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Willie Osborn on Creating a Culture of SDR Success

When Willie Osborn joined Confluent three years ago, it was to spend his days thinking about growth—but not just in terms of revenue. Below, Willie explains why he believes developing people, not just pipeline, is the key to the success of a sales development team, and shares what he does to create new opportunities for Confluent’s sales development representatives—within Sales and beyond.

What do you do at Confluent?

I lead part of our Sales Development organization—specifically the Inbound team; the Commercial team, which handles outbound sales; and our new Cloud team. As in any company, our sales development reps, or SDRs, are tasked with generating pipeline. That’s the most measurable outcome. But the way I see it, we meet those goals by doing the other part of our job well, which is hiring and developing talent. An SDR role can be one of the hardest jobs in Sales. You’re on the front lines. You get 99 “no’s” for every “yes.” So what really drives our team members is the opportunity to grow, and it’s critical that we create paths for them to move up, whether into the rest of the Sales organization or another part of the business, including into leadership roles.

In part, that means constantly improving our processes for onboarding, training, and everything else we need to do to help new SDRs conquer learning curves. Especially in the first few months—that’s such a pivotal period in setting someone up for success. It also means empowering our front-line managers to put a lot of their energy into coaching, having those hands-on, day-to-day conversations. I think we’re really lucky here, because a lot of companies sort of put their SDR organization in a box. They think of it as just a pipeline tool. But at Confluent, the rest of the business really understands how growth and upward mobility can help bring in the best people and continue to motivate them once they’re here.

Tell us what brought you to the team, and what your path’s been since.

I joined as Director of Sales Development (SD) for EMEA three years ago, when I still lived in London. I’d been working for another tech company in a similar role, building out its SD team in Europe, and the company ended up being acquired rather than doing an IPO. It was wonderful for that company, but of course it also naturally meant my job shifted to focus more on efficiency and alignment rather than building and accelerating. After a few months, I realized that wasn’t for me—I missed thinking about how to grow every day. Confluent appeared on my radar right at that moment, and it seemed perfect. It was probably 700 people, but still felt like a 200-person startup; they had an awesome product that was clearly resonating with customers, and the organization was in a race to catch up with that revenue. It was an opportunity to help build the foundation, which is exactly what’s most exciting to me.

Since then, I think the growth in my part of the business has really just been a reflection of the larger organization. I started as a director in name but more of a front-line manager in practice, looking after the first five SDRs in London. Six months in, that doubled, and I started leading the new APAC team, as well. Then we gradually hired managers in each region. It’s been step by step.

I’ve also had the opportunity to move across the world, which I wasn’t even sure would be possible when I joined. I’m from Pennsylvania, and I’m married to a Canadian. We knew at some point we wanted to end up back in North America. Then when COVID-19 hit, Confluent, like a lot of companies, adopted a more flexible mindset toward location. Now our SDR leadership team spans three continents, so we have pretty much every time zone covered.

Tell us about the team culture you try to build as a leader.

There are a few things I’d highlight. The company value I probably talk about the most is “One Team.” We believe a rising tide lifts all boats, and we make it a point to recognize and reward collaboration—including the people who help push us forward as an organization. That’s always 99% of the conversation when we’re talking about a potential promotion: “How has this person made us better?” There’s nothing wrong with coming in, blowing your number out of the water, and going home. We need that. And in some cases, it’s what we call “provocative performance.” Maybe you hit three times your monthly number and help us redefine what’s possible. But provocative performance can also mean mentoring new hires, or hosting peer development sessions, or writing new content for our prospecting approaches. There are lots of ways to send those ripples through the organization and help us all go further.

That goes hand in hand with another cultural value for us, which is taking a learning-based approach to everything we do. It’s about humility and a growth mindset. As our President of Field Ops, Erica Schultz, likes to say, “Always better, never best.” I think that’s such a great approach. Recognize achievement, but then it’s on to, “OK, what did we learn? How do we apply that going forward?”

Finally, I’m a big believer in ownership. We hire smart people and we should trust them. But I think we also need to be very clear about what ownership does and doesn’t mean. Especially when they’re new in a role, people sometimes think it means just doing whatever they think is best. But that’s not how business owners actually operate—they have a finance expert, an operations person, a marketing pro. They spend most of their time communicating with those people, bouncing ideas around and making strategic decisions together. So it’s a balance. It’s helping people understand when they need alignment, how to leverage the support and resources around them, and when they can run with something on their own. And, ultimately, they should know that even if they mess up, it’s OK—as long as we learn.

What’s challenging about your work?

The hardest thing is hiring. I remember in my first job, before I was a manager, senior leaders would say that, and I didn’t really understand. I thought, “I’m sure they have their pick.” But now I know it’s true. Finding great people, helping them be successful, keeping them happy and motivated, and even moving them into their next role in a way that allows you to model your team’s capacity—that’s all incredibly hard.

That’s true everywhere right now, because there are so many opportunities in the hiring market, but I think it can be particularly difficult in a high-growth organization like this one. Confluent is constantly changing. The company you joined a few years ago is a different company today, and that’s tough for some people. Adaptability is a muscle you have to build, which we can help you do. But aligning expectations is important, too. We’re honest with candidates about the amount of change happening here, and we look for people who’ll be excited about and energized by that.

Can you give us an example of how some of that change plays out?

It’s everything from how we align with our counterparts in other teams to what our targets are to what part of the organization we sit in. When I first joined, SDRs were within Sales; not long after that we moved to Marketing; now we’re part of Sales again. One good example from within my organization is the new Cloud SDR role. One of our SDRs moved into a sales engineering position last year, and it worked out really well—so we started thinking about how we could develop other team members who wanted to be customer-facing but were really interested in the technical side. Now we have a career path for those people, which is something a lot of companies don’t offer.

And even now, with 10 people globally in that role, we’re still evolving it every week. It’s a lot of the same questions we asked back when I first started at Confluent, just in a different area. “What are the blockers?” “What do we want to drive?” It’s building something new at the same time we develop our people.

Looking to the future, what’s most exciting to you?

From a company perspective, we’ve obviously evolved a lot over the past few years, and it’s hard to imagine a more attractive market opportunity than this one. But I think there are still so many improvements we can make, whether it’s big strategic ideas or tactical things like how we onboard new hires or process our leads. It’s really the same thing that drew me here in the first place—building something new, having an impact, and continuing to learn. Two of the three teams I’m running today didn’t even exist a little more than a year ago.

And ultimately, for me, it’s about the individual people’s stories that come out of all those new projects or new teams. We’ve had so many SDRs go into not only sales engineering or other sales roles, but operations, HR, marketing—really challenging positions that don’t seem on the surface like the logical next step. That’s possible because we’ve built trust with other parts of the business and shown them that being a great SDR doesn’t just mean you’re great at building pipeline. It means you’re trustworthy, you’re accountable, you do what you say you’re going to do. And every time someone takes a chance on one of our people and that person succeeds, it creates a flywheel that leads to the next story, and the next, and the next.

Jon Rye is Senior Vice President of Confluent’s Global Go-to-Market Strategy and Operations Team. The GTM Strategy & Operations team is responsible for the strategy and planning for Field Operations and is focused on driving efficiency, productivity, and overall operational excellence of Field Operations’ customer facing teams. Jon has been in sales strategy and operations leadership roles for the past 19+ years at companies such as Oracle, McAfee, Polycom and most recently Domo. Jon began his career in Mergers & Acquisitions and Private Equity for Hambrecht & Quist and Whitney & Co., respectively.

Willie Osborn is an SDR Director at Confluent, leading the Growth SDR Organization globally (and current interim Global Head of SDR). SDRs are responsible for building a pipeline of highly qualified sales prospects through inbound and outbound prospect engagement. Additionally, SDR is the entry point into the Confluent sales team for people early in their career, with a heavy focus on learning, development, and progression. Prior to Confluent, Willie helped build and scale similar teams at a number of tech companies.

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