{"podcast":{"title":"The Skip Podcast","slug":"the-skip-podcast-5971055","podcast_index_feed_id":5971055,"rss_url":"https://api.substack.com/feed/podcast/92860.rss","website_url":"https://theskip.substack.com/podcast","image_url":"https://substackcdn.com/feed/podcast/92860/2324e9fa0532ff478716907ce9057e09.jpg","author":"Nikhyl Singhal","episode_count":51,"summary":"Career advice for tech professionals","last_synced_at":"2026-06-11T04:19:45.900997+00:00","page_url":"https://stenobird.com/podcast/the-skip-podcast-5971055"},"episode":{"title":"10 Job-Search Rules That Just Broke","slug":"10-job-search-rules-that-just-broke","published_at":"2026-05-20T14:00:00+00:00","page_url":"https://stenobird.com/podcast/the-skip-podcast-5971055/10-job-search-rules-that-just-broke","show_page_url":"https://stenobird.com/podcast/the-skip-podcast-5971055","url":"https://theskip.substack.com/p/10-job-search-rules-that-just-broke","audio_url":"https://api.substack.com/feed/podcast/196624701/2723af2ab667dd9dc6d37b8d41d7ba32.mp3","summary":"In this episode, I sit down with three senior product leaders who just came through the senior job search in this market: Dana Ingraham from Harvey, Briana Ings from Atlassian, and Pei-Chin Wang, who’s founding her own company. While the search itself continues to be exhausting, I was surprised to learn that everything else has changed: the playbook is completely out of date, in at least ten different ways. All three reported feeling something I’ve started calling smiling exhaustion: working hard, going long, and surprised by how good it feels. If you're a senior leader, sitting in a stable role debating a move, weighing how you can ride the AI shift, or quietly wondering if founding finally belongs on your career path, this conversation is for you. Key topics: • How AI agents have flipped the first year at a new role from headwind to tailwind, and are even bringing joy to the first year of a new role • The new founding math: fast, fun, and skill-additive, with a much lower downside than it used to be • How to navigate the job search when you don’t live in San Francisco—and remote jobs are dwindling • Why structured AI learning is the wrong move, and what to build instead, so your fluency is hard to fake • How to signal hard boundaries to a new boss, and differentiate between real respect and performative virtue-signalling • Why holding your professional identity loosely matters when the role of senior leader is getting reformatted in real time Referenced: • Airbnb: https://www.airbnb.com/ • Atlassian: https://www.atlassian.com • Claude Code: https://claude.com/product/claude-code • Harvey: https://www.harvey.ai • Loom: https://www.loom.com • Modern Animal: https://themodernanimal.com Brought to you by: • Guru—Trusted knowledge for every AI tool and team: https://www.g…","meta_description":"In this episode, I sit down with three senior product leaders who just came through the senior job search in this market: Dana Ingraham from Harvey, Brian…","key_points":[],"chapters":[],"topics":[],"duration_seconds":3561,"processing_state":"not_requested","actions":[{"name":"request_transcript","method":"POST","url":"https://stenobird.com/v1/public/podcasts/the-skip-podcast-5971055/episodes/10-job-search-rules-that-just-broke/transcription-requests","description":"Idempotently request low-priority transcript generation for this episode."},{"name":"read_markdown","method":"GET","url":"https://stenobird.com/podcast/the-skip-podcast-5971055/10-job-search-rules-that-just-broke.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}