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How VC’s Are Transforming Startups Remotely with SignalFire’s Heather Doshay - ep. 077

• HEATHER DOSHAY, RICK HANEY, KALEEM CLARKSON • Season 1 • Episode 77

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In our latest episode of the Remotely One podcast, our hosts dive deep into the world of remote work, exploring its challenges and successes within startups, especially during the pandemic. Joining us for this insightful discussion is the remarkable Heather Doshay, Partner at SignalFire, renowned Doctorate in Leadership holder, and a visionary in all things People and Remote Work.

Heather's journey is a fascinating tale of resilience and humor, tracing her trajectory from her college days in Greek life to a prominent career in remote work and organizational leadership. She shares candid anecdotes from her past, including overcoming rejection during a sorority election, highlighting the transformative power of setbacks in shaping her leadership skills and resilience.

Venturing into the professional arena, Heather was an early advocate for remote work, recognizing its potential for enhancing flexibility and productivity. Her tenure at Webflow, a pioneering remote-first company, further solidified her belief in distributed work models, positioning her as a thought leader well before the onset of the COVID-19 pandemic.

When the pandemic struck, Heather's leadership at Webflow faced unprecedented challenges. However, rather than resorting to layoffs, she and her team devised innovative contingency plans to preserve jobs, exemplifying Webflow's commitment to its values and leadership ethos under CEO Vlad Magdalin.

Heather's journey is replete with valuable lessons for navigating career transitions and embracing remote work culture. Her experiences underscore the importance of resilience, adaptability, and forward-thinking leadership in the face of professional challenges.

Tune in to gain invaluable insights into the evolving landscape of remote work within the startup and venture capital sectors. Heather's expertise sheds light on both the opportunities and challenges of adopting a remote work culture in a post-pandemic world. Thank you for sharing your wealth of knowledge on remote work, startup culture, and venture capital, Heather!

Learn more about Heather:

Heather:

I am really into puns, and I dress my dog up, um,

Kaleem:

sorry. You said you're really into what?

Heather:

Puns.

Kaleem:

Oh, like PENs. I thought you said I'm really into the puns. Oh, okay puns. Yeah. I love puns. Okay. She's

Heather:

So I named my dog Charles Barkley, for the barks. Um, and,

Kaleem:

me hard with

Rick:

I love it!

Heather:

the water.

Kaleem:

puns

Rick:

I had a little Pomeranian dog named Scotty Yippin.

Heather:

It was about Oh yes, Scotty Puffin is what I want to name the next

Kaleem:

as you can for one minute straight. You ready?

Heather:

About what though?

Kaleem:

Anything you want

Heather:

Okay, so let me tell you about Charles Barkley. He's a baller. He is a Powerfurward. That's the way you would spell it out. And for his holiday gift, we got him this cute sweatshirt, which is like this green little hoodie. He doesn't like it at all. But he's afraid of stairs. His parents don't love it. They have to pick him up from all the places he goes. But he does have a ball living around in the backyard, so.

Rick:

Oh my lord, this is amazing!

Kaleem:

I think the wordle thing's pretty good, but I feel like loving puns and naming her dog Charles Barkley for some reason just

Rick:

Oh, that is so

Kaleem:

It's so good,

Rick:

just so you know, this is not going to get old. I

Kaleem:

Yeah.

Rick:

Welcome back everyone to remotely one I am your co host Rick Haney joined by my well moisturized esteemed colleague Kaleem Clarkson. Hey,

Kaleem:

What's happening, man? I love those glasses, bro, when you got those

Rick:

Oh, these are new.

Kaleem:

Oh, you look like a sophisticated lumberjack. Like you're gonna chop down some wood, but you're gonna be real smart about it, dude.

Rick:

Well, I used an expensive handsaw on this wood right here, you see. I came right in from the forest. Yeah.

Kaleem:

Such a bob, dude. You're such a

Rick:

So, if anybody doesn't know, that was my Maine accent coming out. Kaleem and I are both from Maine. You'll figure that out. But hey, everybody. Welcome back. Thanks for joining us. Since you know how to find us now, do us a huge favor. Go to RateThisPodcast. com forward slash RemotelyOne and just leave us a review. That's all we ask. Again, RateThisPodcast. com forward slash RemotelyOne and we would be ever so thankful. Since 2015, RemotelyOne is one of the largest communities of remote work professionals with over 3, 000 Slack members and 5, 000 email subscribers. That number has got to be higher by now. I would imagine, right? Yeah, so go check it out at RemotelyOne. com where we do not have 5 foot longs, but you'll be just as happy.

Kaleem:

That's true.

Rick:

with that out of the way, Kaleem, give us a tease or two about today's guest.

Kaleem:

And you know, Rick, every single time we interview these people, I start sweating like I'm in the movie airplane. Oh my gosh. We have the sweat towel hanging out, the moisture's building. I got my four sweatshirts on and today's guests, they know some things, they've done some things.

Rick:

we're going to get learnt.

Kaleem:

Oh my gosh. Learned and educated. Our guest, they grew up on the left coast in Los Angeles, Los Angeles. My favorite teams, the Lakers, R. I. P. Kobe. I love the Lakers. Let's go. Let's see. They currently reside in Portland, Oregon, you know, the second Portland Rick, which we know it's really the second Portland.

Rick:

It's number two.

Kaleem:

number two that I mean the record books state it. Okay, Portland Mains

Rick:

Everybody was born in the east and moved west.

Kaleem:

Rick. Every single time though, we get people on the show. I feel like I need to go back to college

Rick:

Oh, we're definitely out college on this one.

Kaleem:

Yes. Check this out. Our guests today, they're addicted to education. They're just addicted to learning

Rick:

is great.

Kaleem:

It is great. It is great. First, they got the Bachelors of Literature and Writing from UC San Diego, University of California, San Diego, because you didn't know what that was. They got their Masters in Adult Learning and Higher Education from, you ready? Columbia. Just a

Rick:

Oh!

Kaleem:

tiny, just a small, tiny, little school. Columbia's Ivy, isn't it? Is that one of the Ivies? Is that one of the Ivies? Okay. Okay. Okay. And then Rick, she just couldn't stop there. She just had to keep learning and she got her doctorate in organizational leadership from the University of San Francisco. So one, two, she's a trifecta.

Rick:

Yeah. Yeah. We're going to have a lot of questions. A

Kaleem:

She started a career off in higher education, had a great career. There was a faculty member worked for teaching center. She transitioned to a few different startups. She's an official member of the Forbes HR Council. Rick, her partner is a geek,

Rick:

Okay.

Kaleem:

Is a self proclaimed dork. I don't,

Rick:

We're going to have to define the differences there because this is an important topic.

Kaleem:

exactly, but you know what? She says it because she loves puns. She absolutely loves puns. And listen to the name that she gave her dog. Audience, you ready for this? Her dog's name, Charles Barkley.

Rick:

I love it.

Kaleem:

Charles Barkley. Why am I so old in this fucking game? Like, it just makes me want to crack up. Woof! Woof! Charles Barkley. Sorry, sir. Charles. How many dogs are named Charles Barkley? I would love to know. Oh my god That'd be funny as shit. We got to see if we can get sir. Charles on what did you say scotty puppet do? Oh my gosh. Listen. Our guest uh used to be the senior vp of people at places in rainforest q a the former vp of this tiny Little company, they're small, you might not have heard of them, they do these websites, the company's called Webflow, she's the former VP of people at Webflow.

Rick:

Oh, that's my website. That's what I use to build my website.

Kaleem:

think I have a website on that as well. Rick fantastic. Shout out Drupal though. Shout out Drupal still. and then she's an advisor, so she loves to share her knowledge. She's an advisor at people text partners. She is a partner at signal fire, which is a venture capital firm that helps early stage founders, listeners and viewers, please give a warm welcome to Heather Doshie!

Rick:

Alright! Woo hoo hoo!

Kaleem:

Woo!

Heather:

Thank you. That was the best introduction I've ever had, and my dog got an intro. the best part.

Rick:

I mean, can you hear these people, Heather? They're crazy. about you. This is insane.

Heather:

I feel like a contestant on The Price is Right.

Kaleem:

Whew. Oh.

Rick:

down!

Kaleem:

That was intense.

Rick:

Yes.

Kaleem:

the accolades. Heather, thank you so much for joining us. Thank you.

Rick:

Yes, great to have you on the show. And thank you for tolerating our juvenile sense of humor. It's amazing.

Heather:

Oh, I'm like a 14 year old boy. It's perfect. We'll have a great time.

Rick:

I love it. You're gonna fit right in around here. So we have, obviously, I mean, who knows where to start with your experience, your education, and all the things that you've done. You have such an impressive background. And where you and I have some things in common is Greek life on campus. And as, as you and I both know, Greek life tends to promote, leaders and whatnot, but in, in your experience, your background leaning so heavily in, in leadership and human connection, how does that all come into play at such an early stage in life, especially in college, when people are just trying to figure out who they are and where they want to go professionally and why are those topics so critical to remote work?

Heather:

Great question, and complex question, too. So, um, Well, for me personally, I joined Greek Life because I went to a school where the first few weeks I had a hard time really finding the right connections and community where I was. And so for me, joining a sorority was a way to build in a group of people that I could do the activities I wanted to do. And I sort of took it for granted, but I worked my way up. I did a bunch of leadership positions and found myself graduating college and trying to figure out what do I do with it. And so I actually became a Greek advisor for my first few jobs out of school advising fraternities and sororities in colleges. And, watching it from the other side, in some ways you kind of see, How silly and petty it can be because it's taken so seriously and it can be relatively exclusive. And people say, like, you buy your friends, even though there are so many benefits. But on the other hand, it's a really critical, formative experience for a lot of people. And there are places for everyone to go if they want to join one. It's just that a lot of people think it's not for them, so they maybe don't even put themselves there in the first place. But it's funny, when I actually studied my doctorate, I didn't know that this was gonna be a finding in my dissertation research, but I looked at women going into the career workforce because we understand women earn less than men. There's all these pieces out in the world that we know about work, and I wanted to understand how does college serve or not serve as a great equalizer for people from underrepresented groups? And I focused in on women for this particular study. And for women, it found that next to student athlete and internship and, student government, sorority life was almost exactly equal to those in terms of what will most likely have someone be most successful in their career. And the kind of truth of why might surprise you a lot of people will say, Oh, it's because it teaches leadership skills and there's all these positions. That's not what people said in the study. What people were saying was I thought rejection for the first time, but I got past it, right? Like, the more you get rejected in your life, the more you realize I can grow past this and it makes you kind of thicker skin and stronger, less afraid to go for jobs, less afraid to negotiate all those things. So for me, ultimately, that's what it did for me. I think, even though I didn't know it at the time.

Rick:

so it's like a lot of people don't realize how much rejection can actually be a confidence builder when everyone else sees it as like a detriment,

Heather:

Mm hmm. Absolutely.

