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What are your SaaS company's current growth marketing challenges and wins?

November 21, 2023

How B2B SaaS Marketers Should Be Using Thought Leadership, Documenting Decisions for Full Company Transparency, & Making Async Work Across Time Zones With Tara Robertson of Chili Piper

In this episode, Jeanna chats with Tara Robertson, Head of Demand Generation at Chili Piper, about all things remote work and B2B marketing.

Tara Robertson is the Head of Demand Generation at Chili Piper, a scheduling and lead-routing solution that helps revenue teams book meetings faster. Tara is a 10-year B2B marketer who’s worked in various marketing roles. Before joining Chili Piper, she led the demand generation team at Top Hat, an educational software company that makes active learning come to life. Tara hosts Chili Piper’s Demand Gen Chat podcast, which discusses tactical methods to improve marketing, and writes the monthly newsletter, The Sauce.



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

  • The importance of thought leadership in B2B marketing
  • How to leverage LinkedIn thought leadership ads to increase demand
  • How to take advantage of working across time zones 
  • The importance of documenting decisions and creating an accessible records system (especially in remote work!) 
  • Tips to stay productive and get things done while working remotely 

In this episode…

Thought leadership in B2B marketing is a content marketing approach that positions a company as a trusted industry leader. The goal is to increase brand visibility by establishing the company as an expert in its field. How do companies benefit from thought leadership?

Seasoned marketing expert Tara Robertson affirms that using thought leadership drives results and reduces marketing costs. It also increases brand awareness, enhances credibility, and improves lead generation and customer retention. She emphasizes the role of thought leadership in building a personal brand, as it lets you promote your reputation and skills and attract potential employers. Generating thought leadership content can be as simple as writing blog posts, LinkedIn content, newsletters, or hosting a podcast.

In this episode of the Remotely Cultured podcast, Jeanna Barrett chats with Tara Robertson, Head of Demand Generation at Chili Piper, for an insightful conversation about B2B marketing. Tara discusses the importance of thought leadership in B2B marketing, tips for working asynchronously and leveraging time zones, and how to create an accessible records system.

Resources mentioned in this episode


Jeanna: Hey, everyone, welcome to Remotely Cultured. I'm your host Jeanna calling in from Roatán, Honduras, where I run FPS and I host this podcast. This episode is brought to you by First Page Strategy. At FPS, we use data and big ideas to produce exponential growth for product-led brands who need to nail their acquisition goals and want to work with a flexible, non-traditional agency. For example, in one year, we've grown a client's total revenue 197%, their organic revenue by 300%, and their paid revenue by over 1,000%. If you're a SaaS, FinTech, or startup and need to hit your 2023 high-growth acquisition goals, check us out at firstpagestrategy.com. All right, today on the podcast we have with us Tara Robertson. Tara is a B2B marketer with over 10 years of experience in various marketing roles. As the head of Demand Gen at Chili Piper, she also hosts the podcast Demand Gen Chat and writes the monthly newsletter The Sauce. Tara is powered by pizza and negronis. Welcome Tara to the pod today. Where are you calling in from?

Tara: Thanks so much for having me. I'm calling in from Toronto in Canada. So pretty far away from you.

Jeanna: Yeah, right. Maybe somewhere along the same plane but like very far north, a little bit colder perhaps. What's it like in Toronto right now, are you guys heading into fall, like what do we got going on?

Tara: It's pretty warm. I'm wearing layers just because my air conditioning is really working hard today. So I'm waiting for fall personally, I'm a big fan.

Jeanna: Yeah, me too. I'm a big fan of fall also which is hilarious because I live in the Caribbean so I do every single year make a trip back to the US or some other colder location for fall, I'm big fall fan as well. Um, and what about Toronto is unique, like for people that haven't been there? What is special to the culture of Toronto? What's the city like? What should we know?

Tara: Oh, um, I think it really depends where you're coming from to compare it to something. But for me again, I'm a huge fan of fall. I'm a big person that just loves seasons. So I think it's, we have really distinct four seasons here. So I think for a lot of people that would be really unique if they're coming from other parts of the world. 

Jeanna: Cool.

Tara: And we have a really great restaurant and bar scene here in Toronto. So I live on the west end of the city and there's a ton of great restaurants breweries, distilleries, just a lot happening in the kind of small business and restaurant scene.

Jeanna: Nice. And what's the work culture like in Toronto?

That's a good question. So I've always been more on the startup side of things. So kind of a hustle culture, not necessarily the straight-up nine to five. But there is a pretty thriving remote work scene here especially now that kind of post-pandemic people are more open to working at international companies. In the past, it was a pretty small scene here. So I felt like you would run into the same people all the time. But now I've got a lot of people who are working for US companies working for European companies, just because that door has really been opened for us.

