Right now is not the norm. Tons of product marketers have been thrown into remote working from one day to the next and understandably, lots of people have lots of questions.

We spoke to Sapphire Reels, a Senior Product Marketing Manager at Pluralsight, about how PMMs can adapt to working from home in light of COVID-19.

Full transcript

Bryony Pearce - PMA  0:04

Hi everyone, and welcome back 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 pod’s sponsored by the Product Marketing Festival. For those of you who haven’t heard about it yet, it’ll be coming to a screen near you between June 8th and June 14th, and will featuring headline acts from companies like Amazon, Uber, Adobe and Facebook, talking about everything from research all the way through to optimization. To get your ticket, just head over to the site, festival.productmarketingalliance.com.

As part of this series, we’re connecting with product marketers all over the world about topics they’re super passionate about, and in this episode, we’ll be speaking to Sapphire Reels, a Senior Product Marketing Manager at Pluralsight, about working remotely as a PMM.

Sapphire first joined Pluralsight as a PMM back in April 2017 and progressed to her current position in October 2019. Before joining Pluralsight she held product marketing roles at Patientco and HubSpot and she’s also one of our PMA ambassadors. Anyways, that’s all from me for now, let’s pass over and welcome Sapphire to the show!

Sapphire Reels  0:22

Hi, thank you so much. I'm so excited to be here today to talk a little bit about product marketing and working remotely. I've been remote for the past four years, both at my current company Pluralsight and my previous company, PatientCo, and it's pretty crazy times we're all living through right now. And so I'm excited to just kind of chat about some things that have worked for me and also some simple tools and methods for others to figure out what works for them working remotely as well.

Bryony Pearce - PMA  0:50

Awesome. Well, it's great to have you here today. And I guess could we just kick off with just a bit of a background on your role at Pluralsight and then the company itself?

Sapphire Reels  0:58

Yeah, that's a great question. So Pluralsight is a technology skills platform. So we allow individuals and businesses to improve their tech skills. So let's say an organization has an initiative to migrate their data and applications from on-prem to the cloud. We provide content and assessments to their technologists that will help them upskill. And then we provide a suite of analytics to their leaders that will inform where their skills are, where their skills gaps are, so they know if they're actually ready to take on these initiatives. When I first joined Pluralsight, we were traditionally a B2C company, we've shifted into the B2B space and over the three years I've been there, we've really gone heavy into B2B Enterprise. And then so product marketing was brand new when I joined as it exists today. Today we sit within portfolio marketing, so portfolio marketing includes brands, content, customer advocacy, and analyst relations. We have 10 product marketers, I am the only remote, work from home, product marketer, usually - not right now, obviously. And then we have one product marketer in Dublin and one in Boston in our offices there. In terms of my role, we like to think of product marketers as full-stack product marketers. So there are four core pillars we think about for product marketing at Pluralsight, which is market intelligence - so that's obviously, what is the market saying? Who are our buyers? What do they care about? We have messaging and positioning - so how do we talk about the product that we're selling? And we also work with our brand team on brand positioning as well. We then have sales enablement - so how do we make sure that our sales team have all the knowledge and assets? And we work with sales enablement to figure out how do they have the tools and processes to effectively do their job and sell our product? And then the last piece is obviously, launch strategy - how do we take our products to market? And within our product marketing team we recently reorg'd and have more niche focuses. So one, the team that I'm on, is called the prod squad - product squad, we really focus heavily on building product relationships and launching products to market. Of course, as a product marketer, that includes all the things I talked about already, so still coming up full-stack. We also have a go-to-market team that really coordinates across marketing and sales plays and operationalizes some of our launch strategy. And then we also have a sales squad, which works on our sales relationship and working with sales enablement as well.

Bryony Pearce - PMA  3:34

And then you mentioned the rest of the product marketing team they're not remote workers, so how do you find that kind of being the only one that works remotely do you find there are any roadblocks there, or?

Sapphire Reels  3:45

Yeah, that's a great question. So when I first started, there was a VP, three directors, and then I was actually the first product marketing hire and I think it was an interesting time because they actually wanted everyone to be on-site, and then along came Sapphire and being on-site just wasn't an option for me. And so when I first started, we really had to look at some of the processes and templates and just all the team working and functions that they had set up and really re-evaluate for somebody who's remote. I think one of the benefits is I was that first PMM and I was remote. So I had a lot of influence on how we did things. But that being said, our team grew very, very quickly, we hired four more people in a matter of a couple of months. And so what was really important for me, and I think it's important for anybody who's moving into this remote world is to consistently provide feedback on your experience. Most people have never worked remotely until now. And so they just inherently did not understand some of the challenges I was going through. And so for me, it was really critical for me to talk to my boss, my leader, my team about what was difficult. So some of the things were around communication, engagement in team meetings, like we have a weekly standing meeting. And it's really hard to get excited when everyone's in the same room and they're talking and it's kind of loud, and it's hard for you to get a word in, I had to be really cognizant to voice that, you know, "hey, it's hard for me to feel excited and to be engaged in this moment". And so, for me, it was really critical to just make sure that I was voicing that to my team, and that takes a lot of trust to be able to do that.

Bryony Pearce - PMA  5:34

And then after you voiced those challenges, what kind of steps were taken to overcome them?

