Taking Osano to the Next Milestone (and Beyond)

“What got you here won’t get you there.”

When I founded Osano in 2018 with co-founder and CTO Scott Hertel, we knew we had to put this common truism into practice if we wanted Osano to truly succeed. We did so after Osano got its first customer, after we secured Series A and later Series B funding, and now it’s time to think about what’s going to get us to the next milestone.

In that spirit, I’m excited to announce that I will be stepping aside as Osano’s CEO to make way for our new CEO, Bobby Jaffari.

Bobby is an experienced, savvy operator who knows how to scale software businesses like Osano, and I am confident he’s the right person to get us to our next “there.”

I am not leaving Osano—this start-up is my baby, and I want to be there for every step of its journey. Instead, I will be redirecting my focus as Osano’s first Chief Innovation Officer (CIO), ensuring we continue to deliver solutions for the new and emerging challenges businesses are facing.

Since everyone reading this won’t have the opportunity to ask Bobby questions, I figured I’d serve as your stand-in. I sat down with our new CEO to speak with him about his experience and perspective. But before we jump into that, I wanted to say a few things about how I reached this decision.

Why I Decided to Make This Shift and Why Now

I'm a founder who loves to build from zero to one.

As a founder, my job is to make sure we have the right leaders for the right stage of growth. I've always been most passionate about early-stage growth, product innovation, and finding that next big idea. As we've scaled, the CEO role has become less about that and more about operational excellence for a company of our size. We've reached a scale where we need an expert operator to steer the ship—someone who can take Osano to the next level.

This became apparent to me earlier this year. I knew that we needed to proactively seek out the leader we needed.

Bobby came to us on the heels of leading Freshworks’ launch in North America as the company’s General Manager. Freshworks is a successful customer helpdesk product and faced a large incumbent in Zendesk. Under Bobby’s leadership, Freshworks went from zero presence and zero employees in North American to a $10 billion valuation and a very successful IPO.

The leadership team and I interviewed many interested, qualified candidates, but when I saw Bobby’s experience, his humility, and his enthusiasm for Osano’s mission and people-first culture, I knew we had found our next CEO. Our board of directors unanimously agreed.

How This Feels

I have no doubt that others (and especially other founders) will be deeply curious about why I chose to hand off the CEO role.

I said it before, and I’ll reiterate: Osano is my baby. Any founder would think the same of the business they built. It’s tempting to think that because you built it, you could never give the chief executive role away to somebody else—somebody else couldn’t possibly care about your baby as much as you do.

I’m passing the torch to Bobby precisely because I care deeply about Osano. As big as my ego can be at times, I knew it had to play second fiddle to Osano’s success. And now, I get to contribute to Osano’s success in the way that I do best: By building exciting, innovative new things from the ground up as Osano’s CIO.

There’s a lot about my new role that I’m excited about, and I could write a whole blog post (or two or three) just about the new things we’re going to build. But this post is about Osano’s CEO—past and future.

Without further ado, let’s hear from Bobby.

Questions and Answers from Osano’s New CEO

Arlo: What drew you to Osano?

Bobby: Data privacy is a very personal matter and one that continues to evolve in importance as technology and AI become part of our lives. What you and Scott have built speaks to your entrepreneurial vision, and it aligned with what I was looking for. The opportunity to drive the next stage of growth and continue innovation in the category were some of the key reasons I decided to join the team.

Arlo: One of the things that stood out to us when we were looking for Osano’s next CEO was your experience at Freshworks. Could you tell us a little bit about Freshworks’ North America launch?

Bobby: Freshworks was a phenomenon success story, and the first India-founded SaaS company to go public in US. I have always believed that exceptionally successful companies win because they excel and execute well across product, go-to-market (GTM), and operations. Having a bold vision and clear strategy for how to grow at every stage was key to our success.

These principles were the key pillars in our company and specifically in the Americas region, which I led. Freshworks executed well across all of these areas while also having a high-performance and fun culture.

Arlo: What do you have planned for the future of Osano?

Bobby: First, it's very important to have a multi-year strategy on who we want to be as a company and who we serve as our customer profile. Aligning across product and GTM strategy will be a key area of focus to ensure we build a high-performance business.

My role and the rest of the leadership team is to ensure our vision is clear and that we align across every function to deliver the best results. Obviously, culture is a key part of any successful company, and we will need to continue to develop that.

Arlo: I’m sure our customers and partners have a lot of questions about this change, so I’ll ask on their behalf: What does this all mean for them?

Bobby: Trust, innovation, and customer delight are and will continue to be at the core of our focus. From the time a customer engages us to learn about how we can help their privacy program to the time when they build and scale their program, our goal is to deliver exceptional results. We’re going to ensure every touch point delivers the value our customers and partners expect. Customer success is our north star.

Arlo: To wrap up, is there a fun fact about yourself that you’d like to share?

Bobby: English is a second language for me and when I moved to US in ‘83, I went from not speaking a single word to fluent within 6 months. I guess it's easier when you have 3 hours of ESL! Also, my path to US came through Japan and I've wanted to go back ever since but unfortunately have not prioritized it. I love the Japanese culture and food 😊.

What’s Changing, and What Isn’t

This is a big shift, and it’s going to have a correspondingly big impact. The important thing to know is that the things about Osano that our customers, employees, partners, and you love—our friendly, user-centric attitude, the thoughtful approach we take to product development, our commitment to your compliance—those things aren’t going to change.

What is changing is how we operate as we continue to grow and scale. Ultimately, this means a better product, a better customer and support experience, and a better Osano. We're not going to make the mistake of thinking that what got us here will get us there. As we continue to climb to that next milestone, I want to thank you, sincerely, for coming along with us for the journey.