Full transcript:

Bryony Pearce - PMA 0:01

Hi everyone, and welcome to the Product Marketing Life podcast, which is brought to you by Product Marketing Alliance. My name’s Bryony Pearce and I’m the Content Manager here at PMA. This week’s podcast is sponsored by Product Marketing Core...meta, we know. PMMC is our very own product marketing certification program, and it covers the A to Z of product marketing essentials. With 11 modules, 68 chapters, 87 exam questions, 10+ hours’ worth of learning and official PMA certification, it’s a course not to be missed. Head to https://pmmalliance.co/PMMC for more info. Back to today’s show...to give you a glimpse into the world of other product marketers in this show, we'll be talking to Chris Winkler, a Senior Product Marketing Manager at DocSend, about what a day in his shoes looks like. Chris joined DocSend back in October 2018 and before that spent time at Glassdoor and Groupon in a blend of product marketing and account representative roles. He’s also one of our Founding 500 members and a PMA ambassador. As many product marketers know, there isn't really such thing as a standard day in this industry and because of that, we're going to be focusing on Chris's most recent working day. Before we get stuck into 'a day in the life of' though, welcome to the show, Chris.

Chris Winkler 0:14

Thank you so much. Glad to be here.

Bryony Pearce - PMA 0:16

It's our pleasure to have you, I guess, could we just kick off with a bit of an introduction to you and DocSend?

Chris Winkler 0:23

Of course. So I am the Senior Product Marketer here at DocSend, I'm a part of a product marketing team of one. So sometimes somewhat lonely. But here at DocSend, we are a secure file sharing platform for primarily startup founders, VCs and financial professionals that really helps them have more control over the sensitive information they're oftentimes sending externally while also providing them with analytics and insights to help them inform business strategy as well as their follow up for after they share those documents out.

Bryony Pearce - PMA 1:01

And you mentioned it's you and one other product marketer. Out of curiosity, what's your ratio with product managers at DocSend?

Chris Winkler 1:08

Oh, I'm sorry it's just me on the team, and then I have one product manager.

Bryony Pearce - PMA 1:13

Okay, gotcha. Okay to add a bit of context then before we move on to your day yesterday, could you just give us a bit of a background into the current stage of the product life cycle that you're in at the moment?

Chris Winkler 1:27

Yeah, it's a great question. I think it's two-part really, currently with the next product that we're looking to release, it's really honing in on that positioning messaging and what's unique about this next feature that we're releasing is it's more of a functional release, then kind of a glitzy big advertisement, new product release. And so, really, on our end, it's really kind of focusing on the internal processes involved, making sure everything's set up. Because what this will do is really open up new opportunities for how our users use the product, as well as really how they can expand and grow their use of DocSend externally. So really, it's getting towards that launch period, ideally mid-March, so really making sure we have all the internal reporting squared away, we have the positioning and messaging really focused in on, and then also the internal enablement. So really heading up, making sure CS, our support team, our sales team all know the right way to talk about this feature and some of the edge cases that we could see. But on the flip side, I think there's always an earlier stage that myself and my PM are working on which is around like gathering data and just doing more and more analysis to inform what those next products and features are that we're going to be building for our users and how each different use case or persona might use that feature differently. And really understanding like what that MVP looks like, as well as like what that full-blown, fully built product looks like at the end of the day, and like really where we can start to focus. So at a high level it's always I feel like planning for the next launch while making sure the current launch is getting ready to go out the door.

Bryony Pearce - PMA 3:32

Yeah, for sure. And then with a launch like this, that's going on in March, how long ago will you have known that this was coming? Like do you get much oversight into the product roadmap at DocSend?

Chris Winkler 3:43

Yes, so I'm very fortunate here at DocSend to work closely with both my CTO and product manager and really they have kept me in the loop and allowed me to do research and help them out in terms of really understanding what should go on to that product roadmap. And so this was a feature that we've known about, likely since, I guess Q4 of last year, maybe even earlier than that. However, it really hasn't started coming to fruition until earlier, I guess the beginning of this quarter, really. And so I think one thing I really like about how DocSend develops the product roadmap is they really try to focus on six months at a time, however, they focus on themes for the rest of the year past that. So while Q1 and Q2 this year is solidified to an extent, then we have a bunch of these ideas that we're trying to validate for Q3 and Q4, which ties back into your last question around like how we're just always, I feel like in this analysis phase to make sure we understand really what that looks like and then we can prioritize those products and features based off of the intel we gather.

Bryony Pearce - PMA 4:58

Okay, cool. That makes sense. So I guess next up in the main theme of the podcast is looking at your most recent working day. So this is obviously an area of product marketing that just changes so much from day to day and one product marketers day can be vastly different from another's. So I guess focusing on yesterday, can you just talk us through what that looked like for you in terms of what meetings you were in, what sort of tasks you were working on what teams you were interacting with, and that kind of thing.

Chris Winkler 5:26

Of course, so yesterday was an interesting one. A very exciting thing happened, believe it or not, we have not launched an NPS score yet and so yesterday, myself and my marketing ops manager finally got all the pieces together to launch that. So that took up a big portion of the day and was a very exciting one because I think NPS is a very important data point to consider, especially when understanding your users and how they use the product. But more than that, I think I met with, of course, my PM to really continue to fine-tune the messaging and positioning and more so for me really to get a deeper, deeper understanding of the upcoming release and that product functionality, so that I could continue to fine-tune and educate the rest of the departments on how that product and feature should work. I also had meetings with sales in CS on the CS side, because we're starting to shift our target audience and our target personas, I'm working with them to help them understand really how to prep to talk to these new personas that we expect them to start managing, as well as how to develop a health score to really help them understand like, is this a good client? Or is this someone that might be at risk? Because obviously with CS, retention is a big goal for them. And then on the sales side, and these go hand in hand, we are currently using an outside SDR agency. And so having meetings with them to make sure, really well, I guess just checking on progress, refining messaging where we need to, and continue to iterate to make sure we're getting the best response and putting out the most effective messaging to target and attract these new personas to get them into sales. I think then on the more creative side of things, and something I really enjoy, I am responsible for creating all the product videos that we do, we use another outside video agency for that. And so yesterday I spent a good chunk of time developing a creative brief and putting together like really what I want the underlying message and theme of this upcoming video to be focused on and then working with that outside agency to talk that through, see what's viable, answer any questions he might have. And then the last two pieces, which are a little bit more, I guess, just easy ones are one I kicked off, had a new vendor, we just purchased a new competitive intelligence vendor. And so really working with them to talk them through the competitors you want to target more importantly, give them the background knowledge of why we're targeting these competitors, and what insights I'd really like to focus on when they provide those insights to me. And then the last piece there was I'm currently also developing some surveys to identify and like understand, well identify users in our other use case, because I think this is a mysterious black hole for us right now. We have a lot of people come into DocSend that select this use case so we really want to understand who they are, what they're using us for. And then really like taking a step back and then creating that survey and then spreading it around the rest of the teams to make sure if there's any other insights or inputs they want to pull out of this survey, getting that feedback and filling in the survey. So, yesterday was kind of an interesting one. It was just a bunch of different things going on at the same time. And I would say that's almost like how every day is, it seems like there's just a bunch of different tasks that need to happen. But as long as you're moving things forward, I think that's my daily goal is to at least focus on getting these things to the next step on a daily basis.

Bryony Pearce - PMA 9:36

Yeah, for sure. It sounds like a packed day. How did that NPS launch go?

Chris Winkler 9:43

So far, so good. I'm seeing the results coming in by the minute actually, I just got another one. And they have been so far pretty strong answers, a lot of promoters, a couple of neutrals in there. And so I think what we decided to do this time because we haven't done it yet is we did a soft launch to about like 1000 users, just to make sure everything's working. And we'll do the bigger launch to all our current customers, I think this afternoon seeing as everything looks to be set up properly. So yeah, really excited to get that data back into our system so we can do some further analysis on that.

Bryony Pearce - PMA 10:23

Yeah. And then what's actually, on your side, what's involved with that launch internally and externally, what assets for example did you need or what kind of messages did you send out?

