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SaaStr Podcast #367 with Zoom Head of Global Sales Operations and Enablement Hilary Headlee

Ep. 367: Hilary Headlee is Head of Global Sales Operations and Enablement @ Zoom. Prior to joining Zoom, Hilary was VP of Global Sales Operations and Productivity @ MindBody and…
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Ep. 367: Hilary Headlee is Head of Global Sales Operations and Enablement @ Zoom. Prior to joining Zoom, Hilary was VP of Global Sales Operations and Productivity @ MindBody and before that enjoyed similar roles with Alteryx, Invoca and Lynda.com. At Lynda.com, Hilary grew the support teams from 6 to 60 people and supported more than 60 net new reps in just 3 years. If that was not enough, Hilary is also a Limited Partner in Stage 2 Capital, the venture firm focused purely on go-to-market.

In Today’s Episode We Discuss:

* How did Hilary make her way into the world of SaaS and come to be the sales leader she is today with the global communications leader, Zoom?
* When thinking about sales ops vs revenue ops, what are the 4 key points to consider for founders? How does lead management and onboarding alter the question of sales ops vs revenue ops? Where does Hilary see operational debt the most? How does she advise founders on removing it?
* Given the broad scope of sales ops and engagement, is it not just rebalancing culture, comms, and change? As a business scales does there not come a time where it unbundles and scales out of sales vs revenue ops? How do the roles change with time and scale? Where do the breakpoints occur?
* Why does Hilary believe documentation is so important today? What is the toolset Hilary uses for documentation? How does Hilary train her team around the right strategy to document their processes? Where do many go wrong here? Where can you pick up small wins?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
SaaStr
Harry Stebbings
Zoom

Below, we’ve shared the transcript of Harry’s interview with Hilary.

Harry Stebbings:

We are back for another week in the world of SaaStr with me, Harry Stebbings, and last week we had Kyle Parrish on the show from Figma, unpacking the world of scaling into enterprise sales. And today I want to get one layer deeper into sales operations itself, and who better to have that conversation with than Zoom’s Head of Sales Operations and Enablement, Hilary Headlee.

Harry Stebbings:

Prior to joining Zoom, Hilary was VP of Global Sales Operations and Productivity at MindBody, and before that enjoyed similar roles Alteryx, Invoca, and Lynda.com. And at Lynda.com Hilary grew the support team from six to 60 people, and supported more than 60 net new reps in just three years. If that wasn’t enough, Hilary’s also a limited partner in Stage 2 Capital, the venture firm focused entirely on go-to-market. I do also want to say a huge thank you to Eric Yuan at Zoom, some fantastic question suggestions today. I really do so appreciate that.

Harry Stebbings:

But that’s quite enough from me, so now I’m thrilled to welcome Hilary Headlee.

Harry Stebbings:

Hilary, it is so great to have you on the show today, I’ve heard so many good things, both from Eric and Janine on your team. So thank you so much for joining me today, Hilary.

Hilary Headlee:

Thank you so much, Harry, I appreciate it.

Harry Stebbings:

Not at all, I’ve been looking forward to this one. But before we kind of dive into the meat of the show, I do want to start with a little bit of context. So how did you make your way into what I call the wonderful world of SaaS, clearly I need to get out a little bit more, but also come to be head of global sales ops at the juggernaut that is Zoom today?

Hilary Headlee:

Sure, I got into SaaS actually back in Minneapolis, Minnesota. I was starting at a consumer research and advisory firm that was doing qualitative research, which sounds very fancy and in a way it was. There were two wonderful co-founders, Mary and Vickie, and I just loved what they were doing in the research field. And it ended up that they were starting on having an ACV, or an annual contract value, and that’s where I first started to understand that type of repeatable business. And I fell in love with it.

Hilary Headlee:

Luckily, a couple of the gentlemen that I worked with were in Santa Barbara, and they were at a small company at the time, Lynda.com. So about 13 million in revenue on the B2B side, and they needed someone to come and run sales ops, and training, and customer success, and they gave me a call and that’s how I got up to California, and then it’s been about 10 years going to different SaaS companies, usually pre-IPO, a little bit crazy, a little bit chaotic. And they want me to come in and try to help operationalize and make sure that the sales reps have everything they need to be successful.

