Delivering Market-Changing Products

Shawna Wolverton is an Executive VP at Zendesk. She is an experienced Product Management Executive focused on leading great teams. In this podcast, Shawna talks us through all things related to product, product strategy, culture, and delivering market-changing products.

Watch the episode here: Delivering Market-Changing Products

Question [00:02:21] What is an EVP of product, and how do you make it happen?

Shawna [00:02:27] I think it’s one of the most interesting things about this field of Product Management to me is that there isn’t a well-worn path to this place. My career definitely is a reflection of that. I got my degree from a university in Political Science and Russian Studies. And as my mom likes to remind me, I was qualified to do nothing. Anyway, here we are.

So I fell into an interesting corner of software, product development localization, because I had a sort of language affinity. What gave me the opportunity was really to get this fascinating view into how software was developed. It never occurred to me, and getting in the guts and running builds and understanding UI. And I was like, Oh, this is cool. And I got really lucky because it was the first.com boom. And I lived in the Bay area, and I started helping marketing departments build the first sort of rudimentary websites.

And one of those websites sort of morphed itself into a product. And they suggested that I might want to be the Product Manager. I was in a place where I was like, “sure, yes, sounds great!” and as soon as I started doing that job, it was like, Oh, this, this is amazing. I really started to super thrive in that job. And then, you know, almost immediately, the.com bust happened. There were a whole bunch of people who had actually been Product Managers longer than 18 months who were out on the job market. But I got lucky.

And one of the guys who worked on my engineering team when I was the Product Manager was at Salesforce and called me and asked if I wanted to do localization again, which I definitely did not want to do. But it got me in the door. And from there, interestingly, there was a glitch in the case management system, and I used to get product bugs routed to me. I was so terrified that I was going to screw up and do the wrong thing that I just started reproducing them and figuring out how to fix them. Then I would go to developers and ask them to check it for me. And finally, they were like, please stop harassing our engineers. We’ll give you a team

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Question [00:04:59] When you got those first jobs, who did Product Managers report to?

Shawna [00:05:06] I reported to the CMO in my first job. Once I got into Salesforce, the sort of chaos of that early product development explosion that was happening everywhere, and into more of a sort of professionalism, there was a Head of Product and Engineering.

Question [00:05:38]Coming from a non-Engineering background, how many non-Engineers were they in the product team?

Shawna[00:05:45] Not a lot. But I think it’s one of the biggest misconceptions about what it takes to be a great Product Manager is that you have kind of deep, deep technical expertise. And what I hooked into very early was about wanting to make customers happy. And like, that’s the fire in my gut. I want to delight customers. I want to give them a thing that they love using. And with curiosity and relationship building, it was never, ever an issue for me. Even in my multiple years of working on a technical platform, I couldn’t code my way out of a wet paper bag.

Question [00:06:57] How do you supplement the lack of technical skills to prove and continue proving that you can lead products from end to end?

Shawna [00:07:05] I think so much of it is about how you build relationships with the people on your team and then across an organization. Fundamentally because the output is software, we think of it as a technical job, but it’s actually such a relentless people job. You don’t get to tell everyone what to do. All you can do is sort of try to tell a really good story and try to get everyone to come with you.

It took me a while to realize all the bugs, and I was trying to understand what was happening. I learned about how to talk to developers when I knew they were being straight with me. And when maybe not so much. And how to have those conversations and talk about outcomes. Wins on the board, right? Say you’re going to do a thing, do the thing, tell everyone you did the thing, and sooner, rather than later, people start giving you more things to do.

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Question [00:08:29] How Does Product Work at Zendesk?

Shawna [00:08:35] Well, it’s a really interesting setup at Zendesk. Through acquisition and some organic growth. We have product development teams in 12 countries. So from Krakow to Singapore, we are doing product development almost 24 hours a day. Trying to figure out how we coordinate across all of the time zones, how we collaborate across all the time zones has been one of the most interesting parts of my now two year journey so far at Zendesk.

What’s interesting is that it sort of necessitates a balance between some strong top-down directives and then a lot of trust in the bottoms-up that’s happening in the regions, right? I’m not sitting next to the product team in Singapore and sort of understanding their day-to-day. I have to give them a strong sense of where we’re going from a North star point of view from a big picture, high level. These are the most important things for the next task for the next year, for the next 18 months. And then trust that when they have to make decisions day-to-day without me, or even one of my directs, in their time zone that they’re, they have the information they need to do it.

