The Estee Show - Product Management & Business Insights

Estee Goldschmidt
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The Estee Show - Product Management & Business Insights

Estee is a product management expert with an MBA who's navigated the startup world from the IC trenches to the VP role. She is a veteran of business initiatives that generated millions, but her biggest lessons came from failures that didn't pay off. From prioritizing short-term wins over long-term value or launching features without solid data, Estee has seen it all in Product Management. From big paychecks to unceremonious firings, Estee knows the highs and lows of this industry.   Her outspoken approach brings you great conversations with industry leaders and the latest in the world of business and product management. Enjoy a product management and business program that is not afraid to be honest and rough around the edges. Welcome to The Estee Show!

  1. 4 DAYS AGO

    43. Unpacking Antisemitism on College Campuses with Shai Goldman

    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.

    36 min

  2. 30 OCT

    42. The Paradox of Service: Can Great CX Mean No Service at All? With Ben Segal

    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.

    1h 6m

  3. 15 OCT

    41. Bad Managers and How Not to Be One with Rachel Windzberg and Dave Lifson

    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.

    57 min

  4. 23 SEPT

    40. Inside Fitbod: Habit Building in Fitness Tech with Josh Gnanayutham

    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.

    34 min

  5. 3 SEPT

    39. Weightlifting Insights from a Product Manager with Arianna Hoffman

    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.

    35 min

  6. 20 AUG

    38. The Anti-AI vs. Pro-AI Debate with Shane Ursani

    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.

    42 min

  7. 30 JUL

    37. Deep Dive into Fractional Product Management with Aakash Gupta

    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

    1h 6m

  8. 16 JUL

    36. How to Conduct Effective Reference Checks with Allison Yamamoto

    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/

    1h 9m
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About

Estee is a product management expert with an MBA who's navigated the startup world from the IC trenches to the VP role. She is a veteran of business initiatives that generated millions, but her biggest lessons came from failures that didn't pay off. From prioritizing short-term wins over long-term value or launching features without solid data, Estee has seen it all in Product Management. From big paychecks to unceremonious firings, Estee knows the highs and lows of this industry.   Her outspoken approach brings you great conversations with industry leaders and the latest in the world of business and product management. Enjoy a product management and business program that is not afraid to be honest and rough around the edges. Welcome to The Estee Show!

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