Meet Calendly’s new Chief Product Officer: Welcome, Stephen Hsu!

Today, we’re thrilled to share that Stephen Hsu has joined Calendly as our Chief Product Officer. 

Stephen was most recently the Senior Vice President and General Manager of Salesforce’s MuleSoft division; prior to that, he led Salesforce’s Sales Cloud engagement portfolio and the core productivity capabilities. 

As CPO at Calendly, Stephen will be executing on our ambitious product roadmap — we sat down with him to talk more in depth about what’s in store for Calendly, and to learn a little more about his approach to product organizations. 

What drew you to this role, and what are the biggest opportunities you're excited to tackle? 

Calendly has built a powerful product and PLG-driven business that serves millions of users in a simple and practical way. As a productivity and collaboration platform that helps people connect, it’s now incredibly well-positioned to become an engagement layer for artificial intelligence, go deep with departmental solutions for the enterprise, and expand its already robust ecosystem to new markets. 

As CPO, I’m excited to help evolve our product strategy to meet the opportunities of the next level and take Calendly to the next stage of growth, expanding the aperture to move upmarket and meet the needs of enterprise organizations. The creativity, focus, and execution are all what thrill me about joining the Calendly team.

On a personal note, I’ve discovered I have many ties to people already working at the company, and as a result, there is a familiarity that makes me feel that I’m a part of the Calendly culture already. When I first met our CEO and founder Tope Awotona, what was supposed to be a 30-minute coffee turned into a 2.5-hour walk through the hills of San Francisco. It felt like a fit from the start. And we also became more fit in the process!

As a product leader, what part of Calendly's platform are you most inspired to focus on? 

Calendly is the #1 scheduling automation platform in the market, helping 10+ million users connect around the world to get business done. It has also now evolved into an engagement layer upon which people are beginning to rely for more than just scheduling. This ultimately means that we have a unique and massive opportunity to leverage the tools of generative AI to help drive business outcomes around the entire meeting lifecycle, for any use case or workflow. We are going to seize this moment!

And there are so many other areas I’m most eager to explore at Calendly. These priorities are so compelling:

• Making Calendly even more useful to the departmental users who get the most value out of the platform, like the sales, CS and marketing teams who benefit from features like Calendly Routing, and the recruiting teams who need scheduling automation built just for them.

• Embedding Calendly in enterprise automation workflows, enabling customers to build apps with Calendly APIs, and other platform extensibility and ecosystem improvements.

• Evolving Calendly’s data strategy to become a unique source of meeting-specific data, and providing AI-driven insights to meeting participants that help drive them to business outcomes.

• Expanding into adjacent product categories — Calendly is already so much more than a calendar link; it’s a sophisticated scheduling platform offering shared availability, extensive integrations, advanced security features, and more. I’m excited to continue that evolution.

How should B2B companies think about innovation, with the growing number of productivity apps in the enterprise space? 

To be successful, B2B companies today should revisit the pain they are aiming to solve for their customers and rethink the best interface for providing the painkiller. As we move forward into the future, we’ll see the constraints of Web 2.0 holding companies back from providing the most effective ways to help their customers. Forms and rigid apps won’t cut it. 

Add to it the proliferation of productivity apps over the past several years, and it's no stretch of the imagination to see there will be diminishing returns on productivity as the costs of integration, context-switching, and siloed teams slow down meaningful business impact. Consider that the average enterprise today has over 900 different systems in their application network, and only ~30% of them are integrated. The future requires a painkiller for the disconnected experiences produced in this environment.

Enter: generative AI. The surrounding media buzz, the multitude of hackathons happening around the world, and the flurry of companies looking to leverage the technology for business productivity are warranted. With the rise of generative AI, you could have a bot that orchestrates connected experiences for users, regardless of where the data lies. If you have a user interface like that of Calendly’s, it doesn’t matter that data is strewn across multiple systems on a company’s backend. Calendly’s AI could take care of any meeting objective for you so you can focus on meaningful business outcomes.

Right now, tactically, B2B companies should think about what role their application plays in an orchestration of workflows across multiple applications. They should think about which other applications should be more tightly integrated in their target persona’s user experience, when to build versus when to partner, and how these multi-system workflows affect where data gravity resides and where the users prefer to engage. 

Ultimately, companies need to factor all of this into the value they provide to their customers if they want to provide the winning solution.

What’s one of the greatest lessons you've learned from your career to date? 

As a product leader, I’ve reflected on many experiences in my career, both successes and failures. Recently, I’ve boiled them down into three guiding principles: 

Prioritization: Always ask, “What is the one thing I should do right now, that makes every subsequent priority easier to achieve or completely unnecessary?” I learned this from The One Thing, by Gary Keller, and it has greatly accelerated how fast I’ve accomplished professional and personal goals the past few years. As an example of how I might apply this, I believe culture is the most impactful in achieving every subsequent priority when joining a new organization. As I join the Calendly team, I will prioritize fully embracing Calendly’s values with the team: Start with Human, Find a Way, Focus Wisely, and Strive for Excellence. 

Curiosity: Ask questions that prompt high-leverage answers, as these answers will help with creation of strategy, negotiations, building trust among people, and identifying what may help accelerate execution (see Prioritization above). Conversely, you can also learn a lot about a person by the types of questions they ask, sometimes more than from their answers.

Communication: Always learn how you can improve your communication skills. Clear communication and the ability to calibrate to the right altitude of your audience make maximum impact in any leader’s charter. As I’m always looking for the easiest way to communicate ideas, I also believe storytelling is the best way to make ideas stick in people’s minds and for them to carry those ideas forward to the rest of the organization.

If you could have anyone's Calendly link, whose would it be? 

As May is Asian American & Pacific Islander Heritage Month, I choose Justin Lin, director of the Fast & Furious franchise, Star Trek Beyond, Better Luck Tomorrow, and various TV shows. I studied filmmaking as a digital art major in college, and to this day, my “What if … ?” career question is “What would life be like if I had gone into the film industry?” Justin broke through barriers in Hollywood to create and direct his films. I’d love to hear his stories about the journey and get some inspiration for creative projects of my own.

Follow Stephen on LinkedIn.

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