The Way of Product with Caden Damiano #130 On Becoming a Product Leader: Dean Phillips, Head of Product Strategy @ ClickUp
Hey listener! I just dropped a podcast episode with Dean Phillips, Head of Product Strategy at ClickUp. I enjoyed this guest so much I added a second hour of time to talk shop on product strategy.
In this episode, we want to discuss Dean's notable journey from indy wordpress developer to leading product strategy at ClickUp and explore his unique, tailored fit role at the company.
We'll also take a closer look at the company's community engagement and its impact on his current position. He shares how ClickUp tackles being an all-in-one platform without sacrificing quality and how they're using AI to make work smoother.
We also chat about leading through influence—something Dean does masterfully.
If you're into tech, product strategy, or just love a good career pivot story, give it a listen!Time Stamps
01:43 Joining ClickUp: The Early Days
18:35 From Music Side Hustles to Product Strategy
24:52 The Origin Story of ClickUp
33:35 Senior Leadership at ClickUp
34:01 ClickUp's Contrarian Success
35:13 Challenges and Innovations in All-in-One Apps
38:25 Team Structure and Collaboration
45:41 The Role of Obsession in Product Management
54:16 Building ClickUp's Chat Tool to Replace Slack
I have DOUBLE the takeaways. There is so much good stuff here.
Obsession as a Catalyst for Success
Dean Phillips' path to success embodies the power of obsession. From the early days when he was just a highly engaged user of ClickUp, his unwavering dedication and deep-seated curiosity drove him to evolve into a pivotal figure in the company's strategic direction.Dean's love for creating and improving products was evident when he first pitched an idea to ClickUp's CEO. His unique insights and passion were recognized, leading to an unexpected role offer.
"I sent it. I was like you should execute this. Please do this. The response was “this is amazing. Do you want to come and execute it with us?"-Dean Phillips
Actionable Takeaway: Let your obsession guide you. Find a problem you can't stop thinking about and immerse yourself in it. This level of engagement can be the difference between being good and becoming exceptional in your field.
The Role of Intuition in Product Management
Dean describes his journey into product management as unorthodox. He relied heavily on his intuition and creative instincts, often sketching his ideas and engaging deeply with designs processes. Despite lacking formal training in product management, Dean's ability to connect dots and foresee product pathways became his strongest asset.
"I kind of had that intuition. But I didn't realize how to do that when I first joined. I didn't realize that is what I have to do, if that makes sense."
-Dean Phillips
Actionable Takeaway: Trust your intuition. Even without extensive experience, your unique perspective and insights can introduce innovation. Don't shy away from presenting your ideas—you might offer the missing piece your team needs.
Strategic Innovation at ClickUp
Dean's role at ClickUp expanded as he took charge of aligning various product components within a cohesive strategic framework. His leadership was crucial in the development of ClickUp's integrated chat feature, which addresses the fragmented nature of workplace communications by bringing context and communication into one place.
"It's my role to oversee every single team, every single feature, and like stitch them all together and make sure that we're building with everything kind of coming together at the right time."
-Dean Phillips
Actionable Takeaway: Focus on integration. When developing strategies, ensure that your ideas foster collaboration and innovation across various components. Aligning different projects under a unified vision can significantly enhance overall productivity and user experience.
Embracing the “Super Individual Contributor” Role
An intriguing aspect of Dean's role at ClickUp is his position as a super individual contributor. He thrives on influencing without formal management authority, collaborating closely with diverse teams to drive innovation and achieve strategic goals.
"I'm a super IC. I'm not involved in the managerial side of things. That was by choice. I wanted to be deep into the weeds helping all the PMs and designers create things. I'm a creator."
-Dean Phillips
Actionable Takeaway: Embrace the super IC role by finding ways to contribute significantly without the need for direct reports. Influence and leadership can come through expertise and collaboration, rather than formal hierarchy.
Overcoming Challenges through Leadership
Dean acknowledges the challenges he faced as he transitioned into a leadership role, emphasizing the value of stakeholder management and influence without formal authority. This journey was not just about personal growth but also about fostering an environment where creativity and innovation could thrive.
" "It's my job to bring a vision together for each area that ties to the greater vision of ClickUp and where we want to go.We wanted to build a strategy which made everyone work together and we had checkpoints. A big part of how we build now with all these features is, we have different teams.
-Dean Phillips
Actionable Takeaway: Cultivate influence. Even without formal authority, you can lead by example and influence others through your work ethic and vision. Foster trust and communication within your team to drive collective progress.
Adaptability is Key in Product Strategy
"It was a big learning curve when I went to ClickUp. But once I had the title of product manager I latched onto that and dove right in to figure it all out." - Dean Phillips
Action Tip: Be open to learning and adapting in new roles. Embrace challenges and seek to quickly understand and integrate new knowledge to drive product strategy forward.
Developing Contextual Solutions for Product Development
"We built ClickUp chat for different kinds of people. We built it for people who love async communication and people who like async communication." - Dean Phillips
Action Tip: Tailor your product features to address varying user needs. By focusing on diverse use cases, you can create more inclusive solutions that improve user experience and engagement.
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