Sapphire Reels  5:39

Totally. So, things take time, when we originally had our team meetings, everyone would be in one room who was in one office and then I would join remotely and I kind of just grinned and bared it for a really long time because that's a personality trait of mine and once we got our product marketers who were in the Dublin and Boston office, our Dublin based product marketer, she actually said, "Hey, it would be great if everyone joined this team meeting remotely". So Monday morning for us, obviously end of her day Monday, she's in Dublin, we all now join that meeting remotely. What that does, it gives everyone a taste of what it is to work remotely and to have to communicate over that. And they saw some of those challenges of being engaged and how the meeting was run. So I think giving people an understanding of what you're going through, can really help them take some small steps, so that's just like a small example. Another example I would point to is just documentation. When you are remote, you have to really live off of documentation and that can take many many different forms from a project review to specific meeting notes to you know, general marketing or department or company information. Because people were in the office, and they didn't need that documentation because they can just jump over to someone's desk, I really had to influence how our team, even just from how we collected information, how we disseminated information and how we organized it in our G-Suite Drive, really just being an advocate for myself and saying 'this is what would be helpful for me as a remote employee, for you all to do'. It does take a lot of effort on my part to surface those things. But I find that if I just voice that feedback that my team has been pretty receptive to working through those things.

Bryony Pearce - PMA  7:38

Yeah. I really like the idea of you all doing your team meetings in isolation as well. I think that's a nice touch.

Sapphire Reels  7:45

Yeah, obviously times are different right now, but I know that there are a few other companies like HubSpot, they just recently they had a week where the whole marketing team goes remote. So I think the situation right now will give everyone a taste for what it is to be remote. And I think, how long this lasts, or as we think about going back into our offices, what I would really encourage people to do is to make note of the things that they're going through right now. And as they go back into the office, or they think about keeping people remote, just really being cognizant of some of the challenges and struggles that they went through, and remembering that when the old sense of normal comes back.

Bryony Pearce - PMA  8:29

Yeah, sure. And then I guess going back to when you first started at Pluralsight, how did the onboarding side of things work when you were remote?

Sapphire Reels  8:39

Totally, so at Pluralsight all new hires go through onboarding on site. Obviously, we are doing that virtually right now. But we have a really great people team who coordinates that and what that looks like is traditionally everyone would go to our Utah headquarters, and then you have a couple of days, usually it's three to four days, of onboarding with your onboarding cohort and you get presentations from across the company. So product marketing does a presentation on like, what is our market? What is our product? Who are our buyers? Our product team does it, everyone across the company presents to the team and really tries to help them understand who's doing what and how do we work at Pluralsight. So that was really awesome for me to just get a feel for the company. And then as I mentioned, I was the first PMM under three directors, new VP. That team was started in December of 2016, and I joined in April 2017. So as a team, we were still trying to figure out, how do we do onboarding? A couple of things that worked really well, 1) if you do have co-located teams, make sure you're bringing your product marketer to some sort of HQ or if you're all remote getting scheduled get-togethers, like right now if you're bringing a new PMM on it's really critical that you just make the space and time for people to get to know them. When we actually do interviews, we have a couple of different... we do like a professionally your experience, and we do evaluation, but like many companies, we do a cultural evaluation. And that's just a meeting where we throw this person in a lunch with all of us to see how they handle it, do they mesh with the team. And so I think that's really important when you're actually bringing someone on is to make that space, especially if they are remote, they're not going to feel comfortable asking for it. So I would say definitely make sure you bring them into your meeting so they understand how that works, but also make time for that social piece. So that's kind of within your own team, as you think about like cross-department, cross your marketing team or cross-departmentally. Something we always do is we have a marketing team channel, we use Slack, and we always have their leader introduce them. We obviously highlight their professional experience and what they're doing but something that's always really valuable is highlighting personal interests, right? You want to really make immediate connections for this person. So sometimes we'll do like two truths and a lie or fun facts about this person. And these are really simple things that people probably already do, but when you're remote, it's even more critical. Because you really need to make sure that somebody is getting a feel for 'who is this person?', and, 'can I jive with them?'. A couple of other things that I would say that were really, really helpful is being really intentional, intentional about the first project that somebody gets. So when I came into Pluralsight, one of the first things I did was implementing our sales enablement tool, and this was something that was really really high visibility. It was a really natural way for me to build relationships across some key departments. So I had a list of people that I had to go out and meet with. And through working on this I had to work across marketing to see what content do we have? What needs to get updated? I had to work across sales to see how did they want information? Am I building the right solution? I had to work across sales ops to get it integrated into Salesforce. So being really intentional about that first project that you're giving to a product marketer is really critical, because it's going to pave their way, I think things that focus on giving them a deep understanding of how the business works, of who they need to be influencing in the business. And if you can combine that with the natural onboarding of learning about the product and the market, that's really great. And so something that we do as a team is, again, we make a list of people for them to talk to, we give them the 'Hey, go talk to them, ask them to walk you through their role'. And then one other thing that we do that's really effective is we ask our new hires to run through a what is product marketing deck with people in the business and so this kind of reframes the expectation. I know, as product marketers, we often hear, 'what is what is product marketing, what do you actually do?', we have them run through that deck with people that they're working with as well.

Bryony Pearce - PMA  13:02

Okay, and then I guess like focusing on the social side of thing as well do you feel like you have to put more of an intentional effort behind... so a lot of the time, if you're in the office, for example, and Monday morning rolls around, it's natural for the first thing you might talk to someone about being "How are you? How was your weekend? What did you get up to last night?" That kind of thing, I feel like with remote workers, from personal experience as well, those general kind of day to day interactions that you miss out on and sometimes don't realize that you miss until you kind of have it again.

