In the technology industry, there is an ever-present opportunity to build products that affect the entire world. But scaling a business to a multi-billion dollar valuation requires a fundamental shift in thinking. For Dennis Woodside, the CEO of Freshworks and a tech veteran with 25 years of experience in Silicon Valley, the transition from building modest projects to driving massive global impact comes down to chasing the biggest dreams.

Woodside, whose career spans leadership roles at Google, Motorola Mobility, Dropbox, and now Freshworks, recently shared his insights on the crucial mindset shifts needed to hunt down $100 million ideas, the responsibilities of a CEO, and the common mistakes founders make as they scale.

The Shift from Linear to Exponential Thinking

Before joining Google in 2003, Woodside was trained as a lawyer—a profession built on linear thinking and applying past case law to new situations. Technology, however, demands exponential thinking. It requires asking: If this technology works the way it could, how does it change the lives of millions, or billions, of people?.

When Woodside joined Google, it was still a relatively unknown company with about 1,000 employees and only one product: a search box. But founders Larry Page and Sergey Brin envisioned a future where everyone on earth would be connected to the internet. Woodside learned that while he might not be the person to invent the grand vision, his strength lay in organizing teams and executing that vision flawlessly.

Today, as the CEO of Freshworks—a multi-billion dollar SaaS leader with 75,000 customers ranging from industrial businesses to universities and baseball teams—Woodside applies that same exponential lens. “It’s easy to come up with an idea that might have a $2 million impact,” he notes. “That’s not going to move the needle for us anymore. You have to really focus on the big things and accept a little bit of inefficiency in some of the smaller things that might be going wrong.”.

The Uniquely Difficult Job of the CEO

Woodside joined Freshworks after meeting its founder, Girish Mathrubootham, who built the company in Chennai, India, and successfully took it public in 2021. As Mathrubootham looked to his next chapter—investing in the next generation of Indian entrepreneurs—Woodside stepped in to scale the company further.

According to Woodside, the role of a CEO is to focus strictly on the problems nobody else can solve. These include:

• Strategic Direction: Deciding exactly where the company competes, which products deserve attention, and making the hard choice to abandon products that no longer align with the company’s future.
• Business Models: Evaluating and setting pricing and revenue models.
• Organizational Structure: Ensuring the company has the right people in the right roles.
• Acquisitions: Finding external talent or nascent products that can benefit the customer base.

“Don’t do someone else’s job,” Woodside advises. “Constantly be thinking about, well, what’s next? What’s the next decision that I need to be thinking about that’s going to transform the business?”.

The Most Common Founder Mistake

Founders often build deep loyalty with the core team that helped start the company. While loyalty is an excellent trait, Woodside notes that a common mistake founders make is staying attached to early employees when those individuals may no longer be the right leaders for the next generation of the company’s scale.

An employee who thrived when a startup had 100 people might not possess the skills to manage a division when the company grows to 60,000 employees. Leaders must be willing to find new talent to supplement the team while transitioning early employees into roles that better fit their capabilities.

When hiring for a scaling business, Woodside looks for two distinct traits:

1. They have seen “Growth”: The candidate needs to have experience in a business that doubled in size in a matter of years.
2. They have seen “Great”: The candidate should have been trained at world-class organizations. For go-to-market roles, Woodside looks for experience at companies like Salesforce, ServiceNow, or Google. For engineering, he looks for rigorous backgrounds from Google or Amazon.

Embracing the AI Revolution

Woodside draws a parallel between the early, mind-blowing days of watching YouTube on a mobile phone and the current AI revolution. Hyperscalers are projected to spend over $700 billion on AI infrastructure this year, and an estimated $1 trillion next year, building data centers and acquiring chips globally. This massive investment is expected to yield unprecedented productivity improvements.

For Freshworks, this means adopting an AI-centric approach to everything they do, allowing them to ship code at a significantly faster pace than they did just 12 to 24 months ago. In a world where AI is leveling the playing field and generating startups that didn’t exist two years ago, Woodside’s advice to professionals is simple: embrace the change.

“If you embrace it now, you understand how to use AI to make you better at your job, you are going to be better than others,” Woodside says. “The competitive dynamics are going to change… I think the best mindset is to say, look, I can know as much about this as the world’s experts, because the world’s experts have only been around for a handful of years.”.