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In this episode, Estee and Shai delve into the unsettling rise of antisemitism on college campuses since the fall of last year, triggered by chants and protests calling for violence against Jews. They discuss a significant Congressional hearing involving leaders from top universities and their controversial stance on whether such chants violate school policies. The conversation includes an exploration of the ideological environment within universities, comparing it to the educational values in Orthodox yeshivas. The guest shares insights from his experience at Columbia University and reflects on the broader implications for Western values, student behavior, and institutional integrity. The discussion also tackles the role of administration, faculty, and the potential long-term consequences for American society, emphasizing the need for awareness and action against these growing issues.
00:00 Introduction and Topic Overview
00:31 Protests and University Responses
02:35 Comparing Educational Experiences
04:49 Critique of University Attitudes
08:55 Historical and Cultural Context
13:08 Normalization of Anti-Semitism
24:18 Future Implications and Solutions
31:22 Final Thoughts and Takeaways
Shai’s article: https://www.tabletmag.com/sections/arts-letters/articles/tale-of-two-academies
Bio: Shai Goldman is a software engineer based in New York City. He spent three years studying Talmud at Yeshivat Har Etzion in Alon Shvut before going on to receive his B.A. from Columbia University in 2024. His article, "Tale of Two Academies," was recently published in Tablet Magazine and explores the difference between the yeshiva and university models of education in order to explain why today's top American universities are subsumed by backwards ideologies and pedagogical missteps.
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Transforming Customer Experience: Insights from Ben Siegel
In this episode, we explore the critical role of customer experience (CX) in business success with Ben Siegel. The discussion highlights the importance of integrating CX with product management, engineering, and marketing to create a cohesive customer-first approach. Ben emphasizes the significance of empathy, proactive service, and strategic investment in CX to not only retain customers but also to create brand ambassadors. Through real-life examples and actionable insights, Ben demonstrates how exceptional customer service can provide cost savings and enhance loyalty, even when product limitations exist. This conversation is essential for understanding the multi-faceted impact of CX on long-term business success.
00:00 Welcome and Introduction
00:11 The Role of Customer Service in Product Management
02:09 Examples of Exceptional Customer Service
05:57 Creating a Customer-Centric Environment
08:46 Investing in Customer Experience
12:14 Balancing Customer Service and Profitability
21:12 Empowering Customer Service Teams
25:26 The Impact of Good Customer Service on Retention
29:22 Handling Customer Cancellations with Care
30:00 The Frustrations of IVR Systems
31:36 Amazon's Approach to Customer Service
34:13 The Role of AI in Customer Service
36:12 Cost Savings Through Good Customer Service
39:26 Building a Feedback Loop Between CX and Product Teams
42:36 Examples of Exceptional Customer Experience
54:30 The Importance of Empathy in Customer Service
58:10 Final Thoughts on Customer Experience
Bio:
Ben Segal is a dedicated advocate for customer experience (CX), renowned for his ability to turn challenges into opportunities. With over a decade of experience in the dynamic sectors of sports, entertainment, and technology startups, he has established himself as a key player in the CX landscape.
His career includes significant roles at high-growth companies such as Freshly and Pair Eyewear, where he advanced from managing a small in-house contact center to developing a comprehensive global operation. During his tenure at these organizations, he was instrumental in scaling customer experience operations, contributing to substantial improvements in customer satisfaction.
At Thesis, where he served as Vice President of Customer Experience, Ben played a crucial role in enhancing CX strategies that led to impressive growth metrics and elevated customer satisfaction levels. His leadership was marked by innovative project implementations and fostering a culture centered on customer-first principles.
Currently, as the Chief Experience Officer (CXO) at Create CX, Ben spearheads initiatives aimed at transforming customer experiences across a diverse portfolio of brands. His responsibilities include overseeing customer interactions, driving service delivery innovation, and integrating AI and automation tools to improve operational efficiency. He is committed to nurturing a customer-centric culture and leveraging data-driven insights to refine the customer journey continually.
Outside of his professional endeavors, Ben enjoys traveling across the U.S., attending Goose concerts, and cherishing time with his children, Dylan and Emma, while also exploring fine culinary experiences.
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Mastering the Art of Management: Insights, Challenges, and Strategies
In this comprehensive episode, we delve deep into the multifaceted world of management. Drawing from personal experiences and professional journeys, Rachel, David, and other speakers examine the defining traits of good and bad managers, highlighting the impact on mental health and job satisfaction. They stress the importance of trust, clarity, and genuine care in manager-employee relationships and explore how effective one-on-one meetings can boost team dynamics and psychological safety. The conversation also touches on the role of managers in aligning team goals, acting as multipliers, and navigating challenges. Topics such as the pitfalls of promoting untrained high-performing ICs to managerial positions and the effects of organizational changes like removing middle managers are also discussed. This episode offers valuable lessons for both managers and employees aiming to foster a collaborative, productive work environment.
