Atlassian Former CPO on Transitioning successfully from operator to investor | Joff Redfern | E224 | #TheProductPodcast

"I love learning new things. I've been a product leader my entire career, pretty much... So I'm decades into it and I wanted to try something different."

In this edition of #TheProductPodcast newsletter, we dive into the world of product leadership and venture capital with Joff Redfern , former Chief Product Officer at Atlassian and current partner at Menlo Ventures . With a rich background in product management at companies like Yahoo and LinkedIn, Joff shares valuable insights on leadership, innovation, and the transition from operator to investor.

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There are many incredible lessons to learn from Joff. Here are a few of the top ones:

➡️ The Evolution from VP to Chief Product Officer

"At the highest level, you get closer to becoming both a general manager and a people manager... The job that I had at the CPO was that of hiring amazing talent, making sure that talent was running their respective areas of the business really well."

As Joff explains, the transition from VP of Product to Chief Product Officer involves a significant shift in responsibilities. The role becomes more focused on talent management and general business operations. CPOs are tasked with hiring top talent, ensuring their success in their roles, and making tough decisions about team composition. They also become more involved with shareholders and the board, emphasizing the importance of building not just great products, but great businesses. This evolution requires a broader perspective on the company's overall strategy and a keen ability to balance product innovation with business growth.

➡️ Embracing Flexible Planning in a Fast-Paced Environment

"We created something called the Rolling Four. And the idea behind the Rolling Four is that every quarter, you should look forward to 12 months and you should update your plan."

Recognizing the limitations of traditional annual planning, Joff introduced the concept of "Rolling Four" at Atlassian. This innovative approach involves updating the plan every quarter, looking forward to 12 months. The idea is to maintain a flexible strategy that can adapt to changes in competition, internal learnings, or product deliveries. Joff emphasizes that this method allows for more nimble decision-making and better alignment with the dynamic nature of the tech industry. It's not about completely overhauling the plan each quarter, but rather making necessary adjustments based on new information and market changes, ensuring that the company's strategy remains relevant and responsive.

➡️ Fostering a Culture of Creative Confrontation

"I would describe it as a creative confrontation. And the idea is that you take an idea and you put it on the table. And with a small group of people, you work on that idea and you work on it in an intellectually honest way."

Joff highlights the importance of creating an environment where ideas can be openly debated and improved upon. He refers to this as "creative confrontation," where team members can challenge ideas intellectually without attacking the individuals behind them. This culture of honest, constructive feedback was a key factor in Atlassian's success and ability to make tough decisions, such as shutting down major products when necessary. Joff emphasizes that this approach allows for the refinement of ideas and leads to better outcomes, as it encourages diverse perspectives and rigorous examination of proposals before implementation.

➡️ The Power of Founder-Led Companies in Driving Innovation

"I do think part of that is the founder mentality that exists within the organization just really infects the people that are also in the organization. And they too have a desire to make big changes."

Working with Atlassian's founders taught Joff the value of entrepreneurial thinking within large organizations. The founders' willingness to take risks and support bold initiatives, like the "Rolling Four" planning method, demonstrates how founder-led companies can maintain agility and innovation even as they scale. Joff notes that this mentality permeates throughout the organization, inspiring employees at all levels to think big and pursue transformative ideas. This entrepreneurial spirit allows companies to remain nimble and innovative, even as they grow into large enterprises.

➡️ Transitioning from Operator to Investor

"I love learning new things. Ive been a product leader my entire career, pretty much... So I'm decades into it and I wanted to try something different."

Joff's move to venture capital was driven by a desire for change and the opportunity to combine his love for angel investing with his passion for advising companies. As a VC, he can leverage his operational experience to support founders while enjoying the clear-cut success metrics of investment returns. This transition allows him to stay connected to product innovation while exploring a new career path. Joff emphasizes that his background as a product leader gives him unique insights into the challenges founders face, allowing him to provide valuable guidance and support beyond just financial investment.

➡️ The AI Revolution and Its Impact on Product Development

"We've spent, I've personally spent a bunch of time looking at how the software development life cycle is changing with AI. And there's certainly a lot of activity in that space."

In his role at Menlo Ventures, Joff is deeply involved in AI investments. He draws parallels between the AI revolution and the mobile revolution, noting that foundational infrastructure comes first, followed by transformative applications. Joff sees significant potential in how AI is reshaping the software development lifecycle, particularly in areas like code generation and developer productivity tools. He highlights the rapid growth of AI-powered development tools like GitHub Copilot and the emergence of well-funded startups in this space, indicating a major shift in how software will be created and managed in the future.

➡️ The Future of Product Management Tools

"The thing about product managers is, and there's, you know, there's not a lot of tools out there that cater just to the product manager when you think about it, like that sell directly into it and have a budget."

Joff observes that while developers and designers have a plethora of specialized tools, product managers have historically had fewer options. He anticipates that AI will play a crucial role in developing more sophisticated tools for product managers, potentially bridging the gap between technical and non-technical aspects of product development. Joff suggests that as AI technology advances, we may see a new generation of tools that empower product managers to work more efficiently and effectively, similar to how AI-powered tools are transforming other areas of the software development lifecycle.

🔑 Key takeaways

• The transition to C-level product roles requires a shift towards general management and strategic thinking.

• Flexible planning methods, like the "Rolling Four," can help companies stay agile in fast-changing environments.

• Fostering a culture of creative confrontation enables better decision-making and innovation.

• Founder-led companies often maintain a higher appetite for risk and innovation, even as they scale.

• The transition from operator to investor offers a unique perspective on product development and company growth.

• AI is reshaping the software development lifecycle, with significant implications for product management.

• There's an opportunity for AI-powered tools to enhance product managers' capabilities and bridge skill gaps.

🎧 Check out the full episode here  🎧

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Credits:

Joff Redfern

Carlos Gonzalez de Villaumbrosia

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