Navigate Complex Career Decisions with Expert Guidance

"I'm in final rounds for a CPO role at a growth-stage fintech (300M revenue, 30% YoY growth). The role involves building a 40-person product team. I need guidance on compensation negotiation - specifically around equity terms, acceleration clauses, and what's typical for CPO contracts. I'm also curious about red flags to watch for in the offer structure and how to approach the vesting schedule discussion."

"After 15 years in product management at companies like Google and Meta, I'm considering transitioning to consulting. I've been doing some advisory work and really enjoy the zero-to-one challenges. My concern is whether I can build this into a sustainable full-time income. I'm particularly interested in understanding how to price my services, find consistent clients, and whether focusing on specific verticals (like fintech or marketplaces) would be more lucrative than being a generalist."

"I'm evaluating a VP of Product role at a small-cap public tech company. I'm torn between this opportunity and staying at my current big tech job where I have good work-life balance but limited growth. How should I weigh factors like liquid compensation vs equity upside, the company's competitive position, and the reality of working in a resource-constrained environment? Also concerned about whether small public companies offer the same career acceleration as pre-IPO startups."

"I recently returned from parental leave and made a hasty job change to what seemed like a 'parent-friendly' company, but it turned out to be a poor fit. Now I'm job searching again and struggling to recalibrate my decision framework. How do I balance my need for flexibility with my career ambitions? I'm particularly worried about over-indexing on work-life balance and ending up in another suboptimal role. What signals should I look for to assess if a company truly supports working parents beyond just saying they do?"

"I spent the last 3 years at a B2B HR tech startup after a decade in banking and fintech. Now I want to pivot back to fintech but I'm worried the industry has evolved without me. The job market feels tough and I'm concerned about being seen as someone who 'couldn't make it' in fintech. Should I target roles where I can leverage my diverse background, or focus on 'crushing' a more traditional fintech role to re-establish credibility? How do I tell my story in a way that makes my non-linear path an asset?"

"I have 20 years of experience across scale-ups and big tech. For the past 18 months, I've been consulting and building AI-native applications while co-parenting an infant. The independent path is rewarding but not financially sustainable. Should I double down and try to raise funding, or return to a senior product leadership role? I'm also considering geographic arbitrage - taking a remote role from a lower cost area. The tech job market at senior levels feels brutal right now. How do I make this decision when I need both financial stability and professional fulfillment?"