A focused mentorship session for engineers and tech professionals navigating a transition, preparing for a stretch opportunity, or building a professional brand.
I draw from my experience shipping infrastructure at HashiCorp, teaching at Parsons, and building Chai With Jai into an education platform — plus a structured framework for identifying the cognitive biases most likely affecting your decisions.
Common topics:
• Career transitions (IC to lead, startup to enterprise, eng to DevRel/education)
• Professional positioning and storytelling for technical people
• Learning roadmaps for complex platforms or new domains
• Building in public, content strategy, developer education
You'll leave with:
• A clear diagnosis of what's actually blocking you
• A specific action plan (not vague advice)
• A framework you can reuse after the session