Chris Winkler 10:36

So nothing was sent out as of yet because I think we are still I mean, the product is very close to being done. However, what's unique about this product is it changes. Let's see, the easiest way for me to put this it changes how we identify a user within our system and this is really important because I think a big portion of my job is controlling the lifecycle marketing for these users. And the last thing I want to do, and this new feature opens up this possibility, but the last thing I want to do is re-message something to someone multiple times given that now we might possibly recognize them as three different users. And so really, it's working with my PM, and my engineering team, as well as my marketing ops manager to make sure we can eliminate that possibility. For example, I guess, to give you some insights into what this feature is which would make this all make a little bit more sense, but it allows a user to essentially create a new 'company' within DocSend. However, I think like what we're trying to figure out is how we can recognize what that first company is so that this user doesn't continue to get a new onboarding campaign every time they create a new company. So it's really more on the back end and making sure everything is aligned and set up properly so we can avoid any mistakes. But then on the messaging piece, it is kind of, I've been creating some more so internal slides and decks to help everyone understand like really what the functionality is, what some of these edge cases could be. And really what we hope to see out of this release, which has been helpful I think because I think there's, with something like this that is more so technical than a new full-on product, sometimes there can be a lot of confusion in terms of the functionality and how it's supposed to work and how it could possibly work.

Bryony Pearce - PMA 12:43

Yep, that makes sense. And then you mentioned that you were working on some messaging work with your PM yesterday, in terms of that relationship for that kind of job, what involvement does the PM have with your messaging and positioning work?

Chris Winkler 13:01

Because he is much closer to the product built and understanding like exactly the ins and outs and I think it goes from like really a transfer of knowledge to the engineer to him and then to me and so it's a lot of me bouncing ideas off and making sure you know, is my positioning and messaging aligned with this feature? Am I just completely out of the ballpark and missing something? And so he is a great way for me and a great resource to gut-check what I'm going to say. Because without that full understanding, you can message something completely wrong and that just drives user confusion. And that's the last thing I want to do. And so a lot of times he's a good person to bounce ideas off of and at the same time, I think my PM also has his own ideas so that'll help me sometimes shift viewpoints to look at this product or feature in a new lens, which can oftentimes be very helpful because I think sometimes as PMMs, we can get so focused into a certain positioning angle that you can ignore other ones. And so I think always bouncing those ideas, whether it's a PM or someone else on the team can help you take a step back and think about, okay, maybe there are multiple ways we can look at positioning messages for different use cases. And so he's always been helpful when working with him.

Bryony Pearce - PMA 14:32

Yep, that makes sense. And then my next question was around the meetings that you had with the sales teams. I always feel like this is maybe a sticky topic in product marketing, and especially in the Slack community, we see lots of questions about people asking how they can get sales engaged and how they should best interact with them. How do you go about setting those meetings up and getting that interaction and engagement out of your sales teams?

Chris Winkler 14:56

You know, it's a great question. I think from my experience it's different company to company first of all. I think having come from sales myself, I've been in a lot of those product marketing meetings when I don't want to necessarily be that involved. And I think that as a sales rep actually it comes back to kind of hurt you in a way. But I think, really kind of understanding that that's how sometimes that could make you think, but then also putting it into a position where it's like, "Hey, I'm just here to listen like you guys are on the phones every day. You are talking with these prospects on a daily basis. And so it's important for me to know what these common objections are, what these common questions are, are we targeting the right people from a marketing span?", and so I think more so giving them the power to just provide me with feedback has been a great tool because you know, on one hand, you have to take it with somewhat of a grain of salt, especially if someone just got off a bad call because then they think maybe sometimes the world is crumbling to them. But at the same point, there's also often a lot of truth behind that. And so understanding like how to get to the insight within that feedback, and then go back to your team and apply that insight, whether it's in the positioning messaging that I develop, or maybe the channels that my growth marketer advertises in, I think letting them know that there's actually going to be some sort of next steps and action items that comes from that feedback has helped me build that relationship with them. And I'm also very fortunate to have a fairly small sales team and so it's very informal, they know where I sit, obviously, we're a small company, so whether it's a meeting or they just come up oftentimes to tell me "Hey, I just had this great call. You should listen to it" or, "Hey I just got this objection, which is absolutely new. Have you seen this before?". And so it's a very fluid way of just providing feedback and acting on it.

Bryony Pearce - PMA 17:10

Yeah, sure. And then so you obviously have a lot of kind of variety in your day. Would you say there are any constants for your day to days?

