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Description
Feeling stuck between career paths — like product management, strategy, or PMM — and not sure where you truly fit? This 3-session coaching package is designed to help you move from confusion to clarity, and build a practical, values-aligned career exploration plan. Whether you’re exploring a pivot, planning your next role, or struggling to make sense of what energizes you, this package will give you space, structure, and support to figure it out. Session 1 – Discovery We’ll dive into your career story, what energizes you, and what drains you. We’ll identify your values, strengths, and patterns using tools like the Good Time Journal and values frameworks from Designing Your Work Life. Session 2 – Discussion You’ll evaluate different career options (e.g. PM, PMM, Strategy) using your values and energy patterns. Together, we’ll map which paths align best with who you are — not who you think you should be. Session 3 – Action & Planning You’ll leave with a personalized Career Exploration Plan: low-stakes experiments, networking strategies, and tools to help you move forward with confidence Who This Is For: ✅ You’re choosing between multiple career paths and don’t know how to decide ✅ You’re craving clarity, structure, and reflection with a coach who gets it ✅ You want a real plan, not just vague encouragement
What you'll get from this package
Greater clarity in your values, your strengths / weakness, and your priorities
Better understanding of different roles and how they are aligned with your values, strengths and goals
Actionable plan for career exploration and job searching
Additional details
Coaching delivered via live sessions and .
We will work together over the course of 2 months over 3 live sessions and a few async check-ins.
Can purchase additional sessions as we go.
Services included:
Networking Strategy
Job Search Strategies
Skill Building
Career Planning
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
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Offered by Dillon V.
Joined July 2024
5.0
Career pivots with purpose | Stanford MBA | Ex-Meta
I’m an experienced product manager with 12+ years in tech and strategy, including six years building products at Meta, LinkedIn, and high-growth startups. My career path wasn’t linear — I started in consulting, explored different roles after my MBA, and eventually found my place in product management. That journey taught me how to navigate career pivots, make bold choices, and grow through uncertainty. Now, I help others do the same — whether you’re exploring your next move, building confidence in your career story, or aiming for a leadership role.
$433.59
3h of coaching