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How to sell your ideas and rise within your company | Casey Winters, Eventbrite
42 segments available
The people who rise fastest in product know how to sell their ideas to customers, and also to their coworkers. Casey Winters, the Chief Product Officer at Eventbrite (previously at Grubhub, Pinterest, and advisor to dozens of companies) shares what it takes to be successful as you rise in the ranks within product. In this episode we’ll talk about how to land presentations, how to win over executives with strategic communication, the skill sets that are most in demand in product, and new growth trends. Join us. Find the full transcript here: https://www.podpage.com/lennys-podcast/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/#transcript — Thank you to our wonderful sponsors for making this episode possible: • Coda: http://coda.io/lenny • Mixpanel: https://mixpanel.com/startups • Whimsical: https://whimsical.com/lenny — Where to find Casey Winters: • Twitter: https://twitter.com/onecaseman • LinkedIn: https://www.linkedin.com/in/caseywinters/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: [00:00] What to expect in this episode with Casey Winters [03:23] An overview of Casey’s career [06:21] A look into the most-fulfilling and challenging roles Casey has energized [06:53] Communicating upward [11:21] How to derisk meetings [13:56] Are you properly preparing for your meetings? [19:12] Striving for perceived simplicity [24:25] Justifying non-sexy product improvements [27:50] Protecting what you’ve built vs continuously scaling [31:06] The downfall of functional ops roles [35:24] The CPO role: what it is and how to get there [40:47] The spectrum of product people [45:14] How to level up your skills [47:04] New growth trends, tactics, and strategies [50:35] Casey’s two stages of growth: kindle strategies and fire strategies [51:54] Under appreciated growth strategies [54:05] Where to find Casey
Segments Timeline
Unlocking Growth with Kindle Strategies
Casey Winters introduces the concept of kindle strategies as essential non-scalable hacks that pave the way for fire strategies, which can lead to massive user growth. He highlights successful companies like Pinterest, Airbnb, and Eventbrite, emphasizing the importance of these foundational strategies in achieving significant scale.
"the goal of your kindle strategies these like non-scalable hacks they only exist to unlock the fire strategies to unlock the things that could take you to millions of users pinterest airbnb tinder red..."
The Power of Coda in Product Management
Casey shares his admiration for Coda, a tool he helped launch, explaining its unique content loops that facilitate sharing best practices among users. He discusses how Coda serves as a central hub for his writing and podcasting operations, showcasing its versatility and effectiveness in enhancing productivity.
"winters hey casey winners what do you love about coda code is a company that's actually near and dear to my heart because i got to work on their launch when i was at greylock but in terms of what i lo..."
Mixpanel: Essential for Startups
In this segment, Casey discusses the importance of data-driven decision-making for startups, highlighting Mixpanel's powerful analytics tools. He explains how startups can leverage Mixpanel to find product-market fit faster and avoid costly mistakes, making it a vital resource for growth.
"statement just go to coda dot io slash lenny that's coda dot io slash this episode is brought to you by mixpanel offering powerful self-serve product analytics something we talk a lot about on the sho..."
Casey's Journey Through Product Management
Casey reflects on his diverse career in product management, starting as an analyst at Apartments.com and evolving through roles at Grubhub and Pinterest. He shares insights into how he transitioned from marketing to product management and the challenges he faced along the way.
"access real-time insights with the help of their pre-built templates and know that at every stage mixpanel is helping you build with confidence and curiosity for free apply for the startup program tod..."
The Evolution of Growth Roles
Casey discusses the evolution of growth roles in companies, particularly during his time at Grubhub, where he helped establish a product management function. He emphasizes the importance of adaptability and the changing landscape of product management as companies scale.
"boggles the mind just looking at your linkedin trying to scroll through linkedin and you have to click on see additional experiences on and there's just so many places you've worked so many companies ..."
Leading Growth at Pinterest
In this segment, Casey shares his experience leading the growth product team at Pinterest, where he played a crucial role in rebuilding the growth model. He discusses the strategies that helped increase monthly active users from 40 million to 150 million.
"have product titles either that you know that was kind of a newer idea also it wasn't until i went to pinterest that i was actually formally labeled a product person i ended up leading the growth prod..."
Communicating Trade-offs Effectively
Casey emphasizes the importance of communicating trade-offs within a company, especially during challenging times. He shares lessons learned about the necessity of escalating issues and ensuring that executives are informed about the circumstances affecting decision-making.
"of the things that you mentioned that you're working on is thinking about trade-offs and being very explicit about trade-offs you're making communicating why you made certain trade-offs and then just ..."
The Art of Storytelling in Executive Communication
Casey discusses the nuances of communicating with executives, stressing the need to present information in a structured manner. He advises on starting with the company's strategy and metrics before diving into specific details, ensuring that the narrative is clear and accessible.
