The Way of Product with Caden Damiano

Caden Damiano
The Way of Product with Caden Damiano

A podcast on overcoming the challenges of collaboration within a product team. If you want to develop strong soft skills, product sense, and design taste, this show is for you! www.wayofproduct.com

  1. #132 Modern API Integration Strategies, The Art of Influence, & Balancing Strategic Vision with Day-to-Day Leadership w/ Anuj Jhunjhunwala Director of Product at Merge.

    5 DAYS AGO

    #132 Modern API Integration Strategies, The Art of Influence, & Balancing Strategic Vision with Day-to-Day Leadership w/ Anuj Jhunjhunwala Director of Product at Merge.

    Hey Listener,In this interview with Anuj Jhunjhunwala, Director of Product at Merge, we discussed how it’s easier than ever to develop API integrations between dozens of enterprise systems and how you can create a better API strategy for your products. Connect with Anuj on Linkedin. Listen now on Apple and Spotify. Modern API strategies for enterprise SAAS It's easier to take the time and money to make something custom to your business. But this isn't always cost-effective for repeatable tasks like integrating with CRMs, HR systems, and other business-critical processes that have established solutions. From Anuj's perspective, interpersonal skills and good team stewardship are the starting points of a good API roadmap. These skills play a significant role in bringing out the best in people to execute something as tricky as API integration development. Product managers, engineering leaders, and even designers must be aware of services like Merge to drive scalable and quick-to-market API integrations to HR systems and CRMs your customers need to use your product effectively. Coding and integration into Salesforce from scratch is a problem that has already been solved and could easily be a buy solution for your product. Making the switch to Product Management In past episodes, I’ve been critical of the product management job family, which made me very reluctant to follow mentorship feedback that I should switch from design to product management. He provided some perspectives on my critique that evoked empathy regarding the role of product management. So, Anuj, if you are reading this, Thank you for your patience and gracefulness in addressing my concerns about this career move; this conversation was pivotal in finally making the switch earlier last year. Actionable Takeaways * The Power of Hospitality in Unblocking Success. The Virtue of Consideration. * Influence Without Authority: The One Thing Most PM’s Fail To Do—and Why * Balancing Professional and Personal Growth. How “Getting a Life” is a Growth Hack. The power of hospitality in unblocking success. "As PMs, in many ways, we are in the hospitality industry. There are different customers we serve." – Anuj Jhunjhunwala Action Tip: What does putting yourself in other people's shoes mean? It first requires you to understand your perspective. Understand why you feel a certain way about a direction.Only then can you put yourself in someone else's shoes and see how their perspective has led them to a different conclusion than yours. Finally, asking clarifying questions to reconcile your perspective and their perspective is what empathy is. Influence Without Authority: The One Thing Most PM’s Fail to Do. Every company needs someone who is talking to customers and understanding their pain points and translating that into something actionable." – Anuj Jhunjhunwala Action Tip: Work on building trust and relationships. Trust is the only currency product managers can effectively deploy in a position where they cannot exercise direct authority over business operations.Influence through inspiration rather than assertion, and create a collaborative environment where ideas can thrive.In your role as a product manager, you may not always have formal authority, yet you possess the potential to guide your team. Anuj reminded me that influence comes from inspiring and convincing others, skills he honed at work and home as a parent. Balancing Professional and Personal Growth "Paradoxically, having less time means I need to be more intentional and productive with the time I have." – Anuj Jhunjhunwala Action Tip: Balancing a high-demand role with a personal life and family can be daunting. It's led to many people delaying things like family and hobbies to build their careers. Paradoxically, not broadening your perspectives through things like having children, getting involved in the arts, and having a non-work hobby can make you less effective over the course of your career through Parkinson's law. More time leads to less urgency. Less urgency leads to lazy thinking. Having too much time leads to you filling it with work—effort that might not have needed to happen if you had some health constraints to prevent it from happening. Anuj's experiences as a young parent show the paradoxical benefit of having people outside of work who rely on him to be present and with them. It forces you to prioritize what matters most and establish clear boundaries. Now that you have a fixed amount of time to complete work, you will be forced to understand the true meaning of prioritization. You will do only the one thing that makes the most sense right now and de-prioritize everything else. Cheers! Caden Damiano This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

