Anthony Scarpaci - Former VP of Growth at Acorns and Founder of TUNOMATIC, shares the toughest moments in his career that shaped his leadership philosophy. From navigating high-stakes mistakes to balancing empathy with assertiveness, Anthony opens up about the defining experiences that molded him into the leader he is today. He reflects on his journey across growth roles at companies like Betterment, NerdWallet, and Blue Apron, while offering candid advice for leaders facing their own career challenges.Anthony opens up about:1. Making a massive mistake early in his career and being told it could cost him his job2. Getting feedback in a formal 360 review that he was “too nice” as a leader3. Returning from his wedding in Italy to perform layoffs at 8 AM the next morningThings to listen for:(00:00) Owning up to an early career mistake(08:38) Transitioning from music to tech & marketing(13:37) The scariest moment of Anthony’s career(19:46) Learning from a crisis: Building trust and accountability as a young leader(25:57) Feedback that Anthony was “too nice” and learning to assert himself(28:21) Thanks to our sponsors for this episode, Navattic and Appcues(31:20) Managing across and up: How to navigate organizational dynamics(36:08) Conducting layoffs and the emotional toll of tough decisions(47:55) Key lessons from handling high-pressure situations(50:46) Giving yourself grace and focusing on what’s in your controlResources:Connect with Anthony:LinkedIn: https://www.linkedin.com/in/anthonyscarpaci/ TUNOMATIC: https://www.tunomatic.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coachingThanks to our amazing sponsors!Learn more about Navattic: https://navattic.com/value Learn more about Appcues: https://appcues.com/value

Tara Goldman, Co-founder of GoldHue and former VP of Product, shares her transition to executive coaching, revealing the pressure of high-stakes board meetings and the masks she wore in challenging environments. She discusses the toll her work had on her personal life, emphasizing the importance of personal values over corporate expectations. Tara reflects on her emotional journey, the realities of imposter syndrome, and the significance of preparation and support. Her insights inspire others to embrace authenticity in leadership.

Gaurav Vohra—a founding team member at Superhuman—reflects on pivotal moments that shaped his career in tech. He shares the highs and lows of scaling teams, stepping back when necessary, and dealing with imposter syndrome. Gaurav opens up about:1. His transition from management consulting to the tech world2. The challenges of leading a large team and recognizing when someone else might be better suited to take over3. Struggling with imposter syndrome and learning to adapt as a leaderThings to listen for:(00:00) Gaurav opens up on his struggles as a leader(05:15) Moving to San Francisco and joining Superhuman’s founding team(09:50) Gaurav’s early tech exposure and the influence of his brother(15:20) Transitioning from individual contributor to leading multiple teams(19:45) The tough decision to step back from managing a large team(25:30) Navigating imposter syndrome in leadership roles(25:44) Thanks to our sponsor for this episode, Churnkey(32:15) The challenge of giving up control and learning from new executives(39:25) The value of stepping off the "escalator" and finding more meaningful work(45:50) Gaurav’s productivity hacks and advice on maintaining balanceResources:Connect with Gaurav:LinkedIn: https://www.linkedin.com/in/gvohra/ Superhuman: https://superhuman.com/Gaurav’s website: https://www.gauravvohra.com/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coachingThanks to our amazing sponsor!Learn more about Churnkey: https://churnkey.co/

Irina Scarlat is the VP of Growth at ICEO (a venture builder) and has built marketing and growth teams at Uber, Revolut, Bitpanda, and Pearson along the way. In this conversation, she reflects on pivotal moments in her career, sharing how they shaped her leadership style and personal development. Irina talks about the emotional challenges of going through corporate restructuring, the importance of maintaining work-life balance, and the tools she uses to combat workplace anxiety.Irina opens up about:1. Being forced to reapply for her job at Uber after a massive shakeup2. The challenges of leading a company-wide restructuring at Bitpanda3. Her journey with cognitive behavioral therapy (CBT) to manage imposter syndrome and workplace stressThings to listen for:(00:00) Irina’s pivotal career moment: reapplying for her own job(01:03) Early life in Romania and societal expectations(07:54) How international experiences shaped Irina’s career outlook(09:18) Transitioning into the tech world and early ventures(12:30) Joining Uber and building the marketing team from scratch(18:44) Leadership changes at Uber and the emotional challenges of restructuring(24:16) Deciding to leave Uber and transitioning to Revolut(29:59) Key feedback that transformed Irina’s approach to work and prioritization(31:15) Thanks to our sponsors for this episode, Navattic & Appcues(38:11) Managing anxiety, imposter syndrome, and the role of cognitive behavioral therapy(52:19) Leading a restructuring at Bitpanda and the impact on team dynamicsResources:Connect with Irina:LinkedIn: https://www.linkedin.com/in/irina-nicoleta-scarlat-30a4b28/ Check out her website: https://irinascarlat.com/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coachingThanks to our amazing sponsors!Learn more about Appcues: https://appcues.com/value Learn more about Navattic: https://navattic.com/value