Sapphire Reels  13:29

Yeah, I think you're totally right. And I think if you've never worked remotely, you don't really understand how impactful and challenging that can be. So a small example is, let's say we all have a meeting, we've all had these situations where somebody, an exec maybe, makes a decision and everyone's kind of like 'what?', 'why are we making that decision?', or, 'I don't have enough context. I'm not really sure what's going on here', right? Like, everyone kind of has this general sense of like, 'Whatever', but in the meeting notes it's 'okay, yes, we'll go do it', and the meeting ends, everyone leaves and goes back to their desk and they have a conversation about like, "oh, that seems crazy, why are we doing this? I don't get it. Can we talk about this?". If you're remote, you don't get that, as soon as the Zoom call ends unless somebody's Slacking you or emailing you about it, you don't see that, so it can create this really strong divide. And even just as a team, like you commiserate on things, that's your work family. And so, you do have to be really intentional. I mean, I think personality plays a big part in this, I am somebody who's pretty bold and forward for better or for worse, I have a pretty strong personality. And sometimes I find myself kind of like hamming it up. Like I honestly think about myself as like, 'how do I market myself to these people?'. And I know that sounds really crazy and like, structured but it's not, I think about like, okay, I want to position who I am and the value I bring, so professionally I want them to know what is my role and what I do but I also want them to know me personally. And I want to make sure that I'm promoting it across the channels they are on and I honestly think about pricing out like my time so for me something that I do is obviously we use Slack, if you use Microsoft Teams or whatever, I put myself in watering holes, like we have a bunch of different topic-based channels that are just off-topic, one I joined this week, it's like 'binge-worthy' because everyone's bingeing on content. And I've just made new contacts, they're just talking about shows that we're watching. We have a 'nerd stuff' channel where we talk about like Star Trek. Um, so putting yourself into those different watering holes is superduper important. I also find that I really have to put myself out there and I have to be very forward with who I am. So whenever I have a new meeting with somebody, obviously we talk about professionally what we do in our role, but I will always make a point to say like, "Look, there are two things you need to know about me and two things I need from you", and the main thing is transparency. And the second thing is communication. And those are really intertwined. Like, 'hey, maybe your boss is giving you a directive and you don't really understand it, or maybe you just found out about something that's coming out, that's okay, I just need to know those things'. So I think from a social standpoint, it's really about you do have to be intentional, and you do have to put yourself out there more than you would. And if you're not comfortable doing that, I think that's something that you have to voice to your team. I know there's a lot of folks that I work with maybe on our product side of the house, who are engineers who aren't as forward and as crazy and people have had experiences like, 'hey, I feel like they're not really engaged on meetings', but I've had meetings with them and the whole time we're laughing it up, and we're doing things so I think it's just about recognizing that people are social creatures, but that manifests itself in very different ways. And you have to be very transparent about who you are, but also have empathy for how others are and how they want to social communicate. You know, some people don't like small talk, and they do it in the office because that's what's expected, but the second you take them out of an office and they're working remotely, you don't get that from them anymore. And you might think, 'okay, what's going on with this person?'. But that's not actually how they like to communicate. They don't like to be social like that, but they felt pressure to do that. So I think it's just about really having a lot of trust and being open to feedback.

Bryony Pearce - PMA  17:20

Yeah, that makes sense. And then on a day to day basis, how do you most commonly interact with people like will it be more so over Slack, you mentioned you use that tool, or is it phone, video call, email or?

Sapphire Reels  17:34

Yeah, it's a combination. We definitely do a lot of Slacks. Again, like I said, I make sure that my work is very visible, and what I'm doing is very visible and my personality and who I am is very visible. So, you know, I'm constantly chatting with my team on Slack and team channels. We have kind of project-based channels, individual DMs, I also have a lot of Zoom meetings, that's for sure. And email. I have my set staple kind of group of calls throughout the week and then ad hoc meetings. I think that, and this is something we can get into later, but I think that as a remote worker, you have to find a balance of what works for you and understanding when a certain type of communication is important. So over the last four years, I've really taken the time to figure out like, 'Okay, what is the most effective way for me to communicate this information or get the information that I need?'. But yeah, I would say most of my time, it's been in Slack and then Zoom as well. Email is less frequent, I would say.

Bryony Pearce - PMA  18:45

How do you find, from in house experience, personally as well, you get a lot of those you know, 'can I just' or 'can you just this', that really kill your flow. Do you find you get that less working remotely or more? Because I find sometimes, although you don't have people physically there asking you for stuff, Slack can sometimes be the equivalent, you know when you can hear the ping going off in the background, how do you find that personally?

Sapphire Reels  19:10

Yeah, that is a really great question. So something that I think people who have never worked remotely and are now working remotely, or in the future when we all go back, and they're working on remote teams is really understanding the difference between asynchronous and synchronous communication. So asynchronous communication is like, "Hey, I'm going to send you this message. And I don't expect you to respond right away". Right? So like, I send you an email and you get to me tomorrow, that's totally cool. Synchronous communication is, "Hey, I sent you a message and I expect you to respond right away." Like I text you about my day, I'm texting my best friend about my day and I expect her to text me back right now. When you're in an office synchronous communication is generally what you thrive off of. You're in a meeting, you get an immediate response from people, you're sitting next to someone at their desk, you can turn to them and ask them a question. So I think there's a really big need for people to be really cognizant of the type of communication that they're trying to send. There's a couple of things to think through, like okay, should I Slack this person? Should I email them? Should I schedule a meeting? Well, it's like, okay, am I just sharing information? Do we need to have a discussion? Like, that could probably just be good for an email. And I will say, like, "Hey, here's just some information. I don't expect you to respond right away", or I will be very intentional and say, "Hey, we have a decision to make, I need you to respond to this email by 5pm tomorrow". There's also decision making is likely happening in meetings. Is that a quick Slack? "Hey, we made this decision". So I think understanding when that type of communication is needed, and I also think that people who are now working remotely who maybe haven't, really just providing feedback around this. So I'm somebody, like I said, I consistently provide feedback. So it's funny a coworker of mine the other day, she was like, 'you know, when I'm in the office like, and I get Slacks, it's really easy for me to drown them out. But when I'm here at home, I feel so much stress to respond'. And there's a couple things that I mentioned to her one, I was like, there are times when I don't respond, you know what I mean? Like, you don't necessarily have to. And so I think there's a couple of ways that you can go about that. One, provide feedback to people. There are times when I've said like, "Hey, sorry, I'm deep in a project like this a little bit disruptive. Is there another way we could possibly communicate?". I also asked about priority, "hey, what do you need? Why do you need it? When do you need it and what's driving that deadline?". It's totally, perfectly acceptable to ask those things. Something else I would say is setting expectations as a team, if you're not talking as a team to say, "Hey, if I send you a Slack I expect an answer or if I send you an email...", like you have to establish the standard as a team as to what you're working for. And I think one of the biggest things is people need to recognize that when you're not in an office, you don't have those visual signals, right? If I'm in an office, and I want to go talk to you about a project and I see you have your headphones on, you're typing away, you have many windows open across multiple monitors, I'm probably not going to bother you. If you're remote, I don't have those signals. So it's up to you to create those, set a Slack status, block off your calendar time. I think it's really important for people to protect their time and also understand that the expectations that are in the office don't apply. So one of the things that a lot of remote workers or managers leading remote people or just those working with me will have to understand is, understanding different expectations. So like you need to evaluate someone based on the outcomes and the results they're driving and not how responsive they are.