    41 min
  2. #131 How American Express Consistently Reinvented Itself for the last 175 years w/ Ryan Cailliet—VP of Research and Design at American Express

    JAN 27

    #131 How American Express Consistently Reinvented Itself for the last 175 years w/ Ryan Cailliet—VP of Research and Design at American Express

    More than ever, we expect more from our technology. With self-driving cars from Tesla, AutoPay, and AutoSaving, as well as same-day shipments and grocery delivery, we expect our technology to think for us, not the other way around. Historically, large legacy companies have failed to make this a priority, thinking that traditional operational models and hand-holding SOPs are enough to retain the business of millennials and Gen-Z. In this episode, we discuss how American Express has reinvented itself over the past two centuries. It started as a freight forwarding company and continued to innovate with traveler's checks, credit cards, and, eventually, a strong digital technology experience. Ryan joined American Express in its next iteration of doubling down on its mobile app experience, modernizing its credit card application offering to utilize all the data available to eliminate the misleading “pre-qualification—all to cater to the new rising market of Gen Z through their “Apply with Confidence” Product. Actionable Takeaways ✅ Redefining Product Management "My job is not to be right. My job is to get it right…and a lot of the product managers (are) so focused on proving their value and how good they are that they can't afford to be wrong. But the longer you go in your career, you find out that being right—out of the gate is probably the worst outcome that you can drive." - Ryan Calliet Pro Tip: Many failed products were based on an influential individual trying to sound smart at the cost of doing the legwork required to find the right solution and get the execution right. Even if Ryan is wrong, the first couple of attempts and the lessons learned in those failures usually give the insights needed to get it right the next time. ✅ Building Trust through Being Considerate in the Design Process "Acquisition is your first experience with a brand. We want to make sure we get off on the right foot, build a trusting relationship and that you come back to us as you grow and evolve over time." - Ryan Calliet Pro-Tip: Ryan's user-centered design fosters transparency and trust, essential for customer relationships amid skepticism. After months of effort, their pre-qualification experience failed because customers lacked trust in it, viewing it as not a guarantee of approval from Gen Z, new to the credit card market. The team refined their plans to ensure successful approval outcomes. This challenging process required collaboration with legal, compliance, and credit bureaus. Ultimately, it resulted in strong adoption among Gen Z. ✅ Taking Calculated Risks "Risk-taking is a part of this job. You can't know how people will react to a product until it’s out there. (Counting on evidence) “Beyond a reasonable doubt” is great because you have to make that judgment." - Ryan Calliet Pro-tip: Being data-driven 100% of the time isn't possible. Eventually, you have to make a judgment call. So, if you feel like you're at least 75 percent confident, which in the legal system is “beyond a reasonable doubt,” it's worth trying out the idea. If you're less than 75% and closer to 50%—or less than 50%, maybe it's time to take the idea back to the drawing board and continue your research until you have more confidence in another direction. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

    46 min
  3. #130 On Becoming a Product Leader: Dean Phillips, Head of Product Strategy @ ClickUp

    JAN 20

    #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. Connect with Dean on LinkedIn 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. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

    1h 13m
  4. #129 Crafting Meaningful Stories, When to Hire a Product Manager, and Leading with the Story w/ Brendan Fortune @ Customer.io

    JAN 6

    #129 Crafting Meaningful Stories, When to Hire a Product Manager, and Leading with the Story w/ Brendan Fortune @ Customer.io