Meredith Rosenbloom - VP of Growth Marketing at Zola, reflects on some challenging moments in her career that molded her into the leader she is today. She recounts her journey from sports marketing to growth roles at companies like Grubhub and Parsley Health while opening up about the challenges she’s faced along the way. Meredith shares the impact of critical feedback, managing career transitions, and returning to work as a new parent.Meredith opens up about:Being asked to take on more responsibility without a title promotion at GrubhubReceiving feedback about her voice inflection and how it made her self-consciousThe emotional and professional challenges of returning to work after maternity leaveThings to listen for:(00:00) Meredith’s early hardships(02:44) Tough feedback on personal traits(06:15) Growing up with a strong work ethic and early career experiences(10:35) Transitioning from agency work to performance marketing(15:10) Navigating a title mismatch and trusting your manager(21:00) Overcoming self-doubt and building confidence with coaching(24:15) Thanks to our sponsors of this episode, Navattic & Appcues(27:22) Returning to work after maternity leave and finding balance(32:50) The importance of mental health and protecting personal peace(39:40) Using breath work and self-care for stress management(46:15) Career goals, family balance, and the value of empathy in leadershipResources:Connect with Meredith:LinkedIn: https://www.linkedin.com/in/meredithrosenbloom/ Zola: https://www.zola.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coachingThanks to our amazing sponsors!Learn more about Navattic: http://navattic.com/value Learn more about Appcues: http://appcues.com/value

Diana Stepner shares three pivotal lessons from her journey transitioning from Product Manager to Leadership Coach. She discusses the importance of making your manager shine, navigating team dynamics, and why building trust is essential for career growth. Diana also reflects on why the characteristics that earned her praise early on in a company consistently turned into points of negative feedback.Diana opens up about:1. Why the same attributes that earned her praise could also create detractors 2. The challenges of being both overqualified and underqualified3. Learning how to balance self-driven success with the importance of recognizing and celebrating her team and managersThings to listen for:(00:00) Intro(03:22) Growing up in Silicon Valley and early exposure to the tech world(06:43) Transitioning from communications to product leadership(12:12) Struggling with being overqualified or underqualified(15:05) Learning how to make your manager shine(21:08) Thanks to our sponsor of this episode, Navattic(25:18) Handling challenging feedback and finding balance in leadership(30:47) When stepping aside wasn’t the right call(35:59) Rebuilding after tough feedback(41:24) Disbanding a future-focused team: the reality of working on the fringe(46:38) The power of slowing down and building trust with your teamResources:Connect with Diana:LinkedIn: https://www.linkedin.com/in/dianas/Product Gold: https://www.productgold.com/ People-First Leadership: https://dianastepner.substack.com/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coachingThanks to our amazing sponsor!Learn more about Navattic: http://navattic.com/value

Natalie Marcotullio, Head of Growth at Navattic, takes us in for a behind-the-scenes look into the process of launching their freemium motion. Going through the strategic reasons behind the shift and how it fits into their overall growth strategy, she reflects on the challenges of aligning the sales team, navigating risk, and measuring success in both the short and long term. Natalie also shares her perspective on the realities of product-led growth, the importance of soft-pitching ideas, and the unexpected lessons learned during the launch process.Natalie opens up about: The excitement and pressure of launching a freemium planThe value of soft-pitching product-led growth strategies over timeThe challenge of aligning a sales team to embrace PLG leadsThings to listen for: (00:00) Intro(03:17) Why Navattic chose freemium over a free trial model(05:53) The impact of freemium on pipeline and user conversion(08:00) Navigating internal buy-in and the importance of soft-pitching PLG(10:01) Testing and experimenting with lower-priced plans before going freemium(12:13) Aligning the sales team with the PLG motion and managing challenges(14:00) Modeling pipeline projections and the impact on MQL and PQL metrics(16:19) The role of customer support in managing increased user inquiries(18:42) Sales engagement with self-serve users and building trust(20:25) Reflecting on early success indicators and word-of-mouth growthResources:Connect with Natalie:LinkedIn: https://www.linkedin.com/in/natalie-marcotullio/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coaching

