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

Diana Stepner shares three pivotal lessons from her journey transitioning from Product Manager to Leadership Coach. She discusses the importance of making your manager shine, navigating team dynamics, and why building trust is essential for career growth. Diana also reflects on why the characteristics that earned her praise early on in a company consistently turned into points of negative feedback.Diana opens up about:1. Why the same attributes that earned her praise could also create detractors 2. The challenges of being both overqualified and underqualified3. Learning how to balance self-driven success with the importance of recognizing and celebrating her team and managersThings to listen for:(00:00) Intro(03:22) Growing up in Silicon Valley and early exposure to the tech world(06:43) Transitioning from communications to product leadership(12:12) Struggling with being overqualified or underqualified(15:05) Learning how to make your manager shine(21:08) Thanks to our sponsor of this episode, Navattic(25:18) Handling challenging feedback and finding balance in leadership(30:47) When stepping aside wasn’t the right call(35:59) Rebuilding after tough feedback(41:24) Disbanding a future-focused team: the reality of working on the fringe(46:38) The power of slowing down and building trust with your teamResources:Connect with Diana:LinkedIn: https://www.linkedin.com/in/dianas/Product Gold: https://www.productgold.com/ People-First Leadership: https://dianastepner.substack.com/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coachingThanks to our amazing sponsor!Learn more about Navattic: http://navattic.com/value

Natalie Marcotullio, Head of Growth at Navattic, takes us in for a behind-the-scenes look into the process of launching their freemium motion. Going through the strategic reasons behind the shift and how it fits into their overall growth strategy, she reflects on the challenges of aligning the sales team, navigating risk, and measuring success in both the short and long term. Natalie also shares her perspective on the realities of product-led growth, the importance of soft-pitching ideas, and the unexpected lessons learned during the launch process.Natalie opens up about: The excitement and pressure of launching a freemium planThe value of soft-pitching product-led growth strategies over timeThe challenge of aligning a sales team to embrace PLG leadsThings to listen for: (00:00) Intro(03:17) Why Navattic chose freemium over a free trial model(05:53) The impact of freemium on pipeline and user conversion(08:00) Navigating internal buy-in and the importance of soft-pitching PLG(10:01) Testing and experimenting with lower-priced plans before going freemium(12:13) Aligning the sales team with the PLG motion and managing challenges(14:00) Modeling pipeline projections and the impact on MQL and PQL metrics(16:19) The role of customer support in managing increased user inquiries(18:42) Sales engagement with self-serve users and building trust(20:25) Reflecting on early success indicators and word-of-mouth growthResources:Connect with Natalie:LinkedIn: https://www.linkedin.com/in/natalie-marcotullio/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coaching

In this episode, Sarah Stockdale, founder of Growclass, shares her journey of overcoming burnout while leading growth teams at tech startups, addressing gender bias in the workplace, and building a thriving community for marketers. She reflects on how these experiences shaped her leadership style, approach to mental health, and entrepreneurship.Sarah opens up about:Witnessing a mass layoff and facing inappropriate comments from a coworkerPushing herself so hard that she had a panic attack on her way to a partnership meetingMaking the bold decision to take a risk on a startup over a secure job because she wanted to optimize for learning.Things to listen for:(00:00) The wonderful humans that shaped Sarah(06:39) Transitioning from a risk-averse upbringing to entrepreneurship(08:04) Turning down a safe job offer for a learning opportunity in a startup(11:26) Not true, but he said, “Sarah wasn’t fired because the boss wants to f*** her”(18:42) Thanks to our sponsor of this episode, Churnkey(20:33) “You get to decide your own worth and impact”(25:33) Busting the hustle = success myth(31:18) Liters of coffee, panic attacks, and burnout(39:10) Sarah’s therapist told her to quit her job(42:39) The impact of frentors (friend + mentor)Thanks to our sponsor!Learn more about Churnkey: https://churnkey.co/Resources:Connect with Sarah:LinkedIn: https://www.linkedin.com/in/sarahstockdale/ Growclass: https://www.growclass.co/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coaching

In this episode, Aakash Gupta shares his journey from a tech-savvy kid in Kalamazoo, Michigan, to a successful product manager and creator in the Product Growth space. He shares his tough feedback experiences, how he’s been able to overcome imposter syndrome, and how building a failed startup impacted his career. Aakash emphasizes the importance of self-care, emotional intelligence, and supportive mentorship in navigating corporate roles and leadership challenges. Aakash opens up about:How the collapse of a startup with 350k users reshaped his career and mindsetGetting specific feedback from a CMO that rattled his confidence Navigating a sticky situation when a team member on a PIP attempted to turn the entire company against him Things to listen for:(00:00) Intro(01:03) Aakash’s journey: From VP to Creator(03:08) Debate skills shaping his product career(05:29) First SaaS job building sports tools(08:07) Lessons from his failed startup(12:26) How mentorship changed his mindset(14:17) Tough feedback from a CMO at Threadup(16:33) The role of emotional intelligence in leadership(28:08) Handling a difficult pip situation(37:01) Dealing with imposter syndrome(44:06) Personal habits for productivity

Ramli John - Founder of Delight Path, shares core memories from his teenage years that inspired his entrepreneurial journey. Explores how attaching his worth to his achievements was making him act like a jerk. Shares stories from the worst boss he ever had. And discusses the toughest feedback that he’s received (and what he’s doing about it).Ramli opens up about:1. Seeing his dad get laid off after 15 years and how that shook his belief in relying on one employer.2. A CEO screaming at their CTO and team members, creating a toxic work environment that pushed Ramli to leave.3. Ramli's realization that he was emulating Steve Jobs' harsh behavior and treating people poorly, which led him to seek therapy for a healthier approach to work and life.Things to listen for:(00:00) Ramli’s new venture: Delight Path(06:26) Ramli’s core childhood memory: layoffs are brutal(08:23) The emotional impact of his dad's layoff and starting his consulting business(18:59) Pressure to rush and overwork leads to mistreatment of others(22:52) The importance of therapy in overcoming our flat slides(28:20) Discussing the need for quiet reflection and the book "Quiet" by Susan Cain(30:58) Ramli’s screamer CEO and sitting in a toxic work environment(38:52) Tough feedback and learning to speak up as an introvertResources:Connect with Ramli:LinkedIn: https://www.linkedin.com/in/ramlijohn/ Delight Path: https://www.delightpath.com/ Product-Led Onboarding Book: https://productled.com/book/onboarding Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Hire Andrew as your coach: https://deliveringvalue.co/coachingThanks to our amazing sponsors!Learn more about Appcues: http://appcues.com/value Learn more about Navattic: http://navattic.com/value

Emma Stratton, founder of Punchy and author of 'Make it Punchy,' shares her inspiring transition from creative writer to entrepreneur. She reflects on overcoming panic attacks tied to money and how life coaching propelled her forward. Emma discusses the pressure of immigrant family expectations and the challenges of toxic workplaces. She opens up about transforming her money mindset and conquering self-doubt while embracing her unique journey. This conversation highlights the power of following your heart and the importance of personal growth in finding success.

In this conversation, Georgiana Laudi, co-founder of Forget the Funnel, shares her background and journey into B2B SaaS. From working in her family’s retail florist business, to becoming the VP of Marketing at Unbounce, and advising a bunch of impressive companies. We explore some of the speed bumps and challenging moments in Gia’s journey along the way.Gia opens up about:Returning from maternity leave and learning someone had been hired above her.The challenges of managing a rapidly growing teamGetting feedback that she’s intimidatingThe importance of clear communication and transparencyThings to listen for:(02:30) Georgiana was influenced by her parents to become an entrepreneur(05:53) Her first business idea was selling martini glasses(11:13) She said “no” all the time because “who has time for that?”(15:21) Her advice to someone who is figuring out their personal brand(19:17) Someone was promoted above her when she was on maternity leave(32:07) Georgiana was told she was “extremely intimidating” by her team(36:52) She never holds back what she’s thinking(39:38) Take notes before confronting an underperforming employee(47:40) How Georgiana learned her communication skills(51:05) She wishes she had learned how to run a business earlier(53:48) Georgiana knows she needs a better work-life balance…Resources:Connect with Georgiana on LinkedInCheck out Forget The FunnelGet your copy of “Forget The Funnel” todayConnect with Andrew on LinkedInWork with AndrewLearn more about AppcuesLearn more about Navattic