00:00 Welcome and Introductions
00:34 Discussing Management Styles
01:55 David's Management Experience
02:43 Good vs. Bad Managers
03:13 Personal Stories of Bad Management
04:29 Characteristics of a Good Manager
10:36 The Importance of Collaboration
14:44 Values and Autonomy in Management
17:11 Reflecting on Management Challenges
17:46 Building Trust and Empowerment
22:09 Effective One-on-One Meetings
26:46 Navigating Organizational Dynamics
32:50 The Role and Value of a Manager
39:42 Challenges in Large Organizations
51:29 The Importance of Good Managers
56:47 Concluding Thoughts and Reflections
David Lifson has led high performing teams at startups, public, and private equity backed companies, delivering high impact outcomes through clear vision, validated product strategy, and collaborative culture. He’s gone 0 -> 1 multiple times, as well as led teams supporting $350M in revenue. His experience leading teams spans 15 years, including four as CEO/GM and eight as Head of Product & Engineering. Dave has a bachelors and masters degree in Computer Science from Cornell University, and is based in Austin, TX.
Rachel started her path to product management as an Engineer in the semiconductors industry. Prior to that, she was a Digital Marketing and Product Specialist at Fiverr, where she was one of the first members of the team to focus on marketing and product research. As a strategy consultant at BCG, she focused on private equity and operations. Rachel joined YouNow as a Product Manager where she focused on broadcaster experience and internal tools, and joined DataDog to lead monitors and alerting product. Rachel holds an MBA from Columbia and a BSC in Electrical Engineering from Tel Aviv University.
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Unlocking the Future of Fitness with Josh from FitBod
Join us in this exciting episode as we sit down with Josh, a seasoned product manager with an impressive background in consumer tech, to explore the innovative world of FitBod. Discover how Josh's passion for weightlifting shaped his career and led him to FitBod, an app revolutionizing the way we approach strength training. Josh shares his insights on habit formation in fitness, the key features of FitBod, the role of AI in personalizing workouts, and the future of fitness apps. Perfect for tech enthusiasts and fitness buffs alike, this episode offers a deep dive into the intersection of technology and fitness.
00:00 Introduction and Josh’s Welcome
00:21 Discovering Weightlifting and Fitness Apps
01:51 Josh's Career Journey to FITBOD
03:57 FITBOD's Unique Features and Habit Formation
07:25 The Science Behind FITBOD's Success
12:26 User Experience and Feature Requests
19:20 Future of Fitness and Personal Training
22:07 Lightning Round and Closing Thoughts
Josh’s Bio: Josh is a product leader who has spent almost 10 years launching and growing consumer products. He started his career at Microsoft and then moved to Zillow where he led their personalization efforts from a nascent stage to a top driver of revenue and traffic growth. Next, he went to Lyft where he helped launch and scale 3 new consumer business lines from 0->1. He’s currently Head of Core Product at Fitbod where he’s responsible for the entire core experience. Josh is also a long-time fitness enthusiast and has competed in bodybuilding.
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From Fitness Class to Weightlifting: Ariana's Journey and Insights on Health and Tech
In this episode, Ariana shares her transformation from a sedentary college student diagnosed with Lyme disease to a committed weightlifting enthusiast and product manager. She discusses the myths around weightlifting, especially for women, and emphasizes the importance of incorporating strength training for long-term bone health. Ariana also provides insights into her career path, the pros and cons of fitness technology, and her experience as a personal trainer. The episode touches on broader health topics, the impact of nutrition, and the role of government and corporations in the food industry. For those new to weightlifting, Ariana offers practical advice on how to start safely and effectively. Tune in for a comprehensive discussion on fitness, health technology, and balanced living.
00:00 Introduction and Welcome
00:08 Ariana's Journey into Weightlifting
02:15 The Benefits of Weightlifting
03:00 Misconceptions and Getting Started with Weightlifting
10:46 Fitness Technology and Wearables
16:40 Nutrition and Processed Foods
27:50 Practical Advice and Final Thoughts
Arianna's bio: Arianna has over a decade of experience in the health and fitness industry training Division 1 athletes in sports like soccer, gymnastics, and field hockey at Rutgers University and American University. She has a Masters in Exercise Science from the University College Dublin in Ireland and has helped hundreds of clients ranging from postpartum moms to kids learning healthier habits. She now applies her health and fitness expertise in the startup world as a Product Manager for a health tech company.
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Navigating the Shifting Job Market and AI's Impact with Shane & Estee
In this episode, Estee welcomes Shane, a director of engineering and AI enthusiast, to discuss the volatile job market and the profound impact of AI on the tech industry. They delve into the hiring booms and busts from 2022 to 2024, the intricacies of AI integration in companies, and the emergence of generative AI tools like ChatGPT and GitHub Copilot. They also explore the future of job roles, the significance of proprietary data, fundraising trends, and speculate on new AI-driven innovations. Tune in for a deep dive into how AI is reshaping the workforce and what it means for the future of work.
00:00 Introduction and Shane Welcome
00:51 The State of the Job Market
06:43 Impact of AI on Hiring Trends
14:58 AI Tools in the Workplace
20:21 Elon Musk and the AI Arms Race
28:49 AI Safety and Future Implications
29:49 Advice for Navigating the AI Revolution
36:30 Conclusion and Future Conversations
Shane Ursani is a technical engineering leader with over 20 years of experience in developing and delivering successful enterprise applications. Currently serving as the Director of Engineering at Vizient, a leading healthcare performance improvement company, Shane has a proven track record of driving innovation and leading high-performing teams across various industries. As an AI enthusiast, he actively follows the latest trends in artificial intelligence, exploring open-source large language models, and building AI-powered prototypes to solve complex engineering challenges and create innovative user experiences. Shane holds an MBA from the University of Southern California and a BS in Computer Science from the University of Alaska Anchorage, combining technical acumen with strategic business insight. On a fun note, Shane was my engineering partner a couple of companies ago - and really showed me what kind of magic can be created when engineering and product work hand in hand.
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Unlocking the Power of Fractional Product Leadership with Aakash Gupta
In this episode of the Estee Show, we explore the evolving world of fractional product leadership with expert Aakash Gupta. This deep dive follows our previous discussion on the topic with Ben Erez and expands on the insights found in an extensive 16,000-word article co-authored by Aakash and Jason Knight, host of the One Knight in Product podcast. Aakash discusses the intricacies of the fractional PM role, from pricing strategies and engagement setup to avoiding common pitfalls and ensuring successful outcomes. He shares lessons from interviewing 20 fractional PMs, offering real-world examples and guidelines. Tune in for an enlightening conversation whether you're in the product management field, considering a fractional career, or simply intrigued by the concept. Additional highlights include tips on balancing life and work, leveraging your network for success, and insights on the latest trends in the industry. Don't miss this chance to learn from one of the most respected figures in product management.
00:00 Introduction to Fractional Product Leadership
00:18 Deep Dive into Aakash Gupta's Article
01:37 Aakash Gupta's Background and Expertise
02:21 Target Audience for Fractional Leadership
02:44 Insights from Aakash and Ben's Experiences
03:37 Welcome Aakash Gupta to the Show
04:01 Understanding Fractional Leadership
04:59 History and Evolution of Fractional Roles
07:25 Challenges and Misconceptions in Fractional Roles
11:52 When to Consider Fractional Roles
15:55 Balancing Full-Time and Fractional Roles
18:46 The Importance of Referrals and Relationships
22:49 Setting Realistic Goals for Fractional Roles
25:39 Fractional Product Agencies and ROI
29:16 Responsibility in Providing Advice
36:33 Navigating the Perception of Product Managers on X
37:08 Controversial Post and Its Aftermath
38:55 Private Likes Feature on X
40:38 Networking and Building Connections on X
41:52 Understanding Fractional Leadership
42:53 Pricing and Strategies for Fractional Roles
43:47 Challenges and Opportunities in Fractional Leadership
50:09 Diversifying Revenue Streams for Fractional Leaders
54:35 Lightning Round: Personal Insights and Reflections
01:03:51 Final Thoughts and Career Advice
Bio: Aakash Gupta is a former VP of product who spent 15 years in product at companies like Apollo.io, Epic Games, and thredUP. Nowadays, he runs the Product Growth newsletter, which is a newsletter on career topics for PM and growth people that goes out to 125,000 plus folks.
Useful Links:
Aakash’s newsletter: https://www.news.aakashg.com/ Linkedin: https://www.linkedin.com/in/aagupta/ X: https://x.com/aakashg0 The article that inspired this episode: https://www.news.aakashg.com/p/fractional-product-leadership
Episode 35 with Ben Erez: https://theesteeshow.com/episodes/episode-35-the-rise-of-fractional-work-in-product-management-with-ben-erez -
Mastering the Art of Reference Checks: Deep Dives and Honest Insights with Alison
In this episode, Alison delves into the intricacies of conducting reference checks, sharing her personal experiences and methodology for obtaining the most valuable insights. The conversation explores the importance of in-depth questions, how to detect sincerity versus bias, and the role of reference checks in the hiring process. Alison also shares practical tips on navigating backchanneling, dealing with potential red flags, and using silence effectively in conversations. Additionally, she touches on her side business focused on health and wellness for high achievers. This episode is packed with actionable advice for hiring managers looking to enhance their interview process and set new hires up for success.
00:00 Welcome and Introduction
00:05 The Art of Reference Calls
00:24 Deep Dive into Reference Checks
01:17 Evaluating Reference Feedback
02:04 Setting Up for Success
03:50 Identifying Red Flags
04:27 Backchanneling Insights
04:57 Cultural Context and References
06:40 Effective Reference Questions
19:23 Handling Biased References
24:10 Importance of Reference Checks
27:51 Backchanneling Strategies
30:40 Understanding Weaknesses in Interviews
31:27 Evaluating Growth Mindset and Self-Awareness
32:13 The Importance of Culture Fit
33:28 Real-Life Examples of Improvement Opportunities
38:31 The Power of Silence in Conversations
42:19 The Role of Reference Checks
54:23 Red Flags in Hiring Decisions
59:04 Balancing High Achievement with Health
01:01:52 Final Thoughts and Key Takeaways
Bio: Allison is a founder, fractional CPO, and product advisor, who's worked at LinkedIn, Oscar Health, and various early stage startups.