Chris Winkler 17:18

I would. And there's somewhat high-level constants, however, I feel like there's always a chunk of my day where I'm doing some sort of research, whether it's on the marketplace, whether it's on specific competitors and really diving into their product to understand the features and functionality and probably more importantly for me how they are positioning those features and functionality. Or it's more internal research when I'm looking at our users and how these users are going through the funnel and since we're a trial first product for the most part, really looking at that user onboarding flow and are people doing the actions that we want them to which we know will actually increase the likelihood of them paying for DocSend, and if not what kind of tweaks or I guess more so what kind of assumptions can we build based off that and how can we test those assumptions to optimize what those flows look like? And so I think like that could be anything from diving into our data platform, or just doing a good chunk of reading and keeping tabs on what's out there. I think the other constant is there's never not a day where I'm pulled into a meeting that's not been scheduled. So the constant is almost that there's not necessarily a full constant I guess.

Bryony Pearce - PMA 18:54

And in terms of those research pieces whether it's kind of competitors or marketplace or users, is that something that you own within the company is a product marketer? Or are there any other teams that you lean on for that kind of thing?

Chris Winkler 19:06

I would say, for the most part, that is something I own. And I think it's a very valuable piece, in my opinion, because I think everyone's busy doing their specific job. And I think that understanding that marketing and competitive research, in my opinion, is a very important pillar of product marketing. And so I do try to make it so I can synthesize some of that research when I find something interesting, and then share it with the proper internal stakeholders. And even if there's not necessarily an action item on it, I think just providing that visibility and making sure everyone is aware of what's going on in the market is absolutely crucial to formulate the next strategy internally.

Bryony Pearce - PMA 19:52

Yep. And then in that first sharing step, how do you actually go about that? Is that a case of pulling everyone into a meeting and chatting about it, or you'll send an email round, or?

Chris Winkler 20:02

Yeah, there was a time when I would spend a good chunk of time trying to get that information, put it into a nice pretty deck to send out and I realized, just really putting your thoughts into Google Docs, sharing an email. And what I like to do is in the email, give my high-level points that I've picked up and then share that Google Doc and say if you're interested in like learning more and getting more granular, like, here's the information in its entirety. And so I find that helpful because whether you just have a couple of seconds to read that email or you actually can get into the document and really dive into those insights, it's something that you can easily digest, depending on your time. And obviously I welcome comments within that document as well. And so I think by doing that, it kind of then fosters this conversation and if we need to have a meeting we can have that meeting, I'm happy to do that. But I think just getting the information is more important than the presentation of that information. And I don't mean that entirely but I think for quick, like competitive insights, I think just getting information is very important.

Bryony Pearce - PMA 21:19

Yeah, no, that makes sense. And would you say you enjoy the variety of product marketing? Do you enjoy that every day is kind of different and you get these curveballs and?

Chris Winkler 21:29

Yes, I absolutely love it. I think it can be sometimes dangerous how much I like it, because a curveball sometimes if I find it very interesting, I need to make sure I don't kind of go down a rabbit hole just chasing that specific thing, especially if it's not necessarily something that will drive the biggest impact. But I think the variety and being exposed to essentially all the business units at my company is something that I really enjoy because I'm a product marketer at heart. I love learning how engineers think, I love learning how my PM thinks, I love learning how my executive staff thinks about like, really the direction of the company. And so being able to shift mindsets on a whim is something that I find interesting, and I think it keeps me more curious. Not just about product marketing, but I think in essence, like how you are really fundamentally supposed to grow a company. So I would definitely say I'm a big fan.

Bryony Pearce - PMA 22:37

Yeah. And then I guess for people who are new to the industry, that lack of day-to-day structure could maybe take a bit of getting used to, do you have any advice for those people who may be struggling with that element of the role?

