Cloudflare TV

Recruiting Corner: Building Out the Mid-Market AE Team in ATX

Presented by Madison McKamey, Tracye Shaw, Matthew DuBois
Originally aired on 

As a part of Cloudflare's Recruiting Corner Cloudflare TV segment, we're going to be talking with some of our Sales Leaders in the Austin office about the explosive growth they've seen in the past year as well as the continued growth we'll have in 2021. Please join us to learn about the growing Mid-Market Sales Sales Team in Austin, how to be successful in this role, and what makes Cloudflare sales unique.


Transcript (Beta)

All right, hello everyone. Welcome to everyone tuning in to our second Recruiting Corner episode of 2021.

On this Cloudflare TV series we use this as an opportunity to discuss all things hiring, recruiting, interviewing, etc.

Today I am joined by a few sales leaders here in our Austin office and we're going to be discussing the growth of our mid-market sales team, why Cloudflare is an awesome place to be and what's in store for 2021.

And hopefully we're ready for some precedented times after all of the unprecedented times of 2020.

Before we get started, I would love just to do some intros and I'll begin.

I'm Maddie. I am on the recruiting team. I'll be hosting this session.

I've been at Cloudflare almost 10 months. I started in June of last year. I've worked really closely with this team, also a lot of other go-to-market functions across the business in the US.

Let's see here. How about you, Matt? What's your story?

Hi, I'm Matt. I've been at Cloudflare for almost five years. Actually, next quarter will make my fifth year.

I started in San Francisco when we were a much smaller company, very much a startup.

I've gotten to see a lot of the growth at Cloudflare.

I moved to Austin to help build that team about a year and a half, two years ago.

I've loved my time here and I've always been in sales, a couple of different roles, but right now helping to manage some of the sales teams out of our Austin office.

Awesome. The Cloudflare veteran. What about you, Jodi? Hi, my name is Jodi Holland.

I am one of the mid-market sales leaders here at Cloudflare.

I have been here just under two years and started out with Matt to start out the sales team here in Austin.

Great to be here. Cool. How about you, Tracy?

I'm Tracy Shaw. I am the Austin sales leader. I'm responsible for the alignment of customer success, mid-market, and the business development team here in Austin.

I have direct oversight of the mid -market teams here in Austin. Cool. Awesome.

Thanks, guys. I'm so happy to be interviewing you all today. Without further ado, I know we have a lot of questions that we wanted to get through and touch on.

I'm just going to kick it off. I think the first question, I wanted to direct this to both Jodi and Tracy, but I know that y'all just went over how long you've been here, but how come you chose to come to Cloudflare?

What about it was exciting to you?

What's your story? Sure. Do you want me to go first, Tracy, or you? Yeah.

Okay. Yes, like I said, it's been about two years that I've been at Cloudflare.

I actually started out as an account executive on the mid-market team. Funny enough, as Matt mentioned, I was the third hire.

I've been here as we've grown and expanded.

Now, we're 30-plus reps, which is super exciting. I think one of the main reasons that it's been so exciting is because of the rapid growth and the career opportunity.

Like I said, I went from an account executive when I started out.

Then last quarter, I moved into a team lead role. This quarter, I've moved into a sales leader role.

The opportunity to advance my career has been exciting.

I think we have a lot of great things going on here in Austin. Great. Yeah.

Why I chose Cloudflare, I had actually had my eye on Cloudflare for a year or two.

I had noticed a lot of people that I'd worked with were coming to Cloudflare.

Including myself. Including yourself. It's really been interesting because there are people that I've worked with here from Apple, from HomeAway, from Rigup, from MessageOne, from Dell.

The one thing they all have in common is they're really smart, really talented people.

Cloudflare has done a really good job of getting the best and brightest from all these different organizations.

I really wanted to be a part of that.

Todd, for example, that you work with closely, Madison, he worked with me at HomeAway.

He's someone I respect enormously. When he called, I was like, heck yeah, I'll listen to it.

Tell me more. Yeah. I love that. It's such a small world too.

I remember when he let me know, he's like, you know, we're hiring.

Tracy's like, that's the best news I've ever heard. It's a small world and we're so happy that you're here.

Awesome. Cool. I know that this session is obviously geared toward just learning more about the team and the growth that we're experiencing within the mid-market group here in Austin.

I would love to open it up to both of you, Tracy and Matt.

Do we have any openings on the team? What does the headcount look like?

Are we going to be like, what's the rest of the year look like in terms of growth?

What's going on? Yeah. We are hiring aggressively. We will be hiring all year long.

Austin is definitely growing. We're the second headquarters for Cloudflare and we're expected to increase the size of the team so that it matches San Francisco and then surpasses it actually.

Definitely have growth.

Definitely need talented, motivated salespeople and they should be reaching out to us.

We definitely have opportunity. You know, I think this is one of the greatest indicators of Cloudflare being an amazing company is I've always been hiring.

For five years that I've been at Cloudflare, it's always been hire, hire, hire, hire.

That's a really good indication of like we're being successful. Teams that sell, teams that continue to innovate and release products need more and more people.

There's never been a time where I haven't had hiring a major focus of my day-to-day.

As Jordi pointed out too, you don't have to wait around for promotions either.

We're always hiring. We're not just hiring new positions, we're hiring whole new teams and whole new offices and the sales team's evolving and so we need more leadership.

We need people, we need good people to promote. So we're always hiring and there's always that career development that goes along with it.

So really good indication of strong companies is that and it's been one of the best things about Cloudflare is seeing the growth and seeing the success which just inevitably means more hiring.

Yeah, for sure. I concur and I can say that I have stayed very busy in my time here.

Y'all definitely keep me busy. So in that vein, what are kind of the mid-market AEs core responsibilities and what attributes in individuals make folks successful in this role?

What is it that we look for?

And I think this is a great question for all of you. So Jordi, if you want to take it away and y'all can just build off of it.

Yeah, absolutely. I think number one, we look for the role in the mid-market team is a hunter role.

So we're looking for people who have more of a hunter mentality.

We're in charge of acquiring new business at Cloudflare.

So we're looking for curious thinkers, creative thinkers.

We are tasked with identifying potential prospects for Cloudflare.

So we strategize on effective outbound efforts, how we can add value to an organization.

I think we like to stay on top of industry trends in order to identify good prospects for Cloudflare.

And I think we put a lot of emphasis on really being customizable in our outreach.

We want to be really thoughtful in our approach so that we can add the most value to new organizations coming on board.

Yeah, I think that's a really good summation.

This is a question I think we talk about a lot and think about a lot as hiring leaders.

We want to be hiring the best people.

So definitely a self -motivated hunter is something we look for.

It's a technical sale too. We're selling to very technical buyers and we're selling a very technical product.

So it's somebody who also wants to specialize in that type of sale and feels comfortable in that type of sale.

We tend to really recruit and look at tech sales reps, people selling all different kinds of applications.

And we're going to be building on that skill set. Generally speaking, this is the most technical sale that our candidates have been involved in and our sales have been involved in.

So if you've enjoyed that kind of aspect to previous sales you've been involved in, then you're going to do really well here as well.

Yeah, I would echo all of the things that the both of them have said. We're looking for people who are curious, who are quick and agile learners.

We want someone who's motivated.

Smart and kind is kind of top of the list too. No one wants to work with a jerk, right?

So we want someone who's humble but driven. This is a role where a relentless follow-up pays off, where being really diligent and thorough pays off.

By making sure that you know your sales math and you know what it takes to get that meeting and you know what it takes to get that opportunity in the door, that hard work pays off.

And this is where when you work hard and smart, you reap the dividends.

Jodi is a success story here. She's not bragging about that, which is pretty typical of Jodi.

So someone who's humble, but you know, she was an AE.

She was relentless. She was that person, whatever it takes, I'm going to get to my number.

When she was a team lead, it was the same way. And then she urged her team to do the same.

And as a manager, she's doing the same thing.

Her team is motivated to hit their number, they're structured, they're organized, but they're relentless about their follow-up and they're scrappy and resourceful.

Those are the kind of folks that will do well here. Awesome. I love it.

I actually have a quick, a really quick follow-up question around the technical sales piece.

How, what does our training program look like for new hires? I know that we started like a new sales incubator.

Like how do we go about training folks up on such a technical product?

Yeah. So let me walk you through kind of what that looks like.

Right now, when someone starts, there's two weeks of full training, the new hire training offered by the company, and then a sales bootcamp, which I would describe more as an overview that prepares you for the newest program that we've rolled out, which we've called the sales incubator.

That program lasts about six weeks.

It's every morning, they come, all of the salespeople come in, they're learning about a different topic every day.

And then during the day, they're applying that knowledge.

And we rolled this out at the beginning of the year, we're gradually building on it, but it's a companion to a manager, kind of four-week play that starts during the incubator.

They have corresponding activities that complement what's going on with the incubator.

So the goal is to make sure that anyone who comes on board with us can be successful out of the gate.

And our goal is to make sure that everyone has close one opportunities by the end of their first 90 days.

So then it's momentum, there's confidence building, you gain the knowledge that you need to navigate those more complex sales that come later on.

Awesome. Cool. That's great. And I know that's a fairly new program that we've rolled out.

And so I'm really excited to see that get kicked off the ground.

I'd add something there too.

I think we've got some really good sales there. I mean, people like Jodi, people who have been in the seat selling as individual contributor, a lot of our sales leaders over the years that we've promoted have come from internal promotions from just really great sales reps.

And so the insight they give our new hires, you can get a meeting.

Yeah, they're not gonna let you fail.

They're gonna guide you along the way. And they're all in the incubator with their team.

Like they're all attending and they're all providing constant feedback.

We've done a really good job with the sales leadership across the board, making sure that it's giving the right support to the AEs.

Yeah, that's awesome.

And I know too, that's also something that we're continuing to invest in as we grow, which is so exciting.

Tracy, I know you and I were just talking about this.

It's like, so awesome to see us like continue building out more programs for enablement.

And this will only continue to get more sophisticated and better.

So it's really awesome to see. Yeah, and I think Matt brought up something that's really important.

Every leader here is really invested in making sure that not only do you feel at home and that you belong, but that you're successful here.

Being the newest office is sometimes a challenge, because you're figuring it all out.

All of the managers are really vested in making sure that we're going to be successful long-term.

And that's our goal. We want to be the best of the best within Cloudflare.

Yeah, awesome. I love it. One thing to add in regards to the incubator that is also important is since we are in this remote environment, I feel like the incubator that we're doing and like Tracy and Matt said, that the managers are taking part of the new hires, maybe even some of the other AEs that are joining.

It's such a great on-the-job training in a remote work environment.

We're all very much in tune. We're a team. We're all really in there brainstorming, working together.

So I think even the challenge of not being in a physical office right now, it's working really well in a remote environment.


Cool. I love it. So my next question, again, kind of geared toward the group here.

What do you think makes being an AE at Cloudflare stand out, apart from other places that you've seen or have been?

What's unique about it? Jodi, why don't we start with you?

Yeah, I'll kick it off since I'm fresh out of being an AE. Yeah, yeah, exactly.

I think what has stood out to me is the high reward. I think it was really, it's a challenging role, but it's also, you know, having, between learning the business, learning the technology, identifying new prospects, but, and also, like we've said, it's a hunter role.

So being challenged to really work hard and be strategic with your outreach and in this, in a team environment that we're in, it's incredibly rewarding once you are successful and, you know, you're hitting your goal.

It's exciting to, you know, see how many new prospects you're bringing on.

I think to learn, we're like innovators at heart at Cloudflare.

So I think for me, it's just been a high work environment, high, you know, effort, but it's been such a high reward, I think is my response to that.


I think if I can go, I think a lot of our AEs, they're really building some new skill sets.

You know, we, I want to hire like really technical sales reps. And there's lots of companies are trying to hire really technical sales reps.