"you know then when you know people inside a company do try to communicate you know upward a lot of times they're so in the weeds that as an executive i just don't understand what they're saying and th..."
Coaching Product Managers for Success
In this segment, Casey shares his approach to coaching product managers on effective communication. He emphasizes the importance of preparation before meetings and role-playing to anticipate executive questions, helping teams to present their ideas confidently.
"that they can follow along with and it's it's a lot of work to really dial that in across different types of people you're trying to communicate that story to because of course upward communication is..."
Preparation Styles for Presentations
Casey shares insights on different preparation styles for presentations among product managers. He explains his own preference for free-forming discussions based on deep knowledge of the material, contrasting it with others who may require extensive preparation. The key takeaway is that understanding the material and anticipating audience concerns is crucial for effective communication.
"that and if you don't have enough experience say presenting to the cfo or the ceo i as the chief product officer do so i can you know impersonate them and help you understand what they're gonna you kn..."
Knowing Your Audience
In this segment, Casey emphasizes the importance of knowing your audience when preparing for meetings. He recounts experiences from his time at Pinterest, where understanding the communication styles of executives was vital. He advises PMs to anticipate questions from executives to ensure they are well-prepared and can confidently address any concerns during discussions.
"communication and what types of frameworks you know what types of structure tend to work you know for eventbrite and making sure that everyone on my team is just really well versed in that and comfort..."
The Cost of Under-Preparation
Casey discusses the high stakes of under-preparing for important meetings. He explains how key decisions are often made in these forums, and the impact of preparation on a PM's career growth. He reflects on past mistakes and the lessons learned, stressing that thorough preparation is essential for achieving desired outcomes in meetings.
"is i'm actually a little bit better if i am free-forming a lot of elements and just speaking from confidence in areas i know versus specifically trying to lay out every exact bullet point i want to hi..."
Building Confidence Through Preparation
In this segment, Casey talks about the confidence that comes from thorough preparation for meetings. He shares how being well-prepared allows PMs to handle any situation, whether it's a board meeting or a discussion with executives. He emphasizes the importance of building intuition and readiness for various outcomes as a product leader.
"pulling from things i know deeply because i've written them down i've thought i've thought a lot about them for a lot of other people they really just need to spend a lot of time on prep to make sure ..."
Understanding Different Executive Styles
Casey elaborates on the different communication styles of executives and how they can impact meetings. He shares his experiences with executives at Pinterest, highlighting the need for PMs to be prepared for specific questions that may arise. This understanding is crucial for building credibility and ensuring successful communication during strategic discussions.
"and you know ben and jack had very different styles of communication jack in particular would very early on ask a few different data questions to get context on the problem and if you as a product lea..."
The Role of Data in Communication
In this segment, Casey emphasizes the importance of data in product discussions. He explains how being knowledgeable about data can bolster a PM's credibility during meetings. He advises PMs to anticipate data-related questions and be prepared to provide context, as this can significantly influence the outcome of discussions with executives.
"somewhat different in that regard but if you haven't thought through all the questions that might be asked from the document that you're sharing or the presentation you're about to present you're not ..."
The Impact of Meeting Preparation
Casey discusses the impact of thorough meeting preparation on a PM's ability to influence decisions within a company. He reflects on the high leverage that these meetings provide for product managers and designers, stressing that under-preparation can lead to missed opportunities for career growth and impact.
"and so this is real good real talk about how long it takes to prepare for important meetings like the ones you're talking about absolutely i mean you know for better or worse um the way that a lot of ..."
Learning from Past Mistakes
In this segment, Casey shares his approach to learning from past mistakes in important meetings. He emphasizes the importance of reflection and continuous improvement in preparation strategies. By understanding what went wrong in previous meetings, PMs can enhance their future performance and ensure better outcomes.
"have the type of career growth you want just go down dramatically and i'm sure you know you and i have definitely made mistakes in our career in important meetings you know in the past but i think you..."
The Challenge of Product Complexity
Casey introduces the challenge of maintaining simplicity in a growing product while adding functionality. He references Scott Belsky's concept of the product life cycle, explaining how products can become overly complex as they evolve. This segment sets the stage for discussing strategies to balance simplicity and functionality in product design.
"team or a meeting with an external partner right and i think that's what you're trying to build you know as any sort of product leader or pm or a product designer or researcher it's that intuition of ..."
Design Hacks to Avoid Complexity
In this segment, Casey outlines various design strategies to avoid the pitfalls of product complexity. He discusses approaches like progressive disclosure and proactive training, explaining how these methods can help manage user experience as products evolve. He emphasizes the need for thoughtful design to cater to different user types.
"yeah you know scott belski who's the chief product officer of adobe he has this concept of the product life cycle you know you're probably familiar with but i'll explain it you know to your listeners ..."
