Cloudflare TV

Yes We Can

Presented by Michelle Zatlyn, Alyson Welch
Originally aired on 

Yes We Can is a recurring series presented by Cloudflare Co-founder, President, and COO Michelle Zatlyn, featuring interviews with women entrepreneurs and tech leaders who clearly debunk the myth that there are no women in tech.

Alyson Welch is the Vice President of Twilio's Enterprise General Business. She also sits on the Board of Directors for Girls in Tech. An expert in organizational planning, she has built enterprise sales capabilities from the ground up for Fortune 1000 companies and early-stage startups. Throughout her career, she’s excelled in scaling go-to-market engines and has successfully designed and executed turnaround strategies for large revenue divisions with more than $500 million in annual recurring revenue.

Alyson is passionate about mentorship; in her free time, she helps tomorrow’s brightest leaders develop their skills and figure out how to advance their companies’ revenue generation strategies.

To watch more episodes of Yes We Can — and submit suggestions for future guests — visit

Women in Tech

Transcript (Beta)

Hi, everyone. Welcome back to this week's episode of Yes We Can. And I'm just thrilled to have Alyson Welch here with me today.

Hi, Alyson. How are you? Hey, Michelle.

Great to see you. I'm doing great. Thanks. Happy Wednesday. Happy Wednesday.

I know. I'm so excited. It's my kids' kind of end of school celebration recently.

So I feel like summer is here. We're still in the midst of it. But we're one more day away from school being out, which is a daunting, sometimes a daunting transition in a parent's life.

I don't know if anyone else can relate to that. I have that same.

I'm both excited and a bit daunted. The schedule, the lack of schedule is both a feature and a bug, I guess, sometimes.

Anyhow, so good. Well, it's so great to have you here.

Let's dive in. So for anyone tuning in, thanks so much for tuning in.

If you have questions for Alyson, there's a way to submit questions and they'll pop up.

We'll try and get through them. And then if you have recommendations of other great people you'd love to see on the show, please email us at YesWeCan at CloudflareTV.

But let's start with Alyson. So you've been a sales leader for over 20 years.

And I love some of these terms, SaaS leader, enterprise, application security, really a lot of hardcore tech.

And currently, you're the head of sales for North America at Twilio, which is an amazing company.

We're going to talk more about that.

But I think that there's a lot of people who listen to the show who aren't exactly sure what enterprise sales means or does.

So maybe you can start by sharing with the audience, what do you do all day, Alyson?


Great. And those are a lot of acronyms. So happy to answer questions on why I put all of that in my background.

So I spend most of my day with my team. I run a team of about 150 people across North America.

And we are focused on building solutions for our customers that help them build great customer experiences.

And so what that means is our target market and enterprise target market at Twilio, which could be very different from an enterprise target market at other companies.

For us, we've defined it as 2,000 employees and up.

So any company in North America, look it up on LinkedIn, has 2,000 employees or more, they would fall into our world.

And we work with those companies to recommend solutions for improving their customer experience, their customer engagement models, et cetera.

That's amazing. That was really good.

I feel like I even know better what that's all about. But thanks so much for sharing that.

And maybe just to give some examples of like, why do you love your job so much?

Like, why do you love helping your customers implement these solutions of these larger organizations?

Maybe give us a sense of why you love what you do so much.

I have worked across different segments, and I always seem to find my way back to enterprise.

In every company I've worked, enterprise has sort of been my core area of focus.

I love the complexity of enterprises.

I love to see enterprises grow. We work with companies that when we first start working with them, they have a much smaller footprint.

And they've either acquired or they've built out different solutions and products over the years to continue to address their customer challenges and their desires.

And I find that there's so much innovation in that category.

And frankly, the other beauty of working with enterprise-size organizations is there's larger access to budget.

So I enjoy working our way into those budget cycles and getting a seat at the table with executives and line of business leaders who are building the next generation products for all of us, from B2C retail experiences that we engage with all the time to behind-the-scenes workflows with financial services.

And looking at Square as a big customer partner of Tulio's, I'm sure you work with them as well as an example.

