
Sydney W.
5.0
(5)
Empowering growth through meaningful career and relationship coaching!

Studied at Stanford Graduate School of Business

Works at Grammarly
Available Monday at 7:00 PM UTC
Questions? Start chatting with this coach before you get started.
Sydney's Coaching Offerings

Career Development Start-to-Finish
Expert help on everything from getting the interview to landing the offer.
$34020h of coaching

Discover a Career Path
Find clarity in your career direction and make actionable goals.
Starting at $855h+ of coaching

Advance your Career
Advance your career with expert guidance and a plan to achieve your goals.
Starting at $855h+ of coaching
Custom hourly · $20/hr
Get help with Interview Prep, Skill Building, and .
Sydney’s Career Coaching Qualifications
Experience level: Executive
60+ people coached for Career Coaching
Welcome! I’m a certified life coach (Erickson Coaching International, ICF-accredited) with 10+ years leading People Operations at companies like Grammarly, CZI, Confluent, and Dropbox. I specialize in career and relationship coaching—because I believe that a better life begins with better relationships, and at the heart of everything we do—whether at work or home—is connection. Coaching has been transformative in my own life, and I’m passionate about creating that same space of clarity and growth for others. There’s no greater joy than helping someone move forward with purpose and confidence. My style is empathetic, intuitive, and rooted in asking thoughtful, perspective-shifting questions that help you rediscover your strength and direction. I’ve supported over 60 professionals across industries and life stages. Education: BBA from Simon Fraser University; executive programs at Stanford GSB and UC Berkeley Haas. If you’re navigating a transition, craving more alignment, or feeling stuck—let’s connect and chart your next chapter, together.
Sydney can help with:
Interview Prep
Skill Building
Career Planning
Cover Letters
Professional Networking
Resume Review
Personal Branding
Networking Strategy
Freelancing
Salary Negotiation
Job Search Strategies
General Exploration
Work Experience

Head of North America People Ops and HR Compliance
Grammarly
2024 - Present
Set the vision and scale Grammarly's People Operations, Global Mobility and Contingent Workforce programs, driving employee lifecycle services, IPO readiness, M&A, global expansion, and other strategic initiatives to support our rapid growth.
Head of People Operations
Chan Zuckerberg Initiative
2020 - 2024
Set the vision and drive the execution of CZI's People Operations, Insights, and Employee Experience function, including employee life-cycle services and experience, people analytics, Workday & HR systems, onboarding, performance review, and other strategic programs to create a better employee experience!
Head of Global People Ops, Analytics & Talent
Confluent
2019 - 2020
Head of Global HR Operations & Contingent Workforce
Dropbox
2014 - 2019
Education

Simon Fraser University
Bachelor of Business Administration (BBA)

Stanford Graduate School of Business
Leverage Diversity and Inclusion for Organizational Excellence
UC Berkeley
Executive Education Program, Leadership
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