Delivering Value: Tough Career Moments - Lessons from Growth, Marketing & Product Leaders

In this episode, Devin Reed, one of the leading voices in content and marketing, opens up about the defining moments that shaped his career—from growing up between two very different cultures in Sacramento to building a name for himself at Eventbrite, Gong, and Clari before stepping out on his own. He shares candid stories of career pivots, from giving up on his dream of teaching to unexpectedly landing in tech sales, and later realizing his sweet spot in content marketing. Devin reflects on the sting of being graded a “seven” at a company that recruited him aggressively, the intimidation of being told he wasn’t qualified for his role at just 25, and the burnout he faced after tying too much of his worth to productivity.Now as a founder, creator, and dad, he talks about learning to measure success not in metrics but in moments—balancing ambition with presence, and re-wiring what it means to “win” in both business and life.In this conversation, you’ll learn:- Why it’s essential to question feedback and define your own worth- How to recognize poor leadership and build a healthier leadership style- What it takes to reset old wiring around ambition and successThings to listen for:(00:00) Intro(01:59) Devin's upbringing and early career(02:47) Transition to marketing and entrepreneurship(03:01) Facing challenges and finding success(06:33) Pivotal career moments(08:08) Thank you to our sponsor, Navattic(11:33) Navigating tough feedback(17:17) The impact of therapy and self-worth(21:28) Dealing with imposter syndrome(26:46) Realizing the importance of empathy in leadership(28:40) Learning from coaches and mentors(34:48) Balancing work and personal life(38:50) Implementing new habits and boundaries(46:20) Setting goals for fulfillment and happiness(49:25) Caution in advice and embracing relatabilityA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Devin:LinkedIn: https://www.linkedin.com/in/devinreed/The Reeder (official website): https://www.thereeder.coReed Between The Lines (podcast): https://www.thereeder.co/content-hub/podcastConnect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coachingJoin Growth OS: https://deliveringvalue.co/growth-operating-system

In this episode, Justin Bauer, former Chief Product Officer at Amplitude and now one of the most sought-after product advisors in AI, talks about the pivotal career moments that shaped his leadership style. From betting everything on a tiny startup with 13 people to navigating layoffs and leveling conversations, Justin shares how he learned to lead with clarity, humility, and courage.He also reflects on what it takes to thrive in a high-growth environment — and how to reinvent yourself every 18 months to stay relevant. This is a conversation about ambition, emotional resilience, and how to earn trust when the stakes are high.In this conversation, you’ll learn:Why preparation and self-reflection are Justin’s keys to confident leadershipHow to navigate the emotional toll of layoffs, leveling, and managing upWhy clarity of expectations keeps your career evolvingThings to listen for:(00:00) Intro(01:44) Justin's early life in Iowa(04:33) First jobs and early ambitions(07:39) Thanks to our sponsor, Navattic & ThriveStack(10:47) A high-stakes decision to join Amplitude(14:00) The reality of startup life(16:00) Advice for aspiring startup employees(18:55) Feedback and career growth(26:41) Overcoming imposter syndrome(27:11) Navigating leadership challenges(29:16) Seeking clarity in a growing company(30:52) Managing up and building relationships(37:50) Handling layoffs and difficult conversations(43:06) The importance of preparation and role-playing(56:05) The value of deep thinking timeThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Justin:LinkedIn: https://www.linkedin.com/in/jjbauer/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

In this episode, Rana Mumtaz, Product Growth Leader, reflects on the defining moments that shaped her personal and professional identity—from quietly adapting to American culture as a soft-spoken engineering student to building products at the New York Stock Exchange and navigating executive rooms as a banking outsider.She opens up about career pivots that required unshakable self-belief, including her leap from civil engineering to software, and the moment she realized her leadership potential didn’t need to follow anyone else’s blueprint. Rana shares how difficult conversations, strategic missteps, and cultural friction all played a role in helping her find her voice and shape her path.In this conversation, you’ll learn:Why empathy matters more than titles when leadingHow to build healthy boundaries with work identityWhat it takes to speak up without burning outThings to listen for:(00:00) Intro(01:27) Growing up and schooling in India(03:37) First impressions of the United States(06:37) Starting a career from scratch(08:35) Thanks to our sponsor, ThriveStack(13:52) Becoming a software engineer(17:08) Honest thoughts on giving feedback(18:22) Executive interactions and leadership lessons(26:32) Dealing with imposter syndrome(29:38) Navigating career challenges and transitions(38:17) Facing hard conversations at work(47:38) Balancing career with identityA huge thanks to this episode’s sponsor:ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Rana:LinkedIn: https://www.linkedin.com/in/ranamumtaz/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

In this episode, Joanna Lord, global CMO, board advisor, and multi-time tech executive, reflects on the moments that forced her to grow the most. She shares how being passed over for a promotion after a colleague threatened to quit cracked open her entire leadership style, as well as the AMA that sent her into a full-blown panic attack just days into a new global CMO role. These moments became turning points, pushing her to shift from a self-focused high performer to a more collaborative and self-aware leader.Joanna also talks about impostor syndrome, recovering from public missteps, and learning to separate her identity from her job title. This isn’t just a conversation about leadership — it’s about resilience, reinvention, and what it really means to grow up in your career.In this conversation, you’ll learn:Why your high performance won’t carry you past your people skillsHow “qualified” and “capable” are two entirely different betsWhat changes when you stop being the hero and start being the glueThings to listen for:(00:00) Intro(01:29) Early life in Vermont and career beginnings(02:24) Joanna’s journalism aspirations(06:56) Receiving devastating career feedback(10:30) Thank you to our sponsor, Navattic(22:50) The AMA that led to a panic attack(29:34) Being capable vs. being qualified(33:14) Imbuing swagger on your team(37:25) A major mistake and avoiding accountability(43:51) Resilience and moving forward(45:48) Unstitching identity from job titles(50:23) Creating a healthy work environmentThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Joanna:LinkedIn: https://www.linkedin.com/in/joannalord/ Official newsletter: https://www.linkedin.com/newsletters/7003840481180749824/ Official website: https://www.joannalord.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

In this episode, Raj Singh, multi-time founder and current VP of Product at Mozilla, opens up about the moments that nearly unraveled his career. From getting called into HR over a side hustle to walking away from a startup after being unexpectedly leveled, Raj shares what it’s like to navigate the highs and lows of building without losing your identity.He walks us through multiple pivots, including the time he turned down a seven-figure exit and the brutal leadership decision that nearly cost him a co-founder. Raj doesn’t just talk strategy, he gets into the emotional rollercoaster of founding: the resentment, the rejections, and the real mental toll of being the one expected to have all the answers.In this conversation, you’ll learn:-Why being a “do-it-all” founder doesn’t scale-How to manage resentment when you get leveled-What it really takes to make hard calls when no one agrees with youThings to listen for:(00:00) Intro(01:04) Meet Raj and his startup resume(02:02) Growing up in the Bay(04:05) First hustle: installing Ethernet cards(07:54) Early failures and impostor syndrome(09:11) Picking product vs. engineering(10:06) Thanks to our sponsors, Navattic & Appcues(12:49) HR call over a side project(16:23) Fear, risk, and side hustles(24:35) Leaving a startup after a new hire(29:01) Facing public failure as CEO(30:06) Rise of IC tracks and redefining success(34:08) Hardest call of his career(44:41) Power of incentives(47:33) His video game theory of growth(52:06) The real risk: not improving(56:00) There’s never a perfect timeThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/value Resources:Connect with Raj:LinkedIn: https://www.linkedin.com/in/rajansingh/Linktree: https://linktr.ee/mobilerajX: https://x.com/mobilerajMozilla: https://www.mozilla.org/en-US/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

In this episode, Gururaj Pandurangi, three-time founder and CEO of ThriveStack, opens up about the near-death moments, pivots, and internal reckonings that shaped his entrepreneurial journey. From growing up in Mumbai with dreams of becoming a scientist to leading multi-million dollar product bets at startups backed by Microsoft and Deloitte, Guru shares what it really takes to build when the vision keeps shifting and the runway keeps shrinking.He walks us through two moments when his companies nearly ran out of money and the uncomfortable decisions that pulled them back from the edge. From flipping into consulting just to survive to gambling everything on a risky conference booth, Guru doesn’t just talk strategy. He talks about fear, team trust, and the mental load of being the one who has to believe before anyone else can.In this conversation, you’ll learn:Why being a “product purist” almost killed the company and what saved itThe mental spiral founders face when bets aren’t paying offHow to keep a team motivated when the vision keeps changingThings to listen for:(00:00) Intro(01:13) Meet Guru: a story of resilience(02:30) Growing up in Mumbai and early inspiration(04:45) Hustling during a solar eclipse(08:16) Engineer to reluctant founder(10:10) 14 years at Microsoft and why he left(10:47) Thanks to our sponsor, ThriveStack(15:20) Taking VC money (and the fear that comes with it)(23:03) Pivoting to consulting to survive(28:05) Spending nearly $1M on the wrong product(30:25) A pivotal meeting with Microsoft(34:45) Battling imposter syndrome(39:37) The pivots behind ThriveStack(44:19) Redefining the product for real customer needs(47:08) Losing team members as the vision shifts(51:18) Why founders should share failures(54:04) Guru’s biggest mindset shift(55:41) A real take on VC fundingA huge thanks to this episode’s sponsor:ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Gururaj:LinkedIn: https://www.linkedin.com/in/gururajp/ThriveStack: https://www.thrivestack.ai/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

Can you be too nice to lead?In this episode, Michael Leibovich, GM and Head of Growth at Adobe, shares the career pivots, personal awakenings, and leadership lessons that shaped his unconventional journey from touring musician to executive. Michael opens up about getting fired, receiving feedback that questioned his approach to leadership, and learning how to balance empathy with outcomes. From scaling growth teams at Vimeo, Mindbody, AppFolio, and Abstract to navigating the emotional weight of letting someone go, Michael brings clarity to the messy, human side of leadership.We explore how feedback becomes identity-shaping, what it means to truly “drive clarity” in a role, and why building a career is more about learning from missteps than chasing perfection.In this conversation, you’ll learn:Why “you’re too nice” was the critique that stuck—and how Michael worked through itThe surprising lesson a failed VP stint taught him about agency and self-worthA simple question that brings clarity to tough calls as a managerThings to listen for:(00:00) Intro(01:24) Growing up in an artistic blue-collar SoCal home(02:30) First jobs and career aspirations(04:29) Journey into music and touring(05:44) Transitioning to tech and SaaS(07:24) How being in a band helped in learning business(11:02) Thank you to our sponsor, ThriveStack(12:20) Being too nice as a leader and finding a balance(21:27) Paying impactful feedback forward(23:38) Navigating imposter syndrome(26:46) Leadership challenges and job insecurity(29:27) Reflecting on career transitions(31:45) A costly mistake and learning experience(36:17) Managing team dynamics as a leader(44:42) A useful shift in perspective(46:46) Driving clarity and embracing intuitionA huge thanks to this episode’s sponsor:ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Michael:LinkedIn: https://www.linkedin.com/in/michaelleibovich/ Adobe: https://www.adobe.com Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

Steph Pennell, founder of The Event Critic and a former marketing leader, shares her journey from disillusionment to self-discovery. She discusses the pivotal feedback that made her reevaluate her career and values, including the impact of a shocking lipstick comment. Pennell also dives deep into how ADHD, manifestation techniques, and human design have helped her regain control and find alignment in her life. Her insights on navigating misalignment, feedback challenges, and the balance between professional and personal values offer a refreshing perspective for anyone feeling overwhelmed.

What happens when you finally land the leadership role you’ve been working toward—only to realize it’s not what you imagined?In this episode, Shannon Curran—former VP of Marketing at MadKudu and now founder of SSC Consulting—opens up about the real moments that shaped her career. From growing up as a risk-averse high achiever to becoming a solopreneur trusted by founders, Shannon shares the feedback that shook her, the environments that helped her grow, and the human-first leadership lessons she learned the hard way.We unpack why cultural fit isn’t fluff, how to build trust in hard conversations, and why you don’t need to have all the answers to be a great leader. Whether you're in-house, managing a team, or building something of your own, this conversation offers something real.In this conversation, you'll learn:Why Shannon left higher ed and nonprofit work for techThe real story behind inheriting a leadership team without trainingHow to navigate feedback that questions your identityWhat she learned from a rocky client relationship early in her consulting careerThings to listen for:(00:00) Intro(01:25) Business education for the risk-averse(05:04) Career beginnings in tech(09:12) Thank you to our sponsors, Navattic and Appcues(11:50) Facing speed bumps and feedback(20:48) Managing and letting go(26:49) Sensing trouble and taking action(27:45) Navigating tough conversations(30:10) Handling team changes and communication(31:48) Learning from mistakes and setting expectations(45:33) The myth of the all-knowing leader(52:59) What’s next: parental leave, peace, and building enoughThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/value Resources:Connect with Shannon:LinkedIn: https://www.linkedin.com/in/shannon-sweeny-curran/SSC Consulting: https://shannonscurran.com/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

What makes someone walk away from a PhD, a career in law, and the startup that made them?In this episode, I sit down with Else van der Berg—a former head of product turned solopreneur—to unpack the hard-earned lessons from the burnout that nearly broke her. Else shares how working 80-hour weeks and tying her identity to performance pushed her to the brink—and what changed afterward.We talk about how startup culture, pressure to “always be on,” and even toxic leadership can distort your sense of success. Else doesn’t just reflect on the crash—she offers a clear, honest roadmap for building back stronger, with boundaries and intention.In this conversation, you’ll learn:- Why Else left a high-growth role after a massive burnout—and how she rebuilt her career- How early startup culture trained her to overwork and ignore red flags- What she looks for now in leaders, teams, and work environments—and how you can tooThings to listen for:(00:00) Intro(07:06) From law to tech: Elsa's career transition (08:59) Thank you to our sponsor, ThriveStack(20:22) Challenges in the job market (25:44) Burnout and recovery (29:11) The persona of hard work (30:55) Sexual harassment in tech (33:15) Support systems and reporting issues (38:51) Burnout and recovery (41:03) Choosing the right work environment (49:06) Leadership and self-reflection (55:12) AI and the future of work A huge thanks to this episode’s sponsor:ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Else:LinkedIn: https://www.linkedin.com/in/dr-else-van-der-berg-42b8b6a2/ Substack: https://elsevanderberg.substack.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching