Anneka Gupta, Chief Product Officer at Rubrik and Stanford lecturer, shares her insights on navigating 'founder mode' dynamics in organizations. She discusses the importance of a positive mindset in team management and the delicate art of summarizing complex ideas. Anneka emphasizes effective decision-making, strategies for handling difficult colleagues, and the value of giving and receiving feedback. She also outlines pathways into product management, highlighting the significance of relationship-building and embracing a culture of learning.

Career transitions are filled with dozens of questions and pitfalls. Join Nikhyl Singhal and four product leaders from the Skip CPO group to discuss the challenges associated with big career decisions. Briana Ings (ClickUp), Anneka Gupta (Rubrik), Shirley Lin (Divvy Homes), and Annie Pearl (Calendly) bring dozens of years of leadership experience to the conversation, as they discuss when to leave (and not) leave your company, how to research the next opportunity, manage the interview process, and successfully interview and land that great next job. Don’t miss their inside tips on what they look for in interviews, common mistakes to avoid, and how they evaluate opportunities.Connect with The Skip: Newsletter | Podcast | CPO GroupFollow Nikhyl Singhal on LinkedIn | TwitterFollow Anneka Gupta on LinkedInFollow Annie Pearl on LinkedInFollow Brianna Ings on LinkedInFollow Shirley Lin on LinkedIn Full Show Notes:[0:00] Welcome to The Skip![1:30] Introducing our guests Anneka, Annie, Briana, and Shirley![3:30] Shirley Lin describes the company culture differences between Divvy Homes and Airbnb[6:00] The Skip Community for CPOs[8:30] “The head of product or a CPO role, it can be very lonely. You have a lot of pressure on you.”[12:00] Career errors, specifically in times of transitions into and out of roles[13:30] What to do when a company changes dramatically in size and/or in culture[14:30] “It was actually the point where I was frustrated, where I worked through those frustrations and helped solve those problems where I had the greatest growth. Both in terms of my title and getting responsibility, but also just from a personal level and having to figure out a way through those difficult times.”[17:30] Do good companies pass on good people?[21:30] Should you ask for feedback after an interview? Or after getting turned down for a position?[25:30] Pregnancy, life changes, and other times of absence[30:00] There really is no “one size fits all” for every career situation. Every person has a unique and personal journey to creating the career of their dreams[34:00] When looking for a new job, what is the process and where should you look first?[39:00] What does crafting a career framework look like?[45:00] A name with a well-known brand VS. a company that is a great unique fit for you[48:00] “It’s always easier to find a job when you have a job.”[54:00] Factoring in your seniority when thinking about finding a job (and leaving your current job)[1:01:00] Biggest pet peeves NOT to do in an interview![1:06:30] Interviewing and the “take-home” interview[1:13:00] How to decide which of your references to use for your interview and resume[1:15:00] Finding references for the company you are interviewing with or in other words interviewing in reverse.[1:16:30] Wisdom in determining if a company is worth joining or not[1:22:00] “Your boss doesn’t need to be your best friend.”  (And respect over friendliness)—-----The Skip podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. He coaches more than 100 executives, managers, and rising stars navigate important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life.

In this podcast episode, Nikhyl is joined once again by Anneka Gupta, Annie Pearl, Briana Ings, and Shirley Lin. The group explores the topics of how to recognize and recover from burnout, as well as to achieve a healthy work-life balance. They discuss the personal nature of burnout and how it's not simply a matter of comparing the two columns of “work” and “life.” The group suggests that if you're feeling burnt out or unsure if you're on the right path, it's time to reflect on your work and make changes to achieve a more balanced state. Nikhyl advises aiming for the "yellow" as a North Star and taking corrective action to prioritize tasks and achieve a healthier state.Overall, the episode provides practical advice for anyone experiencing burnout, emphasizing the importance of self-reflection and taking action to achieve a healthier work-life balance. Nikhyl's advice to aim for a more balanced state and prioritize tasks is a helpful reminder that perfect balance may be unattainable, but making incremental changes can lead to significant improvements in mental and emotional well-being.Thanks to this group of incredible women for joining and sharing their endless wisdom. We hope to have further discussions on other big career topics. Please share the podcast with your friends :) Connect with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | FacebookAnneka Gupta: LinkedIn | TwitterAnnie Pearl: LinkedIn | InstagramBrianna Ings: LinkedIn | InstagramShirley Lin: LinkedIn Full Show Notes:[0:00] Welcome to The Skip![0:10] Introducing our guests Anneka, Annie, Briana, and Shirley![0:30] Starting with Anneka Gupta, CPO of Rubik, Inc. - how does she handle “work/life balance?”[0:45] “I would phrase it not as ‘what do I have to fit into the box of my life’, but what do I want to fit into the box of my life?”[2:30] Brianna Ings - VP of Product at ClickUp - how does she handle work/life balance?[2:30] “I have a four month old daughter. And so the big thing for me is figuring out my new normal. So I really wanna prioritize spending time with my daughter, my husband, we used to have dinner together every night, and I wanna maintain that.”[4:00] How does Shirley Lin find joy in her life?[4:30] “my husband and I try to make sure we're connecting, but we confess, there are some nights where we kind of stand at the kitchen counter and we're eating a dinner of Salami, cheese and a glass of wine, and we're saying like, that's pretty good; good enough.“[5:30] Does being an experienced Project Manager help Annie Pearl, CPO of Calendly, decide how to effectively optimize her time?[9:00] As part of the new norm for Executives in the Zoom era, Briana vividly narrates her experience of multitasking; juggling between an important meeting, and keeping an eye on her baby daughter as she pumps breast milk.[11:30] Has anyone ever had to hold back professionally because of the need to balance time and commitments, even if it meant passing up a great opportunity at a top company?[15:45] In a graduation speech, Shonda Rhimes talked about the challenges of being a working parent. She said that whenever she appears to be succeeding in one area of her life, it often means she's struggling in another.[17:00] The additional pressures of being a working parents and the worry of the expectations of others[22:30] Many people are struggling with burnout and a sense of failure. To overcome this, it's essential to examine our relationship with work and make changes that will lead to a more fulfilling and sustainable path forward.[24:30] Nikhyl advises those feeling burnt out to aim for a more balanced state, using the "yellow" as a North Star. He emphasizes the importance of taking corrective action to prioritize tasks and achieve a healthier state, even if perfect balance is unattainable.[26:30] “There's always things that are going wrong, but can I find joy in growing and trying to get through the hardship?”[31:00] How do you make sure you prioritize yourself?[34:00] Briana struggled with saying "no" in her career, including a time when she was asked to travel for work despite not wanting to leave her daughter. She learned to prioritize her own desires and set boundaries by saying "no" when necessary, allowing her to feel more in control of her time.[36:00] Nikhyl shares his thoughts on the challenges of outsourcing and asks for personal tips from the group who are all working moms with busy schedules. Are there any "executive hacks"?[38:00] How does this group plan and schedule vacations?[46:00] Nikhyl advises leaders who are considering bigger, more demanding roles to check in and test their capacity before taking the plunge to avoid burnout.—-----The Skip podcast is designed to help tech professionals take control of their careers and achieve their professional goals. Hosted by Nikhyl Singhal, a successful founder, head of product, and executive, the podcast offers guidance on navigating important career decisions, management challenges, and personal crossroads.Nikhyl has helped hundreds of leaders in the tech industry maximize their happiness and professional life. He understands that career is one of the most critical parts of a person's identity and that many people struggle to navigate the complex landscape of job transitions, skills development, and long-term career planning.

Anneka Gupta, Chief Product Officer at Rubrik and former leader at LiveRamp, shares her insights from nearly two decades in tech. She reveals how LiveRamp skyrocketed from $30M to $200M ARR in just three years. Gupta discusses the balance between specialization and broad expertise, the significance of mentorship, and the complexities of migrating Fortune 500 clients post-acquisition. She also highlights the need for product managers to enhance their commercial sensibility and the value of diverse experiences in product leadership for effective decision-making.

Former CPO at Slack and Partner at IVP, Tamar Yehoshua, along with Anneka Gupta, CPO of Rubrik, share top secrets for building great products at SaaStr. They discuss building trust with CEOs, aligning on vision and strategy, staying focused on customer problems, navigating misalignment, and building great teams.