Hilary Headlee:

And that’s a lot of how I got to Zoom, it was a little bit on accident, I was actually researching job descriptions at the company I was at to hire a few more people and saw they needed a head of sales ops, and about fell off my chair. I loved the product, I loved what I was able to do with Zoom. And ended up reaching out to a gentleman that I knew and said, “Hey, is this really for real?” And from there the rest is kind of history, and I feel really lucky to be there.

Harry Stebbings:

I absolutely love that, and also I didn’t know that early at Lynda, I mean, what a journey that was as well. But I do want to start this on a topic that’s so important for so many founders today, and it’s kind of the [inaudible 00:05:00] of sales ops versus revenue ops.

Hilary Headlee:

Yes.

Harry Stebbings:

And you said to me before that it’s not that simple and there’s kind of multiple points to consider. And so I really want to kind of touch on that first. Like what are those main consideration points, do you think?

Hilary Headlee:

Yeah, I get asked this, I want to say it started to be a couple times a week of either revenue leaders who were thinking about should they maybe consolidate their organizations, or different vendors kind of want to have you talk about that, and just in general I think there’s a lot out there. I put together like 10 questions that keep floating around in my head about what you need to consider as an organization, or an ops leader, or maybe as one of those sales leaders that’s considering it. I think a couple of them that popped out is just how do you define sales ops, marketing ops, and customer ops at your organization today? What I mean by that is in marketing ops, you could have a very strong like B2B marketing ops, and a B2C marketing ops, and maybe even an e-commerce side there. I mentioned Lynda.com, we had a really strong B2C and B2B side. That would be a lot to take on all of those operations, plus sales ops, plus customer ops in that arena.

Hilary Headlee:

When you look at sales ops, are you looking just at direct or is there indirect as well? Those can be really big depending on how your distribution really marries out. And in customer ops, that can be cut a couple ways. Customer success operations might be more of that one to one, or one to a few alignment and assignment for onboarding and ongoing support. You could also have things like professional services, or managed services, you could have all of your technical support and more of your call center support operations as well, which to me are different disciplines and skillsets in their own right. So I think there’s some companies it makes sense to maybe smoosh all those together, and get the right kind of speed and synergy, if it’s there. I think in other companies it might be a little big. And for you to have that speed it might be better to kind of specialize and separate.

Hilary Headlee:

So that’s one of the first questions that I just encourage people to think about, is how do you really define those, and I think sometimes the smaller you are and the simpler you are, I think you can get a lot of speed out of that, maybe the more complex you are in ensuring the other kind of levers are all in place, then you can totally make sense as well. But that’s one of the first questions I always want folks to consider when they’re asking that question of is it sales ops or [inaudible 00:07:06] ops?

Harry Stebbings:

Can I ask, just on that point, in terms-

Hilary Headlee:

Yeah.

Harry Stebbings:

Of like the … non fragmentation, but kind of the clear silos that one has with those, at what stage do you find they tend to segregate and it’s no longer the quick and dirty, so to speak, where it’s all kind of jumbled in together? Is that 100 people, is that 50 people, is that five million in ARR, 10 million in ARR, I know it’s a hard benchmark to ask for. But in that kind of clear point where it tends to start specializing.

Hilary Headlee:

I personally don’t think so. I think it depends also how many people you have on your operations team. So there’s many times back in the day, Harry, I’ve been in sales ops, what is it, 15 years now, and back in the day we were managing marketing ops, and we were managing customer ops, and it was just called sales ops. So you can … Or at least I found that I was able to do it better at a smaller company and those companies were usually sub 100 million. And there was maybe only a handful of us on a team, I mean, less than five. So I think it just really depends also on company size, and how you want to go to market and support all of those areas.

Hilary Headlee:

So there’s not a magic number for people, there’s not a magic number for ARR. And to me, that’s part of why I try to come up with questions to consider, is I just don’t think there’s a one size fits all, again, of size in either of those to say that’s the time to do it. I think there are dependencies when you look at your people, your process, and other areas that you need to take a look at.

