Delivering Value: Lead like the top 1% in growth, marketing, & product

In this episode, Luke Wallace, founder-turned-fractional growth leader and former Chief Growth Officer at Zipline Education, opens up about the moment high-visibility mistakes hit customers and forced him to rebuild his operating system. He shares the CEO feedback that drew a line between being nice and being kind, why he chose to hire an executive coach instead of switching jobs, and how he moved from heroic execution to scalable systems that don’t break under pressure.Luke talks about over-communicating up and across with data, rebuilding trust after public misses, and setting binary outcomes that make expectations unambiguous. He also gets tactical on giving direct feedback without becoming a jerk, navigating team changes when a beloved generalist no longer fits the stage, running customer interviews to unlock stalled growth, and managing imposter syndrome as the stakes rise.In this conversation, you’ll learn:How to turn painful, public mistakes into long-term fuel for resilience, credibility, and trust.How to use systems, documentation, and managing-up rituals to scale beyond “hero mode.”How to build a support loop (clear feedback, mentors, and customer interviews) to stay grounded and effective.Things to listen for:(00:00) Intro(02:00) Luke’s early dream of becoming a pilot(03:22) Into tech via school IT program(05:00) Startup wins, scrappy realities(09:15) Thank you to our sponsor, Navattic(12:23) Direct feedback versus being nice(23:54) Building a data-backed recommendation(24:27) Handling high-stakes leadership talks(25:01) Working through imposter syndrome(27:19) Systems for scale over heroics(30:19) Why Luke hired an executive coach(34:42) The hardest conversations as a manager(36:45) When the team and role evolve(40:00) Giving clear, actionable feedback(40:32) One-to-one coaching offer from Andrew(43:20) Lessons learned from real failures(44:26) Customer interviews as the unlock(46:34) Key takeaways and ways to connectA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Luke: https://www.linkedin.com/in/lukewallace805/ 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, Diego von Söhsten, immigrant operator, product leader, and Director of Product Growth at Jobber, opens up about the “after you’ve already proven yourself” flavor of imposter syndrome. He recounts a moment when a senior executive publicly tore down his work (and blamed his accent), and how he rebuilt confidence, created alignment without air cover, and ultimately earned a promotion while shipping a freemium foundation that mattered when COVID hit.Diego talks about learning to over-communicate up and across, turning anti-role-models into fuel for the leader he wanted to become, and building a growth org that prized clarity, storytelling, and psychological safety. He also shares practical ways underrepresented builders can find mentors, ask for help without shame, and protect their inner game when the ground keeps moving.In this conversation, you’ll learn:How to turn painful feedback and bias into long-term fuel for resilience and credibility as a leader.How to use storytelling and structured communication to create alignment and influence without authority.How to build a support network of mentors, peers, and self-awareness to stay grounded under pressure.Things to listen for:(00:00) Intro(01:53) Diego's career beginnings(06:01) Diego’s experience being criticized for his accent(10:43) Thank you to our sponsor, Navattic(15:05) Overcoming and growing from adversity(24:04) Understanding user drop-off and alignment(24:46) The power of storytelling in product management(26:38) Building and leading effective teams(29:31) Diego’s advice to those struggling to find their place(33:13) Working with a good team member who just couldn’t fit(44:58) Balancing passion for work and professional boundariesA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Diego: www.linkedin.com/in/diego-vs Diego’s official website: https://www.vonsohsten.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, Kelly Gillease, two-time CMO, daily meditator, and former search marketer turned executive leader, talks candidly about the inner game behind durable leadership. She traces her path from debating podiums to performance marketing at Hotwire, through scale-up chaos at NerdWallet and post-acquisition life at TripAdvisor/Viator—sharing how mindfulness, therapy, and a “true, kind, necessary” feedback filter helped her steady teams when everything felt on fire.Kelly opens up about a tough DEI misstep, how she took the feedback without getting defensive, and why she chose to “run toward” hard conversations instead of retreat. She gets tactical about cross-functional influence (and why debate training still matters), building reputations through appreciation rituals, and choosing environments that actually fit you, even when the shinier title says otherwise.In this conversation, you’ll learn:- How to use “true, kind, necessary” to deliver (and receive) feedback that lands, and what to do when it doesn’t- Practical rituals for team resilience: appreciations, mindful pacing, and calmly problem-solving without losing speed- How to pick the right work environment for your wiring. and navigate the politics, pacing, and trade-offs of big-co vs. startup lifeThings to listen for:(00:00) Intro(01:47) Kelly’s roots, early influences, and formative values(03:51) Where creativity meets ROI: loving both art and math(09:05) Thank you to our sponsor, Navattic(13:50) Scripts and mindsets for hard feedback and conflict(24:23) Owning a DEI misstep, pausing, and moving forward(29:22) Gratitude rituals at work and at home that build morale(39:58) Why big-company bureaucracy wasn’t the right fit(44:20) Radical honesty, necessary conversations, real growthA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Kelly: https://www.linkedin.com/in/kellythepea/ 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, 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