And I think what we find is we hire really smart people, people that are motivated, people who have been in technology for, in their career, but throughout their quarters, they become vastly more technical in their approach, selling to like our buyers, again, are, it's not uncommon to be in a technical sales role.

And there's a technical influencer who's deciding whether you're selling some kind of like sales tool or HR tool or recruiting tool or what have you.

Our buyers, they are those technical influencers with other products.

So I feel like the sales rep becomes much more technical.

And that's the way we differentiate amongst our, the other technical sales positions out in the market is you are going to become a stronger technical sales rep while at Cloudflare.

And this is going to, you know, make you very attractive in the market.

Don't say that. It's true. It's true.

We're all looking for very technical sales people. And that's what you will become at Cloudflare.

I would also say retention rate is extremely high. We don't lose a lot of sales reps.

It's a phenomenal company to work for. And as Jody pointed out, like you can be very, very successful at Cloudflare, but you're going to be building lots of new skills at your tenure at Cloudflare.

Yeah, I would agree with all of those things.

The thing that I would add, it's our job here is to make you better when you leave us than when you whether that's to a promotion, a lateral move, you leave the company, whatever that is, our job is to make you better.

And I do think here, AEs learn to build a portfolio of good accounts. They learn to prospect thoroughly.

They really hone their sales skills. They know how to, they're going to learn how to manage a complex sale as well as they would a simple sale.

And by the end of it, they are going to be expert salespeople if they aren't already.

And so that kind of, you know, to Matt's point, it does make them attractive on the job market, but that means that we are successful.

You know, we are here to make them successful and they are here to learn.

And we are getting better at doing that every day.

So it's a learning curve for us too, but we're also getting better.

And so the better we get, the better leadership they're exposed to. So it's a win-win for a salesperson.

Yeah, totally. I love that. Awesome. Cool. So, you know, outside of what makes being an AE at Cloudflare stand out, what do you, like in general, what do you, what do you all think makes Cloudflare a special place to be in general, just from a culture perspective, from a team perspective, what do you all love about, about working here?

Who wants to go first?

I'll go first. I'm the one who's been here not quite six months, but what I love is that you work with really smart and talented people and you see potential every day.

You know, I think when you're in a job every day, it's really hard to see upside and it's really hard to see opportunity.

I think here, that actually is the thing that I do, that I can't help but see.

There's so much potential and upside here because of the type of people we work with.

We're just getting started.

We really are. I mean, Austin is what, a year and a half old, this office, about.

We're really just getting started. So it's an exciting time to be here because a lot of the things that were in place when we were a startup are transitioning into things that we need to do to scale.

And that's always a time of high change and high velocity.

And for me, that's a fun environment. Like that velocity, that excitement, that level of change is something that I really enjoy.

So that to me is why it's cool to be at Cloudflare right now.

It's a really exciting time to be at Cloudflare.

Totally. I can jump in.

What makes us special? So I've seen Cloudflare now for five years. And I think most businesses have really audacious goals, both in their product, revenue goals.

Cloudflare is the same.

We've had some really big goals. And early on, sometimes it's like, sometimes I almost felt like it was just Cloudflare saying those things because they're supposed to say them when you're like an earlier startup.

But I've seen and been a part of us hitting those goals.

The new product releases that we were trying to get out, the revenue goals, which are constantly increasing, but we continue to hit them.

It's not easy, but we've hit them every year quarter since I've been here.

And to me, that's really special because everybody wants that kind of trajectory.

It's hard to pull off. It's hard to execute against. So seeing that success, very special.

And the other thing I'll point to, which is I've worked at other companies where they say, we're really innovative and we're releasing all these great things that's going to change the world.

And for the most part, like other tech companies, like the least cool features, Cloudflare has done an amazing job releasing new products that introduce whole new industries for me as a seller, new people, new buying personas that I can now sell to, new companies that I can now engage with.

And that's also really hard to do. And Cloudflare very much has this culture of like, we're a strongly positioned product and we're going to make products that just work.

And seeing that being a part of that, and then on top of that, again, seeing that those products have been successful both in their usability and we're able to sell them, that to me is a really strong combination of there's something really special happening at Cloudflare.

As a sales rep, you want to be at those type of companies. Definitely. Yeah.

And I would just lastly, to add on to that, I think as far as when you mentioned, Maddie, the cultural aspect, I think our team, our sales team in Austin in the mid-market, we, and we're, I mean, looking back fondly pre-COVID, how much fun we had in the office and how much we worked, how we worked hard, we collaborated in the office and dealing with those challenges, moving remote has, has been a challenge, but we've also, we've kept that culture vibe of having fun, collaborating.

It's still a competitive environment because we were in sales.

We want to do well. We all want to be at the top. We all want to hit our goal and go beyond a hundred percent.

And then I think it's just great to have colleagues that you can lean on to brainstorm to, you know, whether we're using our chat channels or team meetings, of course our video calls, but there's a lot of collaborative efforts and we're still trying to make it as fun as it can be.

And I think I really enjoy our team.

We have a lot of different personalities, a lot of different kinds of people, age groups, experience, and we all come together and help each other out.

I love it. Yeah. I mean, I can also even speak to that on my end.

I actually started fully remote at Cloudflare and so did basically. Yeah. And it was something that I was quite nervous about, to be honest.

I've never, you know, not like met my team before.

And I was so pleasantly surprised with how seamless it was to feel like I was apart.

And it's awesome to see that that's kind of the theme across all teams.

And it feels like I've known my team and have been on the team forever, but even though I haven't actually physically met them in person.

So that's awesome.

Cool. So I know time check, we only have about four minutes left.

I do have one more question that I would love to ask y'all and then I'll let everyone get on with the rest of their afternoons.

Um, but in the, um, kind of in the, in the spirit of growing, growing your, your career, like what, um, I think this is actually a great question for, for you both, uh, maybe Matt and, and Jody, but what are some things that you have learned at Cloudflare that you think will just be very beneficial for you for the rest of your career?

Like what will, what are the nuggets that you'll take with you?

You first Matt. Um, I think it's a couple of things.

I mean, I kind of touched on a little bit ago. I, I have gotten much more confident in, uh, like speaking to CTOs, CISOs, just the technical buyers of the world, IT, network engineers, security engineers, um, very specialized, like technical engineering departments.

Um, I've gotten really comfortable speaking with them, understanding their world, um, and, and, and having those conversations.

Um, um, I have no plans on leaving Cloudflare anytime soon, but I feel based on the number of recruiting emails I get that, uh, I, our kind of buyers are, are, are sellers are, we're just very attractive in the market.

So, um, that's the big one for me.

For sure. What about you Jody? Yeah, I think, uh, one thing that I, I definitely think will, will stick with me through my career is really, um, and, and Tracy mentioned it earlier is, is being agile and being creative and being scrappy.

Um, I feel like that was something that I had, you know, touched on and done in previous roles, but here at Cloudflare, there was something, um, about being here that I just, I, no matter what it, what it took, I just wanted to find a way, creative thinking, creative messaging, whatever, uh, sort of accounts I could find, uh, I was really persistent.

And so I feel like finding a way, um, any way I could to get to my number.

And I think having that, you know, at all costs kind of mentality, I just, I really want to get scrappy.

I want to hustle. I want to make sure I'm making the most of my day to get there.

And so I think that has really tightened my skills and my, uh, my drive.

Yeah, I love it. Awesome. Um, well, I know we're about at time and I apologize for my barking dogs.

Someone knocked on the door, lose their minds.

But, uh, I wanted to thank you all so much for sitting down with me today and chatting through all of this.

Um, as a reminder to anyone who's tuned in, we are hiring across the board.

Um, and in, in Austin and on our, our mid-market team, um, you can find our job at, um, Cloudflare careers.

Um, it's been so, so awesome getting, um, getting to work with you all and, um, let's do this again soon.

Thanks Maddie. All right. Thanks guys. See ya. Bye.

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