She's built and led high performing product teams, and coached other product leaders uplevel in their career and navigate the uncertainties in the job.
Allison is passionate about women's health and has also developed a support program for high achieving women struggling with their relationship with food, exercise, and irregular periods.
Allison's company: https://www.theallymethod.com/
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Transforming Tech Careers: The Rise of Fractional Work with Ben Erez
In this episode, we explore the revolutionary concept of 'fractional work' and its impact on career trajectories in the tech industry. Our guest, Ben Erez, shares his experience transitioning from a full-time product manager to embracing fractional work. He discusses his roles with Continuum, benefits of fractional engagements, types of fractional roles such as advisory and interim positions, and strategies for building a successful career in this field. The conversation also highlights balancing personal and professional life, especially as a parent, the value of maintaining a diversified portfolio, and the importance of pursuing work that energizes and excites you.
00:00 Introduction to Fractional Work
00:20 Personal Background and Initial Exposure to Fractional Work
01:02 Understanding Fractional Work
01:43 Real-World Experiences with Fractional Work
05:24 Financial Viability of Fractional Work
07:24 Advisory Roles in Fractional Work
16:25 Interim Roles and Their Challenges
28:28 Part-Time Product Management
30:58 Balancing Fractional Engagements
31:23 Challenges of Context Switching
33:01 Choosing the Right Tribe
35:00 The Owner's Mindset
36:54 PM and Interview Coaching
46:22 Navigating Parenthood and Work
51:16 Building a Fractional Career
58:31 Final Thoughts on Career Fulfillment
Bio:
Ben is a fractional product leader, interview coach, podcast host and newsletter author. He has been a 1st PM at 3 startups, and also worked for large companies including Meta. Ben is frank and insightful, and full of practical tips for anyone interested in fractional leadership.
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Navigating Product Management Through the Lens of Political Strategy In this bonus episode of the Estee show, David Lifson, a seasoned Chief Product Officer, joins the conversation to extract lessons from the recent presidential debate from June 27th, 2024. The discussion focuses on how product managers can learn from high-stakes political scenarios, touching on themes such as the importance of hypothesis-based thinking, planning for contingencies, managing expectations, and the necessity of effective communication. They also discuss leadership qualities, the need for adaptive strategy, and the value of surrounding oneself with diverse viewpoints. Lifson provides actionable insights for product managers on aligning strategy with execution and the critical role of messaging in achieving organizational goals. 00:00 Introduction and Guest Introduction 00:28 Analyzing the Presidential Debate 01:17 Hypothesis-Based Thinking in Politics 02:06 Lessons from the Debate: Execution vs. Strategy 05:50 The Importance of Setting Expectations 08:48 Leadership and Adaptability 10:55 Surrounding Yourself with the Right People 22:04 Effective Communication and Messaging 28:18 Final Thoughts and Takeaways
Bio: David Lifson has led high performing teams at startups, public, and private equity backed companies, delivering high impact outcomes through clear vision, validated product strategy, and collaborative culture. He’s gone 0 -> 1 multiple times, as well as led teams supporting $350M in revenue. His experience leading teams spans 15 years, including four as CEO/GM and eight as Head of Product & Engineering. Dave has a bachelors and masters degree in Computer Science from Cornell University, and is based in Austin, TX.
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Gaurav Discusses the Power of Napkin Math for Product Management
In this episode, Gaurav Hardikar, VP of Product at HomeLight, talks about his journey through the real estate and startup scenes at companies like Zillow, Trulia, and now Homelight. He dives into the concept of 'Napkin Math' for Product Managers, advocating for quick and efficient decision-making over extensive financial modeling. Gaurav explains how this approach informs product prioritization and testing hypotheses swiftly. He also discusses his course on Maven, which aims to equip PMs with actionable growth strategies. Throughout the conversation, Gaurav emphasizes the importance of continuous learning and adapting new approaches within various business processes.
00:00 Introduction and Background
01:53 The Concept of Envelope Math
03:46 Practical Applications of Napkin Math
05:46 Failing Forward and Iterative Testing
06:25 Prioritizing Features and Roadmapping
12:17 Training and Mentoring Product Managers
15:19 Integrating AI in Business Processes
19:33 Collaboration with Engineering Teams
29:10 Course and Educational Initiatives
32:34 Lightning Round and Final Thoughts
Bio:
Gaurav is a Product Executive with over 10 years of experience building digital products. He started at Trulia and Zillow Group with a reach of 50MM+ monthly users, grew an established mobile commerce app (Shopkick), and helped take Brilliant Smart Home 0 to 1 across SaaS, embedded hardware, and mobile app platforms. He's currently VP of Product, Consumer at HomeLight where he owns Product, Ops, and Growth.
Gaurav’s course - https://maven.com/insider-growth/pm-impactLink to Gaurav’s original post that inspired this conversation: https://www.linkedin.com/posts/ghardikar_as-a-product-manager-using-data-in-every-activity-7206363910474506242-BFxr
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Creating Quality Products: A Candid Conversation with Toma on Design and Product Management
In this episode, Estee converses with Toma, the first designer guest on the show, about the integral relationship between design and product management. They reflect on how they connected through a humorously truthful LinkedIn post that Toma put up about the dilution of design quality during product development.
The discussion delves into the challenges of aligning different stakeholders' priorities, the importance of shared values in achieving extraordinary outcomes, and the pitfalls of compromising on quality for fast metrics. Toma talks about the significance of maintaining high-quality standards and the impact of values-driven decision-making in organizations like Apple and Microsoft.
The conversation also touches on the detrimental effects of MVP culture and how true product management focuses on creating excellent products rather than just checking boxes. The episode concludes with a lightning round exploring Toma's views on design podcasts, his admiration for Steve Jobs, and key takeaways for product managers to prioritize quality and fight for the product.
00:00 Welcome and Introduction
00:24 The Designer's LinkedIn Post
02:44 The Importance of Aligned Values
04:54 Design in Tech Companies
08:34 Quality vs. Metrics
10:20 The MVP Debate
19:22 Top-Down Quality Culture
22:22 The Power of Value-Driven Decisions
23:13 The Problem with Compromising Quality
24:10 Top-Down vs. Bottom-Up Culture
25:18 The Importance of Using Your Own Products
26:40 The Role of Product Managers vs. Project Managers
31:06 Creating a Strong Product-Design Partnership
33:59 Evaluating Quality in Popular Apps
37:45 Lightning Round: Insights and Inspirations
About Toma: Toma’s journey to becoming a designer was unexpected. Originally from Australia, he studied law and business before life took a turn in 2006, leading him to Italy. There, he moved his first pixel and wrote his first line of code. Since then, Toma has brought his design expertise to tech companies across multiple continents, focusing on product and organizational strategy and design. Now based in Amsterdam, he is a Design Director at the European hospitality unicorn MEWS, where his teams spearhead the creation of outstanding guest experiences.
Link to the image that inspired this episode: https://www.linkedin.com/posts/activity-7188806639368462337-QDrv?utm_source=share&utm_medium=member_desktop
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Leveraging AI in Product Management with Rachel: Insights Beyond the Basics
Rachel, an experienced AI product manager, shares her journey from electrical engineering to working at esteemed companies like Microsoft, Facebook, and Instagram. She discusses her career transition, the rise of AI, and the essential paper 'Attention Is All You Need.' Rachel dives deep into practical applications of AI for product managers, emphasizing productivity, personalization, and real-world examples like Spotify and e-commerce. She also explores the future of product management and engineering roles amidst AI advancements, providing valuable insights and advice for professionals in the field.
Referenced in the episode:
1. Article about Shein: https://www.linkedin.com/pulse/how-data-science-artificial-intelligence-helped-shein-keep/2. Air Canada forced to honor refund policy invented by AI chatbot: https://indianexpress.com/article/technology/tech-news-technology/air-canada-ai-chatbot-9170822/
00:00 Introduction and Welcome
00:04 Rachel's Career Journey
01:21 Impact of AI in Product Management
01:49 Deep Dive into LLMs and AI Technologies
06:26 AI for Productivity and Personal Use
18:21 AI in Professional Settings
31:33 Future of Product Management and AI
35:48 Personal Insights and Hobbies
38:57 Final Thoughts and Farewell
Rachel's Bio:
Rachel started her path to product management as an Engineer in the semiconductors industry. Prior to that, she was a Digital Marketing and Product Specialist at Fiverr, where she was one of the first members of the team to focus on marketing and product research. As a strategy consultant at BCG, she focused on private equity and operations. Rachel joined YouNow as a Product Manager where she focused on broadcaster experience and internal tools, and joined DataDog to lead monitors and alerting product. Rachel holds an MBA from Columbia and a BSC in Electrical Engineering from Tel Aviv University.
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Decoding Corporate Jargon and Navigating Workplace Dynamics
In this episode, David Lifson returns to discuss the complexities and humor found in corporate jargon. The conversation covers the differences between real-world language and corporate speak, the creation of in-groups and out-groups through jargon, and the challenges faced by non-native English speakers. The hosts analyze popular corporate phrases and their hidden meanings, sharing their own experiences and observations.
They also delve into the toxicity of certain workplace cultures, the impact of poor management, and offer insights on how to identify healthy work environments. This engaging discussion provides both comedic relief and valuable advice for navigating corporate communication and dynamics.
00:00 Introduction and Guest Welcome
00:12 Corporate Speak vs. Real World Language
01:23 Types of Corporate Jargon
02:09 Cultural Implications of Jargon
02:30 Literal Interpretations and Misunderstandings
03:59 Common Corporate Phrases and Their Meanings
04:28 Disagree and Commit
07:04 Digital Transformation and AI
15:40 Executives and Accountability
17:41 Breaking the Cycle of Toxic Work Environments
18:14 Red Flags in Job Offers
18:55 Defining Yourself Beyond Your Resume
19:41 Learning from Career Setbacks
21:29 The Reality of Startup Culture
22:42 Recognizing Toxic Job Descriptions
25:36 Effective Feedback in the Workplace
30:15 Understanding Communication Styles
34:54 The Problem with Bad Managers
35:17 Conclusion and Farewell
Bio: David Lifson has led high performing teams at startups, public, and private equity backed companies, delivering high impact outcomes through clear vision, validated product strategy, and collaborative culture. He’s gone 0 -> 1 multiple times, as well as led teams supporting $350M in revenue. His experience leading teams spans 15 years, including four as CEO/GM and eight as Head of Product & Engineering. Dave has a bachelors and masters degree in Computer Science from Cornell University, and is based in Austin, TX. See former episode with David here: https://theesteeshow.com/episodes/episode-24#spotify -
The episode covers Ali Sipher's experience taking a 7-month career break. She discusses the importance of setting clear goals for the break, such as self-discovery and exploring new directions. Financial planning for 1.5-2x the intended break duration is recommended to avoid undue pressure. The initial months involved decompressing from the fast-paced work mindset and pursuing personal interests like getting certified as a phlebotomist. A major realization was how much time actually exists in a day without the constant urgency of work. The break allowed Ali to rediscover her core identity beyond her job and gain clarity on her values and interests. She advises taking at least 6 months for a true mental reset, and beginning the re-entry process 1-2 months before the intended return date. Overall, an intentional career break can provide invaluable self-awareness and perspective.
Planning for a Career Break Set clear goals for the break - e.g. self-discovery, exploring new interests Financially plan for 1.5-2x the intended duration of the break Determine responsibilities to hand off or cover during the break Embracing the Break Allow time to truly disconnect and decompress initially Pursue personal interests, projects, certifications Expect a mindset shift - days feel longer, less urgency Rediscover your identity beyond work Lessons from the Break You have more time than you think for what's truly important Savor the mental break from constant urgency Gain self-awareness about your core values and interests Decide if/when you want to re-enter the workforce Re-Entering the Workforce Start considering re-entry 1-2 months before intended return Don't wait until burnout to take a career break Plan for a bit more break time than you think you'll need Expect to miss using your brain for problem-solving eventually Key Takeaways Career breaks allow valuable self-discovery and mindset shifts Proper planning (financial, responsibilities, duration) is crucial Be open to the break taking you in an unanticipated direction Decide when you're ready to re-engage based on your goalsAli Sipher: Ali Sipher is an accomplished product leader who loves complicated and unglamorous problem spaces (think: supply chain, healthcare, accounting). She’s delivered innovative products, unlocked new revenue streams, and optimized operations in leadership roles at Parsley Health, Walmart, and multiple startups. After taking a six-month career break, Ali started working as a product management consultant. This helped her realize how much she loves owning the day-to-day product work.
Ali is actively looking for her next full-time role solving complicated and unglamorous problems. Interested in connecting? Reach out: [email protected] -
The Boiling Crisis at Boeing: Unpacking Five Years of Turbulence In this episode, Kathryn and Estee dive into the ongoing crises and challenges confronting Boeing and the airline aviation industry. From crashes, the tragic suicide of a whistleblower to damning congressional hearings, Kathryn, an expert journalist with extensive industry experience, provides a detailed timeline and analysis of the pivotal events since January 2024. The conversation explores multiple Boeing aircraft incidents, including doors flying off mid-flight and wheels falling off upon takeoff, and scrutinizes the cultural and management issues that have plagued Boeing for years, emphasizing the shift from engineering excellence to profit obsession. Kathryn highlights the importance of public pressure on Boeing to enact meaningful changes, advocates for a complete overhaul of Boeing’s management, and urges passengers to vocalize their concerns to legislators and consumer organization.
Bio: Kathryn B. Creedy is a veteran aviation journalist and author who has covered every facet of commercial and business aviation. Kathryn has written for Forbes Online and is the author of Time Flies – The History of SkyWest Airlines. Her byline has appeared in Smithsonian’s Air & Space Magazine and top aviation publications such as Air Transport World, Aviation Week and Space Technology, Flightglobal, Centre for Asia Pacific Aviation and Airline Business. In addition, she has written for BBC Capital, CNN Travel, The Los Angeles Times, AFAR.com.
