Product leadership in a startup environment is a challenging yet rewarding journey. Jason Dea, the SVP of Product at Uberflip, has driven success through his hands-on, data-driven, and customer-centric approach. With extensive experience leading cross-functional teams and having co-founded his own startup, Jason brings a wealth of knowledge on identifying, validating, and scaling product orgs.
In this blog, we will delve into the critical relationship between a first-time founder and their Chief Product Officer (CPO). We will explore what a healthy dynamic looks like, warning signs of trouble, and key indicators that it’s time to bring in a CPO. Additionally, we’ll discuss the strategic role of a startup CPO in a founder’s long-term exit strategy and the evolving importance of AI in product leadership.
Tell us about the relationship between a first-time founder and their startup CPO. What does a healthy relationship look like? What are the warning signs that things are not quite right?
Like in all relationships, trust is imperative. This is uniquely true when considering the relationship between a founder and a CPO. At the end of the day, the product you’re inheriting is the founder’s baby. And while nobody’s baby is ever ugly, the reality is that it’s a product leader’s job to have the hard conversations with all the stakeholders involved (customers, employees, partners, investors) to understand where that baby might have a few warts. I know that’s a terrible analogy, but that’s the harsh truth.
A great founder/ startup CPO relationship must be based on a level of trust and respect, where conversations of that nature can be had, and when they occur are brutally objective. Your shared goal is to grow the business, full stop. The absolute most important puzzle piece in that growth equation is your product. A great product leader understands this and needs to be given the agency to act on what will be best for all stakeholders.
But things may not always be smooth sailing. Some warning signs to watch out for include whether the founder or CPO feels the need to keep things close to the chest, not share important info, or if the founder is constantly looking over the CPO’s shoulder and not letting them do their job. Another issue to look out for is when either side gets defensive about feedback; we all need to be open to constructive criticism. These relationship rifts can stifle innovation, slow decision-making, and ultimately harm the product and business growth.
Recognizing and addressing any potential issues early is crucial, as is understanding that the relationship will evolve. As the company grows and changes, so should the way the founder and CPO work together. Maybe the founder needs to take a step back from the day-to-day product stuff, or perhaps the CPO starts to take on a more big-picture strategy. It’s all about being flexible and doing what’s best for the business.
What are the signals/indicators that it’s time for a founder to hire a CPO?
There are a few signals that it might be time for a founder to bring in a startup CPO. You might notice the product development process getting increasingly complex or struggling to prioritize features and manage everyone’s expectations. You may realize you need more sophisticated metrics and analytics to really understand your product’s performance. Or you’re facing challenges in aligning your product strategy with your overall business goals. When these issues start popping up, it’s often a sign that it’s time to bring in some specialized product leadership.
Let me explain this transition using an analogy I find helpful: I like to think about a startup as a soccer team. In the early stages, the initial growth of a startup is often like a soccer game with little kids. For anyone who may be a parent (or aunt or uncle) you’ve probably seen it. While little kid’s soccer is just about the cutest thing ever, from a strategy and execution perspective, it’s also pretty rudimentary. All 10 kids on the team crowded around the ball like a swarm of bees. All hustle. 1000% effort. And every once in a while, a goal.
Eventually, every business hits an inflection point. Suddenly, your soccer opponents are bigger, faster, stronger. Having more finesse in your approach to the game matters at that point. You need to understand positions and plays and how the different positions make up a broader strategy to move the ball down the field. The best way to do this would be to bring in someone who’s already learned those nuances of the game. A startup CPO can be like an experienced coach who can help organize the team, work with you to develop strategies and nurture each player’s strengths.
A typical example of this evolution for emerging product organizations is looking at their product roadmap. The question founders often need to ask themselves is – Is my product roadmap just a list of to-do items? Or is it an articulated way to map out the steps to take your product and company vision through to day-to-day execution? A skilled CPO can help transform that to-do list into a strategic roadmap that aligns with your company’s vision and goals.
What advice do you have for a first-time founder whose long-term strategy includes an exit, whether to a PE firm or otherwise. What implication does this have on the role of the CPO and product strategy?
For a first-time founder with a long-term exit strategy, the product roadmap is a critical tool to guide the company from vision to execution while building value for potential acquirers. Here’s how to approach it:
- Product Vision: Define the enduring problem and unique thesis, ensuring alignment with potential acquirers’ interests or market trends.
- Horizon Milestones: Break the vision into clear, validating steps. Include metrics and achievements that would be attractive to PE firms or potential strategic buyers.
- Capability Themes: Identify capabilities needed to achieve each milestone, focusing on building a strong, differentiated product that creates unique value in the market.
- Execution: Prioritize and sequence-specific features for delivery, emphasizing those that foster growth, market fit, and customer retention.
This framework has several implications for the CPO role and product strategy:
- Market Positioning: The CPO should focus on building a product that fills a clear market gap, making it an attractive acquisition target.
- Metrics Focus: Implement strong analytics to showcase product success and market penetration.
- Flexibility: Build a product that can pivot if needed to align with market demands or potential acquirer interests.
- Intellectual Property: Where possible, develop and protect unique IP that adds value to the company.
That whole chain of planning has to work in concert. For a founder eyeing an exit, it’s not just about building a great product; it’s about crafting a narrative that can make potential buyers take notice. Your CPO needs to think two steps ahead, balancing the day-to-day shipping features with the long game of building real, lasting value. At the end of the day, your product strategy isn’t just a roadmap for your product and engineering team; it’s the blueprint for your company’s future value.
Because everyone is talking about AI, what advice do you have for product leaders who need to add AI to their “skills?”
Perhaps more than anyone, product leaders need to stop adding AI as a skill we can check off. We need to get comfortable incorporating AI into our thinking, how we approach our work, and how we solve customer problems. AI isn’t just a widget; it’s an enabling technology.
Today’s LLMs allow us to go beyond investigating and analyzing data and actually have a “conversation with data.” A mentor of mine once told me that the hardest part of the role of a CPO is reading the tea leaves of data to literally predict the future. Having an active conversation with data rather than just looking at graphs and printouts is a way to fundamentally change and accelerate that element of fortune-telling that we product leaders are tasked with.
For instance, a product leader might use AI to analyze vast amounts of user feedback, identifying patterns and sentiments that would be nearly impossible to uncover manually. This could lead to more quantitative justification for feature prioritization or reveal unexpected use cases. Another example could be using AI for predictive modeling to anticipate market trends or user needs, allowing for more proactive product development.
It’s important to note that the field of AI is rapidly evolving. What’s cutting-edge today might be table stakes tomorrow. Great product leaders are lifelong learners and driven by curiosity; the rapidly changing world of AI should be an ideal space for us to sink our teeth into.
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Thank you to Jason for his insight and highlighting how the relationship between a founder and their CPO is pivotal to the success of a startup. Building a foundation of trust, open communication, and mutual respect is essential for navigating challenges and seizing opportunities.
Recognizing the right time to bring in a startup CPO and understanding their strategic role in the company’s growth and exit planning can significantly impact the trajectory of a startup. As the landscape of product development continues to evolve, especially with the integration of AI, staying adaptable and forward-thinking is crucial for product leaders. By leveraging these insights, founders and CPOs can work together to drive innovation, foster growth, and build products that stand the test of time.