Chris Winkler 22:50

100% and I think kind of like I alluded to on that last part sometimes you can get into a dangerous rabbit hole. I think it's important to just consistently prioritize. I think and this is something that I learned somewhat the hard way early on in my product marketing career, but if you're trying to do 1000 things at once, you're not gonna really do them either well, or complete many of them. And I think really being able to take a step back, when you might be feeling overwhelmed or when there's a lot of things you need to do and really reprioritizing like, 'Okay, what do I think and drive the biggest impact in the short term? What can maybe wait a little bit longer? And then what can I maybe de-prioritize or push off?' Or now that our marketing team has grown, I think what can I delegate to other people within the marketing team? So I think that's the biggest piece for me, is really taking a step back and reprioritizing for sure. And well, I guess another piece is, I also learned this the hard way, but the importance of saying no to things. It's an art form I've learned, you can't just say no, like that doesn't necessarily always come off the right way. But really kind of having that conversation and understanding what the underlying motivating factors are to that ask of you. And then really again, then seeing where that fits into your priorities as well as your scope for the quarter. Maybe it makes sense, but sometimes it just says, I think given that we've agreed on focusing on these things, in this quarter, that doesn't necessarily fit in scope, but most times when you phrase it the right way, people are very receptive to that. So that's definitely a crucial piece.

Bryony Pearce - PMA 24:54

Would you say there's anything that you still sort of struggle saying 'no' to, to this day?

Chris Winkler 25:04

I think it's the pieces that I find personally very interesting or very curious that maybe don't drive the biggest impact but I want to know the answer to. I think there are sometimes questions that I feel just like personally motivated to get the answer to. And I think even then I need to take that step back and be like, 'Chris, even if you get this answer, like, what's going to come of it? And what is this going to impact down the line?' And yes, there have been many times where it's been an hour into me trying to find that answer and I'm like, why? I need to take a step back and focus my attention on the things that matter most and so I'm a naturally very curious person. So stuff that piques that curiosity can lead me into that rabbit hole that I need to get back out of.

Bryony Pearce - PMA 25:54

Okay, cool. Well, thank you for giving us a bit of insight into your day. I'm going to move onto next a few questions just to help people get to understand you and your drivers and your experience a bit better. So first off, if you could go back to the start of your product marketing career, knowing what you know now, what advice would you give to yourself?

Chris Winkler 26:19

I think it goes back to that artful way of saying no, I think there was an early time, especially when I wanted to prove my ability to be a good product marketer that I looked at just saying yes to everything as a way to prove myself and I think that can lead to just, I mean, you just get tired when you say yes to everything and you put some unwanted pressure on yourself. And I've seen people that I've worked with that are just getting into product marketing say yes to everything and they just kind of burn themselves out. And so I think consistently understanding how to identify what items will make the biggest impact and then using that measurement to then lay out what you're going to focus on is something I wish I could have told myself years ago.

Bryony Pearce - PMA 27:18

I feel like that kind of saying no piece can be a bit of a trap for a lot of product marketers, especially when you first start in a new job because I imagine in the first few weeks or months, it's all about kind of building those relationships with those kind of stakeholders and teams that you're going to need to rely on. And it can feel unnatural if you're thinking, "Well, I'm going to need to work really closely with this person, but as soon as they come to me I'm going to tell them no", and it can maybe feel a bit counterproductive, but obviously it has to be done.

Chris Winkler 27:44

Right. And I think you know, I guess there is a caveat to that. And I will stay strong on my stance on like, hey, what makes the biggest impact but I do also see you can define impact in a couple different ways, right? You could have impact on the business, but you could have impact on internal alliances and internal trust. And so if there's an ask of you that you think you can get done really fast, but it's gonna, like improve a relationship that you have with an internal stakeholder, like, I see that as a high impact action, because when it comes back to maybe you might have an ask of them, it's now, okay, like, we are partners in this, and we can rely on each other when things come up. And so it's a tricky game, one that I think changes from company to company, and I think, unfortunately, there's not a full-blown, you know, methodology to it. But like you said, it can be kind of a trap. But I've also seen myself saying no to someone that also builds trust with them because they understand, you know, I do know how to prioritize and I do know how to identify things that attract the biggest impact. So it's one of those things. It's very case by case.

Bryony Pearce - PMA 29:04

Yeah, it works both ways, I guess doesn't it? Okay, so next up, can you think of any sort of mantra or belief or behavior or tip, for example, that has most influenced you in your product marketing career?