In this conversation, Wes Bush, the founder and CEO of ProductLed, talks about his background and journey in the product-led growth space. We start by exploring his childhood, entrepreneurial drive, and transition into the tech world. Then, Wes reflects on being fired from his job at Vidyard, how that experience fueled him to start his own business, and how he navigates being a leader today. Along the way, we explored some of the speed bumps in his journey: from making tough decisions as a leader, maintaining emotional distance from his team, managing anxiety, and finding balance while traveling.In this episode, you’ll hear about:Why Wes was fired from Vidyard - and what he learned from the experienceHow he navigates being a leader today and approaches tough convos with his teamWhat gives Wes anxiety, and how he manages itThings to listen for:(01:21) Wes shares what his new book is about (03:48) His entrepreneurial spirit and itch from a young age(06:55) The moment Wes realized that any job that didn’t use his brain was a waste of time(11:25) When he got fired for challenging his leadership’s approach(17:53) Wes was told to stop sharing ideas(23:05) Being glad he got fired because it wasn’t the right environment to be in(30:30) Wes’s advice to a younger individual who needs to make a tough decision(35:46) His experience spending 19 weeks of traveling in 2023(41:00) Dealing with down days and anxieties(46:30) He describes how his job has opened new doors and opportunities(49:38) Which skill Wes wishes he worked on earlierResources:Connect with Wes on LinkedInCheck out ProductLedConnect with Andrew on LinkedInWork with AndrewLearn more about AppcuesLearn more about Navattic

In this episode, Talia Wolf, CEO and Founder of GetUplift, shares her experiences growing up in a family that valued hard work, her early jobs as a waitress and skydiver, her transition into the tech, marketing, and CRO world - and many of challenging moments along the way, including balancing her career and motherhood, the need to ask for help from your support system, and navigating critical feedback.In this episode, you’ll hear about:Staying in a CMO role she didn’t like because she was afraid to start her own businessBeing a woman in a male-dominated field and how she overcame her imposter syndromeReceiving a “slap in the face” piece of feedback from someone on her teamThings to listen for:[06:20] Talia's diverse career path, from skydiving to wedding planning and tech[12:48] The challenges of being a woman in a male-dominated industry[18:05] The creation of a supportive group among women to share vulnerabilities and experiences[24:37] How having children changed Talia's perspective on work-life balance[28:52] Learning from critical feedback and using it to improve as a leader[33:17] The importance of accepting and building upon experiences or letting go in business[37:44] Talia's upbringing and how it influenced her unconventional approach to CRO[42:56] Struggling with self-doubt and imposter syndrome when starting her own business[47:19] The impact of a supportive network in overcoming fears and boosting confidence[52:03] Balancing the identity of a driven career woman with motherhood[56:28] Learning to trust her team and achieve a better work-life balance after having childrenResources:Connect with Talia on LinkedIn: https://www.linkedin.com/in/taliagw/?originalSubdomain=ukGetUplift CRO Agency: https://getuplift.co/Connect with Andrew on LinkedIn: https://www.linkedin.com/in/andrewcapland/Work with Andrew: https://deliveringvalue.co/get-startedLearn more about Appcues: http://appcues.com/value

Yuriy Timen, a SaaS advisor and solopreneur, shares his unique journey from finance to leading tech companies like Grammarly, Canva, and Airtable. He reflects on how his upbringing during the Soviet Union's collapse shaped his strong work ethic and values. Yuriy opens up about career mistakes, overcoming self-doubt, and the importance of empathy in leadership. He discusses the lessons learned from tough feedback and highlights the significance of intentional networking and work-life balance, aiming to be 'empathetically intense' in his professional relationships.