Harry Stebbings:

Totally get it. I think we always all love the kind of clear silver bullet of oh, it’s five million in ARR and then suddenly-

Hilary Headlee:

I know.

Harry Stebbings:

Amazing what happens at these milestones, it’s very funny for me. Tell me, what’s another main consideration thing?

Hilary Headlee:

Yeah, I think you need to take a look at what’s happening with what I call operational debt. So I frameworked out this cheesy sales ops pie, which has six pieces of the pie that I think just in relate and really go through what happens in operations, and the operations part of the pie is your process systems and data. And I think most people would agree that that’s a core part of operations. From data though, you get insights, strategy, and then hopefully some planning, and your planning should drive processes, and those go into your systems, data, and so forth.

Hilary Headlee:

So it works like a circular pie in those areas. But when I think about operational debt and ask that question, I think an easy way to identify that is to, if you want to, remember something like this. Do you have an ocean of data and a desert of insights? And if that’s what you’re dealing with, you might have some operational debt, because your data might be cumbersome based on systems that weren’t maybe architected or put well together, or too many fields, or duplicate fields, which really to me is symptomatic of process. And I think that’s one of the last pieces of the pie that sales ops as you talk about the fragmentation that we might see in operations with other folks jumping in, and IT, and sales FP&A, which are really important, I think, also to consider for rev ops or sales ops. If you look at it, that process can help come in and be that master kind of sweeper and vacuum cleaner, I think it can go a long way.

Hilary Headlee:

So that’s the other one I really want people to consider, is how much operational debt are you carrying, especially if you’re an ops leader coming in. Because there’s only so much that you might be able to clean up, and do, and fix, and still be considered a success at the organization.

Harry Stebbings:

Couple of questions I have to ask there.

Hilary Headlee:

Sure.

Harry Stebbings:

How do you balance between like handling and managing operational debt versus progressing in terms of instilling further rigor in sales ops, and instilling further discipline? How do you kind of balance between like solving the past, but also plowing forward with the future?

Hilary Headlee:

Yeah, it’s hard, I’ll say that. I think I’ve tried to, especially at a place like Zoom, I try to hyper categorize on some of these areas. And so when we look at our key critical success factors and what we need to do to be successful. There’s times that we’ve tried to put them in what do we need to do to be just ready for some of the foundational items, what do we need to do to scale, which is basically clean up some of that operation debt. And then what do we need to grow, and make sure that folks have a buy in on the mix of projects to keep moving forward and making that happen.

Hilary Headlee:

Like you said, I don’t think there’s a silver bullet on how to do it, and I know fast growth companies sometimes you have to trade off scale. And I think scale … This is probably a whole separate topic, I think it’s overused. If you could make it once and use it sometimes just a second time and not 200 times, that can be scale in some areas that you need to do. And so it’s just finding the right balance at the company you’re in, and what their appetite is for continuing to fix some of the things that need to be fixed while also taking on all of the things that will help you grow. Because you can grow even if you have some operational debt, for sure.

Harry Stebbings:

Can I ask, I’m sure you have so many founders and operators come to you with operational debt inherent within their organization. Where do you see it most commonly? Where are you like, ah, this is where I always see it?

Hilary Headlee:

I think you can see it a lot when you’re looking at something around a meeting, and there’s data pulled up, and everyone’s brought their quote, unquote “own data” to the table. Or, “Where did you get your data?” Or, “I don’t trust that data.” Data as defense I think is one of the early signs that I’ve found in companies where people just don’t trust the numbers, and they want to align around facts, but really it’s around feelings. And I think that can be one of those signs that there’s a challenge there that you need to be digging into.

Harry Stebbings:

I totally agree with you there in that challenge. What’s the other one in terms of another major consideration point?