Rick:

when you learn something like that at an early age, you, 19 years old and you've experienced that, but you're around people who are also there to support you. So that when you get out into the real world and you're in an office setting and you're trying to find your way professionally, you already have that thick skin already going into it. That's amazing. What a discovery.

Heather:

An embarrassing story, but when I was in college, I ran for my sorority president of my particular sorority, and I lost. And I was on the couch with, like, A pile of tissues being pathetic, crying for like days afterwards. This is so sad when I look back on it. But it was my same sorority sisters who came to me, brought me things, like took care of me. And I ended up applying to be the Panhellenic president instead, so for the sorority system. And I won that. And so it's like each time you fail, if you don't give up, you sort of fail up and you get something better and better. And that's honestly a theme throughout my career that I learned there is like, it feels like shame and embarrassment that you were rejected. But it was just one opportunity. There are thousands of opportunities all around you at any time if you just kind of know where to look for them.

Kaleem:

yeah, what's interesting is uh, One of the presidents at the university I used to be a part of. I'm a former president. We're kind of standing around talking and He actually can't talked about this concept of keg learning the idea that you can learn around the keg. So, yeah, don't act like you're not learning how to, you know, use the kegerator in a sorority or fraternity either. I mean, there's a lots of skills, Rick, that you've, you know, learned from the kegerator. So I'm just saying,

Rick:

I built a career around kegerators.

Kaleem:

Yeah, so this president was like, actually, believe it or not. You know, we'd be all around the keg pouring a beverage and somebody would say something about political science. And we would have, you know, let's say an insightful conversation around the keg around that. So it's pretty interesting. Um, I have a question.

Heather:

Yes.

Kaleem:

I noticed that you did a lot of your career was in higher education. And I noticed that. You worked at a teaching center. Not very many people know too much about the teaching center. Was it actually named the Tracy Seely Center? Was that the name of the center or the Center for Teaching Excellence? At what

Heather:

University of San Francisco. It might be now named that, but at the time it was just the Center for Teaching Excellence. Yeah.

Kaleem:

Yeah. So I also worked at a faculty development center at Kennesaw State University. We had, you know, did for 12 years as director of operations in strategic initiatives. So I would love to know, what did you learn in that experience? You know, managing programs Helping faculty learn how to teach better. What lessons did you take from that to kind of move on to your next career?

Heather:

Well, and not to turn back on you, but I want to hear the same from you after it's because you also have that same experience. And I'm curious if we came up the same way, but, I would say, like, teachers make a huge difference on people's lives, not just in, like, the curriculum they build, but the way that they show a belief in a student, and it can make or break somebody. And so it's like such a critical role. People don't realize that they play is when, You actually believe that your student can achieve whatever outcome it is and you even if it's a hard Like kind of tough love the student actually performs better to it than if they didn't And so those unconscious biases that exist for students are so critical at every stage through college So I think that was my biggest takeaway And then I think personally as I also say that job was the first time I realized I wanted to do remote work because Faculty they go on sabbatical for like a year at a time or, they really work during the school year, but in the summers it's quiet, but I was on the program side. So I was in this sad little office with no windows, all year round. But for the summer, I like, would like send an email each day and be like, I'm not going to hear back for three months. I don't want to overwhelm their inbox. So I just like would sit there and I started working on my graduate school studies instead because there was like really nothing to do and I kept thinking. I'm sitting in this office like four by four office by myself, and there's nobody here. I could be doing this from home like why do I have to commit and like check in at 8 a. m. And out at 5 p. m. Every day when I'm sitting at a computer and not talking to anybody so I will say professionally Teachers are so important if you are a teacher, and you're listening or if you know a teacher like give them a hug and They do incredible work professors and all the way through K through 12 But also whoa like this was 20 2012, 2013, I think is when I was in that program. And remote work didn't seem like an option. I never even knew it could be. But I was like, wait a second, something's wrong here. So.

Rick:

So when the pandemic came around, You are obviously well ensconced into this way of life. So Can you talk a little bit about how that? You know, like you had to have been watching people around you and in other industries Just flipping out like we were at the time, right? But you probably weren't because you were well prepared So talk to me about what that was like

Heather:

Yeah, so I guess how I got into remote work first and then kind of how it was for me at the pandemic. So I was at Webflow then, by the way, and very beautiful story of how we were able to handle it. But for me personally, I was working for a company that was remote friendly. And so Rainforest QA, about 30 percent of the team was globally distributed around the world and 70 percent was in the office. And I was the VP of people. And I thought, HR isn't the job that gets to go work remote. Like, HR has to be in the office, but I really wanted to work remote. Like, I had wanted it ever since I was in the university world. And so, I kind of just got an exception to work from home, like, one or two days a week. And every time I do that, I loved those days. There's something about, Having the flexibility to just start working, and then maybe take breaks as you need maybe you work a longer day, like, that flexibility for me is so huge because I think in spurts get energy in spurts. And I love that flexibility. I'm also kind of an introvert. I'm an outgoing introvert, so no one ever thinks that's the case. But I lose energy, like, spending my lunch break talking to people. I want to sit by myself and talk to nobody. And so I realized like this is good for me and when I wanted to go remote I remember I thought I should move permanently and it actually wasn't just to go remote It was because I wanted to move to Portland and my company was in San Francisco My sister had moved to Portland. I was looking to buy a house houses in San Francisco are ridiculous If you've ever looked at the listings could not afford one, but my sister showed me Portland I was like, oh I could actually buy something there. And so I Basically made this big like Google slides presentation for my CEO about like how I it was gonna be effective if I went remote And here's why and here's all the things and it was like slide one and I showed him and he Am I allowed to swear on this podcast?