Bryony Pearce - PMA  23:06

Yep, no, that's great and something that I should probably take on board myself, I didn't even think...

Sapphire Reels  23:10

We all need to remember! There are times I'm like why is this person not responding to me? And then I'm like, oh, they're probably busy, right?

Bryony Pearce - PMA  23:20

Okay. So you said not too long ago that you have kind of staple calls that you'll have in the diary. What kind of calls would those be kind of week to week?

Sapphire Reels  23:31

Yeah, that's a great question. So I guess kind of what my week looks like. So every Monday morning, we start with the team sync. It's something that's time-zone friendly. So again, as I mentioned, we have someone in Dublin, Boston, and then Utah and I'm in Los Angeles. And so we have it in the morning when the time when everyone comes so that everyone you know can get the same information. In that team sync we have rotating hosts, so a different PMM or Director hosts it every single week. You know, we clock the agenda the week before, we'll invite people in, but it's kind of a place for us to just connect and start our week. So as you mentioned before, right, generally people come into the office, they have their coffee, and then they go to their meetings. This is that time for us who are remote or co-located to connect. So we'll have that kind of meeting a lot of the time it's awkward, and I think that's one of the things about remote work that people don't understand is it's awkward, and you honestly just have to embrace it. And that's kind of like our team culture, we almost thrive on that brand of like, "Okay, well this is really awkward. So time of death is 8.30. Okay, bye everyone". Like it's just how it is, but like, it works for us and we embrace it and we love it. And like, you know, after the meeting, we're like, 'why did we have that meeting' but that's the purpose of it. It's just there for us to connect and have that moment. So that's kind of the start of my week. And then I would say consistently, I have meeings with my product teams. You know, I've worked with different product teams, I work with about six different product teams right now. And so we kind of establish the cadence that works for us. So I have one that's really gearing up towards launch - we are meeting on a weekly, sometimes twice a week basis. I have other teams who are very early in discovery and product development process and so we may only be, you know, every other week, once a month. So it just honestly depends on the product. I also have project meetings. So we are kind of a project-based team in my work. Although I do the same kind of responsibilities, the work that I'm doing every single quarter definitely changes. And so I'll have project-specific meetings, like for a launch, for example. And then one-on-ones are definitely something I have and I think, you know, this is something I was reading William Chia's article about remote work and he mentioned this as well. And I think there's kind of two distinct meeting types and sometimes they can bleed together but they're really important. So one of the things when I first joined, I had a manager who hadn't had a remote team member before, we would have one one-on-one a week, and it was an hour. And after a couple of months, he was just like, "Hey, I'm feeling like inundated by information from you we come on the call, there's so much for me to wrap my head around, I don't feel like I'm able to effectively get you what you need". And so one of the things that I started doing was I started a one-on-one Doc, and I would have the agenda at the top, so I want to talk about these three projects, I would have like a summary of what I did, so here's an update on what happened this week, and then I have a very explicit action item of like, this is what I need you to do. And sometimes that's like, I need you to review this document or I need you to go talk to this person because they're not doing what I need them to, and I need somebody to help me. So very project, professional focus one-on-ones and kind of figuring out when that works. And then the second thing, which I think is one of the most valuable things you can do as a remote worker, as William mentioned, is a coffee type meeting. I have a standing weekly call with some of my teammates. Some of them are together. Some of them are one-on-one. And it's just time for us to chat. And I know William was talking about, like, "Hey, this is a time where we don't talk about work at all". For me, I take a little bit of a different approach. And if the work comes up, work comes up. As I mentioned before, where you have that water cooler talk, where you'll commiserate as a team. If you're remote, you don't get that. So sometimes you can be like, 'I feel crazy, why? Why do I feel one way and it feels like everybody else feels this other way?'. So I have this standing, and I look forward to it every single week. I have a standing Friday meeting with one of my co-workers, her name is Lisa, and we just talk and sometimes we talk about work and challenges we're going through sometimes we talk about our weekend, obviously during quarantine, we're just talking about what Netflix shows we want to look at. But it is the highlight of my week because I just feel like I get to connect with this person, as a remote person it brings in so much value, as somebody who's generally in office she also loves it because when somebody is remote they're on your team but it's also kind of like they're a third party, right? Like they're not caught up in the craziness and madness of an office. And so we both get a tonne of value out of it. And so I think that there's sometimes people think like, I don't want to force that social communication and connection, but I think it's really, really valuable. And really, really important to set aside that time, especially if you have somebody who's new, or if you are newly remote, it's really important to make sure that you make the time because one of the other flip sides of that is, you know, I'm somebody like, I'm pretty straight to the point of business, if I schedule a meeting like, and we have the first 30 minutes to get through the content, right? Like, we can spend five minutes doing the updates. And right now, that's really important, as we're all working remotely, and there's a lot of anxiety and stress, we'll do that. But you have to be a meeting moderator and you have to steer back to what you need. And people have to understand like, 'Hey, I have 30 minutes with you to get the information that I need. And I scheduled this on Monday for Friday and all week I've been waiting to get this information from you'. So I think it's just, you know, understanding that the need for the social understanding, need for the business type meetings, understanding that they can bleed together. But really making sure that you get what you need out of them and that you voice that back.