Jeanna: Right, love it. And so how long have you yourself been remote? You work remote now for Chili Piper, yeah?

Tara: Yeah, so Chili Piper has actually been remote since the beginning. Which is pretty unique for a startup. But I joined two years ago, at my previous role obviously I kind of had to shift remote during COVID, I was working in Toronto office. And honestly, we started getting the emails saying, "we're going to come back to the office soon, get ready," and that was when I started talking to Chili Piper because I just, I had a great routine working remote and I couldn't picture going back to an office so I got lucky when I found this role.

Jeanna: Cool. Yeah, I love that. Good for you. Because if I would have gotten an email telling me to go back to the office after COVID I would have done the exact same thing. I read on your bio, it's probably changed now, that Chili Piper is distributed in more than 160 cities and 35 countries across the world. That's incredible. How big is Chili Piper now, like can you tell us a little bit about what the work culture is like there?

Tara: Yeah, because we're so distributed I feel like it's hard to pin down the culture.

Jeanna: Oh yeah, okay. 

Tara: Again, people all over the world. But we are just under 200 people and yeah, very spread out. So I think I'm the only person in Toronto but we have people across Canada, we have a lot of our CS team is actually in Brazil, so they bring a totally different culture to the team, which is really fun. And we have a lot of Europeans as well. So super spread out. But one thing that we like to do is we encourage people to meet up for team dinners and things that they can expense and that gives people a chance to meet up in person and we have a Slack channel where we all kind of celebrate those, we call them Piper meetups, and we celebrate making those meetups happen.

Jeanna: Okay, so if anybody is like, a little bit easier when you have people in 160 cities or a larger company, but if you're going, perhaps you might be traveling somewhere where there's a coworker, then Chili Piper allows you guys to expense a meet-up together and you guys share it back. I love that so much.

Tara: Yeah, and some people like to get together and work from their WeWork that week. I personally work from home full-time, but some people like to meet up if you're in London, we have people there, if they're in Paris, so you could meet the team and work for a day from their WeWork and just experience what it would be like to work from Paris or Lisbon every day.

Jeanna: Yeah, that's so cool. Yeah, I'm particularly really interested — right now we're way smaller than Chili Piper. We have about 30 people distributed and we're just now at the cusp of like, how do we really make in-person events happen, because there's a lot of conversation in remote work that while you're remote, you still need in-person strategies. So how is your team meeting each other? How are you building relationships and bonds and that can be really challenging when you're smaller because in-person events where you're like flying the whole company out and putting up in hotels and paying for airports is very expensive. And so I love that idea like just allowing people to facilitate their own meetups. We do have that kind of happen in our company a little bit more organically, but that's really cool. I love it, that it's kind of a thing and you guys named it and it's part of your culture, internally. That's great.

Tara: Yeah, it can be tough to do the whole company. We try to do one a year where we get every single person together. But again like some people have issues with visas and it can be tough to pick a place so if you let it happen organically but kind of give it a little bit of encouragement that can help.

Jeanna: Right. Love it. What else about working at Chili Piper is unique to you guys, your remote culture or any systems or processes or ways of working that you haven't experienced before?

Tara: Yeah, I would say one thing, because this was my first time joining a company that was already remote, I was unsure how that would go. But really, we have pretty radical transparency, which I think a lot of companies say that they have that. 

Jeanna: Yeah, right.

Tara: But in my experience, I don't know if that was true. But we actually do have that here. So everyone's calendar is fully open, including the co-founders, you can see like when they have like their kids swimming lesson or when people have therapy, it's on everybody's calendar. And I think that transparency, obviously, when we're working across time zones, it's important for scheduling because yeah, I need to know what my peer in Lisbon is doing so I can book a meeting. But it's also helpful to see that people have like their whole life on their calendar, which I'm a huge calendar person. So my whole life is on my calendar. 

Jeanna: Same, same. 

Tara: So I really appreciate that transparency. I have like my dog walks on my calendar, I have lunch, and it just helps across the team to have that just full transparency.

Jeanna: Cool. Love it. We'll talk a little bit more about remote work in the podcast but I want to shift a little bit and just have you explain to our listeners about what you're up to at Chili Piper. Like what is your role? What does the company do? Like let's give the listeners a little bit of background.

