Critical Moments

In this episode of Critical Moments, Mark Josephson interviews Emmanuelle Skala, a seasoned executive who shares a pivotal leadership moment that changed her career trajectory. Facing feedback from her CEO that she was “not well-liked,” Emmanuelle reflects on the challenges of balancing results with relationship-building in high-stakes leadership roles. Key themes include: • The power of radical candor in executive feedback. • Transitioning from a results-driven mindset to a relationship-focused leadership style. • Practical lessons for CEOs on fostering authentic connections while driving growth. This conversation is packed with actionable insights for CEOs, startup founders, and senior leaders looking to enhance their self-awareness, improve team dynamics, and drive long-term success. Key Moments: • [00:01:53] Emmanuelle’s background and global leadership role. • [05:22:44] The career-altering feedback from her CEO. • [10:07:75] Reflecting on leadership style and its impact. • [18:33:59] Insights on radical candor and its role in growth. • [22:27:48] Building authentic relationships as a leader. • [28:43:97] Emmanuelle’s three takeaways for CEOs and leaders.

In this episode of Critical Moments, host Mark Josephson talks with Cristina Miller, former COO of Goldbelly, about a critical moment in her career that tested her resilience, leadership, and problem-solving skills. Goldbelly, a rapidly growing food marketplace, faced a logistical nightmare during the peak of the holiday season: 70,000 packages at risk of not being delivered due to shipping delays caused by COVID-19 vaccine distribution. Cristina shares the high-stakes decisions, the scramble to escalate the issue with UPS, and the leadership lessons she took away from navigating this career-defining challenge. Key timestamps and insights include: • [01:06] Cristina introduces Goldbelly and her role in scaling the company during the pandemic. • [02:17] The meteoric rise: 5–6x sales growth as Goldbelly became a lifeline for food makers. • [07:04] The crisis unfolds: A phone call from UPS with devastating news about holiday shipments. • [10:53] High-stakes logistics: The challenge of delivering perishable goods at massive scale. • [16:00] Critical moment: Strategizing solutions while battling time constraints. • [22:40] Escalating the issue: Reaching UPS CEO Carol Tomé to resolve the crisis. • [31:55] The outcome: How leadership, collaboration, and swift action mitigated the disaster. • [35:43] Leadership takeaways: Staying calm, escalating effectively, and delivering bad news with a plan. • [38:00] The value of relationships: Building goodwill with partners for when you need them most. This episode offers a rare behind-the-scenes look at how leaders tackle unexpected challenges, make tough calls, and ensure success in the face of adversity. Cristina’s insights are invaluable for anyone building businesses, managing teams, or navigating high-pressure moments. Listen now on Apple Podcasts or Spotify and join us for real stories from leaders making critical decisions that shape careers and companies.

In this inaugural episode of Critical Moments, Mark Josephson sits down with Matt Blumberg, the former CEO of Return Path and current Executive Chairman at Bolster, to discuss one of the most defining moments of his career: the near-sale of his company that fell apart at the eleventh hour.Matt takes us behind the scenes of a nine-figure deal that was so close to closing, the champagne and cupcakes were already delivered to offices worldwide. But a single phone call changed everything, forcing him to navigate the fallout, rebuild his team, and learn invaluable lessons about leadership, resilience, and the art of the deal.Key highlights include: • [03:12] The critical moment: Almost selling a 17-year-old SaaS company, only to have the deal fall through at the last minute. • [07:01] “I can’t believe I’m making this call”: The phone call that stopped the deal in its tracks. • [10:12] The immediate aftermath: Matt’s physical reaction and the challenge of informing his team, board, and family. • [13:44] Salvaging what’s possible: Pivoting to secure a strategic investment at the valuation agreed upon in the failed deal. • [25:48] Rebuilding and recovery: Lessons learned, team departures, and selling the company two years later for a lower valuation. • [32:18] Retrospectives and pre-mortems: How structured reflections and anticipating risks can help leaders avoid repeating mistakes. • [33:50] Key takeaways: The importance of meeting decision-makers, identifying potential deal-killers, and fostering a bias for action.This candid and insightful conversation captures the highs and lows of leadership in a way that’s relatable, human, and rich with actionable lessons for anyone building a company or leading through uncertainty.Listen now on Apple Podcasts or Spotify, and join us for a deep dive into the critical moments that shape careers and companies.

Critical Moments is where we dive deep into the pivotal moments that define careers—and lives. Hosted by Mark Josephson, a tech veteran with 30+ years of experience leading companies like Bitly and Castiron, this podcast isn't just about business—it's about the whole person. We explore how leaders navigate high-stakes decisions at work while balancing health, family, and personal life. With candid conversations, we'll uncover the real stories behind the successes and struggles that shape the people who build the tech industry. Expect laughter, lessons, and a lot of honesty.