Discussing career transitions with Heads of Products from Calendly, ClickUp, Divvy Homes, and Rubrik

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.

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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)

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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.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com