But they are building new digital solutions to manage how payment processes are occurring in the industry.

And it's just totally transformative.

And it's really interesting to see that evolution. So I get energy from our customers, and I get energy from the people I work with within Tulio that we've hired and helped build careers for.

I love that. There are a lot of things that I think that sometimes when you think about enterprise sales that you don't really pop up.

But when you were describing, it's like the collaboration with your customers.

And Tulio has amazing technology and how your customers use that to help solve problems for their customers.

And it is a very collaborative relationship.

So thanks so much for giving us a little bit of insight on that. That's great.

And we're going to come back to people who do really well in this sort of environment.

But before we get there, let's zoom out. Because again, you said you've worked with a lot of different sorts of customer segments, different stage companies.

So Tulio today is a public company, large. You have a large team growing really quickly.

You've had a lot of large customer company experience, high growth experience.

But you've also been an earlier stage startup. So I love that breadth of experience.

And so if you take a step back and you think about, OK, the last two decades, what are some things that are similar to these larger companies and startups?

And what's kind of different? And it's really for an audience to get a sense of what the differences are between those types of companies.

Yeah. And I'd say Tulio is about 4,000 employees now.

I don't have the exact number, but around there.

When I started, we were probably just over 500. So we've grown. I've been there about four and a half years.

I've been with Tulio about four and a half years.

And so I find that I get involved in sort of that growth stage of from a 200 million to a billion plus.

That's really where my expertise lies. I did work with pre-revenue startup.

And I work with pre-revenue startup companies to advise all the time on their go-to-market strategy.

And the key differences that I noticed are really just around the infrastructure.

The ability to go back now that we've been through this growth phase that we have at Tulio and similarly with my experience of growing with Akamai, we have the ability to go look at our data and our trends.

And in a startup, you don't have that, right? Because you're just building the product market fit.

And you're just getting your first customer stories in the door.

And you're really iterating and learning. So that infrastructure is something you're having to be much more creative in coming up with solutions and approaches.

Versus at Tulio, we can lean on some of our signaling and our data and our customer behavior and trends to make decisions.

And I think that's really a core difference.

To me in tech though, the similarities of the people and the type of profile that does really well in technology, at least the stages that I've been a part of is pretty similar, whether it's startup or hyper growth company like Tulio, where intellectual curiosity is really critical for success.

And if you don't have intellectual curiosity in the technology world, it's probably not...

I wouldn't encourage you to step into necessarily our category.

You might be better suited to start into an organization that's a little bit further along in terms of development and stability or predictability.

You have to really have a willingness to solve problems, roll up your sleeves every day, no day looks the same.

And that goes for my experience with Tulio as it goes to my experience with the startup world.

And I would add, it goes with my experience at Cloudflare too of this building.

And there's just a long list of things to do. And as soon as you think you've done it all, there's a new long list.

And what you built two years ago is no longer what you need for now.

And you got to go back and do it all again.

And it is super fun, but it is constantly changing and learning and rethinking decisions and assumptions along the way.

So I think you did a good job describing my experience as well.

And we'll come back to that intellectual curiosity.

And when you're saying about ability to look at the data, to make it repeatable, I think that's, as you get to a larger company, you want things to be repeatable, especially in sales.

I think that is one of the things that were kind of the most surprising to me as I've learned more about enterprise sales.

Actually, success is predictability, being able to, with high degree of confidence saying, this is what we're going to get to by this time.

And here's how we're going to do it.

That's kind of the name of the game. And when you're starting a company, I don't think you less likely have that lens.

You're just like, I just want, will somebody buy this?

And so it is that predictability and repeatability that becomes so important.

Definitely. We're modeling all of the time and we're doing best case, worst case modeling.

It's quite a math oriented role at this point with a lot of assumptive inputs that then tell you, this is what we think the numbers are in terms of the amount of people you can hire and the coverage that you can expect.

And sometimes you certainly see changes in the year.

You see COVID, gosh, we never predicted that. And that was a real adjustment that we had to make to our business planning.

