Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
Work 1:1 with an AI career coach to identify, scope, build, and present AI projects that demonstrate your skills and make you a stronger candidate for the roles you want. Possible uses of coaching sessions, but not limited to: - Identifying the right portfolio projects for your target roles - Scoping projects to be completable and impressive within a realistic timeframe - Technical guidance and feedback throughout the build process - Presenting your projects on GitHub, LinkedIn, and in your resume - Coaching on how to walk through your projects confidently in interviews - Building AI fundamentals and skills through hands-on project work
A clear strategy for which portfolio projects will have the most impact for your target roles
Polished, well-documented AI projects you can walk through confidently in interviews
A GitHub and LinkedIn presence that signals to employers you're ready to contribute
The ability to talk about your AI projects clearly and handle technical follow-up questions
Coaching delivered via live sessions and .
Services included:
Interview Prep
Skill Building
LinkedIn Review
Resume
AI Fundamentals
AI Agents
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
Get help with Cover Letters, AI Fundamentals, and .
Jenny also coaches for Product Management, AI Strategy & Transformation, and Technical Program Management. View all.

Joined March 2026
Decode AI career paths: expert guidance to navigate and break into AI
With over 6 years of experience at Microsoft as a Product Manager, I have extensive experience leading cross-functional teams and aligning on hard problems while ensuring all voices are heard, especially in innovation spaces like AI and agentifying products. I work directly in the AI space to define and build AI features, as well as build the underlying system to support AI. I've successfully coached over 30 individuals across varying levels of experience and backgrounds, where they have landed roles in Apple, Microsoft, Google, Slack, and more. I have also been closely involved with recruiting to bring in interns/new grads and industry hires for our next wave of talent. Whether you're looking to break into AI, understand the various opportunities available to you based on your background, advance your career, or more, I'm here to provide tailored guidance and support. Please feel free to reach out, I would love to be part of your journey~
5h - 8h of coaching