Tara: Sure, yeah, so at Chili Piper we work with Go-to-Market teams to help them essentially drive more demo requests and meetings from their existing site traffic. So you already have qualified people coming to your website, we help you qualify them and route them to a meeting with the right rep, right then in there. So no back and forth with an inbound SDR team. We're essentially skipping that whole step in the process of booking a meeting. And we enable outbound teams do the same thing. So if you're reaching out to your prospects outbound, they can book a meeting with you in one click instead of going through kind of a whole discovery call process if you're going outbound call already qualified, so helping you a lot of those steps.

Jeanna: Cool. Love it. And what do you do in your role specifically?

Tara: Sure, yeah, so our marketing team is pretty lean. In my roles today, I manage all of our paid advertising. So obviously, because we're B2B, LinkedIn is a huge focus for us on the organic side, but on the paid side, as well. All of our paid search, and then we also, because we're a lean team, all the content that we produce, we tend to recycle it on the paid side as well. So I run our newsletter that we call The Sauce and our podcast called Demand Gen Chat where I get to chat with other marketing leaders and I'm lucky that that podcast existed before I joined Chili Piper but I was really excited to kind of pick up that torch and keep it going.

Jeanna: Nice. And so what are some of your favorite like demand gen tactics you're seeing that have been successful for you like in the past year, even like the past two years? What's working for you that other brands should be listening to?

Tara: Yeah, so one that's actually very new, so I can't say for sure that it's going to work for everyone, but we're actually testing out on LinkedIn, their new thought leader ads, which is basically allowing you to run —

Jeanna: Oh, I just saw you post some, like metrics on that, yeah, so let's let's talk about that. What is it?

Tara: Yeah, so if you've ever been on LinkedIn, scroll your feed, you'll probably see a lot of promoted posts from brands, companies. But one really new feature in the last couple of months is you can actually promote content from people within your organization. So we're running a test where our co-founder, who is also our CMO, we're putting some paid behind her posts and the goal is, obviously, we want to bring qualified traffic to our website, but we also want people to follow her and follow us on LinkedIn and kind of build that audience that way. So, so far, it's looking very promising, but it's only been a couple of weeks.

That's great. Yeah, that's definitely something I'm gonna like get off this podcast and go talk to our Head of Marketing about to start testing because we're like jumping into the thought leadership game pretty hardcore. I think that a lot of marketers already understand that that's like where content is going and where lead generation is going. And a lot of people are having success on LinkedIn through thought leadership bringing in leads — is that what you're seeing for Chili Piper as well?

Tara: Yeah, so I was pretty lucky when I joined that our co-founders are both very open to being thought leaders. I know not everyone as a marketer is in that position. 

Jeanna: That's like the tricky part, right? Because we're an agency. So we try to do this for our clients and we definitely have come across clients that do not want to be the face of their brands and that's difficult. So yeah, that's great.

Tara: Yeah, and I think at Chili Piper we've always led kind of with people first, if you see any of our ads, or even our website, it's very focused on our people, the voice of our customer, customers faces, and I think that's helped us stand out on the ad side, but one thing that's fun working with the co-founder is immediately she came to me and said, "Why can't I run ads for my LinkedIn? I want them to come for me," and I said, "Well, that's not how it works." And then months later, it is a feature now.

Jeanna: Oh great, yeah, someone was listening, right? So is that your top producing channel for leads, or like what produces the most leads for you guys?

Tara: Yeah, so for us, organic is huge, which obviously it's a little bit of a black box can't always describe where that traffic is coming from. And then the other big source, which is kind of just tied to the marketing industry now in general is a lot of marketers, either were laid off or went into new roles and now they're at a new company, and they're saying I need Chili Piper again, I had it in my last and I want to get again.

Jeanna: Yeah, referrals. 

Tara: Yeah, exactly. So we call them returning customers, referrals. You can bucket it however you want. But those are two huge sources for us, which has changed pretty dramatically year over year just because of how turnover has been in the marketing space.

Jeanna: Right. Right. Right. That's great, kind of that word of mouth marketing, right? That's not really a channel that like a ton of marketers talk about when we're talking about a marketing toolbox. Like we are an agency so we have kind of our core services that we provide people but like, word of mouth marketing is one that's come across in my career, and it really works, but it's like, how do you truly get that flywheel going? It takes like a long time, and it's kind of all the things you do right, like great customer service, an amazing product that you've built like, so. That's cool, but it's a little bit hard to do, I think. What would you say, why have you guys been successful with word-of-mouth marketing? Is that some of the things that I just listed?

Tara: Yeah, I mean, I think it's all of the above. Plus, we've always had a concerted effort on communities in general. So obviously organic LinkedIn is huge for us like I mentioned, but also just partnership communities, Slack communities, events, we've always made that a real focus. And I think I was again, lucky coming into a marketing team where that was already a priority. And I didn't have to make the case to say like, Hey, we can't put all our money into AdWords or LinkedIn. We need to be spreading it around into these other channels. And we've just been able to prove that over and over with self reported attribution. When we ask people how they heard about us, it's often events, communities, things that, again, you can't flip a switch necessarily, which is tough sometimes to make the case to the executive team.

