9 Questions with Kelly Watkins - Docket

9 Questions with Kelly Watkins

Former Slack VP and Abstract CEO, Kelly Watkins, recently joined the Docket Board of Directors to provide guidance and consulting to the meeting platform.

Kelly is the CEO of Abstract and previously served as the Vice President of Global Marketing at Slack, where she helped the business grow to more than 10 million users globally and led expansion efforts internationally. She was also Head of Brand and Product marketing at GitHub, VP Marketing at Bugsnag, and worked in nonprofit communications. 

Kelly’s product-led experience, marketing accomplishments, and developer background add a critical facet to a board of directors on a mission to help support Team Docket as they accelerate their product growth and significant customer base.

Charlie: You led Marketing at Slack through an era of meteoric growth, including laying the foundation of the Where Work Happens brand strategy. Tell us a little about the opportunity you saw and what you did to accelerate the growth.

Kelly: When I joined Slack, the company already had a pretty amazing growth trajectory, but much of the initial storytelling was oriented toward early adopters. For example, Slack’s homepage was about NASA’s Jet Propulsion Laboratory, and how Slack was used to put the rover on Mars. Early adopters were motivated by the idea of working like a rocket scientist, but we wanted to get beyond this audience to bring a broader set of people to Slack. 

We started by trying to understand our new audience and how they worked. The biggest theme we identified was around the idea that work was missing a place. Historically we had offices, but offices were being disrupted by all sorts of things—remote work, digital tooling, and globally distributed teams and companies. We felt there was a very strong opportunity to tell the story of Slack being that one place where your team and your tools all came together.

The second ah-ha was that Slack requires behavioral change for people to use effectively. If you think back to a time when you were primarily working through email, working in a real-time collaboration platform like Slack can be confusing. So we tried to answer the question, “Why does this matter to me?” and use role-based messaging to do so. The goal was to enable everyone to understand Slack as a digital workplace in the context of the work that they were already doing. 

To accelerate growth, we used all these insights and blended them with a set of programs built around the dynamics of human behavior and how humans come to know about and use products. In short, we thought about awareness, consideration, and intent as steps that people go through, and tried to take people on that journey as effectively and as efficiently as possible.

Charlie: What would you say was the biggest challenge in educating your users?

Kelly: Email, as an example, is an environment that’s very tailored to your own set of controls and experiences. You’re working alone in an inbox, and you’re the center of that world. In the context of Slack, work all happens openly in a channel and there are other people around. Helping users make sense of what it meant to work in the open—what it meant to think about work with lots of folks participating rather than just from one vantage point—was a huge part of our educational efforts around channels.

Charlie: You wrote that much of your success at Slack was found in your approach of ‘practicing courtesy and caring about craft.’ How have you seen other brands lean into that these last few months?

Kelly: The takeaway from courtesy is that it’s about putting other people before yourself and creating the most value for them as a first-order priority. With craft, it’s about how you create product experiences, marketing experiences, and sales experiences centered around excellence. 

Basecamp recently came out with a new email product called Hey, which I think is fascinating—specifically the guiding principles they’ve used to build it. It seems like they started from a vantage point of exploring how email can be better for people. You can tell from the product that it’s very craft-driven to meet people’s needs and give them more control to improve their email experience in a frictionless way. 

In the consumer space, I’ve loved a lot of the stuff that Glossier has been doing. Their products are incredible, so the craft is off the chart, but it’s not just the product. It’s also the design, packaging, and the community that they’re building. The way that they are thinking about approaching their audiences also has such a thread of courtesy. The checkout experience on their site is awesome, for example, and some of the stuff that they recently have done around putting money into supporting Black-owned cosmetic companies has been incredible.

Charlie: You’ve noted in a previous interview how organizations rely on their leaders to set the tone for their team and continuously “fine-tune that emotional frequency.” What role do meetings play in that?

Kelly: For any leader, meetings are powerful opportunities to be authentically-human and to connect in an authentically-human way with the people that you work with.