And then when we actually found that we were quite relevant during the COVID, especially during the initial phases of remote work and supporting remote workers and agents who were supporting customers in a distributed fashion, Twilio suddenly had this demand, but we didn't know what we were going to expect during that initial period.

So things like that, you're just always iterating and you have to be comfortable with experimentation.

I love that. I love that. When you're saying how it's actually a lot of math, all I think about it is it's not just meeting up with customers on the golf course.

Since it's like, you know, which sometimes people think about sales.

Yeah, no, that's something I actually am pretty passionate that it's really not bad.

And that's not a characteristic that I'm like trying to acquire.

I like people who can build true relationships with customers, but that means credible relationships that actually require that you understand their business, not just their hobbies and their personal passions, but that you really are seeking to understand what success looks like for them.

And that's what your focus is.

It's not, let's get about for time on the course or a lunch. The modern salesperson is as much of a data analyst and research leader as they are a personable, um, um, you know, very active listener.

I love that. That, that really resonates with me as well.

As I think about our great sales organization, the best people have those characteristics.

So let's talk about that. Let's say there's someone listening and you're like, oh my God, Alison, this sounds amazing.

I want to work on your team, or I want to, I you've convinced you've sold, you've convinced the audience that I'm going to go and spend more time with customers.

And I want to go look for a role in sales.

And so when you think about the team, you have a large team today, 150 people, you hire a lot.

You look at the best performers. What are types of people that do really well in this role and a high growth environment from your perspective?

Yeah, it goes back. It definitely goes back to the characteristics of intellectual curiosity and, um, comfort with, um, with experimentation.

So I, we've kind of, we've summarized it into this grid concept.

And I think many organizations today leverage the work of Angela Duckworth.

I've talked about this on other, um, conversations that I've had her book, the power of persuasion.

Um, and I think it's actually called grit, uh, bravery.

And it just shows that you don't have to have this profile. There's no perfect profile for someone to take on a role in sales.

Sales is accessible to individuals who are highly curious.

And I've hired, I'm so proud of some of the leaders that I've hired into our organization who didn't jump off the page at first as being, you know, this is the obvious person who's going to be a really successful sales leader.

I've hired people from, you know, financial strategy, uh, backgrounds with product backgrounds with, um, gosh, what was it?

People from different industries who had no tech experience, but just really wanted to learn and break in and committed themselves to doing it.

And they're having successful careers now, um, you know, going above and beyond what we ever expected.

Uh, so it's pretty, it, I want, I want people to, to feel that it's accessible.

It sure takes work. It's not easy. And it's not like, you know, the haves and have nots is, that's, that's life, the haves and have nots of life, but it's really the effort you put in is the effort you're going to get out of it.

And you have to be creative and you have to be, um, somewhat patient.

Patience is a key, key characteristic that I think is really important.

Oh, interesting. I've walked.

Can you say more about the patients? Cause that's something that kind of resonates with me that it feels like it should happen really fast.

But what do you, when you say patients, what do you maybe expand on that a little bit?

I think when you join any organization, in my experience, it takes time to learn the business.

It takes time to learn the company, the culture, the model of what success looks like.

And so that, that doesn't happen overnight. In addition to that, you have to build relationships with your potential customers and you have to build trust and trust can take different, um, different timeframes.

Uh, we have cut, we have some regions where we're not, you know, we, we aren't a known brand or our Nia teams.

Some of my teams in the central region of North America, Twilio isn't a household name.

It's not a Silicon Valley where you drive. Yeah. Yeah. Where do you drive up the one-on-one and you see the red, you know, ask your developer canvas.

We're not canvas there.

Um, in a, in the same way that we are in some of the other markets where there's just a higher, you know, higher percentage of developers or, um, more of a technology, um, mentioned in the, in the markets.

So, um, that takes time and patience and, um, adaptability and, you know, also feedback.

So I, I get a lot of feedback, like, did we think about this, that new thing?

Can we try this new experiment?

Um, and I have to be as a leader, um, an active listener or an active participant to be willing to say, Oh, you know what, maybe in this market, we do need to do things a little bit differently, or we need to stop, or we need to lever, leverage a partner or a channel to be more persuasive.