Series of incidents: Door flies off Alaska Airlines 737 Max (January 2024) Wheel falls off United Airlines aircraft (March 2024) Whistleblower John Barnett dies by suicide (March 2024) Boeing CEO Dave Calhoun announces retirement (March 2024) Concerns: Potential for more technical issues with Boeing aircraft Shift in Boeing's culture from safety-first to profit-driven Lack of transparency from Boeing regarding safety concerns Effectiveness of FAA oversight Historical Context: 1997 Merger of Boeing and McDonnell Douglas - potential cultural clash 2003 FAA recommendation on 787 Dreamliner battery casing ignored by Boeing (later implemented after incidents) 2018 & 2019 Lion Air & Ethiopian Airlines crashes involving 737 Max - questionable design choices and lack of pilot training on new system (MCAS) Blaming the victims (pilots) for the 737 Max crashes Current Investigations: Department of Justice (DOJ) considering criminal charges against Boeing for the 737 Max crashes FAA investigating Boeing's manufacturing practices Congressional hearings examining Boeing's safety culture Uncertain Future: Impact of investigations on Boeing's leadership and practices Need for stronger FAA oversight and passenger confidence
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In this episode of The Estee Show, Itamar Gilad, a former product manager at Google, Microsoft, and IBM, discusses his experiences and insights from his career. Focusing on his new book, 'Evidence Guided, Creating High-Impact Products in the Face of Uncertainty' he introduces the concept of 'evidence-guided' product management, contrasting it with traditional methods that rely heavily on intuition and fixed roadmaps. He emphasizes the importance of gathering and following evidence to make informed decisions, and addresses how his frameworks, including the GIST model and confidence meter, provide practical applications for prioritizing and validating ideas. Through anecdotes and historical examples from industry giants like Apple and Amazon, Gilad elaborates on the role of humility, testing, and iterative development in successful product management. He also shares his thoughts on organizational resistance to change and strategies to foster a more evidence-based, innovative culture. A must-listen for anyone interested in modern product management practices.
Itamar's Bio: Itamar is a coach, author and speaker specializing in evidence-guided product management and product strategy. For over two decades he held senior product management and engineering roles at Google, Microsoft and a number of startups. At Google Itamar worked at YouTube and led parts of Gmail.
Itamar is the author of the book Evidence-Guided: Creating High-Impact Products in the Face of Uncertainty. He also publishes a popular product management newsletter and is the creator of a number of product management methodologies including GIST Framework and The confidence meter.
Itamar is based in Barcelona, Spain. You can find more information on his website: https://itamargilad.com/
00:00 - Introduction and background on Itamar Gilad, author of "Evidence Guided Product Management"
02:20 - Definition of "fake door test" for measuring user interest02:50 - Definition of ICE/RICE prioritization frameworks
03:15 - Definition of OKRs (Objectives and Key Results)
04:00 - Gilad's journey from being a product manager to writing his book
07:40 - Discussing the GIST framework (Goals, Ideas, Steps, Tasks)
10:20 - The importance of humility and not having all the answers as a product manager
12:15 - Examples of successful product launches at Google using evidence-guided approach
15:40 - Proper use of ICE/RICE frameworks and avoiding common pitfalls
19:20 - The role of experimentation and testing ideas before fully building them
22:30 - Leadership's role in embracing ambiguity and disciplined product development
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This podcast episode features an in-depth interview with Alex, a former product manager at Google, now running a business that helps experienced product managers advance their careers. Alex discusses the benefits and challenges of working in product management within the tech industry, emphasizing the value of having top tech company names on one's resume for career opportunities and compensation. He also touches on the cognitive dissonance experienced by product managers, the interviewing process, strategies for job seekers, and the role's requirements at large tech companies. Furthermore, Alex shares personal stories, including starting his YouTube channel and the impact of his advice on others. The conversation also covers topics like strategic ambiguity in tech companies, the importance of organizational and communication skills, and insights into succeeding in product management roles.
Bio: Alex Rechevskiy was a Group PM at Google and has built and run products and product teams of all sizes. He has also coached and mentored hundreds of PMs at all stages of their careers and helped many clients land product roles at top tech companies. Alex writes on LinkedIn, makes videos on YouTube and runs a group coaching program called the Product Career Accelerator for serious tech professionals who want to grow their career and compensation.