A great meeting happens because people know why they’re showing up, so the ability to get everybody aligned on the goals before the meeting starts is key. And then, to be able to connect what’s happening in the meeting with next steps matters so that people can get things moving. This is one of the things I love about Docket. It allows leaders to enable alignment and action with so much less friction.

Charlie: In the first part of this year, we’ve seen a dramatic shift in the way teams collaborate. What should leaders keep in mind as they navigate this new landscape?

Kelly: As it relates to remote meetings, there are two things I strive for as a leader. First, how do you ensure participation? You’re not face-to-face in a room, so there can be barriers to people jumping in and contributing in a remote setting.

Second, how do you ensure clarity of communication? Because you’re not in a room face-to-face with somebody, there may be distractions, or the video connection may be poor and prevent someone from hearing you accurately.

I think these are two important aspects of virtual meetings that are important to not only keep in mind but to find ways to overcome. 

Charlie: Slack is one of the more famous product-led growth stories. For organizations like Docket looking to implement a similar strategy, how does that ‘show-not-tell’ philosophy tie in with fostering an authentic brand message?

Kelly: Product-led growth is about how your product is an accelerant to growth rather than something that challenges it. To do this work well, it’s not about just adopting a product-led growth playbook. It’s about having good principles, asking smart questions, and then figuring the options that best align with your audience, product, and business strategy.

Today there’s more pressure than ever on B2B products to live up to a high bar and to be something that people aren’t forced to try, but actively want to use. The first task of a product-led growth strategy is to know and understand your audience, specifically “Who are your users? What are the things that they do today? What are they trying to achieve?” From there, you can build a set of experiences that are not just going to convert them to sign up for your product, but ones that will enable them to use it in the long run successfully. 

Humans want to be seen by brands, but not as a means to an end or a line on some growth marketer’s spreadsheet. Rather they want to feel the company respects them, their time, their effort, and deeply cares about the jobs that they’re trying to do in the world. Product-led growth, at its best expression, pushes companies to do just that.

Charlie: Have you ever led a bad meeting? 🙂

Kelly: Yes. Definitely. I’ve led several bad meetings. *Laughs*

When I reflect on bad meetings that I’ve led, it stems from not doing the work upfront to identify what was needed out of the meeting. If I’m not sufficiently preparing for the type of conversation we need to have, then the meeting isn’t going to go well and it’s going to take longer to get to action.

Charlie: What specific factors attracted you to Docket, and helped you decide it was a company you could stand behind?

Kelly: Joining a board is the opportunity to be in somebody’s corner and help them achieve their mission. With Docket, I was immediately drawn to the vision for the product because I understand the need greatly. I spend many hours a day on Zoom, and I see tons of opportunities for that to be a better experience—certainly in a time where we’re all working remotely. 

So the opportunity for Docket is to take the meeting experience and make it something that’s more well-rounded and empowering for teams. Bias toward action is a big part of how I think about leadership, and I’m excited to see Docket make that a stronger default for meeting culture.

Charlie: What do you hope Docket achieves in this first year?

Kelly: I was thrilled to see Docket win the Zoom Marketplace competition. It was such validation that there are opportunities to extend Zoom as a platform, not to mention space to make meetings more powerful moments for alignment and action. Zoom has dramatically improved our ability to have high-quality video meetings. Now it’s Docket’s turn to help answer why everyone is in that Zoom meeting in the first place and what they need to do once the meeting is over. 

I also see potential around equipping managers and leaders to be more effective at running meetings. Meetings are here to stay and for good reason. For people to become better educated and enabled to leverage meetings for action is going to be better for everyone at work – myself included.

About the Author

Charlie Holcomb

Charlie Holcomb

As Marketing Manager at Docket, Charlie is on a mission to show leaders everywhere how to make meetings awesome. After hours, you can find Charlie enjoying pub trivia, local music, and rugby.
Docket was named the 2020 Zoom™ App Marketplace ‘Whale Watch’ Competition Winner.Learn more
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