Hilary Headlee:

Yeah, I think one of the other ones to look at is just what is everything happening with your lead management and your onboarding process. So what I mean by that is there are a lot of different ways that you can do lead management. You can do a strict MQL process, and scoring, and attribution, and all kinds of amazing metrics focused items there. Or you can send every lead over the fence like we do at Zoom. And there’s a difference there in how you want to be looking at that and managing that, and making sure that the output is what you needed to have.

Hilary Headlee:

On the flip side, there’s the onboarding process, there are some that you can do a self serve onboarding using tools like WalkMe, and making sure that as you’re onboarding thousands of customers in a week or a month that it’s repeatable and everything’s going. There’s other onboardings where it’s very technical, it takes a clear project plan, project managers to do those. And sometimes those can be another factor to consider if you’re going to have one ops person over all of those very different measures, metrics, margins, and all of those pieces.

Harry Stebbings:

Can I ask, why did you favor the strategy of, in terms of lead management, throwing them over the fence so to speak, versus the intensely rigorous kind of categorized lead management process that we mentioned?

Hilary Headlee:

Well, I didn’t pick it at Zoom, and we also had it at MindBody, and at first it was really odd to me because I was so used to a strict MQL process and scoring and going through it. When I look at the root cause, and you mentioned Eric in the beginning, Eric is a big believer in root cause and doing kind of one thing to solve for it. And what he was trying, I think, to solve for was that it doesn’t matter how you score and maybe what you look like on a website, you deserve to talk to someone at Zoom. And so that’s really how we modeled it, is if you say, “I want to be contacted,” or, “I want to have a demo,” you’re going to talk to someone and have that. And that goes all the way down to various actions you might take as well on the website.

Hilary Headlee:

So for Eric, I think follows the model of customers first and delivering customer happiness, and sometimes waiting until you bubble up or you have the best score. Kind of put that to the side and just go and talk to someone who wants to tell you about Zoom, too.

Harry Stebbings:

I have to say, I do kind of love that perspective. So it’s super nice to hear-

Hilary Headlee:

[crosstalk 00:14:06]

Harry Stebbings:

And it’s unsurprising coming from Eric. I do want to ask, on the lead management and onboarding process, how does your approach here change the question of revenue versus sales ops?

Hilary Headlee:

Yeah, I think the easiest answer is just to look at it in complexities. So I think that is the underlying theme of a lot of the pieces around rev ops or sales ops. If you have a really complex lead management that’s going to take a ton of attribution conversations, and meetings, and what that needs to look like, and you’re looking at different things in onboarding and how that needs to look from the different check ins, and managing those pieces, and the length of time, it may be that in sales ops you don’t want to take that on. You maybe want to look at it as I’m going to own the big eight in sales ops, and when I say the big eight, I mean the revenue plan, head count, territory quota, comp, pipeline, forecasting, and analytics. Just for sales, and not taking on necessarily the kind of lead math that you would want to do on the marketing side, and maybe some of the onboarding and outcomes that you want to have there based on making sure that they get up and running and starting in the renewal side of things.

Hilary Headlee:

So to me it’s a hyper summarized way to say it is complexity, and the more complex it is, the harder it might be as an ops leader to kind of take that on and make the right change that the business needs.

Harry Stebbings:

And speaking of the complexity, it brings in so many different parts of the organization from change, to culture, to communications. I guess my question to you is with such a broad scope of sales ops and engagement, is that kind of scope not just a rebalancing of change, culture, and communications?

Hilary Headlee:

I don’t know if it’s a rebalancing of it, but I do really subscribe to the thought that at the end of the day, if I am to describe my job in sales operations and enablement, it is driving change in the business. And what I mean by that is we’re constantly rolling out different processes, or programs, or products, or positioning that really will make a rep do more or less of something, do it better, and do it faster. And so I kind of joke that at the end of the day, strategies all seem to be around more, better, faster. And I think that’s a lot of what I’m asked to drive and to lead, is just to get those behavior changes across the org, and do that through great change management, make sure that it feels good culturally because there is change fatigue, especially at a company that is growing really fast and trying to meet the demands of the market. And landing the plane on good communication is hard. Making sure that you cut through the noise. There’s so much that goes on between emails, and chats, and other avenues, and making sure that people understand it, and that they get it the first time on what they either need to be aware of, or take action on, or what they maybe need to do to go and like talk with a manager, have those pieces.

