Interview
October 24, 2024

A Conversation with Pavla Bobosikova

Published By
Sarah Mooney

In this insightful conversation, we sit down with Pavla, a seasoned tech entrepreneur and advisor, to discuss her journey from startup founder to post-acquisition leader. Pavla shares her experiences with remote work during the pandemic, which led to the creation of her company, WFHomie. She offers valuable perspectives on the challenges faced by remote teams, the potential of AI in streamlining workflows, and the importance of effective communication in distributed work environments. Join us as we explore the evolving landscape of tech startups and gain wisdom from Pavla's unique vantage point.

Video Transcript:

Sophie: All right. Well, thank you so much for joining Pavla. Super excited to have this conversation today. And yeah, thank you so much for making it after your trip to Vancouver.

Pavla: Thanks for having me.

Sophie: Cool. So let's kick things off by kind of diving into your journey as a tech founder, now as an advisor, and mentor, and just kind of general amazing stakeholder in the tech community. How did it all start? How did you come up with the idea, kind of thesis behind WFHomie? What was the light bulb moment or a particular experience that sparked that initial journey and building that startup?

Pavla: Yeah, for sure. So I think it all comes down to personal experience. That's kind of what led me onto WFHomie. So prior to starting it, I was working at another startup called Nudge.ai that just as the pandemic was hitting, was going through an acquisition. And so I was on the getting acquired side of things. And we were merging with a team that was based down in San Francisco. Our team was based down in Toronto. The vision was for us to kind of start working together in SF and then for us to start a satellite office in Toronto.

And so as Affinity was acquiring Nudge, the Nudge fall kind of went down. And then that was literally the week of the pandemic kicking in. So we got to experience the proper kind of onboarding for the first handful of days. And it was an amazing experience. And I remember thinking like, wow, this is Silicon Valley level. This is how it gets done, all the right stuff. And then we all flew back because the pandemic hit, right? So everybody was kind of just working from their kitchen table or basement or whatever. And it was just so interesting for me to see how it impacted my employee experience as a new employee at a time. And it really made me worried about companies that are hiring or trying to merge and integrate new people into their teams because it was just so much more difficult to do that remotely compared to all the whistles you can have in the office and all the little offsides and lunches together and whatnot. And obviously by now we have figured out some kind of band-aids for some of these experiences, but the drop off the delta was just so striking. And it really made me wonder how our company is going to be able to be successful and get their new employees really excited about what they're working on beyond just kind of like clocking it in during their nine to five, but really thinking about, okay, how could I help push this product forward or push this team forward? Which is something that as kind of at the time entrepreneur at heart, I was like, well, I always want to work with teams that think that way, right? That kind of, even when they close their laptop, like one of the things they might be thinking about is about how they can do something better. And it just seemed like it would be really difficult for leaders to kind of create that type of excitement.

So with that, I started looking, interviewing HR people at the time, people, people, and looking, starting to understand what has changed with them with the pandemic and kind of validating whether this hypothesis is right. And through that discovered, there's a lot of more tactical things that were actually a hurdle at the time. While obviously this is a challenge that has been also present. So this was pandemic times, 2020, an interesting time.

Sophie: Oh, a hundred percent. I remember that time very well. I think that was also when we met at the very beginning of the pandemic when you were trying to figure out what that next step was going to be. So yeah, no, it's been amazing to see your journey with WFHomie. And I think you really kind of realized that dream. I want to also just say again, congratulations on the recent acquisition, such an exciting experience for you to go through. We'd love to know how this transition has been to kind of post acquisition.

Pavla: It's definitely been interesting. I think to be honest, I kind of underestimated what that's going to look like, from a personal founder-like perspective. I think a lot of my friends, investors out of the industry tried to warn me about like how much of a shock it will be personally to just go, you know, back to operator back to just kind of obviously the role is going to shift right with, with joining the acquire and then with whatever activities I might have been doing after that. So definitely on a personal note, it has been somewhat of a, of a kind of like cultural change shock, but I wouldn't necessarily say in a negative way. It's just been very different. So things go, you know, back from having kind of a hundred percent responsibility over your team, your customers, you know, responsibility to your investors, all those things that you're kind of like how 24 seven, every waking second you're kind of, or at least that's how it was for me, feel kind of accountable for everything to while you're now part of something bigger. So obviously you still care and you do have some autonomy, but there's only so much you can influence and impact. So it kind of changes how you think about things or how you approach making changes at that point. So that was me, mostly as I was answering that mostly as the like kind of post acquisition, joining another team in terms of being able to spend more time mentoring, advising, investing, all that I've been absolutely loving this journey. I never thought this would be something I would want to pursue. But I'm really grateful for the opportunities that came along in this direction. And that's been keeping me really excited.

Sophie: A hundred percent. And I think, you know, one of the most amazing things is when a founder becomes a part of the community in kind of a different facet where they're an investor, they're an advisor because, you know, you've been through it. And I know, you know, from my own experience, some of the best advice and mentoring that I've gotten has been from people that have gone through that experience because it's just, it's so unique. But I remember you mentioning it's been kind of, you know, underestimated how crazy a transition is from being founder, CEO, and something I've been definitely thinking about. You know, you kind of think back to how it was when you went from, you know, in-house to a founder. And that was crazy enough. So I can imagine the other way around.

So one of the things I wanted to ask kind of on the advising side, as someone who advises startups, I'm sure you've seen it all when it comes to, you know, challenges, especially kind of internally, whether you're ramping up, you know, your customer success or kind of general like knowledge base and management challenges, what are some of the really common hurdles that you've encountered, especially with remote teams, if there are any?

Pavla: Yeah, I think it's definitely kind of when it comes to, and I mean this genuinely, not because I know what your product does, but genuinely finding the different pockets of information, especially as teams are remote and a lot of the, even kind of the day-to-day on the go, a lot of the knowledge transfer just ends up happening in the DMs and it's kind of between different employees who are like, you know, might be working together on a specific customer or are just kind of helping each other figure out what has been the product update, so how do I resolve this ticket? And then by the time all of this information makes it into some form of a CRM, which I've also seen things from, you know, Google Sheets to much more sophisticated pieces of software there, it feels like a chore to kind of update, you know, what has been done, what have we learned today? So sometimes the information never makes it there, sometimes it does, but I think at this point people have been conditioned to not necessarily treat the company's source of truth when it comes to customer information as an actual source of truth.

So wherever that information might live, I've kind of seen people already treat it as like, it may or may not be true or, you know, this has been last updated by a teammate that's no longer with our team or just kind of people question it to begin with and that's supposed to be the best that they have. So they kind of, you know, go in already knowing that it's not perfect. And so even for me personally, when I'm trying to, you know, as I was joining a new team or when I'm trying to learn about a new company, this is very much like an information getter. I love to understand everything firsthand and really get access to raw data. And I know that it's always challenging and you quickly learn that different types of information live elsewhere with different people. And honestly, in my experience, what has worked best has really been like finding the person that has been one of the superstars on the team, who's been with the team for quite some time. And you're better off talking to this person and kind of learning what they have to say about what customer, their product, how it resonates, this or that, rather than relying on the written set of information that is 99.9% of the time incomplete and or just not fresh.

Sophie: 100%. Yeah, that makes a lot of sense. I think, you know, as we are looking forward to how the tech industry is evolving, I think AI is also becoming such a big part of how we're trying to take those really kind of annoying or cumbersome tasks and kind of revamping them or making them more automatic. I'm really curious in your kind of perspective, I feel like, you know, I'm focusing on Ariglad, so I feel like you have a bird's eye view of what's going on in general in the industry. I'm curious, what are some of the biggest opportunities and also challenges for companies like Ariglad as we harness technology like AI?

Pavla: Yeah, I think the opportunities are definitely in workflow automation across kinds of verticals. So of course, in your case, customer success, I think the same applies to marketing, you know, sales, different roles. And luckily, there looks like new and new companies are popping up in the space or, you know, shifting to leverage AI to really help their customers make the most of it. So I do think that when it comes to, you know, information transfer, automating some flows that are internal that might feel less scary to start with, because it's really just going from an internal person to an internal person to a CRM or to whatever type of type of software, I think that's a very kind of easy way for companies to ease into it when they're considering starting using AI. So it doesn't go straight into customer facing or candidate facing or, or anything like that. It doesn't have to be that way. But definitely, definitely some of that because it's still striking how many tasks that are kind of done mostly internally are done manually and then, you know, lead to incomplete or not up to date information. I think in terms of challenges, I think it's mostly like a self imposed adoption hurdle. I don't really want to speak about how real of a challenge it is. But definitely our concerns around privacy, security, that sort of stuff, like I've seen companies struggle with this to understand like, you know, with whom should we be sharing this data. So let's say, you know, you have a huge customer, customer success data set that goes into information about different accounts, different people on the account, this or that, and it would be great to break it down by product features that you can then pass on to product team that they can work with on their roadmap, you know, when it comes to like, what should we work on next? What really needs improving, etc, etc.

And I know it might feel scary to just dump this, this mega set of information, even if you, you know, delete a few columns here and there into some form of AI. So I think it's mostly around the kind of hesitation when it comes to companies and different people at different companies kind of adopting the software, but I think there are amazing opportunities. And it can really speed up a lot of things and kind of make them more objective, rather than kind of qualitative because, you know, if certain topics do come up all the time, like they might be worth looking into, like AI can be a great friend and just an accelerator of things. So like that.

Sophie: 100%. No, I totally agree. I think, yeah, no, it's a super exciting time. And I really just appreciate you hopping on to talk about this. One last question for you. I would love to ask because of your experience in supporting teams kind of growing, especially remotely. Do you have any advice for us as a fully remote team and anything that we should be kind of incorporating into our company?

Pavla: That is a great question. I think I mean, this has been true since at least the beginning of COVID, probably the beginning of time, over-communicate, right, just open lines of communication, just making sure to instill extreme transparency and honesty among different team members. And then just being pretty, being clear on what processes feel right and experiment with those processes. Because obviously, one thing when it comes to remote work is the question of like, how do I communicate with somebody to most effect in the most effective way, etc, etc. But also, some people just don't know when to stop. And of course, burnout has been an issue for many.

So I just think being very clear about kind of what are the expectations from different team members, making sure that, you know, half of the team doesn't spend their half of their day, emotionally overthinking like, oh, my God, my boss didn't send me an emoji, are they mad, kind of being very clear about what is normal on your team and make sure that everybody's comfortable and kind of confident. And this is how I should be communicating. This is what type of communication I should be expecting to receive. And I think that can really ease the burden of people wondering what's going on where and just lets everybody focus on the subject matter and kind of in a calm face, just keep grinding through stuff.

Sophie: I love that. I actually love the word that you used, kind of over-communicate, because I definitely experienced this as well. You know, when we were starting and kind of growing, we didn't communicate enough. And I think it was because I just kind of assumed that everyone kind of knew generally what I meant, even though I didn't like communicating enough. If I mentioned it once, I'm sure they got it and I'm sure that sunk in. But, you know, I wouldn't work that way. That wouldn't be how I would kind of take in information. So yeah, no, I think now it's like, I want to be able to communicate as much as possible, but rather just annoy everyone with my overload, then accidentally, you know, miss something. So I think that's really good advice. Awesome. Well, thank you so much, Pavla. Thank you so much for hopping on and sharing your wisdom. And yeah, we'll talk again soon.

Pavla: Yeah, thank you so much for everything. Bye.

Sophie: Bye.

As our conversation with Pavla draws to a close, we're left with a wealth of insights into the world of tech startups, remote work, and the transformative potential of AI. Her journey from founder to advisor exemplifies the dynamic nature of the tech industry and the valuable perspectives gained through diverse experiences. Pavla's emphasis on over-communication and transparency in remote teams serves as a crucial reminder for all distributed workforces. Her thoughtful reflections on the challenges and opportunities in adopting AI technologies provide a balanced view of the road ahead. We thank Pavla for sharing her wisdom and look forward to seeing how her insights will shape the future of work and technology.

As we reflect on Pavla's insights about effective communication and the potential of AI in streamlining workflows, it's clear that innovative solutions are key to thriving in today's remote work landscape. This is where Ariglad comes in - an AI-powered tool that automatically keeps your knowledge base fresh and relevant, making your entire knowledge ecosystem smarter, more efficient, and incredibly user-friendly. Ready to see how Ariglad can transform your knowledge base? Book a demo today and take the first step towards revolutionizing your team's information management.

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