HomeInterviewsGlasswing Ventures, Interview With Rudina Seseri, Founder and Managing Partner 

Glasswing Ventures, Interview With Rudina Seseri, Founder and Managing Partner 

Rudina Seseri, Founder and Managing Partner of Glasswing Ventures

Rudina Seseri, Founder and Managing Partner of Glasswing Ventures, replied to our questions about herself, the firm, how they support companies, and shared with us some predictions about the future of tech.

FinSMEs: Hi Rudina, can you please tell us a bit more about you? What’s your background?

I am the Founder and Managing Partner of Glasswing Ventures, an AI originalist fund founded in 2016 to back the technology. Before founding Glasswing, I was a Partner at a generalist fund leading their enterprise AI and data investments. Before VC, I was a Senior Manager in the Corporate Development Group at Microsoft Corporation, where I played a pivotal role in successful transactions and investments.

When I founded the firm and raised the first fund, it took significant effort to convince prospective investors that AI would be a significant technological wave. Against market trends, I secured $112 million for the firm’s first fund in 2018, the largest AI-focused debut fund on the East Coast. The subsequent oversubscribed $158 million Fund II in 2022 demonstrates the maturation of Glasswing’s venture capital proposition. Our Fund II was over 40% larger than Fund I, reflecting our strategic vision and the evolving nature of technology investments.

In addition to Glasswing, I am also very involved in supporting the next generation of entrepreneurs as an Executive Fellow at Harvard Business School and through several mentorship programs at MIT, Wellesley College, Northeastern, and Babson College.

FinSMEs: Can you introduce Glasswing Ventures?

Glasswing Ventures is a first-capital-in venture capital firm backing startups that harness the power of AI and frontier technology within the enterprise and security sectors. Together with my Co-Founder Rick Grinnell, we anticipated the disruptive force of AI and assembled a visionary team with decades of market experience, a disciplined investment approach, and a proven track record of industry-leading returns.

We invest in transformative founders who have the potential to revolutionize industries. Our deep domain expertise across business functions, what we call the Building Partners model, coupled with our world-leading advisory councils, comprised of 54 advisors who are technologists, AI visionaries, successful entrepreneurs, and Fortune 500 executives working with us and our startups on an exclusive basis, enable us to identify and invest in exceptional founders, supporting them as they redefine markets.

FinSMEs: Which is your overall strategy?

Our investment strategy is grounded in a conviction that artificial intelligence will fundamentally change how large enterprises operate. We back best-in-class entrepreneurs utilizing AI to disrupt existing enterprise and security software to provide more value to customers. We strive to be our founders’ first call in good times and bad, creating a culture of alignment and trust. We deliver customers, talent, and expertise beyond traditional support, ensuring our portfolio companies reach their full potential irrespective of market conditions.

We take pride in attracting and funding exceptional founders of all backgrounds and are immensely proud of our DEI metrics that far surpass industry standards. Over 46% of portfolio company executives identify as women/BIPOC, and 48% of portfolio company employees identify as women/BIPOC. 

FinSMEs: Beyond capital, how do you support startups?

Our commitment to startups goes well beyond providing capital—we are Building Partners.

At the core, our approach is the belief that successful startups need more than just financial backing; they require a diverse team of seasoned professionals who have walked in founders’ shoes. As early-stage founders consider their product roadmap, formulate their go-to-market strategy, or identify their ICP, our team provides them with experience, relationships, and support to help them navigate these critical issues quickly and achieve success. From day 1, founders can tap our Building Partners team of experienced investors, successful entrepreneurs, and seasoned operators, providing differentiated value to enterprise AI, cybersecurity, and frontier technology founders in the pivotal early business-building days.

We bridge founders’ operational and experiential gaps by leveraging our Building Partners’ collective expertise and advisor network. This means providing robust support across crucial areas such as go-to-market strategies, product development, engineering, and finance from the earliest days. The depth and breadth of our team mirror the leadership of a successful technology company, ensuring our founders have access to a full C-suite for comprehensive support.

Our commitment to founders is clear—we want to be the go-to partner for visionary founders, providing unmatched value and helping them navigate the critical early business-building days with confidence and success.

FinSMEs: Can you tell us more about Glasswing AI Palette? What is it? How does it work?

