Dealing with role ambiguity with Shirin Bradfield (Optimal Workshop)

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

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 toleranceThings 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 DalioThis 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.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/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 voiceThings 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 growthResources: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-toolkitSubstack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

Maja Voje, a go-to-market consultant and bestselling author of The Go-To-Market Strategist, has worked with over 800 companies, from Google and Rocket Internet to startups and scale-ups. But even with an impressive career, she’s had to make tough calls—like recognizing when it’s time to walk away from a role.Maja opens up about:- The fear of overstaying vs. leaving too soon- How she evaluates whether to stick with a role or move on- Lessons from working with limited resources and competing against well-funded companiesThings to listen for:(00:00) The challenge of knowing when to quit(00:47) Growing up in Slovenia and early ambitions(03:17) Discovering growth hacking and marketing(06:52) Challenges and successes in marketing(08:17) Thank you to our sponsors, Navattic & Appcues(15:33) Navigating career transitions and advice(32:49) Overcoming financial constraints in business(35:12) Advice for professionals facing constraints(36:51) The importance of proactivity and learning from mistakes(40:54) Balancing work, health, and personal life(53:32) Navigating social media and business strategies(59:18) Embracing abundance and supporting othersThis 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 Maja:LinkedIn: https://www.linkedin.com/in/majavoje/Maja’s GTM Solutions: Best-selling Book, Checklists, GTM Bootcamp: https://gtmstrategist.comWeekly newsletter (Substack): https://knowledge.gtmstrategist.com Free resource: ⚡Go-to-Market Power Hour https://gtmstrategist.com/resources/power_hour/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

Yue Zhao, former PM at Meta and Instagram, and Founder of The Uncommon Executive, shares how she struggled with promotions early in her career—until she learned how to navigate corporate politics. From feeling stuck in a startup to learning how influence and perception shape career growth, Yue opens up about the pivotal lessons that changed her approach and ultimately helped her scale to leadership roles in tech.Yue opens up about:-The moment she realized working harder wasn’t enough to get promoted-How she learned to build influence and position herself for leadership-The power of framing, buy-in, and playing the game strategicallyThings to listen for:(00:00) People think politics is a bad thing (02:47) Childhood interests and parental influence (07:34) Thanks to our sponsor, Fullstory(09:24) Career beginnings and consulting at McKinsey (13:18) Joining Thumbtack and early challenges (19:50) Navigating career frustrations and promotions (25:41) Understanding workplace politics (35:30) Questioning career progression (36:36) Efforts to get promoted (38:36) Building influence and strategy (41:05) Creating forums for strategic conversations (44:36) The Head of Growth Leadership Scorecard(45:38) Transition to Instagram (57:46) When to lead vs. when to listen (1:07:35) Habits for high performance This episode is presented by:Fullstory: Surface User Sentiment with Behavioral Data - https://fullstory.com/valueResources:Connect with Yue:-LinkedIn: https://www.linkedin.com/in/yuezhao/-Substack: https://news.yuezhao.coach/-Yue Zhao Coaching: https://www.yuezhao.coach/Connect with Andrew:-LinkedIn: https://www.linkedin.com/in/andrewcapland/ -The Head of Growth Leadership Scorecard: https://andrew-dkbyiqi6.scoreapp.com/-Substack: https://media.deliveringvalue.co-Hire Andrew as your coach: https://deliveringvalue.co/coaching

Mackenzie Hughes, Co-Founder of GoldHue and former Product Ops Leader, shares how she navigated career pivots, overcame self-doubt, and ultimately built a business rooted in purpose. From knocking on doors as a political canvasser to leading product teams at high-growth startups. Mackenzie reflects on the pressures of leadership, the identity shifts that come with climbing the corporate ladder, and the moment she realized she had been contorting herself to fit an environment that was never built for her.Mackenzie opens up about:- The gut feeling she ignored when stepping into a leadership role - Why corporate “professionalism” often reinforces bias and how she stopped playing the game- The hard-won lesson that success isn’t about making more money, it’s about aligning with what actually mattersThings to listen for:(00:00) Changing yourself to fit in (02:06) Why Mackenzie values vulnerability and honest conversations (08:45) Early career: Political and nonprofit campaigns (09:10) Thanks to our sponsor, Fullstory(14:30) Overcoming fear of public speaking (23:35) A career low point: Feeling disillusioned in her last role (29:19) A coach’s insight that helped Mackenzie find authenticity (32:32) Enabling the patriarchy vs. staying true to herself (36:29) The challenge of under-resourcing and lack of support (46:38) Losing herself in a money-driven mindset (51:00) Creating a vision board and defining her ideal state This episode is presented by:Fullstory: Surface User Sentiment with Behavioral Data - https://fullstory.com/valueResources:Connect with Mackenzie::LinkedIn: https://www.linkedin.com/in/mackenzierhughes/ GoldHue: https://www.goldhue.co/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coaching