Hilary Headlee:

So I think, again, those three really tie together for me, and though I have the sales ops pie to describe it, at the end of the day I think that’s what a lot of a leader is doing over these functions, is focusing on those three things. Change management, culture, and communication.

Harry Stebbings:

I have to ask on the change management element, it is off schedule but I’m too intrigued and it’s like it’s such a challenging thing to do well. What does a kind of great change management look like to you?

Hilary Headlee:

I think great change management looks like when you roll it out, folks don’t feel like it’s a change, because they’ve already been looped in, and they also don’t feel like it’s a new process they need to do, it’s just better. It’s a very idealistic approach to it, but I subscribe a little more to I’m not going to come up with all of the change and process items that need to be improved on my own behind a big curtain, right? Like the Wizard of Oz, I did that early on in my career thinking that would be better and people would be so excited that we rolled out this quote, unquote “great change”, and instead people were like, “What are you doing, Hilary, why didn’t you tell us about this? You missed these 97 different things that could have made it better.”

Hilary Headlee:

So I learned early on and failed that that wasn’t the right way to do things. So I try to do a lot of looping in ahead of time, to the point where I think sometimes by the time I roll things out they’re like, “Yeah, yeah, yeah, we get it, Hilary, just keep moving, we already know that that was coming.” And for me, that might be a little annoying that they already knew on their end, but it also tells me that they weren’t surprised by it. And when people are surprised, it’s tough, and so that’s one of the things I do try to subscribe to, is to not surprise my reps, or surprise my managers with big things that are coming. I do try to give them as much of a heads up as possible without kind of overwhelming them as well.

Harry Stebbings:

Can I ask, sorry, again too interested, in what form does that take in terms of like letting people know and getting ahead of the game there? Is that kind of Slack notifications, emails, is it educational resources around the product that’s coming itself? What does that look like in terms of the right way to communicate it?

Hilary Headlee:

Yeah, it’s a couple things. I try to always make sure that my peers and my colleagues at my level are informed first. I try not to skip level, but very quickly from there we go to our heads of, if you will, to make sure they’re looped in, we talk to sales managers, we talk to sales reps. I have my folks on my team go and do kind of like wiring of the house and make sure that we’ve got the right input and feedback on those pieces. It’s a lot of quick conversations, or quick chats using Zoom chat and making sure that we have what we need to know to move forward.

Hilary Headlee:

And so I think when we formalize it, yeah, I definitely follow and subscribe to doing a formal cascade down, but along the way it’s a lot of looping people in and making sure that they understand it, and then more importantly, that we’re not shortsighted.

Hilary Headlee:

I think that’s what hard sometimes of being in a leadership role, is when I was in, for example, in customer success, I was one step away from the customer and I was one step away from reps. I’m not one step away from customers and reps anymore, I’m a couple steps away. I don’t know their job state today as well as I could with how fast things are changing with our customers, and how we’re doing things. And so for me, getting in touch with the front lines on those is important, and finding those reps that you can trust who will tell you is a really important piece, and I think that’s something that I really try to do at every job I go to, is who are the folks that give good, honest feedback and can help move the business forward, and help you not kind of stumble and fall for the greater good of our customers or our reps.

Harry Stebbings:

I love that, that’s fantastic. But it seems like the alignment between like the different roles within the organizations, and the different players within each company, documentation is always touted as kind of being central to that. And you kind of [inaudible 00:20:08]. And so I’d love to hear your [inaudible 00:20:10] how are you thinking about documentation today as a leader, specifically?

Hilary Headlee:

Yeah, I am … If you talk to anyone on my team today, or in prior lives, you’ll hear that there’s a couple key things that I say, and one of them I know I share a lot is we can get clarity and alignment through documentation. And what I mean by that is it doesn’t have to be a 10 page document, it could be a picture that you draw on a sheet of paper, or a whiteboard, or the three kind of key decisions in a meeting. There’s a lot that people hear and not everyone is hearing the same things, and so I’m a big believer that you do have to document to drive for that.

