Delivering Value with Andrew Capland

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

Ty Magnin, former marketing leader at Appcues and UiPath, now CEO at Animalz, made a mistake that could’ve ended his career.While leading a team at UiPath, he accidentally uploaded a private doc that outlined a power shift — and the wrong person saw it. What followed was a firestorm of Slack messages, a panic spiral, and a career-defining moment of humility and growth.In this conversation, Ty shares the leadership mistakes that almost got him fired, the ambition that fueled (and nearly derailed) his rise, and the inner work that helped him become a more people-first CEO.Whether you're a VP, Head of Marketing, or startup operator navigating corporate politics, you'll see yourself in this one.Ty opens up about:How to recover from a mistake at workWhat not to do when ambition clouds your judgmentThe political landmine Ty triggered with one doc uploadWhy money didn’t bring fulfillment after a $50B IPOHow to define success on your own termsThings to listen for:(00:00) Intro(02:44) Growing up fast: raising a kid while studying poetry and film(08:14) Early confidence, creative roots, and startup appeal(08:54) Thank you to our sponsor, Fullstory (14:30) Leaving Appcues for a leap in comp, lifestyle, and pressure(21:00) Learning the hard way who your stakeholders really are(32:00) Uploading a private doc… and the aftermath(40:22) The IPO money moment that changed his definition of success(47:35) The surf van, parenting balance, and CEO tension(53:01) Coaching others, defining legacy, and measuring impactA huge thanks to this episode’s sponsor:Fullstory: Behavioral data that empowers - https://fullstory.com/valueResources:Connect with Ty:LinkedIn: https://www.linkedin.com/in/tylermagnin/Animalz official website: https://www.animalz.co/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

Elena Luneva, VP of Product at GoFundMe, opens up about the hard-earned lessons that shaped her leadership journey—from navigating layoffs early in her career to building a business unit from scratch at Nextdoor. In this episode, Elena shares how receiving career-altering feedback about her confidence changed her trajectory, why moving from “being right” to “being effective” became a career mantra, and how she learned to lead through massive uncertainty.Elena opens up about:The feedback that hit her “like a freight train” and what she did nextHow growing up as an immigrant shaped her relationship with vulnerabilityWhy psychological safety and hiring rigor became non-negotiables for her as a leaderThings to listen for:(00:00) Learning tough career lessons through feedback(01:16) Growing up between Russia, Canada, and New York(04:29) Early signs of curiosity and connecting different worlds(07:01) Perfectionism and cultural expectations(11:20) Building a new business unit at Nextdoor(13:39) Processing painful feedback and working with a coach(15:35) The shift from being “right” to being “effective”(29:08) A hiring mistake and its fallout(35:23) How to speak up when it’s hard(40:37) Leading a business unit through the COVID-19 crisis(49:04) What’s missing from a LinkedIn-perfect career story(50:18) How reframing fear helped Elena move forwardThis 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 Elena:LinkedIn: https://www.linkedin.com/in/elenalunevaSubstack: https://elenaluneva.substack.com/aboutElena’s Maven course: https://maven.com/elena-luneva/business-impactConnect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

This episode is presented by:AppUnite: The right dev partner can make or break your product. AppUnite embeds with your team to build apps that scale. - https://bit.ly/3QOKHtTFullstory: Behavioral data that empowers - https://fullstory.com/valueApril Dunford, author and globally recognized expert on product positioning, reflects on her unconventional journey from aspiring doctor to tech executive to in-demand consultant. In this episode, she shares what made her finally walk away from VP marketing roles, how she reinvented her career in her late 40s, and why teaching, not advising, is at the heart of her business today.April opens up about:The burnout and politics that pushed her to “fire herself” and leave startup lifeHow imposter syndrome nearly kept her from recognizing her true superpowerWhat she learned from one of her toughest client sessionsThings to listen for:(00:00) The challenges of a VP of Marketing role(08:14) Breaking into product marketing(09:25) Thank you to our sponsors, AppUnite & Fullstory (12:01) Navigating career decisions and public speaking(19:33) Transitioning to consulting(31:38) The importance of disqualifying bad clients(33:39) Handling political traps in big companies(38:45) Transitioning from startups to big corporations(42:14) The importance of management training(45:47) Navigating layoffs and job security(54:59) Managing up and leadership skillsResources:Connect with April:LinkedIn: https://www.linkedin.com/in/aprildunford/April’s official website: https://www.aprildunford.com/ April’s newsletter: https://www.aprildunford.com/newsletter April’s podcast: https://www.positioning.show/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching