Jill of All Trades: Lessons from Ashley Wilson on Growth, Change and Embracing Uncertainty
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You're listening to the Uncharted Podcast. Today's guest is Ashley Wilson, who's the co-founder and COO of Momentum. We talk about how they're differentiating themselves and positioning their offering in a competitive space. More importantly, we talk about the importance of transparency and how they're driving engagement and ownership within their company, as well as some tips and tricks that I think is applicable for anybody. We had a ton of fun, so I hope you enjoyed today's episode. I have absolutely

Ashley Wilson from Momentum. Welcome to the Uncharted podcast, Ashley. How are we? I'm good. Thank you so much for having me. Really excited to talk to you. Pleasure's all mine. I love getting a quick intro, personal business bio. So give everybody some context on who Ashley is. I'm Ashley Wilson. I'm the co-founder and COO of Momentum.

We are in kind of the sales tech space and we've been working on this for the last couple of years. I'm also a mother of three young kids. I am married to one of my co-founders and we're three co-founders, one of whom is my husband. And I live right now in Argentina. I'm American, but I've been living in Argentina for almost the last two years. Why the move to Argentina? Obviously, marrying somebody from another culture, started learning Spanish.

Started to think, oh, I would like to live in another country. We met in San Francisco. We met at work, a company called Sauce Labs back in 2010. So I felt just from visiting here a lot, his family didn't speak really much English when we met at all. And so just seeing that the immersion that you get from living somewhere is just so rich in its experience. So that was the motivating factor in the back of my head.

And then we decided to do it at the beginning of 2020 for a couple of factors. So we've been building out our SDR team here in Argentina, in Rosario where we live, which has been awesome. We've got a team here. So we thought we actually would have people we could work with in person versus us working out of our house in San Francisco.

Three kids now, we had two kids and a baby on the way. So we figured San Francisco with kids is starting to get expensive and challenging. And we didn't have a lot of my family there. So just getting more support. And then the intention was to move for a year. So do a sabbatical year, and then we'll come back to San Francisco, we put our stuff in storage.

And we're going on two years and really honestly, the combination of having a team here to work with every day, which is just very rewarding to be in person again in office with the family and just lifestyle support from a cost perspective. It's just made it a...

unexpected life change that we're just in the flow with and seeing where life takes us at this point. - I love it. I've gone to a couple of different regions over the last, let's say 18 months, like Belgrade being one, Croatia being one, even London reminds me of 2012, 2013, when SAS was coming up, everyone was in the office and that energy where everyone's learning.

Now that you've done it for almost two years with the team in Argentina, do you think you can get the same productivity and output with a team, especially like a customer facing go-to-market team? Because that's a little more rare abroad as let's say like an in-person team that's in San Francisco or in general in the US. It's a great question. We've been building out our SDR team here, and we're promoting some of our SDRs to be junior reps to work with us, but we're

We just hired our first enterprise rep in San Francisco. We just hired our director of CS in San Francisco, director of CSM. We obviously just raised our Series A, which is why we have this money to start hiring these folks. But we are recognizing our customer bases in the US or North America, primarily. We have a couple of European customers. And we really are, in our DNA, San Francisco SaaS company. We all met in 2010 in San Francisco. All three of us co-founders, we kind of rode that kind of tech

way for the last decade plus there that we think that there's a real value to kind of having both. So having a team that can, from a cost perspective with doing an outbound motion, it's pretty hard to scale that in the US as an early stage company. So we get the luxury of doing that here and testing and working with our team on messaging. But I think from a go-to-market accounting executives, head of sales, CS perspective,

You have to be where your customers are. And for us, we're not a LATAM company. We are a US company. We've also been building up engineering in Canada, where our CTO is and co-founder. So I think we're just more thinking of where do we build our hub? We'll see how it evolves as we grow. I don't know what we'll look like in another four years, but so far, that's how we're thinking about it. The case of change has been remarkable in sales tech. I remember specifically you guys in 2020,

came on my radar because I was at Saster, a couple of people. And even since then, it's just changed so much. And I say this with love, but the last couple of B2B events I've gone to, every new startup, the pitch is the same. And as someone that's had a product marketing background, how are you learning to position yourself and differentiate yourself? I feel like I've gotten...

I was schooled in doing that in practice. I know I had product marketing background. I started product marketing consultancy. I did this with founders and being a founder now and writing this 2020 to 2024 kind of timeframe. We raised our seed in 2021 on a very kind of

similar premise but different i think what i have learned is that the rate the pace at which you have to reevaluate your positioning has gotten so much shorter and you have to be comfortable with that you have to make that part of your strategy you have to invest in that that might mean that you're changing your website three times in the year whereas before maybe we change it once a year

Back in the day, we'd change it every two years. So that's a big thing that we have come to embrace is that we're using our positioning as the means to the go-to-market strategy, which is the heart of positioning. But recognizing that as a constantly evolving effort that we have to do, me as marketing, founders, make sure the SDRs know it. So you feel like you're always sprinting to stay ahead. But I think that's what's being asked of companies today.

these days. You pointed it out, we were very early on jumping on the AI bandwagon. So we were able to ride the AI for sales messaging for a good, I would say, 8 months, 9 months. But towards the end of last year, we're like, okay, everyone's doing AI for sales. And then in the spring, it was like, okay, let's do customer intelligence. And now we're thinking of rolling out our next wave of positioning. And I think the other angle of it is your customers do help inform the positioning.

And so if you're listening and talking to your customers and what are they wanting to solve for, what are they thinking about for next year? You start to, just like it involves your product roadmap, it should absolutely inform your product position, your brand positioning.

And I think that's something that now as a founder, I maybe didn't understand that so closely when I was a marketing consultant because I was working with the team, not necessarily the customers. So any early stage founder would say, you're going to talk to your customers all day long in year one and year two and year three. Keep doing that. We cannot rest on our laurels anymore and just keep riding these waves. As you're talking, like part of it is like talking and getting the anecdotes. And part of it is like,

doing it at scale using like data. But sometimes you said it, the pace of change is so fricking fast that the data can be outdated, right? What do you do there? I'll give you what we're doing. I don't know if it works for other people. We were just at the pavilion, the GTM conference two weeks ago.

did our first booth, rolled out our next positioning that we're doing, which is enterprise listening. So the way we're talking about enterprise listening is that especially as you move up market, it's very hard to listen and take action on what your prospects and customers are saying. So we plug into your conversations. We use AI to extract the data out on scale.

So a couple months ago, I was thinking that was like customer intelligence. Oh, we're the platform to gather customer intelligence. And then Amish, who is our partner at FirstMark, who invested in our Series A, when he made some customer introductions, he started introducing us as this magical tool for enterprise listening. And we were like, whoa, that's cool. We never heard that. It's different. It's out there.

But in the last two months, we decided to just rally around because we all had a visceral emotional reaction to it. It's not like that came from a customer. It's not like that came from the data. It did come from a very smart investor. So it was like a reason to listen. But we started to say, if we did enterprise listening, what would that mean to us? What would the story? And we just did a whole new kind of brand positioning exercise. And what would the messaging be? And if we were to start telling that story, which we believe is a story of the future,

How would we talk about it today? What do we tactically do? Yes, we plug into your customer conversations and use AI. But what is the emotional story? Oh, it's enterprise listening. We help anyone in the organization listen and take action on their customers.

And then we go and validate that. So we've been rolling that messaging out of the conference on our whole new intro deck is that our website in a couple of weeks will be that. And until they get more data that says to go in a different direction, we'll just keep kind of battle testing that in the market. And until the next amazing thing comes out, which it will, I'm sure in six months, somebody will say something else. We'll change it. So I just think that's what I mean by you have to be really listening. And a part of it, you're right, is that

You got to go off of some gut feeling here. Like you're making things up as you go. You're creating the future. So there's got to be some just trusting and what gives me emotional resonance.

Great. Let's lead with that. Love it. Some folks just can't handle the pace of change. It's been so much the last four years and I sympathize with that. But the one thing I've learned is you just got to roll with the punches and go. What do you do in those circumstances? Do you just move on? Do you try working with them and getting them to adjust and change their behavior? What's the secret sauce you've learned? I think you have to be more judicious in your hiring.

especially early, probably sub 50 people to really get the startup folks. But what does the startup folks mean today? I think it means a lot more of they're quick on their feet,

highly autonomous. They thrive in kind of creating something out of the white space. You can't have a lot of like process people at this stage. We're about 40 people. I think we're starting to bring in a little bit more structure to some of our roles and sales or CS. But even then, we're hiring people who've worked at startups. We're hiring people who have understood

the name of the game. And I think you also need to be in your hiring process, in your onboarding, say, guys, things are going to feel like they're changing a lot and that's okay. We just shifted now that we're a little bit bigger to monthly all hands, but we were doing biweekly all hands with the company. We're a remote company. We value being very transparent when it comes to roadmap and financials and runway. And that was a way to stay on the same page, but also not have any surprises,

One quarter later. So I think you have to over communicate because that way you need to have the freedom to make the changes. Also, as a leader, I think you need to be strong in your opinions amongst especially your founding team and your leadership team to say, I'm sorry, guys, like I am going to steer the ship differently. We are going to go in this direction. And I think you get people bought in if you are bringing them along step by step. That's something we try to do.

Love it. One thing we glanced over, but I'm curious when I was just looking at your background. So right before this, you had an agency, product marketing agency. And at some point, you decided to make the transition full time to becoming a founder of Momentum. I do event sponsorships and I'm very good at it, make decent money. But I've pondered, is this a good time to go do something? I'm curious just to get your perspective. Was there an aha moment? Did it happen gradually? Talk to me through your experience and any advice you may have. I think in my case,

Pandemic hit in March 2020. Agency business went almost to zero, basically zero. Marketing budgets got cut immediately. My husband, Santi, wanted to start another company. He previously founded a company. We were living off of the agency income for a couple months. And I was like, okay, now what? My co-founder, Ray at Olivine, we actually came on as a third co-founder part-time.

Agency stuff, we're not so busy, but we'll keep that going as we get more clients. And we luckily closed a couple of clients that year. But we've got time. So we actually, I did name momentum. We did the branding. We did the persona workshops. This was all pre-seed. And then in the fall, when we went out to raise the pre-seed round, October 2020, I actually had a moment where...

I'm doing the deck with Santi and Moise. I'm talking about the positioning, but I'm not on those calls. I'm sitting on the couch listening to the calls because we're in the same room. I realized I didn't want to be behind the scenes. It's hard as the partner of a founder because you are the one who's kind of the rock. You're involved. You hear everything, but you're not going to get any credit.

And I think given my background and given my skills or things I wanted to develop and learn, I realized that I'm probably going to be upset if I stay behind the scenes. And maybe there's an opportunity to just get into this and we go all in. So in our case, we just decided once we raised our seed round,

in August, 2021, we felt, okay, I'm going all in. We're going all in as our family. And I started to transition out of Olivine and we brought in somebody to run the day-to-day and Ray stayed involved for another year or so. She has a startup as well now. And it's honestly been such an amazing transition because it's really fun to do your own. So my advice to you would be, if you're curious about it, keep listening to that because I think sometimes the universe will show you when it needs to happen. It's very rewarding in a,

not worse or better way than the consultancy, but it is rewarding in a very different way that feels

very engaging to me. I've worked with so many founders, but I really did not sympathize being a founder until I became a founder. And I had to learn how to get my own clients overnight. Like what you went through, I was in events. So March, 2020, I went to zero and I've learned to be so sympathetic with founders. And as a result, pretty much like worked with some of them for six, seven, eight years. And I think that's because I have that ownership mentality. Now,

Now that you're a founder, I think you sympathize with some of that. But I've had a really hard time over the last two years to be the middle person between founders and sometimes employees for a wide variety of reasons, because the incentives are a little different. Some of them, frankly, have been burnt with the layoffs. I'm curious, what have you learned to educate people?

your staff or people like what it's like to be a founder? Because sometimes I just think it's education and it's like learning that without having to go through it. So I'm just curious if you have any advice. - Great question. I'm thinking back to when we worked at Sauce Labs in 2010 and we were all early. Sanjay was the first employee. I was like employee number 10 or whatever.