Hilary Headlee:

I also think, Harry, my gosh, we sent everybody home a couple months ago, at least in the United States, and we sent them home without a clear plan, because it happened really fast. And I think for a lot of us, we were forced to be more formal. And there’s only so many meetings, even Zoom meetings, that a person can have in a day and continue to operate. And so I try to be very keen that we’re forced to formalize, document what you can do, the one who really documents is going to be able to drive for the results that we need, and especially in operations. That’s what we need to do, that’s what we have to be able to do.

Hilary Headlee:

So I think that’s at the core of a lot of what I have, and a key principle of mine, is finding folks that can synthesize, document, communicate it out, and then drive for the results through that inner organization.

Harry Stebbings:

Can I ask, where do you think many people make mistakes when it comes to documentation? Because it is a tough new habit to suddenly just document every part of your life. What do you think about like the mistakes that ones makes in documentation?

Hilary Headlee:

I don’t know about mistakes, I think that there’s one way to document. So I think sometimes when I say documentation, people hear, “I have to do a three page like dictated meeting notes piece,” and I don’t think that’s the case. I’m a big believer in, again, if you talk to anybody who knows me, I love a good matrix, I love a good two by two, things that really hyper simplify and get folks aligned on that. It also can be as easy as for meetings you attend, what are the three decisions that were made, and the three key action items. And I take those in our own Zoom chats, in the meetings, so everyone can see it and frequently people will say, “Hilary, you didn’t get that right. It’s actually three instead of seven,” or whatever it might be. And right there then we’ve sped up, and we’ve course corrected, and we’ve aligned.

Hilary Headlee:

And then I flip those into a regular chat for anybody who couldn’t be there, and again, I’m able to loop people in, get that clarity, get that alignment, and continue to help move the business forward. So I have found it a key skill to be able to have, and so again I think the mistake might be that people think you have to like over document. It can be three quick things that are just keeping people going forward.

Harry Stebbings:

Totally get you in there, I’m very happy to hear that it can be brief. But I do have to ask, in terms of the people there, adding the very best people to your organization is the single most needle moving thing that anyone can do. And you said before that there’s five key things you look for in an employee, and it’s such a good hook, but you kind of left me hanging there. So what are the five key things, Hilary?

Hilary Headlee:

Yeah, they’re probably going to sound really cold and op-sy when I say them. I don’t know that I can always hire for and then find it, but I think there’s five ingredients that I’ve found are important for folks that at least are on my team and I’ve started to really share it because I’ve talked about it enough.

Hilary Headlee:

But time management is the first one, and it sounds really easy to be able to manage your time, but it is really hard, especially working from home, working from home for many of our parents that don’t have childcare to support them and just their usual kind of circumstances. But being able to manage your time I think is an underrated, under valued piece that needs to be there.

Hilary Headlee:

I think along with time management, you have to be able to prioritize. And that is hard, we work at a company where everything is a priority because so much is changing and happening, and we want to connect the whole wide world. But that also means that we have a lot of projects that we have to decide on, and so knowing how to prioritize and not always pick the easy, low value thing to do, and do maybe some of the harder, unwieldy pieces to move the business forward, that’s a key piece. So I tie those two together.

Hilary Headlee:

Documentation, we talked about that. Being able to synthesize complex or multiple meetings, and share that, and capture that, and know how to then communicate that out in a way that people can hear it and drive forward I think is a really … is another kind of really big one. So documentation and communication are three and four.

Hilary Headlee:

The fifth one then is adaptability. And I say this in a lot of interviews of folks who are coming to Zoom of I sometimes feel like I threw 15 years of experience out the window because we just do everything differently at Zoom. And so being able to adapt to such a crazy fast culture, and just a really fun pace, but a lot of priorities and a lot of speed. We have to be adaptable and to have them move forward and make sure that we’re still going to be hopefully a company that can continue to support a lot of folks as we move forward.

Hilary Headlee:

So time management, prioritization, documentation, communication, adaptability are the big five that I think if you can land the plane on those, there can be a lot of success in both an operations and an enablement organization.

