Our Investment in Glassbox: Bringing Financial Modeling into the AI Era
For over 40 years, Excel has been the backbone of global finance — powering everything from billion-dollar M&A deals to structured derivatives. It’s one of the most effective and enduring software tools ever built, transforming financial modeling and decision-making at an unprecedented scale. But as AI revolutionizes industries, finance remains constrained by Excel’s original design. Its data isn’t easily interpretable by LLMs, and its manual workflows create inefficiencies in a world that demands automation, speed, and precision. Our perspective is that the next evolution of financial analysis isn’t about replacing Excel — but rather augmenting it with intelligence, transparency, and automation to unlock its full potential in the AI era.
It’s for this reason that we are so excited to announce our lead investment in Glassbox, a Toronto-based startup that is challenging this status quo. The $1.2M USD pre-seed round was co-led by NY-based The Fintech Collective, with participation from LA-based Watertower Ventures.
A $410 Trillion Industry Stuck in a 40-Year-Old Workflow
The problem Glassbox is solving isn’t new. Spreadsheets were never designed for the complex, high-stakes workflows that define corporate finance today. Models are often bespoke, with every intricate formula becoming a potential point of failure. Collaboration is a minefield, riddled with version control nightmares and broken audit trails. And the most dangerous errors? They don’t announce themselves — instead lurking unnoticed until they derail deals, trigger miscalculations, or erode investor confidence. The current state of financial modeling isn’t just inefficient, but an existential problem to an industry that moves over $410 trillion in financial transactions every year. Where speed and accuracy define winners and losers, the “black-box” approach to modeling isn’t just outdated — it’s untenable.
Like Glass — AI-Powered Transparency for a System That Needs It
Glassbox’s secret sauce is FinScript, a proprietary language that transforms Excel’s dense, error-prone formulas into clean, auditable instructions written in human-readable text. It replaces complexity with clarity, making financial models more transparent, efficient, and dramatically easier to debug — like turning a black box into a glass one.
Whereas the unstructured reality of excel makes it a cumbersome partner for AI, Finscript outputs are structured and standardized, turning financial analysis into a legible format that can be understood and acted upon by LLMs. This lets the analyst harness the power of AI for their productivity (generating a model with prompts, automatically updating a discount rate across multiple scenarios), while retaining the collaborative and familial benefits of a standard excel output that Glassbox produces. This approach eliminates adoption hurdles, positioning Glassbox as an evolution of the status quo rather than a complete overhaul. Rather than discarding the tools finance teams know and trust — it’s about making those tools smarter, faster, and exponentially more powerful.
A Team That Lived the Problem
The unstoppable force behind this vision is a world-class founding team that experienced the problem firsthand.
Princeton-trained financial engineer Allison Harris, Glassbox’s CEO, spent years on Wall Street and later as an investment banker, buried in the painstaking, error-prone process of financial modeling. She saw firsthand how much time was wasted, how many costly mistakes went unnoticed, and how much better the system could be if technology actually served the needs of finance professionals instead of forcing them to work around it.
Ian Kennedy, Glassbox’s CTO, is the architect behind the technology making that vision a reality. A seasoned engineer with a track record of designing high-performance, intuitive systems, Ian is building Glassbox to be both powerful and practical.
Together, Allie and Ian are not just iterating on spreadsheets — they’re rewriting the foundational workflow of finance. Their depth of expertise, clarity of vision, and relentless execution have been clear in every conversation we’ve had — this is a team that intimately understands the problem and is uniquely positioned to solve it.
Finance is at an Inflection Point
At StandUp Ventures, we invest in founders who see opportunities where others see obstacles, who are ambitious enough to tackle complex problems, and those who are bold and persistent enough to solve them. We back teams that challenge long-standing norms, not with incremental improvements, but with bold, scalable solutions that redefine how industries operate.
Allie and Ian emobdy this ethos fully. They aren’t tinkering at the edges; they’re transforming how finance teams think, operate, and compete at a foundational level. This isn’t about shaving a few hours off a task or avoiding spreadsheet errors — it’s about giving finance teams a smarter and better way to work.
Our belief is that finance is at the cusp of a critical inflection point. AI is revolutionizing other industries at breakneck speed, yet finance — an industry built on precision and velocity — has been stuck in the past. Glassbox isn’t just slapping AI on top of existing inefficiencies — it’s reengineering the foundation of financial modeling itself. By eliminating inefficiencies at their core, Glassbox is poised to become an indispensable partner to the teams that move markets, structure billion-dollar deals, and shape the future of finance.
We’re incredibly proud to welcome Glassbox to the StandUp Ventures portfolio. For finance teams, this is the beginning of long-overdue progress and disruption. For those of us watching from the sidelines, it’s clear that Glassbox is shaping the future of an industry that’s ready for change.
Welcome to the portfolio Allie & Ian!!!