Kaleem:

Yeah, of

Rick:

of

Heather:

Okay, because his response in his British accent, which I can't do, was like, Fuck yeah, go remote. Like, first slide. I'm like, wait, but I have slides for you. Can I show you the slides? And he's like, sure, show me your slides. But, like, the answer is yes. And so, I show him my ten slides, and then I go remote, and I don't look back. And I was nervous when I Because when I wanted to change roles to a new company, I was like, who's going to hire me when I'm remote in Portland? I'm gonna have to find a job in Portland, but I don't want that. I want to keep working remote and luckily Webflow came into my life at, like, the most perfect time.

Kaleem:

Roughly what year is this?

Heather:

I started talking with Webflow very early 2019, and I joined in March, actually during my birthday, March 18th, 2019. And so this was about 9, you know, about exactly a year before we all shut down for the pandemic. But Webflow was kind of like Rainforest, but flipped in that, whereas Rainforest was like 20, 30 percent remote, 70, 80 percent in office. Webflow was 20, 30 percent in office, 70, 80 percent remote. And so the difference in that is so huge. I think for companies who think about working remote, having more than half of your workforce outside of office makes it so much easier because you do things remote first way. Like, that's your majority. That's who you're planning for. And so I was able to be hired that way. It was outstanding. So we'd like 9 months later, so I don't know. Yeah, I guess the world started kind of shutting down like February, March. Maybe 10 months later after I joined and then I think all the announcements happened like the week before my birthday I think was March 13th at 2020 I mean I had been there for a year but Webflow was already set up to be remote first So that 20 30 percent go work from home and everything would be fine. You know, I always thought It'll be easy. We're already set up for this. I didn't account for The mental health and the civic unrest and all the things that were happening around us all combined together. That was like a pressure cooker, I think, for James. But other than that, because Webflow was such a remote friendly company, and still is, it was much easier to navigate,

Kaleem:

you know, it makes sense because Webflow is a website builder and Needed a lot of developers and traditionally, you know, in my experience too. I learned a lot about remote work from the developer community. But even so you talked about some of the pains that you all experienced already being a remote first company. So what was it like during that period when everybody needs a website and everybody's putting their resources into online, you know, presence? I'm assuming Webflow needed to hire more people. What was it like being the director of people at that time? was there growth in what were some of the things that even a remote first company that was doing this for a while? What were some of the things that you all struggled with?

Heather:

Yeah, it's a great question. So it's funny. March hits. And if you remember, a lot of companies just jumped to doing layoffs right away because they realized, Oh, shoot, like a lot of the world is going to change. We need to like hunker down, save our dollars, like manage our burn. And our team brought up the same thing. And I remember saying like, wait, hold on. Some companies are going to do really well. And some companies are going to do really poorly in this time. And a lot of it's macro and we don't know which one we're going to be at. We need to wait and see. So I remember I worked with our finance leader. We built a bunch of contingency plans to kind of figure out if this happens, this is how I'll respond. And I remember, and Vlad Magdalena, the CEO of Webflow, such a wonderful human being. I remember him saying, I don't want to lay off a single person. If I have to take a dollar salary a year, I'm going to do it before we lay off a single person. Like that's kind of the mentality that he had going into it, which was a huge support. Not everybody

Rick:

This isn't the guy from England, right?

Heather:

No, no, well, he's actually born in Russia and then immigrated to Sacramento, um,

Rick:

Oh, okay.

Heather:

The guy from England is Rainforest, yeah. And this one, much fewer expletives. Kind of a very different personality. Couldn't be more different from you. Um.

Rick:

Well, it's quite a cock up. One minute you're working in the office, the next minute Bob's your uncle, you're working from home.

Kaleem:

Cork up a

Heather:

No,

Kaleem:

up.

Heather:

both very remote friendly, but different people. Yeah, no, in, in, uh, in a California accent. No, but he said, you know, I don't want that to happen. And so we figured out like, okay, what could we do before we ever laid off a person? Like executive team can take pay cuts. We can do optional furloughs. Like these are all the things we can do. If these things happen, I remember it was like this huge spreadsheet we had made with every possible thing. And then the opposite happened. So as you mentioned, like, businesses go online. We didn't know if that would happen, but it did. And our company completely blew up during that time for the positive. Like, if you watch a hockey stick, like, you know, up and to the right, that was happening, way more than we expected. And so, we ended up hiring a ton. We grew from Gosh, maybe we were maybe 150 or 200 people, um, growing into 200 people, like, at the time that the pandemic started, and we're 400 a year

Kaleem:

Wow. Doubled. So what was the biggest challenge like when you saw that growth from a remote work perspective? What was, what do you remember being like the really big challenge?

Heather:

Yeah, I think a couple of challenges. One is compensation. It's a hot topic. It always has been. And the idea of, like, people perceiving of, hey, I should get the pay the same no matter where I live because. That's what I'm worth. Without acknowledging maybe some of the other dynamics at play of how, you know, benefits have to work in different places, or how laws work for parental, parent family leave, those kinds of things and the complexity and nuance of just Navigating all of that. So that was one big piece. I think the other big piece is some leaders that we had hired to help us really scale. We're not as big fans of remote work as the founding team and myself were. And so some teams felt like for my team, I want them in an office. And so we actually did have to make some shifts and changes towards that. And where we had to figure out like, well, what is the way we can be really true to ourselves and figure out like, When does a job actually require and benefit from an office space? And when do we want to leave the freedom and flexibility? And like, let's default to freedom and flexibility, but acknowledge when we need something different. So, for me, those are probably the two hardest things because they're all about nuance and complexity and completely different perspectives.