Bryony Pearce - PMA  29:13

I feel like I wish we did this podcast a lot sooner because I'm getting loads of tips.

Sapphire Reels  29:18

That's awesome.

Bryony Pearce - PMA  29:24

Okay, so next. So I guess this is kind of an industry-wide pain point. Like regardless if you're remote or in house, I guess getting sales teams engaged sometimes kind of pre-launch can be a bit of a battle, perhaps more so when you try to do it remotely? Would you say so and if so, like, how do you combat that?

Sapphire Reels  29:41

Yeah. Definitely a pain point. Um, so I've been at Pluralsight, as I mentioned for three years and I've definitely seen it evolve. So when I first joined we had like a sales training productivity team and it was like one person then it was two then it was three. And so initially, I was owning a lot of it and now we have a giant sales enablement team, very thankful for them and the work that they do. And so it's really a transition. A little bit of context. We have sales reps in Utah, Dublin and Sydney, in-office generally. And then we also have sales teams remotely across the world. So we already kind of have this co-located environment. One thing to mention is our sales onboarding. We do do that, we make every salesperson come to headquarters. So you do do a Pluralsight onboarding and a sales onboarding, generally we try to make those happen the same week. So you do three days of company onboarding, you know, two, three days, whatever of sales onboarding, how it splits out. So that's just a little bit of context there. I think there's a couple of critical components, getting sales teams ready and engaged in a launch. So first of all, I really like a push and pull model. You have to really make sure you're pushing information but also give sales reps the ability to self-service. I like to think of my sales folks as my customers and if you think about your customers like you have those customers who go really deep on research and you know, when they're using your product, they're in the help center, they're pulling what they need, they're figuring it about, they're calling you up, like, right, they're really engaged and they're the go-getters, and the people who want to do it. And then you have people who are the go-getters, but like, they're not necessarily, they're not going to be digging through your help center, they're not going to do those things like they want you to bring that information for them. So you need to really think about that with your sellers. So first of all, I always start with a what's in it for you. I think that's something that product marketers, you know, when we go and we work with salespeople, we're like 'yeah, we have this awesome new product and it's great and our customers are gonna love it'. And yes, at the end of the day salespeople do want something that's gonna make their account happy but they also want to know what's in it for them. Like, 'hey, I want to know that this product is going to increase stick you know, this feature we're launching is going to increase stickiness, which means more retention, which means your customer is going to renew so that means more dollars for you'. So always starting with the what's in it for you, and that's the first line of my communication. I'll send a slack message that's like, "Hey, do you want to increase your deal size? Do you want to improve your retention numbers, then listen up, and I'll link to the information". In terms of push and pull, I think it's really important to be in sales watering holes. Our sales teams, they have their team meetings, they have the regional meetings, we get time in those. We've talked to sales leaders, and we've negotiated to say, "Hey, when we have a launch, we need time in your team meeting to talk to them". And that gives you a lot of rapport, right? That's something that's challenging as somebody who's remote is to build rapport, coming into their team meeting where they already feel really comfortable talking and working with each other creates a sense of trust, and they'll get to ask questions, they'll get to know you, and make it fun - don't make it like some stodgy thing, be interactive, be excited about it. You have to be the one who's super excited about this thing and like leading the charge. So definitely going into team meetings providing that information. Making it really simple. I also will generally do some sort of like on-demand type webinar, that could be a recording from a team meeting, right? Like that might be the right thing, but having something that they can refer back to. And then for those who want to self-service, I'll do like a checklist, like, here are the 10 things you need to do. And then I'll also do like, okay, you know, here's a link to more information on each of those steps. So I think it's really about just deeply understanding the types of sales personas that you have in your organization and how they want to receive information and making sure that you have a good balance of here's what you need to know really simply because you will have reps that that's all they're going to listen to. And then also you have those reps who are going to want to dig deeper and making sure that you have something there. I think another thing that's really critical to building trust with sales is if you have a sales kickoff, make sure you bring your product marketers, I've gone to our last three sales kickoffs and honestly, it's the highlight of my year because our EMEA team comes over and we just have a ball with them. But also, it just creates a lot of trust and rapport. And you know, I have people who I, you know, they're all over the globe, and they've met me in person. So SKO is a really, really great time for product marketers to build that trust as well.

Bryony Pearce - PMA  34:17

So how often would you say you actually have that get together, HQ, all of you?