And that's okay.

That's not, that's a good thing. That's the next phase. So, um, patience is, is something that I think it comes and goes.

Sometimes you'll have immediate, you know, success and results, but to be truly consistent and successful, it takes time to build upon, um, an initial, initial opportunity with the customer.

I love that.

You know, I have the saying, I hadn't told you this ahead of now, but I, I have over the years said, I'm very impatiently patient because it does take things do take longer.

They just, they, they just do. And, and, but then you also want to be impatient in the, in where you can be making changes or actually listening or not resting on your laurels too.

And so it's sometimes I'm like, okay, be impatiently patient, but I agree that the, the patience is really, really important and having this long-term perspective, okay, we're building a long -term business for the long-term.

Let's make good decisions for the long-term and not just take a shortcut.

So that really, um, uh, uh, resonates. And so the, you know, one of the things is, you know, you talked about bringing people even from outside the technology industry or with the technical skills to come join your team at Twilio, again, really technical company and, and others.

How do you, when someone shows up without maybe a really heavy developer background or without a computer science degree or without years and years experience working at some other big tech companies, what advice do you have for them?

Obviously it says highly curious to learn, but what other advice do you have for them to help get up to speed on the technical aspects?

I think sometimes that's what scares people away from technology.

It's like, I don't know anything, anything about this. I'm smart and I'm curious, but how do I learn?

Yeah. Um, there's a, there's a lot of, first of all, everything is pretty accessible these days thanks to Google.

So, um, you have a huge library, like, you know, obviously you're coming into a new market, new technology.

You need to learn the lexicon of that market, of that, um, of that company and then of that company's customers.

So what are the customers saying about whatever technology company you're considering?

Go Google it. It's out there.

There's YouTubes on it. There's customer stories. Um, it's really accessible.

You don't have to lean on, you know, the smart person next to you anymore, which is so nice.

It makes it, it helps us because we can scale faster too, but you have to be able to consume that and then figure out how would you put your sort of tweak on it so that it's unique to you and that it comes across credibly and meaningful.

I mean, that's really important. So do research. You have access.

Um, if you see words that you don't understand or terminology you don't understand, don't be afraid to ask.

Um, I see a lot of people like, I don't want to ask a dumb question.

I think it's actually respected more to speak up and ask a question than stay silent in our industry.

And that's a really great thing. Um, so we're, ask questions, you know, find, find us.

Um, in my world, the sales engineer is probably like the, the technical, um, partner who I work with or my team works with most closely.

And so you'll, you'll typically be partnering with a sales engineer, um, in your, in your, uh, responsibilities as a salesperson.

So that's someone that is your trusted ally and build relationships with that person.

My best, um, my best years as an individual contributor were when I really broke it down.

When I didn't understand something, you know, I wanted to be credible with the customer.

I wanted to stand alone. I didn't want to have to bring in a sales engineer to every conversation.

So leveraging that partnership and having them see how you're really trying to, to get the concepts, um, goes a long way for you and for your, your broader team.

They'll, they'll respect you more in the long run.

Um, yeah. And I think what you said too, is like impatiently be patient and don't rest on your laurels.

So there's just so many layers, um, layers and layers of things that you can uncover, but, but, um, continuing to do that and make it part of your day in day out practice to be a learner.

Um, so that you can, you know, can show up and be credible with customers, but you'll be, you'll be far more successful.

You'll stand out versus just trying to get them back on the golf course, which by the way, nobody plays golf anymore, apparently, because I don't know.

I don't know. I don't see very much golf maybe in certain regions.

That's just a Bay area. Um, do you have, what's that? I will get back to the series though, but do you see something replacing golf?

Is it car racing or something?

Well, I hear about that. That sounds like a fun activity, actually.

I haven't done that myself, but I hear a lot about, and I do this with my teams, like walk talks, hikes, um, certainly like a lot of, there's a lot of cycling in the area.

So that might be specific to Northern California bias.

Um, and I, I would say, um, yeah, that's a great question. Like what's the next way to collaborate strategically and like take a pause and think about the long run.

Um, we do a lot of, uh, we do these boundary sessions with our customers, business consulting environments where we move us, we move away from the engineering, like how is the solution going to work?

And we take a step back and we work through what is the outcome?

Like what is the productivity that you're going to gain and realize for this investment?

I think some of those sessions can help you get into roadmap conversations and strategic, um, thinking for, um, where the products may be going that these companies are building.

And so maybe that's, that's the next thing.

It certainly, hopefully isn't zoom forever. I'll tell you that.

Right. I, I, I, I, there's lots of things that I love that I can spin this up and have conversations with people like you, which are always the highlight of my week.

And then there's sometimes we're just meeting somebody face to face is just such a sigh of relief.

So I a hundred percent agree that I hope we don't totally forget what it's like to be in real life as well.

Some of the things that we've seen work, um, in addition to, as you said, kind of zooming out, it's, you know, you're solving a particular business problem, which is obviously those are a need.

You got to do that, but then also zooming out and be like, Hey, big picture.

Cause to me, there's so many shifts happening in technology that it's hard to keep it all straight.

It's even hard for, for people who are experts, keep it all straight.

Cause there's just the rate of change is quick. And so sometimes zooming out and be like, Hey, let's zoom out and where, where's the business going?

What are some of the trends?

What does that mean? What are the implications and having a conversation about that?

Well, we find that, see that helpful to some of the things we've seen work are, um, well, we started Cloudflare TV to connect with our customers and, and teammates and other people in the ecosystem, which has been wonderful.

But the other one is food. Food is always seems like brings people together, sharing a meal kind of has to the test of, of civilization where it's like, let's share a meal together.

There's something that we all have to eat. Absolutely.

Yeah. Okay. So we have about eight minutes left and we, I mean, you've done such a great job with enterprise sales and Tulio, congratulations, amazing company, big success story.

And obviously they're very lucky to have you part of the team and really hats off to everything you and your team have accomplished.

But in addition to this huge job, I mean, Tulio is almost a $2 billion company.

Like one, you did 1.7 billion in revenue last year, growing quickly, well over 50% large team.

So like that is a lot.

I know you have a family, but you're also on the board of an organization called girls in tech.

So maybe you can tell the audience more about what, what is girls in tech?

Sure. Yeah. Girls in tech. In fact, I have a board meeting right after this.

Okay. So I'm excited to see them. It's, it's an organization, nonprofit organization that was founded by a woman named Adriana Gascovy.

And it's focused around getting women into, into technology, focused on STEM and building empowerment for women to be women, girls, we say girls in tech, but women at large, getting into the field.

So all the things we've been talking about in terms of, you know, technology being accessible, sales being accessible.

We focus on programs.

We have conferences around the world that we sponsor. We have organizations who are involved in sponsoring the initiatives of providing education, access to information, career development, and just ongoing.

If you look on the website, girls in, you can see a number of different programs that are available and they're accessible around the world.

There's different member divisions that we're coaching as a board member, I get involved in supporting Adriana in her business development efforts.

Speaking of engagements, if need be, they've recently launched a job seeking profile, which is really cool.

So they're working with companies to help recruit additional women into their organizations.

And I've just been, I've been really pleased to, it's been an awesome experience for me.

One, because the board is a really high power team of different technology leaders, women and men.

And it's wonderful. The conversations that we have about the changing dynamics, the companies that are shifting focus to support DNI initiatives across the board and the board work that's happening along those lines as well to help influence diverse board participation.

So it's, it's been really rewarding for me to see just in the five years that I've been doing it, the transformation that's happening in the industry and the focus on the importance of diversifying teams.

That's amazing. I love, I love that you, that you're so optimistic and that you're seeing progress, which is great.

Cause sometimes you read some headlines and it feels like we're not making any progress.

So it sounds like things are going really well and you are seeing progress.

And I think that's an important message for all of us to hear.

Yeah, no, I am. I am really optimistic about that.

And I do think that it's, it's happening and I think it's all merit-based.

