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A blueprint for career strategies in product and design leadership.

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Learn how Anshuman Kumar, former SVP of Design at Asana, drove $10M in annual recurring revenue by gamifying product optimization and owning the P&L.

The Evolution of Design Executive Anshuman Kumar

For many designers, the transition from practitioner to manager feels like a natural progression of craft. But for Anshuman Kumar, former SVP and Head of Design at Asana, the leap from manager to executive required a fundamental shift in perspective. It wasn't just about leading a team of 100+ designers; it was about shifting the "output" of design from pixels to business decisions to maximize design leadership and business ROI. As Anshuman shares in my book Leading by Design, becoming an executive meant moving beyond the screen to influence the company's financial trajectory.

In his career journey from Yahoo to Google and to the helm of Asana’s design org, Anshuman mastered a skill many design leaders struggle with: speaking the language of the business. This shift is essential for bridging the gap between UX and the bottom line.

One of the most profound realizations he had was the change in "time horizon." While a manager might focus on the following product cycle, an executive must look much further ahead; at Google, he lived six months in the future, but at Asana, his horizon moved to three years, allowing him to drive product optimization and gamification strategies that resulted in a staggering $10M revenue impact.

This shift meant moving away from the "unannounced Figma visit," which he learned can accidentally intimidate some designers, and moving toward multi-million-dollar budget accountability and long-term organizational health.

📖 Case Study

Gamifying the P&L to Drive $10 Million in ARR

The most striking example of his business-first leadership occurred when Asana set Annual Recurring Revenue (ARR) as a North Star for R&D. Anshuman saw this as an opportunity to prove his design team's worth in a language the board of directors would understand.

1. Identifying "Revenue-Sensitive" Surfaces 💰

Drawing on his early career experience at Yahoo, where changing a font size on an ad product could immediately impact the bottom line, Anshuman knew that certain "surfaces" (user interfaces) were more sensitive than others. He focused his team on payments, new user adoption, and retention.

2. Doing 30% of the Work for Others 👷🏾👷🏾

Instead of waiting for permission, his team audited critical surfaces and identified every UX bug that could be hindering conversion. They identified problems and provided solutions. From the documented list of solutions, he invited the stakeholders to choose what to optimize.

3. Gamification and the Leaderboard 🎲

To drive momentum, they created a leaderboard to track experiments conducted by cross-functional teams. This turned a technical backlog into a competitive game, motivating teams to fix "P2" (moderate-to-high-priority bugs affecting core functions or user experience) and "P3" (low-priority minor bugs, cosmetic glitches, or single-user problems) that had been ignored for months. 

4. The Result: A $10 Million Success 🤑

When Anshuman approached the Chief Product Officer, he didn't talk about "user delight" or "aesthetic consistency." He said, "We’re going to make $12 million in one year." By the end of the year, the design-led optimization initiative had driven $10 million in ARR (annual recurring revenue). More importantly, it sparked a cultural shift in which the entire R&D team realized that the quality of the product user experience is a direct driver of business growth.

Lessons for Aspiring Design Executives

Anshuman’s success offers a blueprint for design leaders looking to claim a seat at the executive table:

• Own the P&L: Don't wait for someone to hand you financial responsibility. Set ambitious targets, tie your design goals to revenue or retention, and be willing to be measured by those numbers.

• Avoid False Trade-offs: An executive’s job is to find the "third way" when business needs and design vision seem to conflict.

The Short of It Is 🚀

A design leader's journey at the highest level isn't about protecting the "sanctity" of the craft from the "coldness" of business. It’s about using the design process to solve the business’s most complex problems. When you can walk into a room and tie a UX improvement to a $10 million revenue bump, you aren't only a designer, but a business leader who happens to use design as your primary tool.

The full interview with Anshuman Kumar, along with insights from many other design and tech executives, is available in the book, Leading by Design: The Insider's Handbook for Tech Leadership, on Amazon.

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