Sapphire Reels  34:23

Yeah, there's a couple of different opportunities. So like I said at Pluralsight we all do onboarding on site. We have SKO, we also have holiday party at the end of the year, and those are regional. So there's one in Utah, there's one in Boston, there's one Dublin and we actually just opened the Sydney office so I'm sure there'll be one there this year, so you have the ability to travel into the regional holiday party. We also have tonnes of team off-sites. I know that my team has won at least once a quarter. We'll all go to Utah. We did zip lining ones like we've done many many different things. I know that there are some teams like we have a group of engineers that are based in Brazil, we had one team go down to Brazil to do their off-site there. So there's plenty of opportunities and Pluralsight is super open to that. I think the way that we think about it at Pluralsight is like, it's up to you and your team, right? Like if you and your team feel like you need to be connected, it's up to you to vocalize that. So actually, something that I did that was really important for me, and I learned this in my previous role. So the company was based in Atlanta, I started going back there once a month, or every six weeks, and I would be there for a couple of days or up to a week to have that in-office time. That was really, really critical for me, and it was just something that I you know, negotiated or I just talked to my leader about, I would say, 'look I'm feeling a little disconnected from the office. I would love the opportunity to be able to come in every couple weeks to have that in-office time.'. And generally, it's just full of meetings and it kind of feels unproductive, but it's critical for me to get back into like, motivation and mindset. And that's what I did for the first couple of years at Pluralsight and my other company. Now, obviously, not today in quarantine, but previously, my travel slowed down because I built the rapport and I built the trust. So I think it's up to the individual to voice when they're feeling like they need more connection. And I think it's also up to the leaders to create those opportunities and create an open culture where teammates feel like it's okay to say, 'hey, I need more in-person time', because you can't ignore that, you can be a fully remote company, but you can't ignore that face to face time is really critical. And so I think it's just about listening to your team and listening to your employees.

Bryony Pearce - PMA  36:35

Okay, awesome. Thank you. And then so obviously, with everything that's going on at the minute with COVID-19, essentially everyone has been forced into this kind of remote working situation. Do you have any advice for anyone who's either new to remote working full time for the foreseeable, or during the COVID-19 like to help them find their feet during this?

Sapphire Reels  36:54

Totally, yeah, well, first of all, it's funny, a lot of my teammates or friends that I have who know I work remotely will come to me they'll say 'you've worked remotely like, how do I do this right now tell me'. And the first thing I'll say is I've been remote for four years and I know people who've been remote for decades. And the number one thing I'll tell you is right now is not the norm. Don't beat yourself up, right? Like, first of all, if you're working remotely, like there are days when everyone isn't productive, whether you're in an office or your home, there are days you go in the office, and you're like, I'm just not feeling it. I'm gonna go to my meetings but in between the meetings, I'm not really getting work done, something's not right. The same thing happens when you're at home. And people feel this immense sense of pressure to be productive because they are at home and they want to, you know, be responsive and doing all these things, because they don't want to portray this image that they're not doing their job. So I would just say don't beat yourself up around that idea, especially in this current environment. Like I said, you know, I'm somebody who I am super productive from home, I really thrive on working from home. And the last three weeks have been really, really challenging for me because there is a lot of anxiety, you know, not only am I anxious about what's going on, but you have a bunch of people who've never worked remotely that I have to work with. So I would just say, you know, be kind to yourself and have empathy for others, you don't know what somebody else's work from home situation looks like you don't know, all the things that you're going through. So really just take the time to not jump to conclusions. Like that example I gave, if somebody's not responding to you on Slack, they're probably not ignoring you, they probably have other things going on. So that empathy is critical. I think changing your perception, as I mentioned, that idea that somebody is not responsive means they're not productive, I think especially people managers need to understand that they need to set the work with their teams to set the expectations of how they will communicate. And so for me, like I know, if somebody sends me an email, I probably don't need to answer it right away unless it includes somebody who's outside of our organization. I also know that if somebody sends me a Slack, and they know about me that maybe they're not expecting an immediate answer. And I know that if my VP or my director calls me they're expecting me to pick up and it's critical, right? These are things and habits I've just developed over the last few years. And I think people are forced into this situation. So just talk about it. Just create space for your team to do that, and have them give feedback, right? Like, "Hey, I'm having trouble. I'm getting a lot of Slacks. I'm feeling like, I'm not able to prioritize my day, and I'm getting interrupted". So being able to set those expectations and feedback and iterate is really important. Another thing I would say is communication. You know, I think that people underestimate or maybe overestimate how good communication is at their company. And when you're forced into this remote world, the cracks are really quickly exposed. People have very different communication styles, right? If you've never heard of like a disc profile, I highly encourage you to go check that out. And you may not really realize their communication style until you're in this situation like I mentioned like some people don't like small talk, right? Like there are different things like that. Some people are very straight to the point like you don't get that unless you know the person and so something that I just think is really, really critical is to just really be cognizant of how you're going to communicate. Something that really took this off for me was honestly learning how to write emails to executives. You know, if I'm talking to my CMO, she does not have the time to dig through my four-page launch document, she needs like a four bullet-point summary of what we're doing. She needs the two action items that I need from her and she needs it in an email so she can respond to it. I know that about her and that's the type of information I get her. Somebody else I'm working with may need more detail. So be really cognizant of how you are communicating again, it goes back to asynchronous versus synchronous comms. How does this communication need to happen? So if it's, you know, 'hey, I'm just trying to build up a relationship with you', that's great, use Slack. 'I need this feedback right now'. That's great, use Slack. 'Hey, I just need you to know this information', that's an email. So really be cognizant about your communication method. I would say running a meeting is really, it's really, really important to think about how you run meetings, because you are having Zoom meetings, I think meeting pre-reads are really critical for people to wrap their head around things before they get in the room. Whenever I come into meeting, I make sure everyone's read the pre-read and if they haven't, I'll give them some context. Make sure you recap agenda items at the top of the meeting, right? Like, 'hey, these are the things I want to talk about. Does anybody have anything to add?'. You're gonna have to act as a moderator because people aren't in the same room and so like, some people feel really uncomfortable. So you recognize that somebody hasn't talked for a while, be like, 'hey, Sapphire, what's your thoughts?' Right, like 'Sapphire, I see that you unmuted and then you re muted because somebody else was talking is there something you want to say?', if you're on a webinar or like something like that you have to be more of that role. And then after your meeting, make sure you're reporting out. You gotta learn how to document information. I know, William talked about this a lot in his article, being at GitLab, you know, they're all remote and super transparent in documentation, that's something that they all do, they all do it very differently. If you're used to being an office, and now you're remote, you're probably not used to the level of documentation that's needed. So figure out what works for you. You know, making sure you ask people, is this too much information? How did you want to receive that? Is there a better way I could have communicated? And then there are a couple of other high-level tips. One thing I would say is schedule flexibility. So most people work remotely because they enjoy flexible schedules. Like I do it because sometimes I wake up at six o'clock in the morning and I'll do two hours of work and then I take a two-hour break and then I hop back online at 10. Like, that's okay, and I think people expect to replicate their in-office schedule when they work from home. And I don't think that's always the case, especially right now, if you have kids, if you're caring for other people, that is not the reality. So be open, talk to your team, talk to your manager, whatever it is you need to do, make sure you're not rocking the boat, but like someone on my team was like, "Hey, I have two young kids and my wife is also working from home and running a business like, there are times during the day, I'm not going to be available. So I'm going to block out my calendar. And if I don't respond, that's okay". So figure out the schedule that works for you and set signals for yourself. That's really critical. So I'm lucky enough I work from home all the time. I have an office, when it's over at the end of my day, I close my laptop, I close my office door and I take my dog for a walk. And that's my signal that I'm done for the day. My boyfriend's not working from home and his signal is he wears his shoes all day and then when he's done working, he takes off his shoes. I know it's really silly, but you have to just find whatever that thing is that works for you. So like, I know some people are stuck, they're working at their kitchen table like we talked about that before, you know, before we started recording this, and you just have to find some sort of signal that indicates to you, I'm done working for the day, because you can work so, so, so many hours. A couple of other quick things would just be like making sure your work is visible, that goes back to documentation. You know, when you're in-office, people see that you're working, people see that you're doing things, some leaders, again, haven't changed their perception of what it means to be productive and to be a good employee in a remote environment. So make sure that you're making it visible. I send status updates on Slack, I do all that. And the last thing I would just say, is like, I know a lot of people love like the Marie Kondo show, you know, sparking joy, like find ways to spark joy. You know, I'm lucky enough that I have been remote for four years and I'm really comfortable with the current status of working from home and so something I really like, have enjoyed for the past few weeks is stepping up to help others feel comfortable working remote. So a couple of things that we've been doing that have been really critical for team culture is we have something called YDAD on Friday, which is you deserve a drink, and it's a happy hour. And it's been super fun. We'll play games, we did like a baby picture guessing game, I had everyone send me their baby pictures. You know, we all guess who it was. We've done some teams play jackbox TV, if you've ever heard of that. So just making sure that like, you know, posting why you're thankful for somebody, like just doing those things that make people really happy in a culture environment are super important right now.

Bryony Pearce - PMA  45:36

Okay, so that kind of ties into the next question. So before we did this podcast, I put it out to the community because I know obviously a lot of people are asking about remote working at the minute. We've had a fair few product marketers come back and put some questions to you. The first was if you had any tips for how teams can stay connected and communicated, without having to have those forced check-ins and status updates, and I guess the ideas that you just ran through are some of those, were there any more kind of day to day type things you'd recommend?

Sapphire Reels  46:04

Yeah, that's a good question. So I think one of the perceptions to break or the things to understand is that when you are remote communication is intentional, right? Like, when you're in the office with somebody, and you're just chatting, like, it seems so much less formal than like when you're at home, and you have to, like, ask somebody to get on a Zoom. And it's like, I don't want to waste their time. I don't want to do this. So I think it's to be expected that communication has to be intentional. And I think about as a team, it's just about establishing what you want. Like, if you don't establish that and let's say you're a manager and you're working with somebody and you like, send them a Slack message. It's like, "Hey, do you have that thing? Are you working on that thing? Where's that thing?", like that seems really micromanaging to somebody. So if you establish your teams and set expectations, like it works, so like for us again, it works to have, we have, one of the things we do is we have a product marketing stand up channel, and it's just every Monday morning, there's a reminder that says post your three Top Things this week, and it just gives everyone on the team a sense of what you're working on. And let's say my teammate's working on something that I can help with or that overlaps with my project, I'll send them a quick ping in a thread and say, "Hey, I'm gonna DM you about this", or we'll chat it out in the thread. So just establishing that stand up early in the week is super duper helpful. And at first, yeah, sure, it felt like a chore, but I promise you, it will pay off. And then at the end of the week, we do an update. And that goes to our team, like our immediate small team and our VP and that's just like a, here are the three things that happened this week. And that's like things that moved status, challenges or wins. And then here's, you know, the two things I need you to know or what I need help with. And sometimes it's like, I need you to review this document or like, hey, this team isn't doing what they need to do. And then like, hey, have you updated? We have OKRs at Pluralsight, so making sure that you update those. I think it's also about creating boundaries, or just understanding boundaries. So like again, because you're remote, and you only have a certain amount of time with people, and you have to really be cognizant of that. Like, you may want to have a team meeting, that's all business, but you should balance that out with a team lunch, where you guys just come together and have lunch and talk. Um, you know, you may have your team channel or a project-based channel that's very focused on business, but you should also balance that out with some off-topic based Slack channels. So like I mentioned we have binge-worthy, we have nerd stuff we have like, other people's pets where people post pictures of their pets, which is amazing. If you don't have that, you should definitely get one. So I think honestly, like, it's just about talking. And if you ask somebody, hey, what's the best way for you to communicate this? You'll be surprised how much information you get. So everything is going to feel forced right now because it is not the natural way that we work as humans and that's okay, embrace it and lean into it and understand that everyone's going through it.

Bryony Pearce - PMA  48:55

Okay, awesome. And then there's a couple of tool requests. So the first one was what project management tools are the team using?

