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

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

Devin Bramhall has been a VP of marketing, a CEO, a fractional CMO, and now an author, but none of that came without falling on her face multiple times.In this episode, Devin opens up about the mistakes that got her fired (twice), the time she unknowingly helped commit financial fraud, and the zero-tolerance plagiarism incident that backfired in the worst way. Through all of it, she’s held onto her belief that everything from leadership to content strategy is made up, and that’s exactly why you can rewrite the rules.Devin shares what it means to lead with bravery and curiosity, how ambition nearly derailed her career, and why making space for nuance, not just kindness, is the real growth path for leaders.Devin opens up about:- Getting fired from two leadership roles and what she did next- Why "servant leadership" backfired as a CEO- The difference between plans and actual strategy (and how she learned it the hard way)- Escaping financial fraud… and nearly getting questioned by the FBI- The power (and downside) of trying to make work feel “safe” for everyoneThings to listen for:(00:00) Intro (01:37) Devin's early life and entrepreneurial spirit (09:02) Transition to professional life (09:17) Thank you to our sponsor, ThriveStack (10:35) Entering the tech world (19:07) Discovering marketing and content creation (23:56) Major career mistakes and lessons learned (30:36) The strategy presentation disaster (31:25) Learning from painful experiences (32:59) Balancing leadership and empathy (34:44) The importance of boundaries (36:08) Handling plagiarism and setting expectations (37:58) Navigating leadership challenges (39:50) Transitioning to CEO (45:03) Dealing with job loss and resilience (48:35) The power of choice and perspective (54:24) Promoting bravery and curiosity (55:51) Everything is made up and that’s where your power isA huge thanks to this episode’s sponsor:ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Devin:LinkedIn: https://www.linkedin.com/in/devinbramhall/Devin’s official website: https://www.devinbramhall.com/Pre-purchase Devin’s book, B2B Content Marketing Strategy: https://www.amazon.com/B2B-Content-Marketing-Strategy-Media-First/dp/1398622516Connect 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 leave a high-paying product marketing role just before a massive acquisition?In this episode, I sit down with Jason Oakley—founder of Productive PMM and co-founder of Demo Dash—to unpack the bold career decisions that shaped his journey in tech. From leading product marketing at a hypergrowth startup to becoming a full-time creator and consultant, Jason shares the systems, mindset shifts, and lessons that helped him bet on himself.We talk about what it really takes to succeed in product marketing today—and why your biggest edge might come from making uncomfortable moves.If you're a product marketer, startup operator, or aspiring solopreneur, this one's for you.In this conversation, you'll learn:Why Jason left a senior product marketing role before a $2B exitHow he used LinkedIn to overcome imposter syndrome and grow his personal brandThe most common blind spots for PMMs moving into leadershipHow he turned his expertise into a scalable businessThings to listen for:(00:00) Intro(08:54) Jason's early life and entrepreneurial spirit(09:55) Thank you to our sponsors, Navattic & Appcues(12:40) Making hard career decisions as a product marketer(22:10) Real talk for young professionals in tech(28:24) Becoming a product marketing thought leader(30:23) Overcoming imposter syndrome on LinkedIn(32:39) Launching digital products as a PMM(38:29) Why practice beats perfection(43:39) Lessons from managing a team(55:13) Work-life balance and founder mindsetThis 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 Jason:LinkedIn: https://www.linkedin.com/in/oakleyjason/ Productive PMM official website: https://www.productivepmm.com PMM Files Newsletter: https://productivepmm.com/newsletter Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

Erin Balsa’s journey from teaching troubled teens to becoming a solopreneur in content marketing is anything but conventional. After a rewarding but challenging career in education, Erin found herself pivoting to tech marketing, working her way up to director roles at companies like Predictive Index. But the leap from the corporate world to running her own business wasn’t without its hurdles.In this conversation, Erin shares the unique challenges she faced transitioning from a public school teacher to a content strategist, the value of following her heart, and the lessons learned along the way. From managing high-stress jobs in social work to navigating the ups and downs of solopreneur life, Erin opens up about the importance of resilience, adapting to change, and staying true to yourself.Erin opens up about:The surprising path from teaching to techHow freelancing on the side led to a full-time businessThe challenges and rewards of working for yourselfWhy following your heart is the key to successNavigating life as a mom, entrepreneur, and content expertThings to listen for: (00:00) Dramatic rescue (01:05) Erin's unconventional career path (06:04) High school adventures and moving to Massachusetts (08:11) College decisions and career beginnings (09:46) Teaching and working with troubled teens (11:11) Thank you to our sponsors, Navattic & Appcues (13:49) From public school teacher to marketing maven (26:26) The solopreneur journey (28:55) Navigating career transitions (29:17) Freelancing success and challenges (30:16) Balancing family and work (34:16) The importance of mindset (43:59) Health challenges and business impact (48:36) AI concernsThis episode is presented by: Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/valueResources: Connect with Erin:LinkedIn: https://www.linkedin.com/in/erinbalsa/Website: https://hausofbold.com/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching