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

In this episode, Mallory Contois, VP of Growth at Maven and founder of The Old Girls Club, traces her path from hypergrowth operator to community builder. She reflects on the “up, down, up” rhythm of her career, from Pinterest’s rocket ship years to rediscovering fit after leaving Metafy, and shares what she’s learned about ego, feedback, and identity along the way.Mallory opens up about being diagnosed with ADHD as an adult and how that reframed her communication, leadership, and approach to feedback. She explains why no one is an “A-player everywhere,” how environment shapes performance, and what it takes to design work that truly fits your strengths.Now leading growth at Maven while scaling a 2,000-member community, Mallory gets practical about following momentum, hiring for energy, and coaching the edges. She also reframes mentorship, arguing that small, intentional peer communities can be more powerful than chasing a single mentor, and offers practical advice for giving and receiving feedback without losing your voice.In this conversation, you’ll learn:- How to identify your fit Venn diagram (subject matter × work style × company size) and use it to choose roles that compound- A 3-part coaching framework to channel “bulldozer” energy into clear, respectful collaboration- Why building a peer community can be the highest-leverage “career hack” you controlThings to listen for:(00:00) Intro(03:31) First tech job (06:11) Hypergrowth lessons at Pinterest(10:12) Thank you to our sponsor, Navattic(14:37) Realizing no one is an A-player everywhere(17:49) ADHD in the workplace(28:23) Coaching and neurodiversity at work(31:39) Leaving Metafy and its aftermath(43:08) Mallory’s advice to her younger self(47:18) Trusting instincts and following momentumA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Mallory:LinkedIn: https://www.linkedin.com/in/mallorycontois/ Mallory’s official website: https://www.mallorycontois.com/The Old Girls Club: https://www.jointheogc.com/ Connect 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, Ryan McCready, content leader turned Principal Content Engineer at Demostack, opens up about the moments that shaped his path: hacking distribution in the early “monoculture SEO” days, sharpening his voice through roles at Foundation, Reforge, and Whimsical, and facing his first layoff. He shares candid stories about creator burnout after viral teardowns, being the last marketer standing after cuts, and the gut punch of being told he hadn’t delivered on a role that had completely changed. When the market went quiet, Ryan turned the setback into a story on LinkedIn, igniting a thousand DMs, weeks of interviews, and a fresh sense of momentum.Now, as a builder and editor who treats vulnerability like a career asset, Ryan talks about measuring success in relationships, not just metrics, documenting your receipts, keeping your voice, and sending that DM. He breaks down the unglamorous parts of leadership: giving and receiving hard feedback, guarding against plagiarism, and aligning work with products that actually have staying power, while showing how practical AI and automation can clear the busywork so you can create with intention.In this conversation, you’ll learn:How vulnerability, done thoughtfully, can unlock opportunity, community, and your next rolePractical ways to productize your “receipts” with AI or automation so your wins market themselvesHow to deliver and absorb tough editorial feedback while protecting quality and your own voiceThings to listen for:(00:00) Intro(01:34) Ryan’s early career and content creation journey(04:19) Navigating career challenges and feedback(09:37) Thank you to our sponsor, Navattic(11:04) Giving and receiving feedback(14:58) On being a team player(17:41) The importance of adaptability(31:18) The power of vulnerability in job hunting(35:39) Creating a strong online presence(41:57) Difficult conversations in leadership(51:16) Building professional relationshipsA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Ryan:LinkedIn: https://www.linkedin.com/in/ryan-mccready Demostack: https://www.demostack.com/ Connect 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, Kirk Reynolds, seasoned founder and now the creator of Wilder Retreats, opens up about the hardest conversations of his career. From telling his 55-person team that he was selling the company without sharing the real reason, to navigating the identity crisis that came when the acquirer shut it down, Kirk reflects on what it means to lead with honesty, even when fear and burnout make it tempting to hide.He also shares how blunt feedback about being a “people pleaser” reshaped the way he manages, and why processing failure and loss is just as important as chasing growth. This is a conversation about leadership, identity, and the courage it takes to be fully yourself when the stakes are high.In this conversation, you’ll learn:Why trusting your team with the truth builds deeper loyalty and respectHow to process the emotional toll of selling, losing, or reinventing a businessWhy intention and self-awareness can turn difficult feedback into lasting growthThings to listen for:(00:00) Intro(01:51) Kirk’s first steps into entrepreneurship(06:26) Building and scaling Discover Outdoors(08:31) Joining Abercrombie & Kent after exit(11:02) Tough feedback and personal growth(20:48) Balancing leadership with family life(25:26) Lessons from difficult conversations(26:04) Deciding to sell Discover Outdoors(28:14) Telling the team about the sale(30:31) Reflecting on honesty in leadership(34:27) The emotional weight of selling(37:48) Finding gratitude in new beginnings(40:03) Preparing mind and body for conversations(45:32) Setting bold, ambitious goalsResources:Connect with Kirk:LinkedIn: https://www.linkedin.com/in/kirk-reynolds/Wilder Retreats: https://discoverwilder.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coJoin Growth OS: https://deliveringvalue.co/growth-operating-systemHire Andrew as your coach: https://deliveringvalue.co/coaching

In this episode, Heidi Gibson, product and growth leader with stints at companies like GoDaddy, Typeform, and Bill.com, reflects on the pivotal lessons from her unconventional career path. From welding nuclear submarines to becoming VP of Product, Heidi shares how resilience, feedback, and self-awareness shaped her leadership journey.Heidi opens up about the realities of imposter syndrome, learning to present to executives, and navigating tough interpersonal conflicts as a manager, all while building a reputation as a trusted, people-first leader.In this conversation, you’ll learn:Why tailoring your communication for executives can change your career trajectoryHow to confront imposter syndrome with practical reframing techniquesWhy early intervention is the key to resolving team conflicts before they escalateThings to listen for:(00:00) Intro(01:18) Heidi’s early life and education(02:03) Starting career and moving into tech(02:49) Building Kmart e-commerce and ISP(04:37) Joining GoDaddy and career growth(05:20) Developing executive presentation skills(07:28) Thank you to our sponsor, Navattic(13:38) Imposter syndrome in growth teams(22:52) Starting a growth team at GoDaddy(24:30) Applying growth fundamentals successfully(27:54) Strategies for overcoming imposter syndrome(31:46) Navigating difficult workplace conversations(50:01) Seeking guidance and finding mentorshipA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Heidi:LinkedIn: https://www.linkedin.com/in/heidigibsonSubstack: https://heiditheproductgirl.substack.com/ Connect 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, 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