know, it seems like you've started a lot of these teams before you've started and and scaled a bunch of them. With what you guys just said and just the huge lottery list of things that you have to do, how do you sort of prioritize and what hacks do you have for somebody who might be in your position at a smaller company rapidly growing and trying to figure out how they actually should prioritize that blocking and tackling Like what do you look at? How do you prioritize Any advice on that front? I know that was a really long question, by the way.

Speaker 3:

It's a great question.

Speaker 3:

Yeah, so I guess to clarify, in every case where I've been a lead building out Lifecycle or email, I ran basically as a party of one for years before building out the team, and the caveat was I did the agency model where I would start small with an agency relationship, usually to take over technical day-to-day operations, implementations, backend coding, but would be operating pretty lean with the agency model and what I think is really important is to focus on the relationship with your customers and to build towards that.

Speaker 3:

And you need someone with vision that is just ruthless about creating trust with your customers longitudinally and putting a lot of TLC into what they do. Like every single touch point feels important, feels like there's TLC, it's authentic to the brand, to the product. You need someone who acts like a founder that is running your lifecycle program before they try to hire their way out of it to alleviate those pain points. So I would say, like true ownership mindset is important, but also, in an ideal world, they can delegate and outsource some of those tasks so that they can focus more on the creative side. And when I say creative side, I don't just mean like design and copywriting, I just mean like the actual vision for the program strategy, perhaps, and then start to hire and put together a team that you think is going to understand that vision that you've created and be able to, like, live up to it.

Speaker 1:

That's a super super concise and good point. One question that I just thought of we have a lot of for people who are listening. I run a small software company. We work with a lot of lifecycle teams. One thing that I've been surprised by over the last year and a half is just how fluid those relationships seem to be. People are always bringing on different agencies for different things. Where do you think agencies what do I want to say thrive, and what things would you not give an agency?

Speaker 3:

It depends. But one thing I like to do is pick an agency that's full service but within a certain platform. Like there's specialists within Salesforce, marketing Cloud or Iterable or Brains or something along those lines and they understand, because all of them have their pros and cons from, like, a usability and backend and infrastructure standpoint. So I would say the P0 is the technical side of things. If you're hiring just a generalist, freelancer or agency, that's going, they're just going to like figure it out, like I would say that's a yellow to a red flag, that's not going to scale the way you think it's going. They're just going to like figure it out, like I would say that's a yellow to a red flag, that's not going to scale the way you think it's going to scale.

Speaker 3:

But hiring a agency that can be nimble and can grow with you as you grow and like keep the ROI super impressive, that's great and you don't necessarily need them for creative, but it's nice to know that they can do it. Or you know certain other areas Because I do not like. I like I like having only one email platform, for example, that does everything transactional and commercial, and I like only having one third party or you know, as few as possible. I do not like when things get decentralized.

Speaker 2:

That makes sense. I should say I spoke with the agency that you referred me to, drew, and we were talking the last time Drew and I hung out, he had suggested some agencies. I told him that my experience with an email agency was pretty poor recently, where they built it using all image slices. So no live text, no, no, anything. And that includes our footer, which has an unsubscribe button, five social media links, a link to the app store and the play store, and that was one single image. And I was like you just lost access to my email platform. Like you're, you're out, like just wait. They put it in one image. So if you click wait, what? What link did it go to? I mean, they just handed me this template and like you're, you're out like just wait, they put it in one image.

Speaker 1:

So if you click wait what? What link did it go to?

Speaker 2:

I mean, they just handed me this template and like you're good to go now, and I was like you. You just like this isn't, even Figma is more modules than this. Like what are we talking about? So I think you know I've been scared off of the agency side and Drew's been slowly coaxing me back to that there are trustworthy ones and so.

Speaker 2:

So I do think that that's important to to keep in mind, and I think that it was exactly what you, what you just mentioned, the agency that I'm saying you know I'm not going to publicly shame them with their name, but you know that terrible experience was a generalist agency who said, hey, we can help with paid ads, we can help with creative, we can help with email, we can help with all these things. At the time it was a team of one over here doing all acquisition and retention Right, and so I was like, wow, this is a great deal You're going to.

Speaker 3:

You guys are going to take so much off my plate and man that backfired yeah, too good to be true.

Speaker 1:

I guess, yeah, yeah, I guess it makes sense, right, like every single company that I seem to be seeing is trying to do more with less at this point, like part of that is, I don't know, like startups, small companies that whole thing is less sexy. But also, like you know, everyone's trying to use AI in some way, shape or form and it just gets to the point where, like, people are trying to do more with less and you end up just getting you know if your output is measured on the templates that you put out or the just getting things done you're.

Speaker 2:

Just the quality of work is the thing that's going to going to suffer there. Yeah, I mean, I think if you think about the business model, right, agency models are tough, and so to to double down on what Drew said, I would think about your, my, my learning from that is only work with agencies that not only are specialists on a in like a field, but like on a platform and possibly like in a niche. Right, like, if you can find an agency that has a really tight positioning and is comfortable saying, no, we don't do this, you probably found a decent partner there. If the agency const, every time you bring up a problem it's like oh, we can do that too. Now I think you're starting to enter some murky water where it's like yeah, like anybody can do it, but can you do it well enough that it's worth me paying you to do it and all that.

Speaker 3:

Yep, I think a lot of people underestimate just how complex email and multi-channel work is from a technical standpoint as well. So yeah, plus one on everything you said.

Speaker 2:

So we've got, we've got our team, we've got a founder, like Lifecycle leader, who's building a vision. He or she has an agency partner to help them execute, especially on some of the you know more, just like functional executionary tasks. We've worked across four to six major flows to make sure that we've got you know everything from onboarding and activation through engagement and win back and the upsell to you know paid if you're a freemium tool or whatever what's sort of the next wave of growing that team.

Speaker 3:

I'll just assume that kind of, before the agency was hired, that you validated some revenue attribution to the channel. We don't need to get into incrementality and types of testing and all of that kind of stuff, but let's just say that there's noticeable traction in ROI and then you bring on an agency. The next step, you know some of this depends on the complexity of your business. I think you all focus mostly on B2C, d2c, correct, like for this podcast. Your audience yeah, one would be what's the career, growth and goals of your fully badass lifecycle lead? Do they want to become more of a people manager? Do they want to grow the team? Do they want to flex into product marketing or something broader? Is there opportunity for them?

Speaker 3:

Maybe this is a direction you don't want to go in with the question, but that would be one item, for that is the direction you don't want to go in with the question, but that would be one item, for that'd be an input for consideration. The next would just be like how do we increase our investment? How do you five exit, how do you 10 exit and then go from there, cause I'll just assume like that would be probably the goal that you're going to work back from backwards from. Is you validated some traction, what? What is the? What are the missing pieces? And is that a team, internally perhaps? And then, is it like someone focused more on retention that could do really drill down on paid user retention, repeat purchases, that kind of thing? Uh, is it someone more on product engagement, if it's a sass product and you know not, for instance, it just depends on all of those variables.

Speaker 2:

That's cool and I like that. A lot of that consideration starts with with the person and the leader that you have.

Speaker 3:

That that's maybe like, if they are a badass and one of your want to kind of like the all stars of the marketing and growth team at your startup, then you want to. That's your best asset right there. How do you, how do you keep them at your company for another five years? I think that's definitely worth putting into the calculus.

Speaker 1:

So, Drew, one of the things that you mentioned on your LinkedIn page a couple of days ago that I was interested in is is talking about personalization testing towards different user groups in different ways. How do you get, how would, how would one get started on that, Like what's a what's a good place to get started?

Speaker 3:

Part of what I'm known for is Grammarly Insights, which is a flagship program at Grammarly. It's happens to be an email but it's more like product features or an extension of the core product experience with Grammarly and it's a personalized digest. So think of like a Spotify wrapped or a Fitbit type of an experience, but weekly, a weekly cadence, and it's got a lot going on in the back end so that it can be personalized and persona driven depending on whether you are a weekly active user, monthly active user, if you're a lapsed user, if you're a student, if you're a professional, if you're a consumer user, a Grammarly business user. We have different rules and a lot of different copy scenarios, different cross-sell or upsell scenarios and kind of going back to the why did this make sense and why does it make sense to invest in something like this? Because it is a large investment, it's a heavy lift and it's a program you maintain and you iterate on over the long haul is going back to what Grammarly is as a product and what the offerings are, so kind of like a matrix of like what is your product promise and what are your offerings? And for Grammarly it's a utility.