Pranav Piyush, CEO and Co-Founder of Paramark, shares the moments that shaped his journey from scaling a YC startup to facing a co-founder breakup and battling imposter syndrome while fundraising. He reflects on the tough feedback that shook his confidence at Dropbox, the mindset shifts that kept him moving forward, and why resilience isn’t just about working harder, it’s about trusting your instincts, staying clear-eyed under pressure, and embracing the uncomfortable moments that lead to real growth.Pranav opens up about:The wake-up call that forced him to rethink how he navigated internal politicsHow his first startup experience ended in heartbreak but led to an even bigger opportunityWhy founders need a “reality distortion field” to sell their visionThings to listen for: (00:00) Pranav discusses his experience with YC and an unexpected rift with his co-founder (03:39) Developing persuasive skills through debate and their benefits in tech leadership (06:29) The accidental start of an entrepreneurial journey with a student job platform (08:05) Thanks to our sponsor Fullstory (10:08) Receiving tough feedback at Dropbox and its personal impact (24:27) The highs and lows of Pranav's first venture and parting ways with his co-founder (38:21) Viewing setbacks as part of the journey to success (39:36) Handling imposter syndrome during a challenging fundraising period (49:18) The role of manifestation and goal-setting in Pranav's life and work This episode is presented by: Fullstory: Surface User Sentiment with Behavioral Data. - https://fullstory.com/valueResources: Connect with Pranav: LinkedIn: https://www.linkedin.com/in/pranavp/ Paramark: https://paramark.com/Connect with Andrew: LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coaching

Tiffany DaSilva – SEO and PPC consultant, Founder of DaSilva Consulting, and educator with programs at McMaster University and Grow Class, shares the defining moments that shaped her career and personal growth.From breaking into the male-dominated tech space to starting her own business after a near-death experience, Tiffany reflects on her journey with honesty and resilience. With 19 years of experience, over 500 websites, and 300 clients under her belt, she opens up about her struggles, victories, and the lessons learned along the way.Tiffany opens up about:Walking out of a toxic unicorn startup and rebuilding her career from scratchThe importance of creating a “Shine Crew” for support and accountabilityHandling harsh feedback and learning to discern what’s worth changingThings to listen for: (00:00) Tiffany standing up for herself after being overlooked (04:36) Joining a unicorn startup and facing cultural clashes (10:28) Thanks to our sponsors, Navattic & Appcues (21:05) Building a “Shine Crew” to create a support network (26:47) Handling tough feedback and deciding what to change (36:20) Breaking barriers in a male-dominated industry (47:49) Aligning your business with personal values (53:22) Managing imposter syndrome and rebuilding confidence (56:55) Using mindfulness to reset after tough moments (59:07) Listening to her gut and charting her own pathThis episode is presented by: Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/valueResources: Connect with Tiffany: LinkedIn: https://www.linkedin.com/in/tiffanydasilva Instagram: https://www.instagram.com/thetiffdasilva/ DaSilva Consulting: https://www.tiffanydasilva.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

Austin Hay, co-founder of Clarify, shares candid insights into his journey as a startup leader. From navigating a messy exit to overcoming personal loss, Austin reflects on the experiences that have shaped him both professionally and personally.Austin opens up about:His struggles with taking work too seriously and learning to balance ambition with self-careNavigating bereavement while managing a demanding roleBuilding resilience through challenging career transitions Things to listen for: (00:00) Taking everything way too seriously (06:27) Growing up as an academic nerd and entrepreneurial roots (15:22) Lessons from leaving a startup the wrong way (25:50) Coping with personal loss while working in high-pressure environments (30:14) Thanks to our sponsors for this episode, Navattic & Appcues (31:56) Redefining success and finding balance in his professional journey(41:47) Advice for founders on balancing ambition with well-beingThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/value Connect with Austin: LinkedIn: Austin HayClarify: https://getclarify.ai/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

Ciara Peter, SVP of Product at Robin, opens up about the career highs and lows that shaped her leadership journey.From navigating imposter syndrome to overcoming burnout in Silicon Valley startups, Ciara shares the pivotal lessons that helped her find confidence and clarity. She takes us behind the scenes of her time at Salesforce, the mistakes that taught her the most, and how prioritizing trust and alignment transformed her career. Ciara opens up about:Facing imposter syndrome as a new managerHer viral LinkedIn post showcasing 15 years of struggle behind her successAlmost crashing a live demo in front of 10,000 peopleHow working at an early-stage startup impacted her mental healthBuilding trust as a leader and balancing strategic conviction with collaborationThings to listen for: (00:00) Ciara’s early career struggles and viral LinkedIn post (04:09) The turning point that led to her role at Salesforce (12:05) Breaking the code at Dreamforce and the lessons learned (24:26) Why early-stage startups took a toll on her mental health (30:44) How imposter syndrome shaped her leadership style (39:57) Navigating trust and alignment as an SVP Connect with Ciara: LinkedIn: https://www.linkedin.com/in/ciarapeter/Connect with Andrew: LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: media.deliveringvalue.co Hire Andrew as your coach: https://deliveringvalue.co/coaching