Harry Stebbings:

So I couldn’t agree with you more there in terms of those as the big five, but I also am struck by the challenge that now comes through a COVID world and hiring in a COVID world, where you don’t have the face to face time, and you don’t have that sometimes quality of engagement, which just has to happen in person. And I’m interested, how do you think about the hiring process, and how that changes in the world of COVID?

Hilary Headlee:

That’s a tough question. I think for Zoom we’re just hiring a lot more. I think what I’m excited about, and I’ve worked in remote cultures since 2005. So back then when we were all sitting around a conference room talking into one little machine, I’ve worked with remote folks. So for me, working from home and being able to hire more remote is almost going back in time. And I think it’s a really fun opportunity for us to expand who we can hire and how we can hire. I think the tough part is, is there is a piece lost when you’re maybe not interviewing those folks in person that you had before, but that also then gives a leg up to people who maybe weren’t in a high cost area like San Jose and Silicon Valley, that we’re now open to and can be more open to hiring, and having those come in. And for me that’s really I think the exciting part of it.

Hilary Headlee:

I think the other piece is there’s just been a lot that’s changing in the world, and that’s really good. And making sure that our pipelines are different, right, and that we’re not hiring folks that look just like us, that have maybe again been in our same circles that we run in. And I’m really excited about that side of it, too. Haven’t cracked the code on it, but I think that’s another piece that is really exciting about this shift in being able to work from home. And doing it almost anywhere in the world.

Harry Stebbings:

I do want to move though into my favorite element of the show, which is a quick fire round. So I say a short statement, Hilary, and then you give me your immediate thoughts. Are you ready to dive in?

Hilary Headlee:

Ready.

Harry Stebbings:

Okay, so the biggest challenge of your role with Zoom today?

Hilary Headlee:

The pace and speed of business.

Harry Stebbings:

Why is that challenging?

Hilary Headlee:

I have worked at pre-IPO and post IPO startups that were considered fast growth. I’ve never been at something that is the pace of Zoom. And I work fast, think fast, write fast, operate fast. And it’s tough to keep up on good days, it’s really fast.

Harry Stebbings:

I’m sure it’s incredibly fast. But tell me, what makes Eric the incredible leader that he so clearly is?

Hilary Headlee:

He truly cares. It is our core value at Zoom, I’ll give you just a quick story if you don’t mind. We were trying to finalize the revenue plan for FY21, and this was before we were all working from home and I ended up working from home because I’d gotten sick. And he kind of asked like, “Oh, you’re not in the office, Hilary,” and I said, “Oh, I’m just, I’ve got a cold, Eric, I’m not feeling well, I’ll try to be back tomorrow.” And I woke up the next morning and Eric had sent me a chat on Zoom Chat and your heart always kind of leaps up in your chest, like what is this, what did I do wrong, right? And he just wrote a note that said, “Hey, I really hope you’re feeling better, I was sorry to hear you were sick.” And I’m like of all the messages you could be sending to the world, you’re making sure that I feel okay. And I don’t spend a ton of time with Eric, but that was really … He really, truly cares and you can see that in how he still takes all of the questions that we have, and making sure that we’re just healthy, and safe, and good to go, especially during this really crazy time.

Harry Stebbings:

Sign of a really great leader that. Tell me, dirty sales data, what is it, and what’s the best way to rectify it?

Hilary Headlee:

Dirty data to me is just a symptom of your system set up, which typically is a reflection of your process. So I have just a firm belief, and maybe that’s because I hyper summarize that process can fix a lot, but I do really believe that better process can help clean up your data. And I’ve found that especially as Salesforce moves over and has centralized into IT teams that that’s how we can come together on cleaning up our systems and our data, is through really good process that’s going to drive the right things. Could be less fields, different fields, whatever that might be at a very simplistic level around those areas. But process to me is how you best clean your data.

Harry Stebbings:

What’s the biggest surprise for you internally since COVID began? Or externally, actually, let’s give internally or externally.