In this episode, Sarah Stockdale, founder of Growclass, shares her journey of overcoming burnout while leading growth teams at tech startups, addressing gender bias in the workplace, and building a thriving community for marketers. She reflects on how these experiences shaped her leadership style, approach to mental health, and entrepreneurship.Sarah opens up about:Witnessing a mass layoff and facing inappropriate comments from a coworkerPushing herself so hard that she had a panic attack on her way to a partnership meetingMaking the bold decision to take a risk on a startup over a secure job because she wanted to optimize for learning.Things to listen for:(00:00) The wonderful humans that shaped Sarah(06:39) Transitioning from a risk-averse upbringing to entrepreneurship(08:04) Turning down a safe job offer for a learning opportunity in a startup(11:26) Not true, but he said, “Sarah wasn’t fired because the boss wants to f*** her”(18:42) Thanks to our sponsor of this episode, Churnkey(20:33) “You get to decide your own worth and impact”(25:33) Busting the hustle = success myth(31:18) Liters of coffee, panic attacks, and burnout(39:10) Sarah’s therapist told her to quit her job(42:39) The impact of frentors (friend + mentor)Thanks to our sponsor!Learn more about Churnkey: https://churnkey.co/Resources:Connect with Sarah:LinkedIn: https://www.linkedin.com/in/sarahstockdale/ Growclass: https://www.growclass.co/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coaching

In this episode, Aakash Gupta shares his journey from a tech-savvy kid in Kalamazoo, Michigan, to a successful product manager and creator in the Product Growth space. He shares his tough feedback experiences, how he’s been able to overcome imposter syndrome, and how building a failed startup impacted his career. Aakash emphasizes the importance of self-care, emotional intelligence, and supportive mentorship in navigating corporate roles and leadership challenges. Aakash opens up about:How the collapse of a startup with 350k users reshaped his career and mindsetGetting specific feedback from a CMO that rattled his confidence Navigating a sticky situation when a team member on a PIP attempted to turn the entire company against him Things to listen for:(00:00) Intro(01:03) Aakash’s journey: From VP to Creator(03:08) Debate skills shaping his product career(05:29) First SaaS job building sports tools(08:07) Lessons from his failed startup(12:26) How mentorship changed his mindset(14:17) Tough feedback from a CMO at Threadup(16:33) The role of emotional intelligence in leadership(28:08) Handling a difficult pip situation(37:01) Dealing with imposter syndrome(44:06) Personal habits for productivity

Ramli John - Founder of Delight Path, shares core memories from his teenage years that inspired his entrepreneurial journey. Explores how attaching his worth to his achievements was making him act like a jerk. Shares stories from the worst boss he ever had. And discusses the toughest feedback that he’s received (and what he’s doing about it).Ramli opens up about:1. Seeing his dad get laid off after 15 years and how that shook his belief in relying on one employer.2. A CEO screaming at their CTO and team members, creating a toxic work environment that pushed Ramli to leave.3. Ramli's realization that he was emulating Steve Jobs' harsh behavior and treating people poorly, which led him to seek therapy for a healthier approach to work and life.Things to listen for:(00:00) Ramli’s new venture: Delight Path(06:26) Ramli’s core childhood memory: layoffs are brutal(08:23) The emotional impact of his dad's layoff and starting his consulting business(18:59) Pressure to rush and overwork leads to mistreatment of others(22:52) The importance of therapy in overcoming our flat slides(28:20) Discussing the need for quiet reflection and the book "Quiet" by Susan Cain(30:58) Ramli’s screamer CEO and sitting in a toxic work environment(38:52) Tough feedback and learning to speak up as an introvertResources:Connect with Ramli:LinkedIn: https://www.linkedin.com/in/ramlijohn/ Delight Path: https://www.delightpath.com/ Product-Led Onboarding Book: https://productled.com/book/onboarding Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coachingThanks to our amazing sponsors!Learn more about Appcues: http://appcues.com/value Learn more about Navattic: http://navattic.com/value