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This package includes 3 hours of 1:1 coaching time where we'll focus on crafting your career story. I've worked with hundreds of people trying to pivot into tech and startups. Most of them coming from finance or consulting, while some are from government, nonprofits, and other areas. Making the transition is all about speaking the language of the place we're trying to go, so that's what we'll focus on during these sessions – sharing the richness of your unique experiences in a way your target companies will understand. I've found this to be most productive if we use the first session to map out your career and job search strategy, the second to walk through key principles of storytelling and how they apply to your personal situation, and the third to really perfect your story so that you feel confident in your networking conversations and interviews. We can flex this plan based on your personal goals and where you need the most support. Most of our work will be during live 1:1 conversations, but some of it may be async (such as if you're super motivated and want to shoot me a loom of your story to review in between sessions). Let's do this!
Three 1:1 coaching sessions to ensure you're prepared for your negotiation
Personalized storytelling support
A killer tell-me-about-yourself intro pitch
Coaching delivered via live sessions.
You will receive significant feedback during our sessions and have homework you need to do in between each time we meet in order to make our discussions maximally productive. If you're looking for something a bit more chill or you are not comfortable with direct feedback, then we're probably not the best fit for each other! 😅
Services included:
Interview Prep
Skill Building
Personal Branding
Job Search Strategies
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
$987.502h 30m of coaching
Find clarity in your career direction and make actionable goals.
Starting at $1,9605h+ of coaching
Advance your career with expert guidance and a plan to achieve your goals.
Starting at $1,9605h+ of coaching
Get help with Interview Prep, Career Planning, and .
Access a library of videos, templates, and examples curated by Leland’s top coaches.
Joined March 2025
5.0
Negotiation and storytelling coach for tenured startup job-seekers
I've worked with 1,500+ entrepreneurial people figuring out their next career chapters. The first 1,000 of those were through the On Deck First 50 fellowship program I built, and another 500 have joined my NEXT Careers community for tenured startup-focused job-seekers. I work with people through every stage of their job search or figure-it-out journey, but have specific expertise around negotiation (more than 250 candidates who I've worked with on a 1:1 basis), job search strategy, networking and outreach strategy, and storytelling. Apart from directly supporting entrepreneurial job-seekers, I was also Head of Talent at a VC, worked at and built startups, and originally spent over a decade at Goldman Sachs.
3h of coaching