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Maria Karaivanova
Venture Investor
Maria Karaivanova is the Co-founder and Chief Operations Officer (COO) of WhyLabs, an AI observability company based in Seattle, Washington.14 With a background in technology and venture capital, Maria has played a significant role in the development and growth of WhyLabs since its founding in 2019.3
Professional Background
Before co-founding WhyLabs, Maria held several notable positions in the tech industry:
- Head of Business Development at Cloudflare from 2012 to 2017, where she helped grow the company from 25 employees to unicorn status25
- Investor at Intel Capital, focusing on enterprise technologies and cloud security5
- Various roles at Boeing, specializing in intellectual property management and international business development5
Education
Maria's educational background includes:
- MBA from Harvard Business School56
- Undergraduate degree in Finance (BSBA) with high honors from Saint Louis University56
Entrepreneurship and Investments
As a co-founder of WhyLabs, Maria has been instrumental in developing an AI observability platform that allows companies to monitor, improve, and build trust in their AI tools.1 WhyLabs has raised a total of $14 million in funding, with its latest Series A round securing $10 million.3
Additional Roles and Interests
Maria is also involved in various other professional and community activities:
- Director at Sea Citi, a non-profit promoting civic engagement2
- Passionate supporter and mentor of female founders and investors6
- Frequent speaker at technology conferences6
- Occasional angel investor6
Maria Karaivanova's diverse experience in technology, business development, and venture capital has positioned her as a key figure in the AI and machine learning industry, particularly in the realm of AI observability and responsible AI practices.