There's so much talent back to what I was talking about just in terms of like the talent pool that we have access to and the way in which we can adopt and, and, and possibly change our dynamics to employ those individuals is, is that there's, there's really active work being done there.

And I'm, I'm really excited about the future.

That's good. Okay. So if there's someone listening and they're like, this sounds like an amazing organization, obviously they should go to girls in to check it out, but what are, just give us a sense.

What are some ways that not everyone can be on the board, but what are some ways that others who are listening can get involved to help support this initiative?

Well, there's always a call for papers type of activity where we're having conferences and we would love to have participation and just different, different speaking about different concepts.

And it doesn't have to be about diversity necessarily, but just sharing experience.

So, you know, take a look at what conferences are coming up. If you have an interesting topic and you want to speak, put, put a quick blurb together and put it out there, put yourself out there.

So please, please join us to share your knowledge.

And then the members are always looking in different parts of the world.

They're always looking for that type of support as well. So just thought leadership, coaching, mentoring.

You can volunteer for any of those programs and girls in tech.

If you don't hear from them, come to me on LinkedIn. I'm sure you will hear from them.

They're super excited to have more and more support and it's a nonprofit.

So they're operating with a lot of volunteers. Yeah, that's great. That's great.

Doing a lot with a little, but having huge impact outsize impact, which is very addictive to have be part of an organization like that, making such important progress.

So that's great. Thanks for sharing that. Okay. So in addition to Twilio, this amazing career, girls in tech, which clearly you're so passionate about, and you've been on Melvin for a long time, you've also started your own community of women called Poppy that helps with financial wellness.

And we have about three minutes left.

So, but I do want to hear a little bit more about that community that you've created, that you founded and why.

Sure. So it's a group of about a hundred women and we welcome men.

We welcome anyone to join. You can find out more about it on LinkedIn.

If you look me up, we'll just Google popping financial wellness.

And it's basically just a place we meet quarterly.

We we've been meeting virtually because people are welcome to join from all over the world.

And we try and do it global globally convenient times. But we meet about different topics that are top of mind.

So for instance, mortgages, you know, and securing mortgage effectively, some of the women in the cohort are going through the first purchase.

And they're thinking about what is the, what is required in to raise funds, to support, you know, buying a home, buying a first home and some of the things to think about there all the way from there.

So like angel investing and strategies around angel investing.

And I just think it's really for me personally, I was, I wasn't part of some of those conversations without creating this community and, or without spending a lot of time, like seeking the opportunity to be part of those conversations.

And financial wellness, financial independence is a really important strategy for me.

It's something that I've worked really hard to establish.

And I just felt like there wasn't a real place to go or conversation was open, safe, confidential, but like you can be vulnerable and say, Hey, I don't understand this about my taxes.

And I need help to like, think it through.

Can someone, you know, join up and let's talk about things like that.

So it's just really meant to be a place where women can, can come and ask questions and, or explore financial strategies.

And it's become even like more amazing than that for me, some of the thought leaders that we've had present over the last year, you know, experts on Bitcoin and crypto and like way more advanced in the financial wellness category than I ever thought we would be.

So it's been pretty rewarding. That's amazing. There's definitely a theme in your career, Alison, where, I mean, well, in this case, it's just like, you saw an opportunity, you just did it, which I, which I love.

Like, that's just so entrepreneurial creating.

You're like, we need this. I'm going to create it. I don't see it, but just making things more accessible.

It's clearly like something you're really passionate about, whether it's more girls in technology or more people in tech or more people in sales, making it accessible, more financial understanding among, among, among women or, or, or anyone.

I think that that is just amazing.

So I, that's some, a theme that I want to end on. So thank you so much for joining today.

Yes, we can everyone. If you want to learn more, Alison Welch, as she said, follow her on LinkedIn and thank you so much for being here today.

I really enjoyed the conversation. Thanks, Michelle. Have a great Wednesday, everyone.

Thanks everyone. See you next week.

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Yes We Can
Join Cloudflare Co-founder, President, and COO Michelle Zatlyn for a series of interviews with women technology leaders. We hope you will learn, laugh, and be inspired by these conversations.
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