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 life

Things 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 growth

A 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.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join 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 role

• Practical ways to productize your “receipts” with AI or automation so your wins market themselves

• How to deliver and absorb tough editorial feedback while protecting quality and your own voice

Things 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 relationships

A 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.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join 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 respect

• How to process the emotional toll of selling, losing, or reinventing a business

• Why intention and self-awareness can turn difficult feedback into lasting growth

Things 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 goals

Resources:

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.co

Join Growth OS: https://deliveringvalue.co/growth-operating-system

Hire 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 trajectory
• How to confront imposter syndrome with practical reframing techniques
• Why early intervention is the key to resolving team conflicts before they escalate

Things 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 mentorship

A 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/heidigibson

Substack: https://heiditheproductgirl.substack.com/

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join 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 success

Things 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 relatability

A 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.co

Reed Between The Lines (podcast): https://www.thereeder.co/content-hub/podcast

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join 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 leadership
• How to navigate the emotional toll of layoffs, leveling, and managing up
• Why clarity of expectations keeps your career evolving

Things 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 time

This 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.co

Hire 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 leading
• How to build healthy boundaries with work identity
• What it takes to speak up without burning out

Things 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 identity

A 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.co

Hire 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 skills
• How “qualified” and “capable” are two entirely different bets
• What changes when you stop being the hero and start being the glue

Things 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 environment

This 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.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching