CPO PLAYBOOK with Felicia Shakiba

Generative AI may be rewriting the rules, but Felicia Shakiba and Claurelle Rakipovic, Chief Product Officer at Pipe, break down what real product leadership looks like. From customer empathy to AI missteps, Claurelle shares sharp lessons on building products that can actually hold their ground. Chapters 00:00 Building Defensible Products in the Age of AI 01:50 Understanding Defensibility Beyond Automation 04:30 Learning from AI Missteps 09:26 Internal Testing and AI Adoption 14:39 New Competencies for Product Leaders 19:47 The Importance of Unique Data 23:49 Empathy in AI Product Development 27:39 Auditing AI for Value Delivery

In the world of private equity and high-stakes M&A, financials are only half the story. The real differentiator? Leadership. This episode explores what leadership qualities truly drive success in mergers and acquisitions, why most private equity due diligence efforts fall short on the people's front, and how to assess leaders before the deal is signed. Our guest is Cameron Bishop Partner and Managing Director at Raincatcher Investment Bankers. Chapters 00:00 The Importance of People in M&A Success 02:48 Cultural Missteps in Private Equity Acquisitions 05:44 Aligning Leadership Post-Acquisition 08:15 The Role of Communication in Corporate Culture 11:04 Integrating Multiple Cultures 13:37 Data-Driven Decision Making in M&A 16:06 Incentivizing Employees for Success 18:54 Identifying and Nurturing Talent 21:43 Achieving Alignment in Leadership 24:44 The Continuous Journey of Alignment

Matt Lewis unpacks the realities of AI transformation inside organizations — and what happens when AI takes our jobs. He shares stories of employees navigating the emotional fallout of AI, the role of leadership in reducing resistance, and how identity and self-worth shape the success of change initiatives. Listeners will walk away with practical strategies for guiding teams through AI-driven transformation with clarity and empathy. 00:00 Navigating Personal Challenges and Professional Growth 05:30 Real Stories of Emotional Fallout 11:42 Subtle Signs of Resistance 19:55 Communicating Change Effectively 27:32 Understanding Organizational Dynamics During Transformation 34:38 TransferMental: A New Approach to AI Transformation 40:24 Identity and Emotional Complexity in AI Disruption

What does it really take to lead lasting change inside an organization? Lyon Kassab, Managing General Partner at BoCG Ventures, breaks it down in this episode on organizational change management and how the lack thereof, can cost millions. From the silent weight middle managers carry to the culture shifts that make or break transformation, Lyon shares sharp insights on trust, transparency, and measuring what matters. If you’re tired of buzzwords and want the real mechanics of driving change—this one’s for you.

Felicia Shakiba and Vikash Jha pull back the curtain on how private equity really sizes up leadership during acquisitions for business growth. From reading the silent signals to decoding executive chemistry, they reveal the high-stakes art of aligning leaders with ambitious growth plays. Chapters 00:00 Navigating Leadership Evaluation in Private Equity Due Diligence 03:07 Identifying Leadership Fit: Early Warning Signs 07:49 The Strategy Behind Leadership Retention 12:16 Cultural Integration: The Key to Successful Acquisitions 14:50 Investing in Leadership Development vs. Replacement 17:12 Communicating Change: Engaging Leadership and Employees 20:44 Best Practices for Retaining Talent Post-Acquisition 22:33 Checklist for Assessing Leadership During Acquisitions

How can executives build authentic confidence and overcome self-doubt? Kip Knippel, President & CEO of KIP Search, shares actionable strategies for navigating imposter syndrome, embracing risk-taking, and leading with clarity. Discover how mentorship, direct communication, and self-awareness help women thrive in male-dominated leadership roles. Learn how to build resilience, strengthen executive presence, and shape a culture where confident leaders grow and succeed.

How can HR leaders move beyond surveys to drive real business outcomes? Scott Leuchter, Global Chief People Officer at Ideal Tridon Group, shares how predictive analytics uncovers key drivers of performance, retention, and productivity. Learn how data-driven assessments, feedback loops, and smart change management can transform employee experience into measurable business impact.

How can private equity leaders align fast growth with long-term mission? Manna Tree’s Co-Founder Ross Iverson shares how founder-investor alignment drives execution, protects purpose, and reduces risk. From navigating CEO transitions to using Gestalt protocols and trust-building retreats, Ross breaks down how great governance turns alignment into a competitive edge in high-stakes environments.

How can companies harness Responsible AI without losing the human touch? PepsiCo’s VP of People Solutions, Mark Sankarsingh, shares how the company boosts productivity and streamlines HR—while safeguarding trust, ethics, and human judgment. Learn how to lead with integrity as you scale teams and adopt AI in a digital-first world.

What does it take to be a transformational CFO today? Former Citigroup Divisional CFO Roman Labutin shares how the role is evolving—blending data-driven decisions with people-first leadership, cross-cultural trust, and strategic partnerships with HR on comp, succession, and org design.

How can CFOs and CPOs drive better results—together? Robert Bendetti shares how finance-HR collaboration transforms workforce planning and performance. From incentive compensation to cross-functional strategy, learn how data, transparency, and aligned leadership fuel high-performing teams.

Is AI expertise more valuable than industry experience? Andrea Iorio explores how AI is reshaping hiring, leadership, and talent development. Learn why AI literacy matters, how to balance human and technical skills, and what it takes to future-proof your workforce in an AI-driven world.

How can online communities turn connection into capital? Maayan, TikTok superstar with over 1 billion views, shares how authentic engagement, content strategy, and social platforms drive loyalty, innovation, and sustainable business growth—proving you can build wealth from the ground up.

How can companies scale globally without losing local relevance? Hasan Kazmi of Visa shares how global strategy meets local execution—balancing trust, adaptability, and empowered teams to drive growth across diverse markets while staying connected to regional needs.

How is AI redefining leadership and the future of work? Enrique Rubio, founder of Hacking HR, explores how AI is reshaping workforce dynamics, leadership roles, and digital transformation. Learn what skills leaders need now and how to harness AI for innovation and strategic impact.

How can leaders build trust and courage across their teams? Angela Cheng-Cimini shares how psychological safety, emotional intelligence, and assumed trust empower employees to speak up, navigate hard conversations, and thrive in environments where openness and accountability go hand in hand.

What really happens to culture after a company is acquired? Bobby Kingsbury of MCM Capital Partners reveals what most leaders overlook during post-acquisition transitions—and how to re-engage leadership, motivate teams, and turn cultural disruption into long-term growth.

How can leaders build a workplace where people feel truly valued? Ophira Melamed, CEO of Nitrofix, shares strategies grounded in transparency, purpose, and respect. Learn how to boost morale, prevent burnout, and drive engagement through trust, clarity, and mission-aligned leadership.

How can companies achieve operational excellence in a hybrid world? BuzzFeed’s CPO Chandler Bondan shares how to lead with clarity, boost engagement, and build culture while leveraging HR strategy and AI to drive efficiency in today’s dynamic workplace.

How do you scale a startup while managing distributed teams? Valentina Agudelo Vargas, CEO of Salva Health and TechCrunch Disrupt winner, shares how team alignment, executive coaching, and clear communication helped her build culture and drive success across cities.