    Hey Listener, Here's the latest interview with Brendan Fortune, Director of Product Management at Customer.io. Connect with Brendan on Linkedin. Listen now on Apple and Spotify. In it, he shares his journey and insights into building effective product management teams and when it’s time to hire the first product manager. Brendan's Approach to Product Management: Brendan Fortune emphasizes the necessity of creating teams with the right balance of skills and passions. He advocates for the triad model consisting of a product manager, product designer, and engineer to ensure all critical areas are covered, thereby mitigating risks and accelerating growth. Actionable Takeaways 💪 Understanding the role of product managers and how it ties into leadership, particularly in startup environments. 🔥 The pitfalls of hiring product managers prematurely and how to determine the right timing based on product-market fit. ✌️ How customer behavior can inform product flywheels and lead to sustainable growth. Risk Doesn't Need a Title Brendan discusses how risk management should not be confined to a job title but should align with the right person. Leaning into team members' strengths often results in better outcomes. "I think it's on display at every startup that I've worked at. You need to be flexible and figure out how you fit into the solution." "Leaning into someone's skills and passions can lead to amazing outcomes, as the team reforms around that individual's idea." Action Tip:Encourage flexibility within your team by aligning roles with individual strengths and passions rather than strictly defined job titles. The Flywheel Concept When Deciding Team Topologies Brendan talks about focusing on the flywheel—a sequence of customer actions and reactions—to streamline growth and optimize product management. "The idea of having a clear sense of your product flywheel can guide product organization and help plan when to hire new team members." Action Tip:Identify your product's core flywheel and ensure your team is structured to facilitate its natural progression. Pitfalls of Early Product Management Hires Hiring a product manager too soon can stall growth. Brendan suggests waiting until the financial metrics justify the hire, ideally outside VC funding. "Can you economically support a salary for a good product manager? That's a good indicator of reaching product-market fit." Action Tip:Evaluate whether your business has generated enough value to invest in a product management hire responsibly. The Importance of Story: Creating meaningful work often hinges on the story being told. Brendan highlights how product managers can foster excitement and drive within a team by crafting a compelling narrative. "People want to do meaningful work and the best product manager helps make the work feel meaningful." Action Tip: Focus on the narrative that ties your team's work to broader company goals, fostering a shared sense of purpose and clarity. Best, Caden Damiano caden@hey.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

    57 min
  5. #128 Crafting Your Brand, Mastering Work Culture, and Innovating Your Career w/ Tammy Alvarez

    12/30/2024

    #128 Crafting Your Brand, Mastering Work Culture, and Innovating Your Career w/ Tammy Alvarez

    Hey everyone, I recently had a fantastic conversation with Tammy Alvarez (LinkedIn) on the podcast, and she really got me thinking about how we approach our careers. She is also the author of “Escaping the Career Trap,” a guide to taking charge of your career and getting excited about Monday mornings again. Get it on Amazon Listen now on Apple and Spotify. Tammy has been through the corporate grind on Wall Street and now runs the Career Winners Circle; they shared game-changing insights on how we can break free from the corporate rat race and really own our career paths, even if it’s in-house. Here are some of my thoughts from this episode: Actionable Takeaways Table of Contents ✅ Failure is only a moment, not an identity ✅ Your personal brand is key to having career agency ✅ Be the CEO of your own career ✅ Build your power base, your personal board of directors Failure is only a moment, not an identity. Instead of tying everything to success or failure, she suggests viewing every career move as a chance to try new things and learn. It's all about experimenting, seeing what works, and tweaking your approach until you hit your stride. "Too often we think we're either success, fail, pass, good, bad, black, white. Whereas when you do everything in your career, in your life, in your business, taking that experimental mindset, knowing that you're going to iterate." -Tammy Alverez Takeaway: Failure is only a moment, not an identity; if we define ourselves by our bad moments, we will never achieve mastery. Mastery takes grit, resilience, and being willing to keep trying until you master your craft. Your personal brand is key to having career agency Even if you're not big into self-promotion, your reputation—or personal brand—is constantly being shaped. Tammy pointed out that if you’re not defining how people see you, someone else will. So, why not take charge? "You always have a brand, whether you want one or not. And so who would you rather influence your brand, you or other people?"Tammy Alvarez Takeaway: Think about the top three words you want people to associate with you. Make sure your actions at work reflect those qualities every day. Be the CEO of Your Own Career Tammy’s advice to treat your career like a business really hit home for me. Imagine you're the CEO of your own life: you set the goals, figure out the strategy, and pivot as needed to reach your aspirations. By taking ownership, you can align what you do with what truly excites you. "Congratulations, you just got promoted because now you are the CEO of your career and you're the CEO of you incorporated." Tammy Alverez Takeaway: Start seeing yourself as the CEO of You, Inc., and make decisions that align with your personal and professional goals. Every action you take raises or lowers your stock price and your market value. Act accordingly. Build Your Power Base Networking isn’t just about LinkedIn connections; it’s about nurturing real relationships with people who have your back. Tammy calls this your power base—the folks who will champion your ideas when you’re not in the room and help propel you forward. "Who are your sponsors and who are the people who are saying good things in the room when you're not there?" Tammy Alverez Takeaway: Identify key allies both inside and outside your organization who can support your growth, and do the same for them. In short, Tammy’s approach is all about empowerment—finding your voice, nurturing your strengths, and making bold decisions to get where you want to be. If you're itching to shake things up in your career, her insights could be just the push you need. Catch the full episode if you haven’t already, and feel free to share your thoughts on how you're taking control of your career. Happy exploring! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