Our team has proudly led the charge in the AI investment landscape since 2010, propelling breakthrough technologies and groundbreaking companies across various industries. Our thesis-driven approach and focus on early-stage startups developing AI-native products, particularly in the enterprise and cybersecurity markets, stems from our deep expertise and understanding of the transformative power of AI.

By leveraging this extensive expertise, we developed a unique, proprietary framework for mapping AI, the Glasswing AI Palette, which we are open-sourcing today. This innovative tool – a living, breathing framework, is designed to demystify AI by outlining and explaining key architectures, techniques, methodologies, and use cases. By showing how these facets work together, the Glasswing AI Palette is a valuable tool for investors, founders, and executives. It is a comprehensive resource for founders of AI-native startups, guiding them in making informed decisions about developing their products. The launch of the Glasswing AI Palette marks an exciting milestone and is a testament to our firm’s dedication to advancing AI-native startups and fostering innovation in frontier technology.

FinSMEs: What do you like to see in founders?….And what don’t you like to see in them? I mean, is there something which impresses you at a first glance?

In considering backing a founder, I look for a deep understanding of cutting-edge AI and how to apply it to a business problem effectively. This requires a founding team that represents both technical expertise, domain expertise, and a deep understanding of the end user. 

Ultimately, I take a holistic view in considering investment opportunities in 5 key areas when considering AI applied to enterprise or cybersecurity. First, differentiated technology and data, including customized, extended, or wholly novel algorithms or proprietary access to unique data that can be used for fine-tuning. Second, is a high-value area that substantially improves productivity or offers new functionality. For instance, there is little benefit in improving productivity in areas with inexpensive labor (e.g., helping a marketing intern write emails more quickly) but significant value in areas such as question answering on enterprise data stores, code writing, SQL generation for querying for analytics, and design acceleration. Third, I look for deep vertical know-how in a founding team that understands customer needs intimately and thus has built a platform that solves a problem better with AI rather than just relying on AI hype. Fourth, I consider performance and error metrics in a platform. Many AI tools, such as the widely available LLM chat platforms, have a significant error rate and are, therefore most suited to tasks where the outputs are verifiable and editable. Founders must understand the true cost of errors, what performance is necessary to achieve value in a vertical, which metrics really matter, and how those metrics relate to business outcomes. Finally, I consider the workflow of the target user as the AI platform must fit into the existing workflow and function within a human-in-the-loop workflow.  

FinSMEs: Please, tell us a bit more about the portfolio. You can list five startups and their paths that you are particularly proud of….(feel free to customize)          

Two companies that very effectively speak to our strategy of Intelligent Connect, which is focused on building the AI-powered enterprise, and Intelligent Protect, which is focused on shifting security from preventative to proactive, are Basetwo AI and Black Kite

Within our  Intelligent Connect thesis, Basetwo is a no-code AI platform for manufacturing engineers to simulate and optimize processes rapidly to reduce cost and increase output. They utilize machine learning architectures such as physics-informed neural networks to create business value, specifically decreasing cost and increasing output in complex engineering environments. 

Within our Intelligent Protect thesis, Black Kite is the industry’s most accurate and comprehensive cyber risk intelligence powered by AI, with visibility into the risks that vendors introduce into an environment. The company utilizes machine learning techniques such as embeddings and cluster analysis to provide a solution that is both automated and proactive. 

Both these companies and the entrepreneurs behind them represent the best-in-class in effectively combining cutting-edge technology with a deep understanding of the business domain to create differentiated customer value. 

FinSMEs: Which sector/s would you bet on in the next five years?

In an environment of shrinking enterprise budgets, we have been investing in platforms/solutions and founders with the appropriate characteristics for the time, providing cost savings and need-to-have solutions:

  • Cost Savings: With budgets shrinking, enterprises are looking for platforms that help their bottom line, such as Verusen, which saves money and resources in the manufacturing process through materials management.
  • Need-To-Have Solutions: Black Kite is a great example – which addresses the ever-increasing cyber security attack surface through third-party risk analysis with AI-powered automation and granularity.

As you build such a solution, it is pivotal to consider the AI MVP (Minimally Viable Product) you are developing. The solution must be a strong AI MVP, providing initial value to a customer on day one to encourage adoption in a customer’s enterprise.