We'll be right back after these words. 2020 was no joke. It changed the game for everyone. Workplace flexibility is no longer a perk, but an expectation. In fact, a recent study showed that a flexible schedule is more important than salary. Yeah, you heard that right? Employees want choices over cash. If you're a startup or a small business that doesn't have a remote work strategy, stop what you're doing right now and complete our free tree assessment at blendmeinc. com. Since 2013, BlendMe Inc. Has been helping small businesses improve the remote employee experience. Let's stay local, but compete global. Visit us at blendmeinc. com. That's blendmeinc. com. Ever wonder how certain ads catch your attention or get stuck in your head? It's because the person voicing it knows how to tell the story. Maybe they're telling you to stumble over to Sullivan St. Patrick's day for green beers, Irish car bombs, and con beef all freaking day. Don't miss the deal of a lifetime this President's Day at Callahan Ford. Savings like these should be unconstitutional. Or maybe Come wash away your troubles here at Cooters Car Wash. We ain't no soap opry, but you'll be singing high praises. Hoo wee, Cooters! Or, here at Brooks Brothers Mortuary, we put the fun in funeral. Everyone is just dying to join us. Alright, well that's a bit much, but for you, I'll do it. I'm Rick Haney, and if you're a business owner looking for a creative voice in your marketing, look no further. I'll tell your story the way you want it told. Follow along at Remotely We Are One, or visit my website at rickhaney. me for more information. And now, back to the show.

Rick:

Well, you know, in the realm of upper echelon managers and leaders, a few days ago, you posted something about goal sharing and, forgive me if I botched this, but it was something along the lines of, it's great to share your goals, but share them with somebody who you perceive as. Um, higher status.

Heather:

Mm

Rick:

that's what it was, higher status. Can you just talk a little bit about why you feel that is beneficial?

Heather:

Yeah, so I never thought of it actually until I read the literature and the science on it. So essentially, you know, people will say, I really began behavioral economics as a side note. Like my favorite books are those, and I could give a little plug really quick for a book that people should read if this topic is of interest. It's called how to change by Katie Milkman, K A T Y Milkman. Basically this notion of there are different things that people do or don't do that. If they want to make a change, you know, sometimes you fail at your change. Sometimes you don't. What are the things that actually cause you to succeed? And one of the things that's very common knowledge is if you tell somebody a goal you have, there's like accountability built in and a fear of perceived failure or shame or not being liked or respected for doing the thing you said you were going to do. So people are more likely to do it. But also that concept is way less effective when you don't fear that the other person could judge you because you kind of see yourselves as equals or even better than. So just telling a friend. Who's going to support you no matter what may not feel like you have to actually stick to your goal. But if you tell someone who you perceive as Like, I really revere this person. I admire them. you're Kind of afraid to let that person down because you don't want them to look down upon you while you still look up on them. It widens the divide between the two of you. And so, it's like this way of, it's a little bit fear, but like a healthy amount of fear and anxiety to get you to kind of stick with what you want to do. So telling a manager, for example, about a goal versus telling a friend.

Rick:

Wow, it's so fascinating to think like, you know, you're not only challenging yourself, but you're also keeping yourself in check. You know,

Heather:

Yeah.

Kaleem:

Accountability groups.

Rick:

Accountability, exactly.

Kaleem:

Mmm, I think she picked that up from higher education because every PhD has an accountability partner when you're having to write your dissertation My dog my dog, oh my gosh,

Rick:

heh,

Kaleem:

so

Rick:

heh, heh.

Kaleem:

Heather, I, so just kind of recapping you, you started off in this higher ed space. You're learning about these things. You're learning about how Greek life impacts careers and women. You start helping other faculty be better teachers. Then you get into the startup space. You start learning about HR and people are ops and you become a people ops person, then you get the job at Webflow, you're in the startup world, like you are startup people operations at this point. Now, after Webflow, after you scale a company from 200 people to 400 people, you move on to venture capital. Right? The other side of the startup space. And with all of the challenges of, you know, VCs, money drying up and all that stuff. Can you tell me what makes SignalFire unique as a venture capital firm? And how does your role actually support the organization specifically?

Heather:

That's a great question. You know. There's a lot of great VCs out there but I chose single buyer because of how it's differentiated because I really believe in our approach. And like simply put, think of it as like data, technology, people, most venture capital firms are people, right? Like they have people who purport all these thoughts and ideas and, you know, theories about how they want to invest and they go out and they invest in those companies that match that, that theory. But a lot of it's based on just like. Their belief in themselves and their ability to think thoroughly single fire is really different because we think data is the answer. Like, how ironic is it that venture capital firms are investing in startups that are like data platforms and they're asking for all these metrics and data on their growth story, but they're not holding themselves to like that same standard. They're not using the technology that they're even investing in. So single fire was actually founded first of the technology product called beacon before we even raised our first fund. And so this product basically crunches millions and millions of data points across the Internet on people, on companies to help us figure out who do we want to invest in, who do you want to hire for those companies, and how can we help those companies find the best customers and kind of, grow their business. And so we believe in using that data and that technology product that we've kind of put together, but pairing it with recognizing it's not just about tools and products because we still need human in the loop. Like what, who are the humans that we can really bring into the mix? So part of why I joined is there's amazing people already at SignalFire and it keeps growing. My manager is a man named Jim Stoneham who's outstanding. Before he joined SignalFire, he was the CMO at Stripe. You might have heard of that one. And before that he was the CMO at New Relic. And he joined New Relic because he was a founder himself, and he was acquired by New Relic with his team. He's a two time founder really impressive kinds of people that are, that's who's advising our teams on marketing and go to market. We've got Tani Nazario Brands, yeah, she was a CHR at Netflix. So like, you say I have an impressive resume, and I'm like, oh no, I'm like small potatoes compared to these folks.