Question [00:10:36] How do you build go about building a culture that scales?

Shawna [00:10:42] It’s hard work. It takes a lot of intention, right? I think I arrived, and all of these different people and all these different places were working on very specific things. And there was very little thought about how they would all come together in a single experience. They were sold separately; they were used separately. It became clear that for great agent experience – when you want to help your customers go to 4 or 5 different products and trying to figure out yourself how to string them together was inefficient. We had to get the whole organization thinking about how what they’re doing contributes to a whole. And I kind of thought if I just started saying it over and over again, that was sufficient. It turns out, it takes a lot, a lot more effort, and it took a lot of setting a centralized, big vision, big bet stuff.

It took some really strong program management staff to help us sort of connecting dots. Every time I saw it, making sure I was celebrating those kinds of wins and showing everyone how that can work. This year has been terrible. Let’s make news to everyone, but it’s been an interesting leveling of the playing fields. The amount of cross-team collaboration that has happened has really pleasantly surprised me. I’m incredibly proud of my team.

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Question [00:12:44] With the complexity of managing different time zones, how does your day-to-day look like? And how do you make sure the most important things don’t fall through the cracks?

Shawna [00:12:59]I have a fantastic staff of people who help. “Shawna remember! Hey, remember this thing.” In all honesty, my day is almost 100% meetings. It’s about 50% of meetings inside of my product organization. The rest is sort of taking product out into the world, making sure we’re aligned with the leadership in Product Marketing, market partners in sales, with success, having deep conversations with customers. I’m involved in quite a few executive sponsor relationships. I’m often called in if there’s some kind of escalation. We have sort of the regular cadence of the executive staff meetings. Then there are some meetings to get work done sometimes, but it’s a lot, a lot of meetings.

I feel really strongly about that time I spent with people on my team, it´s great. So I have one-on-ones with my team. I have one-on-ones with their directs on a regular basis, and I have quite a few doubled down two layers, three layers down one-on-ones regularly. Especially when we do not see each other in the hallway. I want to make sure everyone on my team feels like they have what they need to get their job done and are having a good time.

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What would you say is the career path for people who love building things? And how can they grow?

Shawna [00:15:13] The first thing is to join a company that has a culture of strong, individual contributor PMs. And understand, is there a parallel career ladder that they’ve written down? This is really important to me. I was an accidental manager. I was in charge of three scrum teams. I was having a great time. I had a boss who pulled me into a conference room and said, okay, these two guys, they report to you now go. And that was my management training. I luckily found out that I loved it. I absolutely got such a thrill out of the success of those two guys that I felt better about what they did than anything I’d ever done.

I love management. I know that not everyone should be a Manager. I know that being a Manager and a Product Leader is an entirely different job than being a Product Manager. If you love Product Managing, don’t follow in my footsteps. I don’t get to do Product Management anymore. It’s really sad. I miss it. I keep threatening to get a whiteboard behind me, and I’m like, Oh my board. And they’re like, no, it’s okay, you don’t need it.

If you did an objective inventory, it’s one of the worst jobs ever, right? If everything goes perfectly and you have an amazing launch and customers love the thing you did, you’re up on stage thanking the multitudes, your engineers and your program team, and your marketing team. And if it absolutely flops you’re up on that stage all alone and all you can visit, it’s entirely my fault. I’m sorry. I figured out what happened, and I will make sure we don’t have that happen again. I tell people like you have to find the fire in your gut about why you want to walk through this particular fire. The joke I have with a lot of my peers is if there was something else we were good at, we probably would have it, but we can’t imagine ourselves doing anything else.

When I’m generous, I like to say that I’m the Product Manager of the Product Management Organization. So sort of understanding what I want the outcomes to be, and how do we get there from where we are, what are the processes, the organizational structure, all of those kinds of things. And I think as a CEO, you’re sort of that for the company.

Question [00:18:59] As an accidental Manager, how can someone learn and make sure to acquire the necessary skills to continue being at that level?

Shawna [00:19:11] I’m very much an experiential learner, but the few places I really invested from an educational point of view were not so much in the mechanics. Because I think sort of the mechanics are vaguely the same, but different enough everywhere.