Speaker 3:

That we all do every day is type Most of us do every day across the globe. And so what do you do every day? You eat, sleep, you know, breathe, walk type. It's in that category.

Speaker 1:

I like that a lot Eat, sleep, breathe, walk type.

Speaker 3:

It's part of who we are as humans, and this was in 2014 when I joined Grammarly and already had the idea for this, and it's coming on the heels of Fitbit, kind of having that moment with the quantifiable self movement. But the why is a lot of people were coming into Grammarly to just solve a very short-term issue, not because they had identified Grammarly as a long-term fit for them, something I like I once I graduate from school and I no longer have a teacher explicitly grading my papers and using, you know, red ink and being penalized for it. I just assume if life's going the direction I'm going, I'm cool with whatever my writing output is, things are going all right and people don't kind of self-evaluate and have a high bar or didn't used to, at least in the mainstream and so the whole point of this weekly reinforcement was to help people self-identify that their output is important and there's room for improvement. And why does that matter? And you can get into brand and all these other things about, like, relationships matter, so I should care more about my delivery.

Speaker 3:

But now these days our message is more around, like at the enterprise and professional level, of limiting misunderstandings. Being more efficient and effective with your communication is better for your career, it's better for your organization, it's better for your mental health, it's better in a lot of ways. So personalization helps that message be served up more effectively. Be served up more effectively Because if we're not relevant, you're certainly not going to want to keep opening a weekly message from us, even if we do, you know, make it more of a living breathing organism.

Speaker 2:

So Actually that last bit, I think, is the one that most caught my kind of ear of. You know relevance and how important that is as personalization. I think so many people equate personalization with some sort of like your name and like how can I prove that I know this is you and only you're getting this email? So it's like hey, drew, since you logged in on Tuesday at 9.34 am, we've done this. You know, like you could have no dynamic fields in an email. If it's segmented down to just the right persona with the right message and context, that is actually a more valuable use of personalization than a one-off message that's purely liquid, just pulling in attributes. You know what I mean.

Speaker 3:

Yep, totally. Personalization, yeah, can speak to the behavior that you're responding to. It can speak to the human innately and or their relationship to the product. But yeah, relevancy is important because we're trying to build and keep trust over. This is also the tough bar for lifecycle retention. Folks is. The aspirational goal is to maintain and improve upon the trust that people have when they register and first try your product. Doing that over the course of years is a tall task so you really have to be dialed into the relevancy because once you get too irrelevant, people are going to stop trusting you and stop paying attention to what you're selling.

Speaker 1:

Love that a ton. How did you guys, out of curiosity, how did you get the sort of infrastructure set up to be able to do that Like? That sounds like a pretty difficult to be able to segment down by that much it sounds. It sounds like a pretty big job. What did the setup there look like?

Speaker 3:

Huge job. I'm going to actually do a little plug now. I've got a course on Maven going live in July and August. We're going to go deep on the Grammarly Insights case study For everyone listening. This was not planned. We're going to go deep on the Grammarly Insights case study For everyone listening. This was not planned. I'm just doing it.

Speaker 1:

because it felt right, we'll put it in the show notes Wonderful.

Speaker 3:

But the shorter answer is we had to build a custom data pipeline. Essentially, all that data comes through into what used to be Salesforce Marketing Cloud. Now we're on iterable in a batch on a weekly basis. Because it's a weekly program, we overwrite the table every week. There are a lot of steps that make that happen and there are a lot of things that can go wrong and have at times, but we maintain that data pipeline. And as Grammarly has grown in scale to, you know, a database of over well, over a hundred million users, those tables become more cumbersome and we keep having to solve for scale. So data pipeline is the short answer.

Speaker 1:

That's crazy. And is it like a data team that just pushes, that creates the table based off of what people are doing every week and then pushes it to iterable somehow?

Speaker 3:

Yeah, the ownership has switched a few times within engineering at Grammarly, but yeah, we'll just say data team and usually one main DRI, with a little bit of redundancy if they're on vacation or whatsoever or whatnot. But it's mostly automated at this point. It's just the monitoring is if a step fails, it needs to be restarted, or something along those lines.