Rick:

I wouldn't say that. Wow.

Heather:

change and strategy and growing their leadership capabilities. Like, these are the people that work there. So you take the data platform and like the product piece and the people. And it's just like, you know, force multiplication. It really helps everyone succeed. And so we helped the earliest stage founders really figure out how to be very successful in the long run and they really believe in helping like our VC is. A much bigger as a percentage of the whole size people in like advisory type roles, portfolio success roles is what we call them compared to just investors.

Kaleem:

Excuse me, Portfolio what?

Heather:

Success. Our team is called Portfolio Success. If you think of it like a CSM model, sort of, like, if you think of a startup, like, they're here to help you really be successful once you're in. And so that's what I see my role as being. It's just a place where I feel like the work and the impact that our team can have is truly valued both by the founders and by the company, which is, is

Kaleem:

Wow. So basically, just real quick, it's like Not only are you a VC, but you're also a network of professionals that will actually provide data with your software to all of your portfolio companies. And you also provide them with services that will make them more successful. Like what you talked about, you know, people ops and marketing, all these people. So you're almost like a network and they're able to utilize all of the resources that you have. You're not just like a VC. That's like, here's the money. And we want our return. Right. Okay.

Heather:

mean when it's hard, like, we don't just stick around when it's going well.

Kaleem:

That's pretty

Rick:

Amazing,

Kaleem:

is really interesting.

Rick:

So I got to ask this one question,

Heather:

Yeah.

Rick:

let's see if I can talk my way through it. So obviously right now there's a lot of headlines about this massive push to bring people back to the office. Right.

Heather:

Mm Hmm.

Rick:

And it seems to me that all these headlines are pretty much owned and really kind of propagandized by a lot of these big, big companies. So, what I'm more curious about is what are startups doing when it comes to working remotely and how do they, how do they kind of avoid the hypersensationalism of all of these headlines that the big companies are driving?

Heather:

Yeah, it's ever present, by the way, even for startups. I would say if you're looking for a balanced perspective on some bigger companies, Dropbox and Atlassian are two great remote first larger companies. Drew Hauston of Dropbox has been like, super outspoken about the problematic nature of the return to office movement. And so like, if he's listening, I, cheers, like, that is outstanding work he's doing over there. I think overall what I'm seeing is a lot of these companies that are kind of at like, Series A ish now were probably founded in the pandemic. So they were founded remote out of. Necessity in short, as opposed to out of choice. And I think that intentionality and choice, like really deciding, like, this is who we want to be. And we think that this is the best way to work. Is a critical piece of the puzzle, or else you're not gonna be successful with remote work. And I think all these companies that started in that bubble, in the startup world who are remote maybe didn't get it right and think, well, let's try an office. That might be the answer. So we're actually seeing a lot of startups also call people back to office or even found themselves that way. I also think this, Gen Z group, because we've got a lot of Gen Z founders too, They went to college in the pandemic. They didn't get the social ties of being in person with people. And a lot of them are craving an office. Like I'm, like, working on thinking about plans, of how do you call people back if you're going to do it thoughtfully, what are the ways you're going to do it. And they're like, everyone wants to come back. They just want to be with other people because they missed a critical social development. So it's, I'm a huge fan of remote work. But I also can understand some of the reasons for it. When the reasons for return to office are the Collaboration happens better. That's debunked. That is wrong. When the reason is like, I don't trust you unless I see you. That's just awful management. But when the reason is, I'm a young professional and I want to meet other young professionals, and I missed out on some of the opportunity due to the macro world, I can feel that. And so I think it's like being really clear on what are your reasons for whatever path you're choosing and then making sure that you have the right plan to do that thing successfully. And recognizing the tradeoffs you're making when you choose, remote world, but it's, it's, sorry, we need to choose an in office world. But it's interesting to see, like, even though people have been calling people back, the broad macro world has not changed, as in the way that you would expect. So if you look at the numbers before the pandemic, it was something like maybe 7 percent or so, 7. 3, depending on like which study you look at, 7. 3, 7. 5 percent of people were remote workers. And then in the pandemic at the height, the most it ever went up to was like about 20%, like 17 to 21 percent depending on how you calculate it. And now it's back down at like 12. 7. But that's still twice. It's like 150 percent of what it was before. Um, and so I am personally frustrated by the number of companies that never got it right with remote work, gave up whether their startup or big company gave up and now they're just going back to office again or saying hybrid is the answer, which I think is kind of the worst of both worlds. I have a hot take on that from most folks but I still see huge gains for the remote work movement overall, and it's much faster than it would have been like if you watch the numbers from 2000 to 2019, 2020, it went from like three ish percent to like 7%. So like, sure, it doubled, like 4 percent of the population over 20 years with all the technological advancements, all the things we're seeing 5 percent just from three years. So, like, I still feel a sense of promise and hope about it, but a lot of startups, I just think have been similar to big companies and they follow suit of what big companies are doing. And so they kind of just go, yeah, it is hard doing remote work. Let's give up. And that's hard to see, but I think it's about intentionality and really advising founders to get what's right for them.

