It’s hard enough to imagine being the longtime CPO overseeing a newly remote workforce during a pandemic. Now imagine becoming the new CPO of Calendly – thriving Atlanta maker of a beautifully simple scheduling tool – during the chaos of mid-to-late 2020. That’s just what Silicon Valley-based Jeff Diana did, joining Calendly in September of this year, overseeing nearly 200 employees in his role as Chief People Officer.
Prior to joining Calendly, Jeff Diana served as Atlassian’s CPO, where he successfully helped drive an IPO and growth agenda over the course of four years, leading the company’s growth from 300 team members to over 2,000. Before Calendly and Atlassian, Diana was CPO at the SAP company SuccessFactors and Chief HR Officer at insurance company Safeco. His HR leadership began at household name companies like Bell South, Microsoft, and GE.
Calendly is the brainchild of Nigerian-born Tope Awotona, who grew up in the suburbs of Lagos, where the nation’s enormous economic disparity offered him a vantage point on extreme wealth and similarly extreme socioeconomic hardship living side-by-side in oft-startling contrast. Awotona moved to the U.S. as a teenager. Knowing his future lay in entrepreneurship, started Calendly in 2013, after spotting what he was sure was a gap in the market for truly handy scheduling software a year earlier while working as a sales rep.
Comparably talked to Jeff Diana about his career in HR leadership, and especially about the “secret sauce” that makes Calendly’s culture so unique.
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Comparably: You come from big companies, Jeff. You’ve played in a big field. What brought you to Calendly?
Jeff Diana: The first appeal of Calendly was the business opportunity was second to none. It’s a rocket ship. What’s amazing about the growth trajectory is that we’re profitable, we’re cash-flow positive, we’re growing 100 percent year-over-year at scale already, and we’re just getting started. If you want to look at a company that’s going to be one of the top companies of the next decade, this is it. It reminds me eerily of when I first joined Atlassian, also because of the product-led growth. The product is what drives customers.
Secondly, I ask, “Who is the founder and leader?” because when you’re a founder-led business, the founder has such an impact on culture and the way you work. The founder gets a chance to put their stamp on things, and Tope is fantastic. I’ve worked with a lot of founders and entrepreneurs, and what’s amazing about Tope is that he’s a genuine, awesome human being with a great core set of values. Most founders are born and bred engineers, but they may not know as much about the business processes as Tope does. Then I look at culture. We have incredible people at this company, and they exemplify our values. And lastly, it’s about the build; opportunities to have an impact are huge on the growth curve. I don’t want to do a startup where there aren’t a lot of people who know how to scale a business. We are at a great part of that growth curve of the build. It’s really cool because we have a whole new leadership team coming together to figure out how we grow together with a shared strategy and vision.
The other thing that really connected me is the mission at this company. Tope will talk about making connections happen where they wouldn’t otherwise happen, and I think about that a lot. I think life is all about the connections you planned to make, the connections that you just bump into along the way, and a whole bunch of connections that never happen that would have taken you in all sorts of different directions in your life. Connections have such impact across our lives, and Calendly is all about making that happen. That mission really fit with me. I had to pinch myself, “Is this company real? How could I not come do it?” I’m seven weeks in, and it’s absolutely awesome.
Comparably: That begs the question: If we’re talking about these connections we make or don’t make in life, how did you bump into Calendly, which is out of Atlanta?
Jeff Diana: After I took the job and switched the info on my LinkedIn profile, it aggregated how long I’ve been with the company. When it aggregated with Tope’s, it displayed a three-and-a-half-year association. I thought, “There’s no way I’ve been connected to him for that long,” but it’s true. I’m a venture advisor for OpenView Capital out of Boston, and Tope reached out to OpenView, who had been courting him. He asked, “I’ve got a 100-million-dollar revenue business here, how do I think about the culture? How do I think about the level of leaders that I need? How do I think about where I should hire and how many people I should hire?” He had some pretty heady, thoughtful questions, so they connected him with me. I knew he was going to build this company right. He’s got the right sensitivities, and we just hit it off. I was just a board advisor to Tope, and finally, the time was right where I could really come in and add value.
Comparably: It’s scary to share that kind of vulnerability that Tope did at that point. How do you think that has played overall in the culture at Calendly? It sounds like it was one of the things that attracted you as well.
Jeff Diana: It really was. Coming from Nigeria, with the things he’s been through, with the shots he took at starting businesses and having failures, and then coming up with this problem that he experienced as a big-time sales rep of not being able to connect with people in the right way. And boom comes this idea for the company. There’s a humility and a humanness in Tope, and when we worked together my job was to help him put on paper the values of the company. The first one was “Start with Human.” And it’s Tope. He’s just a genuine person. “We’re all human beings, let’s respect people, let’s cooperate, let’s treat people the right way.” Part of that is vulnerability.
I think the leaders who know what they’re good at and know what they don’t know have that self-awareness. They are learners, they keep their ego in check, and they can scale with the business. When you stop learning, and you think you have all the answers, you’re done. And Tope is the exact opposite of that. He has the attributes to solve, twist, and turn for the problems that occur on the ride. I’ve seen a lot of the challenges and the traps that come through scaling, and I certainly will help him pattern-match that, but every business is different, and Calendly’s journey will be uniquely Calendly’s. The only way you can get there is with someone who is comfortable, vulnerable, and shares with you, so that you can navigate those things together.
Comparably: How has being in the position of a CPO or people leader changed over the last six to 12 months? And what recommendations would you give to other people leaders based on your experience?