Speaker 1:

Yeah, that's awesome. I feel like in the consumer world, this is like a pretty big choke point for a lot of people where they want to be able to do like really, really powerful things, and it's interesting to see some of the companies that have come out to like to be able to like help you push data in more simple ways, right, like Klaviyo and Interval, and these guys have like their own plugins to things like Shopify and whatever Like if you're, if you're like a CPG company, obviously, but yeah, pushing data from software is a weirdly tricky thing to do, so it's cool that you guys were able to do that.

Speaker 3:

What I think is the secret sauce to being able to really stand up something like this because it is a long-term, complex project is buy-in from leadership.

Speaker 3:

Luckily, when I joined Grammarly, it was a small team. I was in an office with the CEO, the two founders, I had a product, a team of maybe four or five marketers there's maybe a dozen to 15 of us and the head of product and one of the co-founders agreed with the vision and in fact it was seen as like a proof of concept of hey, we should have more insights and statistics in the Grammarly product on, like the core desktop experience. We can't prioritize that right now. We have too many other releases happening for the next few years, but we will support you making, like, building out the data pipeline. Why don't you start going into concepting and then, when you need the backend support, bring us in. If we're excited enough about the vision, we'll support you. A lot of startups kind of leave marketing teams, lifecycle teams to kind of fend for themselves and then you end up running into too many obstacles and you can't stand something like this up. So that is the secret sauce, I would say.

Speaker 1:

Yeah, that's really really interesting Because like yeah, I mean engineering at at least software companies, regardless of whether it's consumer or B2B, you're always like fighting for their resources and like core product is always the one that wins out. So it's really really cool that you're able to, you know, test something, say, hey, I really think this is going to work. Let's like, you know, prove, you know, let's build out something that's a little bit automated so we can focus on other things. That's pretty awesome.

Speaker 3:

I'm indebted to them for forever for that. It was great.

Speaker 2:

Yeah, I mean it does.

Speaker 2:

It goes back to what you were saying, though, about the need to have that right kind of first life cycle hire, who is going to act like an entrepreneur.

Speaker 2:

He's going to be thinking about what are the bets that I have to make, because that that you had no data to show that, like this is going to be worth the investment, right?

Speaker 2:

It was purely like I am confident that this will be a valuable thing to the company in the long run, and here's what we should put into it. You had to think creatively about what are the data points that you'd want and how could you get those, and how will that keep up with the product that you know? The product has its own vision and roadmap, and so, for, if you're the proof of concept for this thing, you had to be thinking about what are the data points we'll want in two years, when we have all these other features, and how can we start getting early indicators, and so it does take a special kind of person to sit down and think through that and plan for that. So it's cool that they enabled and supported you, but it also is, you know, I think they probably had a pretty good inkling that they had the right guy and he was worth placing a bet on, as opposed to this idea you had.

Speaker 3:

I appreciate that, yeah, it was a win-win, and you know I appreciate that, yeah, it was a win-win and you know, I think that's something I'll around this theme in general. We've been talking about founders, heads of growth and marketing, like first marketing hires. I think copying playbooks is a necessity and it makes sense that a lot of times we're looking for those tactical playbooks. But when you hire that first lifecycle or even email channel person, look for somebody that is like no, don't give me a playbook, I'm going to make this as contextual and as unique as I can and try and innovate. Look for someone with that drive. I think that, while more rare, is going to be a better investment and more worthwhile because people will start to notice and there's like an immeasurable qualitative impact that that can have internally and externally.

Speaker 1:

I think that might be a good place to wrap up I think any last minute pubs. Drew, I think we have Maven. We have your course on Maven. Talk to us a little bit about your newsletter.

Speaker 3:

Yeah, so Scaling CRM it's on Substack. I write about strategy, seeing the forest from the trees. It's really for lifecycle and adjacent title, like senior manager and above so leads really can be everything from case studies to recommendations on building out a team to vendor spotlights. I actually do that a lot. What's the future of lifecycle? What's the tech stack Like? What are the new startups in our space that are actually doing things like machine learning at scale that you should be paying attention to? But it's really just whatever I feel like writing about on a weekly basis, and that's why I love it.

Speaker 1:

I think we can find Drew on LinkedIn. We'll put all of the links in the show notes.

Speaker 2:

Yeah, Drew, this was great.

Speaker 1:

Again, thanks so much Really appreciate it.

Speaker 3:

Thank you, guys. I'll send the invoice over soon.