Chris Winkler 29:22

Yes. And it's changed and been refined over time. I think, again, coming from sales to product marketing I felt like I had a lot to prove, however, my initial mantra, which I'm sure there's people out there that might be eye-rolling to this, but it was fake it til you make it for a lot of things. I think it was just kind of like, I'm gonna pretend I know how to do this and even though I don't I'm gonna figure out how to do it. And I think that mantra has helped me just expedite my learning curve, but I think what that's led into is my, and I think this is also another trap people fall into sometimes, but I think that's kind of led into my willingness to accept the fact that I'm going to make mistakes. There is no one in product marketing, I'm sure probably no one in life that hasn't made a mistake before. But I think those mistakes have helped me accelerate my understanding of effective product marketing, and just the role in general, immensely. And so, I've seen, again, the second piece around new product marketers, either kind of a struggle saying no, but also this fear of making mistakes, they want everything to be perfect. And I think it's one of those things that the mistakes are going to help you improve. They're going to help you learn, they're going to help you become better at your job. And I also believe in the Pareto principle around that 80:20, like 80% there's likely going to be as good as 100%, that remaining 20% probably has a little bit of diminishing return. And so that methodology has helped me when getting things out there. Because I think mistakes are inevitable. You shouldn't be afraid of them. You should, in a weird way, look forward to them. Obviously, don't make a mistake that tanks the company by any means, but try to minimize the impact of those mistakes. I think it's a great way to learn.

Bryony Pearce - PMA 31:30

Yeah. And then out of curiosity, you said you came from sales into product marketing? How did you make that transition? And was it very much a case of learning product marketing on the job or?

Chris Winkler 31:41

Yeah, um, it really started with relationship building, I would say. And it started at my previous company, I think I was in sales, it started actually, back to the creative side of things, I was really wondering like, where all this sales collateral came from and again, I didn't really know necessarily what product marketing was. And so I would get this collateral, I would have tweaks and improvements I'd want to make, but I don't necessarily know who to give this feedback to. And so that search landed me with the product marketing team naturally. And so I started talking to them, working with them and that relationship really transpired over several months to be just someone that would just provide feedback to now having regular meetings to then getting to the point where a role opened up for someone a little bit newer, someone actually more so focused on the collateral piece and so they asked me to interview and then that was an area where I was able to step in, really proved myself and then climbed the ladder from there and got moving really from a very much collateral and sales enablement focus role up to the higher-level strategic thinking product marketing role.

Bryony Pearce - PMA 33:02

Okay, nice. Next up, can you think of any bad examples of best practices, or bits of advice that you hear in the industry, but maybe wouldn't recommend others to kind of follow?

Chris Winkler 33:18

I think there are two parts to this, a product and sales piece. I think I kind of touched on the sales piece a little bit earlier. But I've recently read some things about especially when doing win-loss analysis that going to sales sometimes isn't helpful. And I think there can be a degree of truth to that. However, I think, again, going back to relationship building and forming allies and building partnerships within sales, I think being able to identify specific reps that are able to provide critical feedback and helpful feedback and leveraging them can be very helpful, very insightful, because they ultimately, whether the product marketers want to know it or not like, oftentimes are the true customer experts because they are living the ins and outs of this customer journey and identifying all the problems that these customers are uncovering whether it's with the product or service or the process, who knows. And so getting that quick, snappy feedback to me has always been helpful. And I alluded to this earlier, but I mean, there are some times you should take it with a grain of salt. I fully believe in that. But that has been something very helpful for me. I think the second piece and I think this is changing, however, I have been involved some times where product and product marketing want to interview users at the same time, or really combine research efforts and I'm all about combining research efforts. However, I think when doing so, like the questions a product manager will ask compared to what a product marketing manager will ask are extremely different. And so trying to squeeze those both into a 30-minute call will give both people 50% of the answers they're really looking for. And so I think understanding and formulating a plan with your PM because, at the end of the day, you both in a way want the same thing, but it's just the questions you ask that will get you there. And so working with them closely to really, 1) come up with the questions together, isolate and segment who each person wants to talk to. And then 2) formulate a plan to do that with the end goal of sharing the insights back and forth. Because I've had many times my current PM gets off a call gives me some insights that I find extremely helpful that I can take for my product marketing, and positioning and messaging. And then I've gotten off calls that I've provided to my PM that he finds very insightful in terms of like, what areas of the product they can improve and optimize. I don't really know how widespread that is, to be honest with you, but I think it's something just to keep a note of if you're in that research and data collecting phase.

