Delivering Value with Andrew Capland

Andrew Capland
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Delivering Value with Andrew Capland

Candid conversations with SaaS growth leaders about the setbacks, feedback, and self-doubt that almost derailed their careers - and instead shaped their path to success. Hosted by Andrew Capland, former Head of Growth Wistia, Postscript - deliveringvalue.co

  1. She Tried to Be the “Nice” CEO—Here’s What Went Wrong (Devin Bramhall)

    6D AGO

    She Tried to Be the “Nice” CEO—Here’s What Went Wrong (Devin Bramhall)

    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 everyone Things 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 is A 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/1398622516 Connect with Andrew: LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.co Hire Andrew as your coach: https://deliveringvalue.co/coaching

    1h 1m
  2. Why This Product Marketing Expert Walked Away From a $2B Exit—With No Regrets (Jason Oakley)

    JUN 4

    Why This Product Marketing Expert Walked Away From a $2B Exit—With No Regrets (Jason Oakley)

    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 mindset This 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

    1h 1m
  3. She Used to Work With Teens in Crisis—Now She Runs a Content Business (Erin Balsa)

    MAY 28

    She Used to Work With Teens in Crisis—Now She Runs a Content Business (Erin Balsa)

    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 concerns This 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 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

    1 hr
  4. How a Career-Defining Mistake Shaped This CEO (Ty Magnin)

    MAY 20

    How a Career-Defining Mistake Shaped This CEO (Ty Magnin)

    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 impact A 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

    55 min
  5. VP of Product: The Career-Altering Feedback No Leader Wants to Hear (Elena Luneva)

    MAY 13

    VP of Product: The Career-Altering Feedback No Leader Wants to Hear (Elena Luneva)

    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 next How growing up as an immigrant shaped her relationship with vulnerability Why psychological safety and hiring rigor became non-negotiables for her as a leader Things 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 forward This 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/elenaluneva Substack: https://elenaluneva.substack.com/about Elena’s Maven course: https://maven.com/elena-luneva/business-impact Connect with Andrew: LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.co Hire Andrew as your coach: https://deliveringvalue.co/coaching

    52 min
  6. Why VP of Marketing is a Brutal Job - Even When You're Crushing It (April Dunford)

    MAY 6

    Why VP of Marketing is a Brutal Job - Even When You're Crushing It (April Dunford)

    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/3QOKHtT Fullstory: Behavioral data that empowers - https://fullstory.com/value April 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 life How imposter syndrome nearly kept her from recognizing her true superpower What she learned from one of her toughest client sessions Things 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 skills Resources: 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.co Hire Andrew as your coach: https://deliveringvalue.co/coaching

    1h 7m
  7. “You Haven’t Built Anything”: The Feedback That Triggered Imposter Syndrome (Amaan Nathoo)

    APR 29

    “You Haven’t Built Anything”: The Feedback That Triggered Imposter Syndrome (Amaan Nathoo)

    Amaan Nathoo is a former VP of Growth turned fractional growth advisor, with deep experience navigating fast-growing startups and the emotional rollercoaster of career transitions. In this episode, Amaan opens up about how a founder’s offhand remark early in a new role shook his confidence, how imposter syndrome shows up in subtle ways, and why he ultimately chose to walk away from a full-time leadership role to build a consulting practice from scratch. Amaan opens up about: - What happened when a founder questioned if he’d ever “built anything” - Why unchecked frustrations almost cost him his job—and how he turned it around - How childhood dynamics and survival mindsets shaped his risk tolerance Things to listen for: (00:00) A founder’s surprising comment and redefining what it means to build (00:22) Meet Amaan: from durable growth roles to going solo (07:14) Learning empathy and resilience through door-to-door sales (09:26) Thank you to our sponsors, Navattic & Appcues (12:24) A failed startup and the founder who believed in him anyway (15:56) The moment Amaan realized his work environment wasn’t working (20:12) Building is subjective—so is value (24:29) Dealing with imposter syndrome and second-guessing yourself (28:50) A recurring early-career mistake: letting frustration fester (43:36) Navigating the decision to leave a role (52:44) Knowing when discomfort is productive and when it’s not (56:06) Time, autonomy, and the dream of doing work you love (59:03) The value of perspective and what makes a truly great leader (01:00:52) Book recs: Trillion Dollar Coach and Principles by Ray Dalio This 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 Amaan: LinkedIn: https://www.linkedin.com/in/amaannathoo/ Website: https://revenuegrowth.tech/ Connect with Andrew: LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.co Hire Andrew as your coach: https://deliveringvalue.co/coaching

    1h 3m
  8. He Got Laid Off With a Baby on the Way - Then Became One of the World's Best Content Marketers (John Bonini)

    APR 23

    He Got Laid Off With a Baby on the Way - Then Became One of the World's Best Content Marketers (John Bonini)

    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/valueJohn Bonini, founder of Content Brands, opens up about his early struggles building an audience—before realizing the power of original thinking, consistency, and fully owning his voice. From navigating burnout to taking a bold leap into his own creative studio, John shares how publishing online changed the trajectory of his career and personal life. John opens up about: - The moment that sparked his shift from passive creator to publishing consistently - How being a parent shaped his time management and career goal - The power of being “creatively selfish” and trusting your unique voice Things to listen for: (00:00) The unexpected layoff (03:17) The power of content marketing (07:39) Thank you to our sponsors, Fullstory & AppUnite (10:15) The Lady Gaga incident (15:38) Navigating career challenges (28:39) The decision to join Databox (34:03) Going solo: The leap to full-time consulting (36:53) First week wins (38:51) Building resilience and overcoming doubts (40:54) Navigating early career challenges (50:53) The importance of preparation (58:55) Handling tough conversations (01:10:40) Building legacy through personal growth Resources: Connect with John: LinkedIn: https://www.linkedin.com/in/jbonini/ Content Brands: https://www.contentbrands.co/ Connect with Andrew: LinkedIn: https://www.linkedin.com/in/andrewcapland/ Free 5 day growth leadership program: https://deliveringvalue.co/growth-leadership-toolkit Substack: https://media.deliveringvalue.co Hire Andrew as your coach: https://deliveringvalue.co/coaching

    1h 19m
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Candid conversations with SaaS growth leaders about the setbacks, feedback, and self-doubt that almost derailed their careers - and instead shaped their path to success. Hosted by Andrew Capland, former Head of Growth Wistia, Postscript - deliveringvalue.co

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