Jeanna: Yeah, long-term investment. So do you guys have like a specific partnerships team that's working on a lot of those partner relationships?

Tara: Yeah, so we have two kind of distinct roles. We have channel partnerships, which is essentially our agency partnerships. So people that work with HubSpot and Salesforce and help implement those and then they recommend us and implement us for their customers. And then we have a product partnerships team, which is essentially all the big names in B2B that we integrate with. So we integrate with Gong and Zoom and all these big companies and that partnerships team is really focused on hey, let's get our product teams to talk to each other and figure out what we can do together.

Jeanna: Nice. I love it. So what would you say that a lot of B2B marketers don't focus on right now, but they should?

Tara: Oh, um, I feel like this might seem silly, but again, going back to that thought leadership piece, especially in B2B marketing. A lot of us, it's such a small pool, a lot of us follow each other. And if you're at a company, especially where either the co founder or your CMO doesn't want to be that thought leader, I think you should just do it. And I know that that's not what everybody wants to hear or wants to do. But it's a slow burn, but it really, you'll see results if you do that, versus just trying to force someone who doesn't want to do it to take that role. It can be, especially when it's someone above you, you're kind of trying to manage up and push them into that. I think you should just take that chance to try it yourself and put the spotlight on yourself, even if it might not be natural to you because you can take that with you when you go too which is huge. 

Jeanna: Yeah, that's great advice. This is actually, when I was saying we're really investing in thought leadership at my company, this is something that we're doing it through our marketers and kind of teaching them that there is this brand, this personal brand that everybody can be building at a company. Because I see a lot of people doing it now on LinkedIn that I started following or their content comes up in my feed and they have really amazing case studies to share results to share tips to share but they are a role inside of a company right? So then you inevitably are looking at their company. What does the company do? I think this is the way that like a lot of thought leadership is happening now and in an era where we don't really get to meet with each other in person anymore and we're all a lot of us are remote in different cities. And it feels like this is kind of a way to make yourself known in your career, grow your career, have have other brands look at you and want to hire you. So it seems really smart. Is this something you have been focusing on like before your time at Chili Piper, or what is your path been like improving your personal brand?

Tara: I would say it's definitely a newer thing. It doesn't come naturally to me at all. I'm not someone who would raise my hand to go to a speaking opportunity, but I think actually during COVID and doing things remotely the more you do it, the more comfortable you get. So it just kind of comes that way. And other pieces, just especially during COVID when everyone was remote, the barrier to putting things out, like videos that we were creating images we were putting together, they weren't as polished as I was used to in the past. So that barrier to entry to create that content just seemed much lower. And it seemed like well, I could try this and see what happens. And I think that once you try that and see the response, it really helps.

Jeanna: So what else do you do besides the podcasts, which is obviously thought leadership that you own? Are you creating your own videos or like written LinkedIn content or what do you focus on as thought leadership for Chili Piper?

Tara: Yeah, we try to do a mix. We actually have a full-time video producer in-house. So a ton of our content is actually video first, which is a bit unusual for a B2B company, but very lucky for us. 

Yeah, amazing. 

Tara: So yeah, it's often instead of, at least in my past roles, we would have something like say a blog post, and then we would be like, now how do we turn this into a video? I don't know what to do. It's not like natural, but we're almost the opposite here, where we create a ton of video content interviews at events, our CMO Lena does a whole interview video series. We're actually, she's heading to inbound next week, I think, two weeks from now. And she has her calendar just full of meetings with customers and prospects that we're filming and turning all of that into content post-event. 

Jeanna: Amazing, wow. 

Tara: Honestly, it's continuous with us. 

Jeanna: Yeah. And so you have one in-house video person that's doing all this? So do they fly around to conferences? Will they go to inbound with Lena and like do all the recording and content creation with her?

Tara: That's a great question. And he's actually on Pat leave right now, so it's a little bit funny timing, his wife just had a baby. But we work with local just video freelancers who film like typically so he won't always be able to make it. And then he does all the production after the fact.

Jeanna: Okay, that's so smart. I love that. That's incredible. Again, yeah, like just like you said, we build strategies for a lot of brands, but it's really hard. It's, it's really hard to get people to flip that switch of like, creating video content because everybody's used to written word content, right? But what we've figured out is really important as a remote brand is that you need to be offering both types of content to everybody because internally, our people that work at First Page Strategy, they're either video people, or they're, they'll read something, right? And so whenever we do a company announcement, we have to create a video for it and then also write it all out because people consume content in different ways. And like as a brand new you need to be thinking about that too, right? Like not everybody wants to be reading — personally, I am the person that's gonna read a 900 word blog post, but my boyfriend will will not read ever so he'll watch a nine minute video and it's funny like we're very different but brands don't do enough of that now. And it's like, it seems like everybody's kind of having a problem. You know, figuring out the video marketing thing and so do you think that Chili Piper's success with that is literally just investing in that internal person full-time?

Tara: I think that's a huge piece of it. I think going back to your point earlier, I'm also a written word person, I would never default video on pretty much anything even though I have a video podcast, that's not the format that I would choose. But even looking at our own metrics, like we take the podcast, obviously put it on the podcast apps. It takes our video producer, maybe five minutes to put that same video up on YouTube. With like all the right tags and making sure that you can search for it. And those guys will get a couple 100 views with just that on YouTube. So it's just funny seeing the way that people consume things is always going to be different than what you expect because I felt like no one's gonna watch a 45 minute video of me interviewing someone that seems so — 

Jeanna: Right! 

Tara: But it can't really hurt to put it out there for search. And we also make clips available to our guests when we have them. So we send them like really short clips that they can use to promote and obviously those clips make them look like experts, make them look great. So they're going to share that on their LinkedIn too, which helps spread that.

Jeanna: I love it. That's super smart. Let's talk a little bit deeper about the podcast. It's, you know, obviously for some people, it's just done for thought leadership or for you know, founder, thought leadership, whatever. Maybe more fun but for others it is a demand generation channel. Is that how you guys look at it at Chili Piper? And has it been successful in driving demand for you? 

Tara: Yeah, I would say it's multipurpose at least for me personally. Part of the reason I was excited to take it on was selfishly to just meet with people that I thought were really smart and interesting and that's partly how I built the show is I reach out to people that I want to hear from and learn from. So I think that keeps content interesting for people too. For demand gen, if anyone is listening who has a podcast, the metrics are a bit of a black box you can't really say for sure, like this person listened and then they bought from us a week later. It's not quite that cut and dry. So that's why we use things like self-reported attribution, asking people where they heard about us. And so that's been one way to kind of prove that we know that our prospects and our customers are listening, but we can't necessarily tie a straight line back to revenue from that. So again, that repurposing of the content is super helpful because I can package up podcast clips that I know say we have a customer on and they say something that's a gem but how they use Chili Piper I can patch that up into a LinkedIn ad and serve that to our target account list. And then I can prove that like, Okay, this content has been worthwhile, but it's not a straight line from putting it onto the podcast apps and revenue.

Jeanna: Right, I love that. So do you guys have like a format that you follow with, like a blueprint of what you're doing? After every podcast of how many clips you're creating, like where you're putting it out on? Or are you a little bit more organic based on what you're talking about in a podcast?

Tara: It's pretty templated, so we use Asana for project management, I'm a huge fan. I love their stuff. So a lot of the work is sort of templated of okay, Nolan, our video producer will make like four to five clips. It's kind of vague, depending on what the content is. I'll send those off to the guests that we had on and then we also loop in our social media manager to go through and say like, what she thinks would be interesting to our company page audience. So it's pretty templated, the assets, but then it's really a little bit of back and forth to decide what actually gets used. 

Jeanna: Gotcha. Cool. All right, shifting back into the remote work topic. I know you had just mentioned Asana, I think this is something that is core to a lot of remote brands. We ourselves use project management software. And I always think about how funny it is because in my career, like you know, 10 years ago, I remember people trying to use Basecamp and stuff like that nobody would ever sign in and you couldn't get anybody to use it. And now we structure our entire days around it, all of our tasks like all of our projects. We personally use ClickUp, but whether you're using ClickUp, Monday, or Asana doesn't really matter. But what is it, or how does the project management platform like fuel your guys's projects and your job at Chili Piper?

Tara: Yeah, so one big way is I mentioned earlier that we work across time zones, so I try to work ahead on certain things to make sure that I can get it done so that the person editing it can then look at it afterward in Asana and I know you had someone on your podcast talking about how they use time zones that way and I thought it was so smart. I didn't do it intentionally but the way that she explained how intentional it was I was like that is genius.

Jeanna: I love that as well. I was like I've never done that like leveraging the timezone differences to move faster, right.

Tara: So smart. So yeah, just for an example. I write our newsletter usually on a Friday afternoon and the woman who edits it is on the West Coast. So I know as long as I wrap up the draft by the end of my day then she has a couple hours to edit it before I come in on Monday and then I can get it into HubSpot and send it. So that's just one way that we use the time zones but all of that work is happening in Asana, I don't have to Slack her or send her links, like it's all in one place. And I also really love the calendar feature in Asana so we can show, not just for visibility to our execs, but also the team of like, ooh, we're sending way too many emails this week. There's too much going on and we can't always control that — September is super busy with events that we're sponsoring. So there's only so much we can move around. But typically we use that to kind of drag things around like oh, we don't want to email our customers five times this month so just having that visual of the calendar I find super helpful.

Jeanna: Nice. And are you guys pretty pure with Asana, like are you at Chili Piper, is everybody doing all of their work in Asana, like all of their projects, all quarterly goals are built out with multiple steps, multiple people like and you're just signing in every day and following a task list to do?

Tara: That's a good question. I wish. I would love to get to that point. Right now. It's just within the marketing team. 

Jeanna: Oh wow!

Tara: And yeah, and then the agency that we use for our website is also in Asana. So that's super helpful to assign to them, but the rest of the company is not. So we use a tool called Leapsome to organize the company objectives and OKRs and then Asana is really just like the nitty gritty of our marketing projects.

Jeanna: Okay, gotcha. Um, and you have like coworkers everywhere, right? And every, like so many cities, so many locations, do you have any tips for people on how you work remote with so many people across the globe?

Tara: Yeah, so one that I quickly mentioned earlier was the just transparent calendars. So that's a huge one for me. So we have a lot of people have like start and end times on their calendar. Mine isn't that organized, but some people do that. Just to remind you like, Hey, it's 6am for me, please don't put me in a meeting at this time. And we use Slack the same way with statuses to show who's online so before you message someone, you know, okay, probably don't want to bug them at 8pm their time. So I personally use scheduling on Slack a lot to avoid that. So that's a huge tip. If you don't want to bug someone at midnight, their time just schedule it for them to see it in the morning. And then we also use we call them "work with me" docs. There's a couple different terms for it. But when we have someone new start, we get them to write a doc about themselves. 

Jeanna: Amazing.

Tara: Honestly, I liked it when I was joining because I hate that first week when you're kind of sitting there like oh, I don't know what to do yet and feeling a little anxious about not being busy enough. So you can really pour your energy into that doc while you are new. And you just describe everything from like, where do you live, timezones, how do you prefer to get feedback, how you manage your schedule, and you can get into the details on that. And so having that all in one place is super helpful.

Jeanna: Yeah, I love it. We also do that as well. I think we picked that up from ClickUp, or who knows who originated that?

Tara: It's hard to say!

Jeanna: Yeah, I love that so much. Cool.

Tara: Yeah, another doc that we do is I think this was borrowed from Amazon. But for every big decision that we make internally, we document it in a decision memo. So when we're deciding, like, what tool to buy, if we're deciding do we need to hire this role? We put everything in a written document and then we can add to it async so that nothing's decided in a meeting that 10 people couldn't join because of their time zone. So we try to work async as much as we can.

Jeanna: So is that one document that is like maybe pinned and it is like a running list of decisions? Or is there like one doc that has all the decisions or how does that specifically work?

Tara: It's not super fancy, but it's actually a spreadsheet with links to all of the separate decisions.

Jeanna: Okay. I love it. 

Tara: So, you could go look them up and say like, why did we buy HubSpot versus this other thing and you can go look for that document.

Jeanna: And so then every single team across the company is in charge of keeping this up or is it a leadership thing only?

Tara: No, anyone can contribute to them, even for things like when we've in the past talked about changing our pricing model, literally every single person at the company can contribute to that doc and say like, I talked to a customer and they told me this or we can get insights from the sales team, instead of limiting it to the leadership team.

Jeanna: That's incredible. And how do people find out about that process? Like that's obviously core to your culture? It's something everybody has to follow, like when you started, how were you told that this is how it worked and that you picked up that you needed to follow that?

Tara: That's a good question. It's actually again, going back to the transparency when we have one of these docs floating around. Someone from the leadership team at our weekly all hands will usually say like, "Hey, I have a DM on pricing, can you guys check it out?" And they'll actually mention it and link to it at our all hands. So, again, super, super transparent and anyone can jump in and check that out. But I don't remember it being anything more formal in onboarding or anything.

Jeanna: Okay, cool. I'm just asking all these questions because obviously I myself am a founder of a company and so I just love to talk about all these like particularities of remote culture is like, so fascinating to me because there's this really interesting part of the working world where, you know, there's lots of conversations of the pros and cons of remote happening. And I always like to tell people that it's like we don't just work remote, we're remote first. Like we build everything at our company, from our processes, all of our tools, all of our tech stack, how we work with each other, is set up to optimize being remote, right? Like async or having people in different time zones, or making sure that you're using running Google Documents for things. But companies that are like, not really figuring out remote and are just putting people at home but then all following like the same old ways of working are the companies that I think are failing at remote. So I'm just so fascinated with people that are working at companies that are really like nailing remote processes or remote operations like how that's all working because it's so different, right? 

Tara: Yeah, I've definitely spoken to friends who they technically work remote, but they're just on Zoom meetings all day. And to me, that's not really the point. 

Jeanna: Right? That's horrible. 

Tara: Yeah, if you're just on a meeting all day anyway.

Jeanna: Right? Yeah, yeah, we definitely. We have like a big kind of anti — I don't want to say anti-Zoom, because Zoom is like, a great tool.

Tara: It can be great, but if you're there eight hours a day that's not great.

Jeanna: Yeah, it's horrible. That and I, you know, had a year for the first time ever as a founder, seven years I've been running this company, but last year like, the company got really big. We hired a ton of people. We're expanding really fast and I found myself sitting on Zooms six or seven hours a day. And after that, I was like okay, this is insane and we now stepped back and have a very strict like max three Zooms a day. We don't do meetings on Fridays. Like you know, when you're scheduling Zooms for people you need to look at their calendar and like choose a day that they don't already have three calls on or whatever. So we're trying to put some like clear boundaries around it because it is just brain-melting. When you sit on Zoom all day, right?

Tara: I love that. Yeah, we started doing no internal meetings on Wednesdays and I find, I personally love it midweek because that's the day that I know like, okay, if I don't finish it on Tuesday, just move it to my list and I have a running to do list for Wednesday and it feels so good to knock through that list.

Jeanna: Yeah, I have actually done that since the inception of my company on Mondays and Fridays. I do not take calls. And so otherwise I don't you know, I don't know how you'd get anything done. Because when you sit on calls all day you just don't get anything done. So I'm the same way and I love Mondays and Fridays because I know I don't have to talk to anybody and I can just be quiet I can play music I can get through my to do list so yeah, it's like so nice when we're able to work. You know, just to yourself like without being on a video call all day. It's like really important to getting stuff done. Cool. And you say you have a like a little tip that people should schedule their days like their dogs and what do you mean by that? I'm a huge dog fan. So I'd love to know.

I was struggling to put this in writing. I feel like it makes sense since to talk it out. Yeah, we we've adopted a dog two years ago and our previous dog was much older and had a little bit of a slower pace, but our new one just needs exercise or else he is just bouncing off the walls and I feel like when you're, especially when you're working remotely and you can do that to yourself, but it's more like banging your head against the wall just staring at your screen for too long. So I personally just try to start and end my day with, it's almost like a fake commute, but with a dog walk instead. Because I just find especially in the winter, if it was up to me, I would never leave the house and that's probably not very good for you. No matter the weather. We start and end the day with a walk and some people like to do it in the middle of the day just for a breather, but I just find that like helps me be like okay, I'm out of work mode. If I have a couple of things I need to brainstorm. I can do that during the walk. But when I come home, that's when I'm done for the day. And so that's really kind of how I start and end the day on a good note.

Jeanna: Yeah. Amazing. What else do you get to — I mean, that's kind of a big part of remote work, right? I think it's becoming, or figuring out what your routine is. Like, what is your remote work routine? That's something I really struggled with when I went fully remote. I moved to Belize seven years ago and I was like, kind of had this guilt, right? Like I felt like I wasn't working enough or I wasn't being productive enough. And some days I felt really lazy and others I was productive and I was trying to figure out like what does it look like for me to be a remote worker like what is my routine? So I think it's just like those little things like what how do you start your day? How do you end your day? What do you show up like at your computer that really helped you thrive as a remote worker? Is there anything else in your routine that you would share? That's like super important for you when it comes to remote work?

Tara: Yeah, I think going back to your point, it's different for everyone. So my partner has actually worked from home for over 10 years since I've met him and he doesn't start his day with like a shower and getting ready. He has a midday workout and then he showers and gets ready so he's up working, but I'm personally like if I'm going to work I need to like shower. I don't always need to like do a full face of makeup but I need to feel like ready for the day. 

Jeanna: Yeah, I'm the same way. 

Tara: I assumed everyone was like that until I started working from home with him and he's not but it works for him. Yeah, you kind of have to figure it out but for me I need — a shower just wakes me up and I feel ready for the day that way. 

Jeanna: Yeah, I'm the same exact way. I mean, it's funny because I don't know if this is like, and maybe this is for you too, because I know you had an office life before going remote, but I was in office roles for so long before I went remote that it's almost like I intentionally or not follow that still like, I still kind of follow a loose, I don't work eight hours a day, but nine to five. Like I work Mondays through Fridays. I don't want to work on Saturdays and Sundays I want to work during the middle of the day, I want to get up and get dressed and like sit at my computer like I'm in an office but I wonder if that's just because we've been conditioned so long to follow that like, office nine to five life, right? But some people thrive when they're like they want to work on their Saturdays because it's quiet and no one's gonna bug them right or they want to work on their evening. But I think that's the beauty of remote work that people can do like whatever works for them but for me I'm I'm like you I'm much more the traditional.

Tara: Yeah, I have a lot of co-workers that can just work from anywhere. They're more of the digital nomad style remote worker. And at first I thought that looked so interesting to me. But I prefer to just travel when I am on time off and I can explore and then work when I'm home. But yeah, you have to figure out what works for you.

Jeanna: Yeah, right. Yeah, it's different for everybody. I was just telling I just sent my coworkers last week on Slack because I was like, I am a like 32 inch monitor girl like I like to be able to, you know, have multiple things open and giant views of spreadsheets. And last Friday I was like, oh, I don't have calls on Friday. Maybe I'll go do something fun. I'll go work from a coffee shop and I was at the coffee shop for literally 10 minutes and I was like, this blows. I can do nothing. I cannot focus. I need to go back home to my 32 inch screen. So yeah, it's just like some people will hate sitting at home and they gotta get out of their house and they gotta go to a coffee shop. So it's really just figuring out what you like, but I think that's the beauty of it. Right? It's like you just get to do what feels right to you at any given day and there's no like set rule to follow. 

Tara: Exactly.

Jeanna: Cool. Any final things you want to share with our listeners before I go to our final three questions?

Tara: I think the only other thing I would say is we talked a lot about figuring out what works for you. But especially if you're leading a team, I think it's important to give people you're leading room to figure that out too. And it might take some back and forth between the two of you to figure out what that looks like. But I would just think about that. 

Jeanna: Do you think that's grace? So you're saying like, recommending that you just give like people that work for you as a leader grace to figure it out for a little while or what do you think that is the secret to that?

Tara: So we try to get it out quickly by those docs when you start, sort of explaining like how I prefer to work, how I like my schedule to look and we kind of leave that up to people to figure out for themselves. But I think it's almost giving the two of you grace to figure out how that works together. Because if, say you're having someone who's a real digital nomad who's always in a different timezone reporting to you and you're a really rigid work from home person, there might be kind of some back and forth needed to figure that piece out. Right?

Jeanna: And does that usually like a 30 day thing? Or do you recommend giving like 90 days to figure that out or is there any timeframe to that or what what's worked for you? 

Tara: I think it's usually much quicker, at least in our experience, just because we, again, we have that doc where you write it out upfront when you're hiring so it's pretty clear what the expectations are. So I don't think it should even take 30 days but that's just been my experience. 

Jeanna: That's great advice. All right, final three questions. What is your one #workfromanywhere item or tool that you could never live without?

Tara: Oh, um, I feel like this is so basic but AirPods. Headphones. I am not someone who can work in an open space with just noise around me. I know some people find that like, they can do that, but I cannot tune it out. So that's a big one.

Jeanna: Yeah, me too. As we both talk to each other with our AirPods in. What about a remote work productivity hack that you might want to share with everybody? You've already talked about some stuff with like, time blocking your calendar and stuff like that. Anything else that comes to mind?

Tara: Yeah, one thing I do, I know you mentioned that you're not always a work-from-a-coffee-shop person, but one thing I'll do is I'll have a really small list that's like a very manageable list of to-dos and I'll go do that from somewhere else. And I'll kind of say like, I'm not leaving the spot until I've done these two things, these three things. 

Jeanna: Love it. 

Tara: And for some reason, that timeframe just really motivates me versus time blocking. Sometimes I just need to get out of my routine to get that done.

Jeanna: That's great. Cool. And if someone wants to learn more about you and Chili Piper, where should they go online?

Tara: Yeah, you can give us a follow on LinkedIn Chili Piper should be super easy to search. My name too, just @ Tara Robertson.

Jeanna: Cool. All right, Tara, thank you so much for joining Remotely Cultured today. It's been fun to chat with you a little bit about your own remote work culture, what you're up to at Chili Piper and how you guys work together. So appreciate you sharing and we'll talk to you later. 

Tara: Thanks so much for having me. 

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