Bryony Pearce - PMA 36:26

Yeah, I guess that's another one that'll just vary from company to company because the impression I get often in these podcasts is that some people have very different relationships with their product managers than others. So I guess that's a case by case one as well, but it sounds like you've got a good setup going. All right, the next one, if someone was looking to move up the product marketing ladder, and they could only focus on one skill, what should that skill be and why?

Chris Winkler 37:04

I'm gonna say two parts, but it's the same skill I think. So I think knowing how to pull insights from customers, prospects, and data and really understanding where to get those insights. I think if you are anything as a product marketer, in my opinion, you should know the ins and outs of how your customers view your product and how your prospects look to buy and those different solutions. And so the more you know there, you are going to be the best strategic partner to any department internally because you are now the professional of the user as well as the prospect. So you'll be involved in a lot more meetings.

Bryony Pearce - PMA 37:56

Sounds like catch 22 though, then you get in a lot more meetings.

Chris Winkler 38:00

Yeah, exactly. But a lot of times there's a lot of progress that comes out of those meetings. And I think they're very helpful to get everyone aligned on some of the insights that you pull.

Bryony Pearce - PMA 38:09

Yeah, that makes sense. And then I guess, kind of tying into that, so obviously, product marketing is a massively varied role, in a lot of different teams, pulled in and out of meetings, you're kind of at the center of everything. So the impression I get is, it can maybe be a bit of an overwhelming role at times. So if you ever feel overwhelmed or unfocused or anything like that, is there anything that you kind of do or tell yourself to regain that composure?

Chris Winkler 38:39

Yeah, so I think feeling overwhelmed goes back to that prioritization understanding, 'okay, where if I had to choose one thing to focus my time on right now, where would that be?' And so that's step one. If I'm feeling kind of unfocused and overwhelmed I oftentimes try to just get away from my computer, go for a walk, just go relax for a second. Sometimes I'll go grab a coffee because I think I can almost guarantee none of my best ideas or thoughts around positioning and messaging have necessarily come while staring at the computer. It's been very random, I'm walking around, I'm in the shower in the morning, that actually happens more often.

Bryony Pearce - PMA 39:24

I was just about to say in the shower as well, it's like quick I need a piece of paper to write it down before I forget!

Chris Winkler 39:30

Exactly like the amount of times my marketing team has heard me say, "Hey, I was thinking about this that occurred to me in the shower" is too many. That I think is really important, I think there's a lot of studies that also show like kind of disconnecting and pulling yourself away from the computer can be really helpful. And I think if you try to force the thought, in my experience, it doesn't work that well. However, if you let these things come naturally while going about your day or trying to kind of step away from this specific task at hand and think broadly, I find a lot of success with that. And you know, a little bit of fresh air never really hurt anyone. So I think just getting out there and relaxing and freeing your brain up of some of these stresses can really be beneficial not just for that day, but also I mean, even for like an entire weekend. It's really helped me clear up and schedule the rest of my week.

Bryony Pearce - PMA 40:30

That make sense. I remember, this was a few years ago kind of pre-PMA, but I'm quite a keen runner. So I go out running quite a lot. And it was one Sunday morning, I was out on this kind of 10-11 mile run and it must have been about four miles in and I just had this really great idea and I was freelancing at the time so it's for my freelance business. And obviously I had nothing to kind of write it down on, I don't take my phone with me, I didn't have a pad of paper in my pocket. So for the next kind of seven miles of my run, I was just running around repeating this idea in my head, thinking "cannot forget it, cannot forget it".

Chris Winkler 41:04

Yeah, I have Slacked my CTO at two in the morning because I'll wake up in the middle of the night and I don't want to forget something. Like the next day he'll be like, "Were you asleep? Or were you out?" I was like I was definitely asleep I promise you that. But I just jolted out of bed thinking about this. So they come at the weirdest times. But to your point, it's important to write it down or do your best not to forget about it, because those can be some great ideas more often than not.

Bryony Pearce - PMA 41:35

Okay, final few questions. Next one, if hypothetically, your work hours were chopped in half all of a sudden, where would you spend that remaining time you had left?