Perceived Simplicity in Product Design
Casey introduces the concept of perceived simplicity, where advanced features are easily discoverable but not intrusive for the majority of users. He explains how Eventbrite aims to implement this approach, ensuring that the product remains user-friendly while still offering powerful functionality for those who seek it.
"a lot of the more complex functionality until we make sure our users learn the really critical functionality and then we can kind of open up more of the full suite of the product then there's just you..."
Balancing User Needs in Product Development
In this segment, Casey discusses the challenge of catering to diverse user needs in product development. He shares insights on how Eventbrite addresses the varying levels of sophistication among event creators, striving to provide a seamless experience for both novice and experienced users.
"know training so what i found is that just none of these really work that well for the eventbrite um scenario because we have different types of event creators across every possible level of complexit..."
Marketing Automation for Event Creators
Casey highlights a successful initiative at Eventbrite that automates marketing for event creators. He explains how this product simplifies the advertising process while allowing for advanced options for users who want to take a more hands-on approach. This dual strategy caters to different user preferences and enhances overall effectiveness.
"there are advanced features in the product and they are easily discoverable when you look for them but they're effectively hidden if you're not looking for them and of course the majority of users are..."
Empowering Event Creators with Marketing Tools
Casey Winters discusses how Eventbrite has developed tools to empower event creators in their marketing efforts. He highlights the importance of simplifying complex marketing processes for users who may not be professional marketers, allowing them to automate Facebook advertising and achieve better results. This segment emphasizes the balance between simplicity and sophistication in product design.
"app but i remember when i went to brazil all of a sudden i started receiving like voice messages and it was really easy to figure out how to use them and how to do them myself when i needed to learn h..."
Justifying Non-Sexy Product Improvements
In this segment, Casey Winters addresses the challenge of justifying essential but often overlooked product improvements, such as stability and performance. He shares insights on how to build custom metrics, run small tests, and create team principles that prioritize these improvements, emphasizing the need for team buy-in to ensure long-term success.
"awesome another topic that you wrote about that kind of touches on the stuff we were just talking about is is justifying non-sexy product improvements things like stability performance developer veloc..."
Protecting What You've Built
Casey discusses the critical importance of protecting existing product features and user experiences as companies scale. He shares lessons learned from his time at Pinterest, illustrating how market changes can impact growth and the necessity of maintaining product-market fit. This segment highlights the need for proactive measures to safeguard the value already created.
"so what i'm hearing is step one is just get your kind of lead peer leaders aligned behind something that may not obviously be something your lead your leaders uh want you to do is that right absolutel..."
The Dangers of Complacency in Product Management
In this segment, Casey warns against the complacency that can arise in established companies. He explains how user expectations and competitive landscapes evolve, stressing the importance of continuous improvement to avoid falling out of product-market fit. This discussion serves as a reminder that stagnation can lead to significant challenges down the line.
"already built so that's that's another element that i think can be pretty impactful in your post on this topic you have an awesome chart of product market fit over time illustrating the point you just..."
Rethinking Operations Roles in Product Teams
Casey critiques the reliance on operations roles within product teams, arguing that they often signal inefficiencies. He advocates for a focus on automation and process improvement rather than expanding operational teams. This segment encourages product leaders to prioritize efficiency and innovation over traditional operational structures.
"right now that's not the intention but it's a no it's a it's a kick in the butt another post that i definitely wanted to chat about maybe your spiciest post maybe i'm curious if there are others is ar..."
Understanding the CPO Role
Casey Winters outlines the responsibilities of a Chief Product Officer (CPO), emphasizing the importance of leading product development that delivers value to customers and the business. He provides insights into what aspiring CPOs should focus on to prepare for this leadership role, making it clear that the position requires a balance of strategic vision and practical execution.
"product ops whereas what the goal should be is let's use our brains to run experiments to make us more functional with less people we're more efficient we can add more value to the customer and to the..."
Optimizing Product Strategy
Casey elaborates on the CPO's role in defining and improving product strategy processes. He emphasizes the need for a feedback loop to adapt strategies based on customer insights and market changes, ensuring that the company delivers tangible results and value.
"scope of the function a cpu role can lead a few different sub-functions you know in my case i lead product management product design research and growth marketing but you know different roles have kin..."
Path to Becoming a CPO
Casey shares his personal journey to becoming a Chief Product Officer, highlighting the importance of understanding the entire business and focusing on impactful areas. He discusses the balance between functional leadership and company-wide optimization that is crucial for aspiring CPOs.
"things like identifying bottlenecks that prevent us from delivering you know value or quality or you know doing that at the detriment of speed working with people across the company to remove those bo..."
The Importance of Versatility
In this segment, Casey stresses the value of refusing to specialize too early in one's career. He explains how acquiring a broad skill set allows product leaders to engage with various aspects of the business, enhancing their ability to contribute strategically and effectively.