    47 min
  6. Ep #127 Navigating Self-Employment and Personal Promotion with Trevor Nielsen -Founding Designer at Kleo

    12/23/2024

    Ep #127 Navigating Self-Employment and Personal Promotion with Trevor Nielsen -Founding Designer at Kleo

    Hey Listener, I'm excited to share my latest conversation with Trevor Nielsen, the design mind behind the popular Chrome plugin for LinkedIn: Kleo. Listen now on Apple and Spotify.Trevor's journey from a traditional nine-to-five job to successful self-employment is inspiring. This episode dives deep into the nuances of personal branding on LinkedIn, designing a fractional design career, and being a founding designer for Kleo, which just launched its pro plan. **Trevor’s LinkedIn** Building Kleo - Fueling Success for LinkedIn Content Creators In our discussion, Trevor shares his experiences of replacing his previous income post-layoff and nearly doubling it with strategic client work. He's also developing Kleo, a tool designed to assist regular LinkedIn users to get more active on LinkedIn. Highlights: 00:00 Starting Content Creation for Personal Branding 00:44 Transition to Freelance and Building Kleo 01:36 LinkedIn Personal Branding and Self-Employment Wins 02:42 Journey from Layoff to Self-Sustaining Business 04:16 Challenges and Epiphanies in Freelance Work 08:31 Consistency and Strategy in LinkedIn Posting 19:26 The Importance of Content Creation and Overcoming Barriers 23:47 The Myth of Creativity 24:37 Connecting Ideas for Niche Markets 25:34 Content Creation and Audience Engagement 26:26 The Power of Video Content 27:36 Building a Personal Brand 31:34 Leveraging Community and Feedback 41:29 Final Thoughts and Takeaways Listen now on Apple and Spotify. Building a Sustainable Career Path Trevor has created a blueprint for freelancers who aspire to build a sustainable and rewarding career path by diversifying income streams while working on passion projects. His insights into balancing side hustles and main gigs highlight the importance of planning and perseverance. Highlights include: 💪 Trevor’s tactical steps in creating a stable income stream post-layoff 🔥 The exponential benefits of engaging consistently and meaningfully on LinkedIn ✌️ The vision behind Kleo and its potential to transform how creators interact and grow on LinkedIn Actionable Takeaways 1. Embrace Client Work as a Core Commodity: "Client work should not be viewed as supplementary to a full-time job but can be structured to be full-time through strategic partnerships." - Trevor Nielsen Action Tip: Methodically assess part-time opportunities to ensure a stable recurring income, equating to a traditional full-time salary. Prioritize recurring partnerships for stability. 2. Utilize LinkedIn for Personal Branding: LinkedIn isn't just a job board. Developing your personal brand through consistent posting and interaction can open doors you never expected. - Trevor Nielsen Action Tip: Start posting regularly. Begin by sharing insights from your professional journey, and gradually engage with your network by commenting on posts and joining relevant conversations. The highest impact is providing relevant comments on the people’s posts you follow. Post for exposure and comment for opportunities. 4. Transform Setbacks into Opportunities: “Following the layoff, I turned to freelancing, redefining my career and turning what could have been a setback into a successful voyage of self-employment.” – Trevor Nielsen Action Tip: In career transition or upheaval, view unexpected changes as opportunities to pivot and innovate rather than setbacks. Thank you for tuning in, and I hope you glean as much insight from Trevor’s journey as I did. Best, Caden Damiano caden@hey.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

    45 min
  7. #126: The Art of Tech Adoption, Issues of Mini-CEO PM's, and the Human Element in Business w/ Jason Monberg, CEO of Presence

    10/28/2024

    #126: The Art of Tech Adoption, Issues of Mini-CEO PM's, and the Human Element in Business w/ Jason Monberg, CEO of Presence

    I recently spoke with Jason Monberg (LinkedIn Here), a seasoned tech entrepreneur and product leader. Our discussion covered a lot of ground, from navigating the tech industry to evolving roles in product management and the importance of continuous learning. Listen now on Apple and Spotify. Here’s what really stood out to me: Actionable Takeaways Table of Contents ✅ Rethinking Product Management Roles ✅ The Power of Team Chemistry ✅ Embracing Continuous Learning ✅ Simplifying Technology Adoption ✅ Rethinking Product Management Roles We dove into the actual role of a product manager, debunking the myth that they should act like CEOs of their products. Jason explained how the essence of effective product management lies in influence and collaboration rather than authoritarian control. Takeaway: Influence is Key "Ultimately you have to get a team oriented around a vision and they have to buy in on their own. You can't force them to..." -Jason Monberg Action Tip: 👉 Build a collaborative atmosphere where team members feel heard. Your job is to have a vision and sell it. 👉 If you can’t sell it, return to the drawing board; don’t promise things to the leadership team of customers that you can’t sell internally. 👉 If you can’t sell it, you may not be the right person for that role. Product Managment is a leadership position. Make sure you make sure you are pointing everyone is the right direction. ✅ The Power of Team Chemistry Our talk emphasized the importance of team chemistry and dynamics. Successful projects often hinge on how well team members communicate and work together rather than just the tech stack they use. Takeaway: Foster Team Cohesion "If the chemistry with the leadership of the product management team isn't spot on, that's always going to be a mess." -Jason Monberg Action Tip: 👉 Keep tabs on team dynamics and encourage open communication to ensure everyone is moving in the same direction. ✅ Embracing Continuous Learning Continuous learning came up as a must for staying competitive in tech roles. Jason highlighted the importance of viewing yourself like a professional athlete, always training and upskilling for those pivotal moments. Takeaway: Keep Learning "Think about yourself as an elite athlete... take pride in yourself no matter what you're doing." Jason Monberg Action Tip: 👉 Make it a habit to explore new skills and tech platforms weekly. Staying informed helps keep you agile and relevant. 👉 Read “Chop Wood, Carry Water” to learn more about this philosophy. ✅ Simplifying Technology Adoption We discussed the balance between tech adoption and business needs. Sometimes, the best tech decisions involve simplifying rather than complicating your processes. Takeaway: Simplify for Success "I'm excited to see a simplification of technology... You don't need all the technology all the time." -Jason Monberg Action Tip: 👉 Review your tech setup regularly to streamline operations and align them more closely with business goals. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

    52 min
4
out of 5
7 Ratings

About

A podcast on overcoming the challenges of collaboration within a product team. If you want to develop strong soft skills, product sense, and design taste, this show is for you! www.wayofproduct.com

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