Chris Winkler 41:49

I think it goes back to becoming that expert on the client. I would probably dedicate all my time to whether it's scheduling calls with current customers, whether it's trying to run surveys and run focus groups with the ideal target audience that isn't a customer, to understand what makes them tick. That's where I would really spend all of my time because then going back to that earlier point like you continue just to become this expert and almost spokesperson of both your current clients as well as the target audience. And so that just makes you very valuable within the organization. And I mean, if my hours were cut in half like that, however, I was able to bring that value to the rest of my department. I mean, it would still be I think, very impactful.

Bryony Pearce - PMA 42:40

And then next up, I get the impression throughout this podcast the answer to this might be everything. What aspects of product marketing would you say you're most curious about?

Chris Winkler 42:50

Everything is definitely a good start. But something I've been trying to figure out more and more is really the psychology of what makes people act on a specific message or value prop. And I guess a lot of that is almost a little bit more advertising side, but really trying to figure out, how to best talk to people to kind of influence them, really. And that is a very broad term, I think something you can use in multiple aspects of just life in general. But diving into that, and understanding like how you can relate a product or feature to an actual personal impact or emotion that will drive that individual to take an action, whether it's just learning more to talk to you or whether it's actually buying the product. I think that is a piece that I find extremely fascinating. I think I notice it all the time. I think we all do. I think Apple has been doing it to us for years and they've figured it out. But I will see ads or a specific product being advertised and it will just make me feel a certain way. And I'm like, that was interesting. Like, I want to learn more about how I can do that for my audience. And I think depending on the audience and the product, it can be sometimes easier, sometimes extremely difficult. But that is definitely I think, at the high-level something I'm very curious about. And then, of course, being, I think, naturally curious, I think, really understanding ways to continue to strengthen the relationship and connection from product marketing to product engineering, and also just almost more so marketing to those departments. I think the closer those two departments work together, I think, the more cohesive the end product and service becomes and like the positioning messaging is constant, it mirrors the product and vice versa. And that can be very powerful.

Bryony Pearce - PMA 44:57

Yeah. Okay, cool, penultimate question. What would you say the best lesson is that you've learned during your time in the product marketing industry? And what led to you learning that lesson?

Chris Winkler 45:09

Yeah, so especially when I started off, I used to hate OKRs, I used to hate planning. I always felt like I spent more time sometimes planning my quarters than I did actually working on the stuff I put in my plan. However, I've quickly realized that it is extremely crucial. And I think effective planning and getting buy-in from not just your team, but also other internal stakeholders is just going to make your life so much easier. It's going to just help, again back to I feel like I've said prioritization like a million times today but I think like, it lets everyone know where your focus is at and so it also can really help mitigate some of those curveball asks you might receive from people because they were involved in that process, therefore, they know what you're working on and what your focus is. And they agreed to that. And so it can really just help that conversation. And I think the hiccup is, you know, going back to my earlier years in product marketing, again, when I wasn't really a fan of this area, and not getting internal buying, again, led to me trying to chase multiple projects down at any given time, and it can just be very stressful. So that was definitely, I think, a very, very important thing that I have been really valued more and put more importance on for sure.

Bryony Pearce - PMA 46:45

Okay. Awesome. And then final question. What do you think the biggest problem the industry faces is either right now or in the future?

Chris Winkler 46:58

I'm not sure if it's really the industry, maybe it is. There's I'm sure aspects of it in terms of how I think product marketers as a whole, really kind of illustrate the impact. But I feel like a common theme that I've seen when talking to other companies and other product marketers is that many young companies, I feel like wait a very long time to hire their first PMM. They found some sort of product fit with the product they built. And they think it's just gonna keep going that way. And then all of a sudden, that might plateau and they're kind of scratching their head, like what's going on? And so, when that occurs, I've talked to product marketers that've been brought into young companies and it's more so they're trying to fix things that happened versus looking forward and improving and optimizing what this company has built. And I guess on one hand, in the grand scheme of marketing functions product marketing I guess is on the younger side. So hopefully this starts to change more and more. But it's something I find very interesting and hopefully as these more and more young startups grow, they start to shift attention to making product marketing one of those earlier strategic hires, rather than something that they can pull in later on. So, not totally sure if that fully answers the question?

Bryony Pearce - PMA 48:37

No it does! Okay, awesome. Well, that's all my questions for today. Thank you so much for your time, Chris, it's been lovely speaking to you.

Chris Winkler 48:42

Wonderful. It's been an absolute pleasure. And yeah, thanks for having me.