And we thought that we knew it all. And I think that's what happens when you're early is that you as an employee, you're so early and you're doing your day to day. You feel so much ownership emotionally and you're so bought in. And you also feel like you've got the view of everything.

And then you realize that you have the view of your world and everyone has their own world view. And the founders have to see it all and take it all in. And something that I've come to appreciate and empathize and think back to my younger self and be like, oh, you did not know is sometimes you have to say in your head,

I'm not going to work on those things. And they almost can become like other people, like apathetic or you don't care. Like, why are they not fixing X, Y and Z? X, Y and Z is such a problem. And you realize that the founder, you have a thousand problems. Part of the job is being judicious in what you focus and work on that day, on that week, on that quarter.

So until you're in those shoes, it's very hard to see that. So what I try to do with my team is I try to empathize from me how I used to feel. First of all, I think probably the

It's very good to have worked at startups before you found the company. I know that there are like those magical whiz kids who found companies when they're 20, 21, 22. I think they're unicorns. I know they exist. But I think there's a reason that successful founders tend to have worked at other companies is because you've not only done the role, you've experienced, you can be more empathetic as the founder, because you've been in your employees shoes.

when people come and tell me stuff, I try to really listen. I think the other thing goes back to just trying to be transparent about where we're at as a business, what we're focusing on. And that goes back to having kind of those regular touch points of here's the strategy, here are the finances, here's where we're at, here's why we took this money, here's where we're going, here's what the goals are.

It doesn't solve everything. And I think some of this is just natural tension between employees and their bosses. I appreciate you for keeping it real. And I do agree with you. The more transparent and vulnerable I've been over the last couple of years, it's better than the opposite. More often than not, most people are reasonable. And the ones that are not, the universe somehow pushes them out. This has been fantastic. One of the things that we'd love to do before we say our goodbyes, we ask this question every time. If you could go back to any time, what's one piece of advice you would give your younger self?

I would actually go back to my high school days. I went to performing arts high school. So I used to be very involved in the arts, so dancing and singing and creative writing. And I always felt self-conscious and bad that I did so many things because in the arts, the very best people focus on one thing.

And it's so clear from such an early age, like when you're a dancer, by 10 years old, you're on the dance professional track. And I was very good at a lot of things, but I wasn't the best at anything. And I wasn't even drawn to one thing.

So I always felt like kind of the Jill of all trades master of none. And I was like, self conscious, I felt like something was wrong with me. And actually, funny enough, just the other day, I was thinking about that. And saying, Oh, my gosh, it all kind of worked out. Because being a founder is being a Jill of all trades master of none. And you actually get paid to do that. And people celebrate you for that. And I think it's probably one of my best qualities now and sort of thrive in

in context switching and things being chaotic and I'm curious to learn the next thing. So I'd probably go back and tell myself it's going to work out.

In 20 years, you'll be in a great spot. You'll feel proud of who you are. Don't feel bad about yourself right now. And I think that's how it goes. Some of the things that we feel the worst about end up being our best qualities and our best strengths. I couldn't agree more. This has been fantastic. I've had a ton of fun. I appreciate you for coming on. For everybody listening, I will put Ashley and Momentum and whatnot in the show notes. Reach out, learn a little more about Ashley as well as Momentum. And until next time, everybody, be well.

Be safe, and we'll catch you on the next episode of Uncharted Podcast. Hi, everybody. Poya here. I know you have a lot of options. I know you're busy. So I just wanted to thank you for listening to this week's episode and for supporting us. Until next time, be well. And if you get a chance, do something nice for somebody.