Links:
Product Career Accelerator: group coaching program for getting into your next product role and growing your product skills & career (https://www.alexrechevskiy.com/pca) LinkedIn for daily product management tips (https://www.linkedin.com/in/alexrechevskiy/) YouTube for practical and instructional videos (https://www.youtube.com/@AlexRechevskiy)
00:00 Welcome to the SD Show: A Deep Dive into Product Management 00:27 The Unmatched Benefits of Working in Top Tech 04:39 Alex's Journey: From Google to Guiding Product Managers 04:58 The Realities of Breaking into Product Management Today 05:54 The Genesis of a YouTube Channel for Product Managers 11:02 The Interview Process vs. The Reality of the Job 13:50 Navigating the Complexities of Top Tech Companies 15:47 The Strategic Ambiguity of Monopolistic Tech Giants 19:19 The Culture of Respect at Google 20:09 The Impact of Google's Innovations on Humanity 20:46 The Challenge of Innovation and Risk at Google 23:01 Navigating the Job Market in Big Tech 24:33 Mastering the Job Application Process 31:12 The Interview Process: Strategies for Success 35:58 Preparing for a Product Management Role 38:14 Lightning Round: Personal Insights and Final Thoughts -
A Journey from Radio to Product Management and the Essence of Product Thinking The script features an engaging conversation between the host and Brody Clemmer, a former radio host turned product manager, who shares his unique career path from working in radio to eventually finding a passion for product management and mental health. Brody discusses the accidental nature of many peoples' entry into product management, his own experience transitioning through various roles, and the importance of 'product thinking' across all organizational functions. He emphasizes that product thinking focuses on understanding and solving user problems, distinguishing it from product management which requires execution. Further, Brody shares how he implements product thinking in his current role at Koa Health through initiatives like 'product class,' aiming to foster a culture of problem-solving and cross-functional collaboration. The conversation also touches on mentorship versus coaching, the dynamics of therapy and mental health, and concludes with Brody sharing insights on personal fulfillment and career choices. 00:00 Welcome to the Show: Brody Clemmer's Unique Journey 01:38 From Radio Host to Product Management: A Career Evolution 02:34 Introducing Product Thinking: Beyond Traditional Management 03:37 Product Thinking vs. Product Management: A Deep Dive 09:30 Implementing Product Thinking in Organizations 15:41 The Impact of Product Thinking on Company Culture 19:20 Mentorship vs. Coaching: Brody's Approach to Personal Development 22:53 Therapy, Mental Health, and Product Thinking 29:26 Lightning Round: Personal Insights and Reflections Tools discussed in episode: Vistaly for consolidating and mapping user feedback
https://www.vistaly.com/ Bio:Brody Clemmer lives in Philadelphia with his fiancé and their son - and is a generalist at heart. For work, he is currently the Lead Product Manager at Koa Health where he was the first US based Product hire, and is focused on the scalability and delivery of Koa’s products, ranging from mental health education to global clinical networks that support employers, payors, and multinational organizations in delivering mental health care for their members. Brody started his career out of high school, after making the decision to not go to university, first working in Radio, then TV Production, then landing at Apple for five years before starting his own business with a guy he met on Twitter. After selling the business at a personal loss, he found himself as the first product hire for a few “unsexy” companies in unknown industries like Executive Search, Leadership Consulting, corporate Sales Training, and finally making his way into Healthtech startups.
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Product Management in Founder-Led Startups with David Lifson: From Startup to Scale In this episode, David Lifson shares his extensive experience in product management across different stages of company growth, including startups and major companies like Amazon and Etsy. Lifson discusses the challenges of being the first head of product for a first-time founder, emphasizing the importance of knowing what you're getting into and how it can be both a career-defining opportunity and a rollercoaster ride. He gives insights on founders' common traits, the pressures of early-stage startups, and the shift needed once a company reaches product-market fit. Lifson also touches on his journey from Amazon to Etsy, and founding his own company, providing valuable lessons on leadership, decision-making, product strategy, and the dynamics of working with founders. The conversation delves into practical advice for those considering head of product roles at startups, including setting realistic expectations, choosing battles, and understanding the real job you're being hired for. 00:00 Welcome to the SD Show: A Candid Chat with David Lifson 00:07 Navigating the Product Management Journey: Insights from Amazon to Etsy 01:26 The Harsh Realities of Being the First Head of Product 02:07 Traits of First-Time Founders: A Product Manager's Perspective 04:16 From Big Tech to Startup Life: David Lifson's Career Shift 06:52 The Founder's Imagination vs. Reality: Navigating Startup Challenges 08:11 Identifying Red Flags in Founding Stories 09:29 The Misconception of Product Market Fit 11:36 The Complex Dynamics of Founder Decisions and Team Impact 18:37 Evaluating Founders and the Importance of Trust 20:34 Reflecting on Success and Failure in Startups 23:10 Discovering Pregnancy Through Tech 23:44 The Value of Failure in Founding Teams 24:22 Debunking the 'Data-Driven' Myth 25:36 The Misuse of Data and A/B Testing 27:47 Navigating NPS and Ethical Dilemmas 31:16 The Role of a Founder in Product Strategy 34:39 Strategic Execution vs. Blind Action 37:48 Navigating Early Stage Product Leadership 39:55 Choosing Your Battles Wisely 42:54 Ethical Lines and Cultural Health 47:45 Working with Founders: A Multi-Layered Challenge
David Lifson's Bio: David Lifson has led high performing teams at startups, public, and private equity backed companies, delivering high impact outcomes through clear vision, validated product strategy, and collaborative culture. He’s gone 0 -> 1 multiple times, as well as led teams supporting $350M in revenue. His experience leading teams spans 15 years, including four as CEO/GM and eight as Head of Product & Engineering. Dave has a bachelors and masters degree in Computer Science from Cornell University, and is based in Austin, TX.
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