Kaleem:

So, that is really interesting. I was actually surprised by your answer. I would expect that after this experience, a lot of, especially seed startups would be like, no, we don't need an office. We're going to save. But I absolutely hear what you're saying. Like, you know, you're having a lot more younger founders and they want that connection. So let me ask you, like, where do you think this Remote work is heading in the VC space. Do you feel like VCs are cool with it now, as far as funding, like is the VC industry cool with funding remote startups? And then where do you kind of see remote work heading, you know, as some of these startups are progressing to become more mature companies and then going out into the industry, where are you seeing those things kind of colliding?

Heather:

Yeah. I guess to your first question. I don't think there's like a cut and dry. I think every individual venture capitalist has its own set of like, biases and preferences in the world. But typically desire to be remote or not is not a deal breaker as much as, You know total addressable market is or something else that's much bigger. And so you kind of don't see it come up It's just more of like a this is how we want to be And I've never seen it push a deal one way or the other personally, but that could be the case that it exists I think Where it's like heading if that makes sense is I think every company as they get bigger This is the thing that's never made sense to me in this return to office move in or hybrid if you think about it like At least in my experience, working with teams that have more segmentation is so much harder than less. So a company like GitLab 100 percent remote. There's one segment, remote worker, like it's very easy. You're planning for one population or one set of things, like you're saving on real estate costs. It's very clear to me why it works and how you scale it. If you're totally in office, what doesn't make sense to me is that most companies start in one physical office, but then they start to branch out and have hubs. Most companies are hub and spoke model, like a Google or Facebook or anyone, they've got offices all over the world. So if you're working on a team, that's cross functional. You're working with distributed team, no matter what. And so when they require a job to be in an office, they still have to do remote work, right? Because you have a remote connection with whoever it is that you're working with on a project. So it's never quite made sense to me to not invest in remote work. Like if I were founding a company, I would 100 percent found it. Totally remote because hybrid is much harder and in fact, like Webflow and Rainforest as friendly as they were to remote folks, really hard to plan for an office environment and a remote environment. It's double the work. Everything is double the work. And so, to me, it feels so obvious and simple, but of course, I'm probably preaching to the choir here. And I just don't understand. So I think the technology has been historically the limiter, I think, and being excited about remote work and we have the technology now. So how do we. Build the best practices for leadership to feel comfortable with it. And how do we, like, I think the Drew Houston's were like, trust that our team, we've hired adults. Like, that's kind of what he says in all his quotes, and that they can manage their own lives. And so, like, how do we get leadership who is used to the comfort of people coming to them and help them build up the communication ability to be really effective at remote work? I think that 5 percent increase that we saw as hangover from the pandemic will continue to grow. That is hugely meaningful. If you look at the grand scheme of, like, the macro trends and if we're able to raise 5% for the next every 3 years, I think they predict something like. 22 percent of the population will be remote in 5 or 10 years. If that's true, and that's possible, I would be very happy with that. You're never going to 100%, you know, so, because it's like hospital workers, restaurant

Kaleem:

right, right. right.

Heather:

going to be. So.

Kaleem:

And then the thing for that you mentioned, you know, for those startups that really want the connection. One of the things that we talk about a lot on the show is just admit you just want to hang out with people. So design that office experience. If you're going to do that, don't make people drive in to sit there on their laptops and work, embrace this idea of people saying, Hey, I just miss my friends or I miss my colleagues and I want to build this professional network. Like, so if startups are going to do that, just design like Atlassian, like Dropbox, like, like some of these other companies. Yeah. Embrace it. Don't try to force this. Oh, well, you're coming to the office. So, you need to go to your cubicle and do that writing that you could have did at your house. Maybe even better. So, it's it's really

Heather:

Yeah, it's expensive to get it right. But, one of the things we did at Webflow was these off sites every year. So you and I work remote, but every year we'd all come together for a big offset, like a week of intentional programming and thought and connection. And you could look forward to those each year so that you made those connections with your teammate and you could go off and like, let that. I think it's really important to have that goodness stay with you for some time and then have team off sites between those to kind of keep it going with the subgroups. And I think it just takes a lot of work and it's expensive to do it. But if you're saving the money on the office, you have the money to do it there instead. And it's special for everybody. So I think there are lots of strategies and ways to get it right. And most people, it, it's not the norm. And so it's a little scarier to embark on.

Kaleem:

Yeah.

Rick:

Sure. I'm hoping that our show remotely one, a key player in the demise of the cube farm, if you will.

Kaleem:

Yes. Telling these stories, sir. The voice of remote work. People have to hear that it can work. I mean, she just gave you all these examples.

Rick:

my goodness.

Heather:

I think also maybe just a note for you all as you're thinking about like this, folks who are of a higher education level tend to be more likely to work remote. White men tend to be more likely to be able to work remote. There's a lot of trends around pay and pay. Obviously, as a result of those things also tends to be higher when you're remote. Like, the average salary is something like 20 plus percent higher for remote workers than it is for not. And a lot of it's because it's knowledge workers. And these are the trends that unfortunately we have in our society of those things. But the keeping people in the office and then earning this right to go remote eventually makes it seem like a privilege versus a way of working and that hurts my heart quite a bit. And so my hope is that a world where junior jobs can learn on the role. Again, all these students who just graduated who are saying, I want to be together people. They learned college remote. So, like, they're capable of learning remote. Like, how do we get them there in the workplace as well?