Jeff Diana: The biggest change has been going remote. Just figuring out how to create connection, how to up productivity, drive, and engagement in a remote world. I think we all underestimated going into this the value of bumping into people in the office, and how that makes collaboration easier. And knowledge transfer is easier in person. Feeling connected to people and culture is easier. We’re now having to figure that out with a whole new toolset and reimagining the experience for our people and our customers, frankly. The second change I would say is that the fight for talent is a national game now, and it never was before. It was a regional game. And that also means that your people are getting pinged for more opportunities than they ever have before.
Comparably: Coming into Calendly, it seems there were really two major things going on for you. You needed to figure out what was going to be required for that next big step of growth, which is always different for every company. And at the same time, you’ve got to design experiences for the people that are here and the people that you’re going to attract in the future. How are you balancing that?
Jeff Diana: The first thing is a series of questions to ask yourself: “Where are we going? What are the key initiatives that are going to get us there? What are the capabilities we need to get there? Do we currently have them or don’t we? If not, that becomes the skill set we go to hire for. Or could we grow it and develop it in the people we have?” There’s the build vs. buy component, and it’s usually a mix of both. I find the faster growth is happening, the more you end up having to buy it, because it takes time to develop it from within. You still do that development, but you have to find that balance on the planning side.
Outside of that, there are a couple of things that will guide you: the company’s mission, the next chapter of growth, and your values. This will apply regardless of whether you’re part of the first 50 people on the team or number 1000. When I start to dream through what we’re going to build, everything on the people side is going to be driven by that value set. It’s a measuring stick as we build our rewards philosophy, how we give performance feedback, and determine who gets promoted. All of that will be guided by reinforcing those values, and those values mattering as much as what you get done. What you get done and how you get it done value equally, and if you don’t have that in your core, I think you lose your way as you grow.
When it comes to people who can’t be rewarded in a way that satisfies their own personal career growth, we’re about celebrating our people moving on to their next adventure. That is building brand. Part of the value prop we give people is when they leave Calendly, they will leapfrog other people for their next job. It’s what happened to me at G.E. Every person I worked with that was successful there went on to success elsewhere. And having Atlassian on your resume, you can write your own ticket. Calendly is going to be in that same bucket. This is all a virtuous system you need to embrace; you just have to make sure people are making those changes for the right reasons. And, for us, when it has happened, it’s fairly rare and for very good reasons.
Comparably: You have a CEO that is an immigrant from an underrepresented group. How is that reality then infused from a diversity, inclusion, and equality standpoint in Calendly as a company? And how does that muscle then grow to attract even more of that diversity of thought into the team?
Jeff Diana: When it comes to diversity, Tope wants to talk about making progress for everybody; not for one group at the expense of another group. It’s just not his mental model at all. He wants a space where everyone has the opportunity to win. We’re a little bit unique from that standpoint. It’s a hugely emotional, hugely personal, high-impact topic. It’s one of those topics that everyone is invested in and has an exceptionally strong, cemented position on. It’s a challenge to lead through that sometimes, but Calendly’s philosophy matches my personal one. You have to have values that are inclusive, anchored in the “Start with Human” concept. And then ask, “What are all the signals that show we truly are inclusive?” At Calendly, we are a highly gender diverse company, probably in the top 1% in the US on gender diversity. Are we well represented for every underrepresented group? Of course not. But that’s the journey of diversity. I think people in general want to know that you care about it, that you’re creating an inclusive place where everybody can be successful, and that you’re taking different actions along that journey to show you care to make progress.
We want every person, with whatever characteristic you want to look at, to be accepted. Every degree of weirdness or difference embraced. We want people to be who they are, and not have who they are in some way impede them. We want to celebrate those differences. We can do all the things we want to get more diversity in our recruiting pipeline, but it won’t stick if we don’t have inclusion. It’s a never-ending battle on the numbers side, but the inclusion side to me is looking at our culture, our practices, our natural tendencies, and the people that are successful here. I want to make sure there isn’t a defining pattern outside of living our values, that there isn’t a subset of characteristics where you can get ahead and everyone else can’t.
D&I is about transparency, sharing information, and how you communicate. Companies do not spend enough time mapping their soft structure, as I call it. It is actually the secret sauce to organizational performance, not hard structure. We all worry about org charts and who reports to who, but soft structure is where decisions get made, how information flows, and how people can raise ideas. It speaks to how inclusive you are by how transparent you are, and I think we do a really good job with that.
Comparably: What are the three characteristics you’re looking for at Calendly, in terms of the company as a whole? Who are you looking for?
Jeff Diana: I’m looking for people who are mission- and value-driven. I’m looking for people that are learners because we’re going to go through the growth curve, and we’re going to learn along the way. And I’m looking for people that want to collaborate beyond themselves. I think what is special is that the people here not only care about the company; they care about each other in a way that I haven’t seen everywhere. Sometimes in the Valley here we get so entitled, we get so stuck in our own little bubble, and we sort of forget what really matters, and Calendly hasn’t. It’s a really special place culturally from that standpoint.
The last thing I’ll leave you with is this: when people are looking for what journey they want to ride on, you’re not going to find a place that’s truly at this stage or has the growth trajectory that Calendly has. But then add to that we’re at the stage of build where people can really paint on the canvas and do the best work of their lives. And you’re doing that in a place with the kind of culture that supports you, and you’re going to enjoy the experience. You sort of go, “How can I not do that?” I’m honored to be part of the company. I have not met a person at Calendly that I didn’t think was a great talent and a great person, and that’s exceptionally rare.