I think one of the most important skills that is so often overlooked for Product Managers is communication, written communication. The ability to build a great presentation and tell your story, and to do that in a way where you have confidence, and you can absolutely be ready for whatever comes at you. What I’ve seen over and over again in organizations is that PMs maybe who don’t even deliver – so there are two PMs. One heads down, delivering great features over and over and over again. And one there’ll be in delivery, but they are amazing at telling their story in front of an audience, and this person wins. So I think it’s important to – they’re both it’s best, but I think the business sort of will always reward and gravitate the people who can talk about the work they’re doing and frame it in terms of how it impacts the business.

I remember like it was yesterday, my first sprint review, and the executive staff were sitting in the audience, and I knew that if I misspoke or said something that was disagreeable, it was going to hurt. I was nauseous, my mouth got dry, and every time there was an opportunity to get up and talk for as terrified or uncertain as I was about my ability to do that, just saying yes. And doing it over and over and over. I did my first year when I started doing executive briefings; I did 53 of them in a year. The first one, I was sitting at my desk sweating, trying to put slides together, like, Oh, I was just going to go. And by the last one, I think I was like two seconds before the EBC. I was in the lobby like, Oh yeah, we got this, let’s go. So it really is just doing it.

We know so much, and we are connected so well in organizations. And I think there’s a tremendous amount of benefit to us and to our companies when we take the time to give other people access to that network that we’ve created sort of just in the course of doing our jobs.

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Question [00:23:37] How you go about building a team?

Shawna [00:23:53] It’s really important to have an alignment with your recruiting organization and to be really clear with them about the kinds of slates that you want in your candidates. One of my favorite things to do is to take people who have not been PMs before and bring them into junior roles. There is a tremendous amount of talent out there that maybe don’t even know that they would be great at this. I always have my eye out, and engineering managers become very suspicious of me when I ask about their engineers. When you’ve been doing this, as long as I have, you sort of get a sense, so I think it’s about intention.

It’s a virtuous circle, right? When you have women who are in your leadership of the company, in leadership and product and engineering, it’s like a magnet. More women show up to apply, more women stick around, more women grow. I think we have to start thinking beyond. There is tremendous talent across race and culture.

Working with your recruiting teams, building up partnerships. We have a fantastic partnership. We just did a speed mentoring with a whole quarter from black girls code. There is so much young talent out there, and we have to expose ourselves to it. There is no pipeline problem. There’s just a hiring problem.

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Question [00:27:32] How do you go about really building what’s next?

Shawna [00:27:50] We created a new process, and it, it kicks off actually this afternoon. We do a sort of high-level team by team roadmap, refresh where we look out three quarters. The next quarter, we got a pretty good idea that these are definitely the things we’re going to deliver.

Every quarter we do an update. So rather than sort of starting the year and say, this is what we’re going to do for the year. And then despite, whatever happens, we just keep marching. We’re really trying to get more agile. Then I do that review with everyone all around the world. We’ll be done with those by the end of next week and then every month. It’s not particularly scalable, but I love it too much to stop.

We do a scrum team by scrum team sprint review- it’s not really a sprint, but it’s the spirit of it. This is what we were going to do on that big plan for this month. Here’s what we thought we’re going to do. Here’s what we got done. And here’s a demo, and it keeps me connected to all the teams. It allows a whole bunch of my staff and me to understand what’s happening, not just in their own org, but across, and, and spot stuff that might be getting weird. It really helps us sort of keep a pulse check on all the stuff that’s going on.

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Question [00:30:40] How are you thinking about the future? What do you think are the biggest opportunities for people who are involved in building products?

Shawna [00:30:49] We’re in an amazing time of growth, and there are so many companies growing so fast who need product people to come in and help them. CEO and Founders can only run product for so long before weird stuff starts happening. Everything, from startups to megacorps, are looking for people who can come in and sort of figure out how things work there and get to building.

I’m super excited about the role and the future of who’s becoming Product Managers. This idea really does seem to be taking root that it’s not a job that has entrance requirements. I think we’re well past this. That I need to have an MBA to be a Product Manager sort of opening gates for all kinds of people to come into this role. I am very bullish on the future of Product Management and Product Managers.

We’ll be back next week with even more of the latest insights from the Product Management world. Stay tuned for more!

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