"not be that everything we build delivers value but i want most of it to and i want the impact of of that value to be higher and higher over time so you also asked about what it takes to get to the cpu..."
Navigating Executive Communication
Casey discusses the significance of understanding executive perspectives and how to communicate effectively with them. He advises product leaders to view executive inquiries as opportunities for learning rather than tests of knowledge, which can improve interactions and foster collaboration.
"i think one of the things that's different about being a cheap product officer versus you know other product roles is how much of a company leadership role it is versus a functional leadership role yo..."
The Spectrum of Product Managers
Casey introduces the concept of a spectrum among product managers, contrasting innovative thinkers with execution-focused individuals. He explains the ideal balance of skills needed in product teams and the challenges of recruiting individuals who can both generate ideas and execute effectively.
"was just refusing to specialize i thought if i could learn all the skills that would allow me to combine them to work on the most important things versus only work on the thing i knew how to work on a..."
Recruiting for Balance in Product Teams
In this segment, Casey elaborates on the challenges of finding product managers who possess both strategic thinking and execution skills. He shares insights on how to cultivate a balanced team that can drive value while also being innovative, highlighting the importance of mentorship and training.
"runs product at cambly and he used to run a core product at pinterest it's this idea of you know uh any product team is like a gang of misfits right they all come from different backgrounds you know m..."
Developing Strategic Skills
Casey emphasizes the need for product managers to develop strategic skills as they advance in their careers. He discusses the importance of being able to write strategy documents and make independent decisions, which are critical for career progression and effective leadership.
"want people in the middle we want people who are strategic they understand what's going on in the industry they can generate some good ideas but they can also turn it into something real that delivers..."
The Growth Mindset for Product Managers
In this concluding segment, Casey reflects on the essential skills for product managers to level up, particularly the ability to think strategically. He encourages aspiring leaders to focus on developing these skills to enhance their career trajectories and contribute meaningfully to their organizations.
"don't have good ways to kind of turn great executors into great strategists you know as as in general like a product you know uh function so i've started investing in a lot of different things here ob..."
The Bottleneck of Strategy Skills
Casey Winters discusses the critical importance of strategy skills for product managers (PMs) as they advance in their careers. He emphasizes that early in their careers, PMs should focus on delivering real value to customers, but as they aim for leadership roles, they must be able to independently write strategic documents. This skill is essential for driving decision-making and advancing their careers, as a lack of it can lead to stagnation.
"interesting that that's like what you found to be the most essential piece for pms to often level up at like i said it depends on the level right so early on in your career as a pm you're gonna get th..."
Innovative Growth Channels
In this segment, Casey Winters shares insights on the evolving landscape of growth strategies for startups. He highlights the challenges of traditional paid growth methods and discusses the importance of leveraging existing channels through improved customer flows and lifetime value. Casey introduces the concept of 'product-led' growth, where companies unify self-service and sales processes to create a more efficient growth engine.
"listening that are trying to figure out what should i work on it's kind of simple a lot of times just get better at strategy and it feels like it elevates you in so many other ways yeah and of course ..."
Building Growth Loops Early
Casey emphasizes the shift in mindset among founders regarding growth strategies. He notes that many are now considering how to integrate growth loops into their products even before achieving product-market fit. This proactive approach allows companies to establish a distribution advantage, ensuring they can scale effectively once they find product-market fit.
"one larger cross-functional team and building an engine that optimizes all of their skill sets so that's something i'm pretty excited about but we're definitely in the early days there that's that's a..."
Kindle vs. Fire Growth Strategies
In this segment, Casey Winters outlines his framework for growth strategies, distinguishing between 'kindle' strategies, which are non-scalable hacks for early user acquisition, and 'fire' strategies that drive scalable growth. He explains that kindle strategies are essential for unlocking fire strategies, which can lead to significant user growth and should inform when to hire dedicated growth personnel.
"it and it's gonna work um so that's something i'm really excited about on that topic when should companies focus on growth and the second question when do you think they should hire a head of growth o..."
The Power of Data Network Effects
Casey discusses the often-overlooked potential of data network effects in driving growth. He explains how leveraging product usage data can enhance product value over time, creating a competitive edge. This approach is particularly relevant in light of recent changes in advertising platforms, as companies that can generate their own data will have a significant advantage.
"tactic thinks that you're just like oh wow this seems to be working better than people may think um yeah well i i still think data network effects are underrated i think a lot of people confused the i..."
Connecting with Casey Winters
In the closing segment, Casey Winters shares how listeners can connect with him online. He emphasizes his commitment to mentoring the next generation of product managers and marketers, encouraging them to improve their skills and build better businesses. He also invites listeners to check out the Eventbrite app for exciting events.
"record quite a lot lately awesome casey's picks get him here get him here now casey i feel like i was successful in extracting many nuggets in our hours together i really appreciate your time where ca..."