Hilary Headlee:

I’m obviously very surprised by how fast Zoom picked up speed, and the day my mom said that she joined her church service on Zoom I about fell over. And then when we did family calls on Zoom, that was really neat and overwhelming, and also sad, right, because you couldn’t see them for the time periods.

Hilary Headlee:

I think the other piece though is that there’s just been a real uniting of this is hard for everyone, and so it’s kind of you can see that I think on LinkedIn, and see people really reaching out of it’s hard out there, this is challenging, what can we do to make it better? And there’s been really cool new things that have popped up, and I’m a silver linings, try to look at the positive side, and I think that’s something that I think has really changed. And it hopefully is a good thing.

Hilary Headlee:

Also working from home. I think there’s been a lot of benefits for that for folks, and so I like those two things a lot about COVID.

Harry Stebbings:

Totally with you. My favorite story is when I found this kind of sticky tape by my mother’s laptop and she was using it to block the microphone, not realizing that there was actually a mute button.

Harry Stebbings:

A penultimate one, and it’s kind of a heavy one actually, but it’s like what moment if your life has changed the way you think really meaningfully?

Hilary Headlee:

Professionally or personally.

Harry Stebbings:

Let’s give one of each, if that’s okay with you.

Hilary Headlee:

Yeah. I think professionally there’s been a handful of feedback that I’ve been given that just really stick out. And they stung, and it hurt, but I really needed to hear it. I think those have been probably the biggest ones that have really changed that professionally, is when somebody’s really willing to give you tough, hard feedback but like you need to hear it. And again, those like pop out so clearly in my brain like light bulbs going off of what those are.

Hilary Headlee:

Personally, it’s obviously having … To me, it’s obvious in having kiddos and how much that changed. Especially changing how I operated at work. So I quote, unquote “got ahead” when I was in my 20s because I just outworked people. I would work 80 hours a week and I think once, at least for me, once you have that first kid you just can’t do that, so you have to be really good, and this is maybe where my principles come in, you have to be really good at managing your time. I had to go from 80 to 50 hours a week. And sometimes even less. And so time management, prioritization, moving the ball forward and not stretching out those work days, because something bigger and more important was there I think was a really big change I needed to make as well. And a moment that I went, “Wow, how I’ve been successful and valued what I can maybe bring to a business needs to change and change pretty categorically.” It’s not just working more, it has to be working smarter.

Harry Stebbings:

Yeah, it’s a total reinvention really. I’m glad that’s a couple of years away for me right now, I think. So I can enjoy working super hard and not having to prioritize anything at all, and probably being ruthlessly inefficient. But I do want to finish on what do you know now, Hilary, you wish you’d known when you joined Zoom?

Hilary Headlee:

I used Zoom as a customer and loved it, I had a Zoom room in my office and I loved just being able to see all my employees across the globe. I loved all of that piece. I think I thought it was more maybe simple than it is. The usability really shadows, if you will, the complexity behind it and how much you need to know to be successful at Zoom. I underestimated kind of in a silly way how tough it is to teach on it, learn it, understand it, sell it, and really get the right complex, technical sale for companies that want to change their communication and collaboration. And I wish I would’ve leaned in a little bit more on that piece, because there’s a technical aptitude and appetite that you have to have, I think, to keep up and really enjoy what you’re doing at Zoom.

Harry Stebbings:

Hilary, I already said at the beginning, I heard so many good things from Eric and from Janine, so I was really excited for this, and it’s been so much fun to do, so thank you so much for joining me today.

Hilary Headlee:

Thank you so much for having me, Harry, this was really, really great. I appreciate all your questions and especially being able to talk about operations. So thank you so much.

Harry Stebbings:

Absolutely love that episode with Hilary, and what a special talent. And if you’d like to see more from us behind the scenes you can on Instagram at HStebbings1996 with two Bs. I always love to see you there.

Harry Stebbings:

As always, I so appreciate all your support and I can’t wait to bring you a fantastic episode next week.

Published on August 28, 2020

Source: https://www.saastr.com/saastr-podcast-367-with-zoom-head-of-global-sales-operations-and-enablement-hilary-headlee/

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