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Wes Kao
Co-founder of a newco funded by First Round Capital
Professional Background
Winnie Kao is an accomplished entrepreneur and innovator in the field of educational technology. As the co-founder of a pioneering edtech company, she has made significant strides towards creating the first platform dedicated to cohort-based courses, aimed at transforming how education is delivered and experienced. Winnie's passion for leveraging technology to enhance learning has led her to immerse herself deeply in the startup ecosystem, embodying the spirit of mentorship and community-building.
Winnie's career trajectory has been impressive, showcasing her expertise in marketing, brand management, and education. She began her professional journey as an analyst at Gap Inc., where she developed a keen eye for market trends and consumer behavior. Winnie continued to build her skills in brand management while working at global powerhouse L'Oréal, and later at Bare Escentuals, where she honed her marketing acumen and strategic thinking. Her experience at these renowned companies laid a strong foundation for her future endeavors.
Education and Achievements
Winnie received her B.S. in Business Administration from the prestigious University of California, Berkeley, Haas School of Business. This educational background provided her with a solid grounding in business principles, which she has applied throughout her career. Her time at Berkeley equipped her with critical thinking skills and an understanding of the complexities of business operations, positioning her as a leader in the entrepreneurial space.
Post-education, Winnie served as the Head of Digital Marketing at Flite, a company that was later acquired by Snapchat. This experience marked a turning point in her career, allowing her to showcase her ability to navigate the rapidly evolving landscape of digital marketing. She was instrumental in developing innovative marketing strategies that propelled Flite to new heights, demonstrating her capability to adapt in a fast-paced environment.
Her entrepreneurial spirit truly shone when she co-founded and served as the Executive Director at Seth Godin's altMBA, a transformative educational program designed to empower leaders across various sectors. This experience not only solidified her reputation as a thought leader in the edtech space but also helped her develop a nuanced understanding of cohort-based learning — a concept she is now dedicated to advancing through her current venture.
Notable Contributions
Beyond her entrepreneurial ventures, Winnie has also contributed to the startup ecosystem through her mentorship roles. She has served as a mentor at Backstage Capital, a venture capital firm that supports underrepresented founders, and at WeWork Labs, helping aspiring entrepreneurs navigate their early-stage startups with guidance and insights. These roles highlight her commitment to promoting diversity and inclusion within the entrepreneurial community.
Winnie's participation as a Global Solutions Program Fellow at Singularity University is yet another feather in her cap. There, she engaged with fellow innovators and leaders tackling some of the world's most pressing challenges through technology and entrepreneurship. This experience enriched her perspective on global issues and the role technology plays in solving them.
Through her newsletter, which can be accessed at WesKao.com, Winnie shares her insights, experiences, and thought leadership with her audience, empowering them to embrace the innovative opportunities in the ever-changing landscape of education and technology. Her commitment to lifelong learning and her passion for fostering community among educators and entrepreneurs make her a respected figure in the industry.
Highlights
Getting buy-in 101:
🚫 "Trust me. I've done this many times."
✅ "I'm recommending X because [evidence, data points, thought process]. I saw something similar play out with [previous example], so I believe we need to be mindful of Y. This matters because Z."
I used to assume my colleagues should trust me because I was the subject matter expert, and my conclusions felt obvious to me.
Instead, I would get push back, lots of questions, and skeptical comments.
I realized what was obvious to me, was often extremely non-obvious to people outside my own head.
Now, my default is to spend a few seconds to share my logic:
-> Share what's informing my recommendation -> Share how I arrived at my conclusion -> Share why I picked X over other alternatives
I became a lot more compelling once I realized it was my responsibility to help others understand why X was the best path forward.
This doesn't have to be intense. It's as simple as sharing your recommendation, then adding a "because."
It takes an extra 15 seconds to explain your rationale. It can save you hours of friction from avoidable back-and-forth and misunderstandings.
IMO When folks have trouble being concise, the problem isn't usually the delivery.
The problem is you actually don't know your idea as well as you think you do.
Words are the final expression and the way you communicate with others, but the problem isn't the words--the problem is words represent ideas, arguments, decisions, and thinking.
If you aren't sure what you think, it's hard to describe it clearly to someone else.
Therefore, the solution isn't surface-level wordsmithing.
The solution is getting clear on your main point.
When you are clear on your main point, expressing it concisely becomes much easier.