Rick:

Agreed. Absolutely. so Heather. if you would not mind sharing with us a comical or inspiring moment that you may have had while working remotely.

Kaleem:

Mmm,

Heather:

many. It's been years. Okay. Well, I would say that my life is a series of comical and embarrassing moments maybe inspiring, but mostly embarrassing. So I was thinking about your podcast and I heard a guest a few weeks back or months back who shared that, oh, gosh, the embarrassing moment for her was that during the pandemic, everyone wore pajamas to work. And I can't believe we did that. And. I sort of chuckled to myself because I wear sweatpants and or athleisure on the bottom half of my outfit 99 percent of the time, like, unless I'm going somewhere right after work, I'm going to wear sweatpants to work every single day because no one sees me from here down. So, why not? But my embarrassing moment is that I have 2 dogs and sometimes they decide to be guard dogs of the house and bark at things or fight over.

Kaleem:

quick, quickly,

Heather:

Oh yeah,

Kaleem:

dogs names.

Heather:

Barkley and Remy Martin.

Rick:

And what was the other one?

Heather:

Remy Martin, also a basketball player, not the alcohol, the basketball player, Remy Martin. Yeah, they're both

Kaleem:

true.

Rick:

One of these days I'm going to get a Larry

Kaleem:

my gosh,

Heather:

I love that. Yeah. I still think Scotty Puppin is the next name. Oh wait,

Rick:

I love it.

Heather:

in, do you want to meet him?

Rick:

Yes!

Heather:

This is Charles

Kaleem:

Oh, look at the sweater, yo.

Heather:

is his holiday sweater. Yeah, it's his little hoodie.

Rick:

gosh.

Heather:

Yeah,

Rick:

Hi Charles.

Kaleem:

Hi, Charles. Hi, Charles.

Rick:

boy.

Kaleem:

So,

Heather:

you.

Kaleem:

and Remy Martin,

Heather:

Who just ran outside, yeah.

Rick:

Okay. Okay. Ha ha

Heather:

And so my embarrassing story is that sometimes these guys get into trouble. You wouldn't imagine it with a face like this, but this boy is capable of manipulating everybody in the world. He'll do things like cry at the stairs and you think something's wrong, but then he just wants to play with you. So, My embarrassing moment is that one time I was hosting a session, like a learning session for our people leaders in our portfolio. And, this woman we brought in to speak was doing a great job speaking, but I'm kind of facilitating throughout. And all of a sudden the dogs get into like a fight over this tiny toy that they just want to like lose their minds over. So I run out to the side really fast and I'm really good at doing like the, I'll show you here as Charlie jumps down, the slide so you can't see my pants. Like you just sort of like. The slide to hide the workplace mullet, um, as opposed to standing up, but when your dogs are fighting, you just get up and run. And so everyone probably saw my sweat pants on the bottom. So that was embarrassing part 1 and then I run over to break up the dogs. And I come back and I'm like, out of breath and everyone's waiting for me to speak because I had a tee up the next slide on the presentation, but I was like, running back and I'm so sorry. My dogs are in a fight. And I like, changed the slide. So that was really embarrassing and that was only like, 2 months ago. So it's just the most recent example. I think each time an embarrassing thing happens, I just erase the 1 from before. So they haven't, there haven't been more than that, but you kind of master the slide if you haven't done it before.

Kaleem:

Are you kidding me? I have to master the slide right now. I mean, we were all sometimes, you know, we're just wearing shorts, you know what I mean? Dress, shirts and shorts. I totally

Heather:

Oh, I should show you. I have a pair of sweatpants on that I think you guys would appreciate. So, I always, with people I'm close with, I'll share, like, the truth. So, if you, if you're, check out my sweatpants.

Kaleem:

Oh, Webflow. I get

Heather:

a large men's

Kaleem:

Oh,

Heather:

and giant, so, uh, yeah.

Kaleem:

I got work.

Heather:

Yay!

Rick:

Oh

Heather:

you're doing my favorite thing. You're doing the power clash. The power clash is the best way to remote mullet it. So it's, you know, business on top, party on the bottom.

Kaleem:

Big time. That's awesome. Great story. Great story.

Heather:

Thank you. Thank you? for turning my embarrassment into a moment of pride. Um,

Rick:

Ha ha ha Where can our listeners and viewers find you?

Heather:

I don't believe in Twitter or X. I'm a quitter of that one. Um, so you can find me on LinkedIn. I think I'm just the normal LinkedIn slash backslash doshay.

Rick:

Okay.

Heather:

thank you. And I'm happy to respond to messages or friend requests and all of that. And then look out for me on the single fire blog. I'll be posting some stuff this year with some more advice and ideas. Oh, and one more, if you're up for it. We have a great remote work guide available that is authored by yours truly. So, if you're ever looking for how to get remote work right at your company, and you feel like there are opportunities for improvement, and you want to bring something to your company, go to the SignalFire blog, and you can find a very thorough guide on everything from how to do it compliantly, to have interpersonal connections, and more. So, check that out if you're looking to make remote work better at your place of work.

Kaleem:

Awesome. Thank you so much. This was awesome. We appreciate it. You can come back anytime. And next time we're out there in the second Portland, maybe we'll hit you up and say, what's up, but appreciate you.

Rick:

I might need to hit you up for some Greek affairs knowledge down the road, so I'll be in

Heather:

perfect.

Kaleem:

Awesome.

Rick:

Thanks, Heather.

Heather:

Talk to you soon. Thanks so much.

People on this episode

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Kaleem Clarkson

Co-host
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Rick Haney

Co-host