Sapphire Reels  49:05

Yeah, so at Pluralsight we're lucky enough to have, we have an in house creative team and brand team. And so we have creative producers who use Work Front for project management. So if we have launches, campaigns, you know, items that need to go through creative, we actually submit a request with like a brief of like, what do we need, what's the audience, you know, whatever, then we'll have a kickoff call or like a meeting with the creative team to just talk through it and then we'll work through Work Front project management to do like, you know, I need this messaging Doc, we add that there, the copy team writes copy, then, you know, we review copies and design, we review design, and then we put it out. So we're really lucky to have that from like a tracking perspective, in terms of like how our team works. Even if you don't like, even if you're forced into this situation. Let's say you don't have a project management tool. I think there are two key things to think about. One is some sort of system to track changes and delegate work, and a system that provides visibility for everyone who needs it. And that doesn't have to be like an Asana or Work Front. Although those things are perfect and amazing for what they do. It can be done in Google Docs. So generally, we'll have like a Google Doc plan, which has like the objective, the strategy, the tactic, timeline, you know, high-level timeline, FAQ, like the one-stop-shop that somebody can go to learn about a project that's in place. And then we'll also have a tactical spreadsheet which will have like the team and the owner and you know, the key message and the status and the link to deliverable and like a Gantt chart. So I would say, you know, for us we are lucky enough that we have had this process in place if you're looking to start some sort of project management tracking, honestly, G Suite or anything like that, Microsoft 365, whatever you use, like that can work, you just have to communicate it and say, "Hey, this is where everything lives. And if you don't update this document here, I'm not going to know". And so I, as a project owner will say, "Hey, you know, here's the document. Here's the intention, dub, dub dub team, I need you to fill in this thing, social team, I need you to fill in this thing". So as long as you can delegate out work and give that visibility, it will work really well. Something else we do is we have and I know, like, the common consensus is like no more Slack channels, but we have project-based Slack channels where if we're standing something up, we have something so there's like the, again, the asynchronous communication and the synchronous communication. We have a Slack channel where it's like, immediate, I need this thing. But then we also have the documentation where we'll have like an FAQ and it's like, here are the questions we need to answer over the life of this project. But here's, you know, the Slack channel does immediate questions. Um, one other thing that's super helpful, that we have as a team that's not necessarily just about remote work. But as a release and launch tracker, so I work with six different product teams, I track where their features are. And I am responsible for updating that on one spreadsheet that's accessible for various stakeholders throughout the business. So not just product marketing, but you know, solution architects and pre-sales folks and our strategy team, anybody who needs to know, that's really helpful for people understanding where a product is in the lifecycle.

Bryony Pearce - PMA  52:27

Okay. And then final question. So I guess when you're in person working with someone, it's easy to be able to see, you know, if they're overwhelmed, or they've got the capacity to take on more work and that kind of thing. How do you gauge someone's state of mind without kind of seeing them like that?

Sapphire Reels  52:44

Totally. Yeah, that's a really good question. You have to ask, I know that and that's like, that can be uncomfortable, you know, based on the trust you have or the company culture you have, but like you have to be the one who goes out on a limb to say, how are you doing? You know, when you're in the office, it's really easy to see what somebody is working on, it's really easy to get those, you know, body signals even vibe of like, hey, that person seems stressed, don't go bug them. You have to ask people. And that's why it's really critical, as many remote people will say, to have those, you know, here's my business meeting. And here's my social meeting or my social channel, like, that's where you get that information from people. So a really great example of that is my teammate, Lisa and I, we have that standing Friday meeting where we just it's like 30 minutes for us to do and talk about whatever we want to talk about. You know, throughout the week, I'm working with her on projects and things like that. And then on Friday, we'll come together, and I'm like, so how was your week? And she's like, Man, you know, this week was tough, I had this, this and this and I'll be like yeah, same for me. And she's like, yeah, you know, I'm feeling like I don't have the bandwidth and I'm like, same. I'm like, well, we should go talk to Tom, who's our boss, we should go talk to Tom about that and see if we can rebalance things. Right, maybe there are some things that you have that I should be doing maybe some things that I have that you should be doing. So you really need to establish like those informal channels. Another thing that can be really helpful for those managers who are managing remote people is really thinking about your one on one time. So I have a one on one document, I just recently moved managers so this one's shorter, but my one with my previous manager for the last three years was like 100 pages on Google Docs, and it was just like a running Doc, but I literally would just use it to run our one on ones and I would allow my manager to self-service, I would say, here are the three things I'm gonna be talking about, here are the updates, and here's what I need from you and here it is prioritized. You have to think about documenting these things and naturally, it will come out so if you go into a one on one meeting with somebody and they have, you know, three items listed, three high-level agenda items and you see like, oh my gosh, they have so much work, like you know that person, if you've worked with them before, you can probably gauge that it's too much work. So documenting, making the work visible is really, really critical, but have open conversations. That's why again, going back to that previous question of like, how do you have those status updates and make it not feel forced, you have to do some sort of intentional forced communication to really know where people are at and it's not going to look the same for everyone. What my tracking doc may not look the same as somebody else's tracking Doc, but the biggest thing is getting it on paper.

Bryony Pearce - PMA  55:41

Okay, awesome. Well, that is all the questions from me. Thank you so much for your time today Sapphire. I've learned so much myself. So hopefully everyone else listening has as well.

Sapphire Reels  55:50

Yeah, thank you so much. This was so exciting. And anyone can feel free to reach out to me about you know, remote work and what they can do and to chat about it. I really love remote work and it's worked really well for me for the past four years and I'm a huge advocate and it can be super fun. So if you want tips on making it fun and easier, just reach out.

Bryony Pearce - PMA  56:09

Thanks again, Sapphire.

Sapphire Reels  56:11

Thank you.