Investing in GC.AI: a specialized tool for a growing team of in-house experts

As I reflect on the last five years of building Worklife, I’m reminded how quickly Silicon Valley as an ecosystem can collectively align on a problem that needs to be solved such as remote work or an innovation or disruptive force such as AI that within a very short amount of time can (and has) fundamentally changed how people work.?

One of the most exciting challenges as a formation stage investor is finding the right team to collaborate with among the dozens of similar-sounding pitches you see every week.?

It’s never been a better time to start something, and at the same time, it’s never been a more difficult time to raise money at this stage because of the sheer volume of new companies being started.?

There’s a lot of competition, and increasingly, I am most confident in companies with trusted relationships with their ideal customer profile and a unique go-to-market advantage that will not only shorten time to product-market fit, but box out inexperienced teams attempting to solve a similar problem with no connections and no sales experience.?

Our lead investment in GC AI has felt serendipitous from the beginning and has fundamentally changed how we approach company building at Worklife.?

I’ve said before Silicon Valley is a special place where the longer you stay here, the more likely you are to work with someone. When you meet smart people, there will be many opportunities over the course of a decade or more to find ways to work together.?

In the case of GC AI, I’ve had the privilege of working with Bardia at Roam Research & Replit, and Cecilia had been on my list of people I would love to collaborate with in the future for a long time.?

Across the tech industry, there are many unsung heroes with highly specialized experience across multiple successful companies.???

The handful of CFOs who have taken multiple software companies public, Elena Gomez who I had the privilege of working with at Zendesk who has recently taken Toast public immediately comes to mind.?

Elena Verna, the secret sauce behind the scenes at many high-growth software companies like Miro, SurveyMonkey, Amplitude, Dropbox, and many others. Worklife backed companies have had the privilege of working with Elena to set up analytics and full-funnel reporting, implement pricing for the first time, and all of the important foundational parts of a product-led growth go-to-market. You can learn how to do this here.?

For many years, GC AI founder Cecilia Ziniti has been a highly sought-after, experienced GC with an impressive list of startups she’d supported at critical inflection points for the company.?

One of the things that I’ve respected most about Cecilia is her unique ability to educate her peers and her passion for up-skilling the legal industry as a whole. Her class on AI prompting for in-house legal has not only solidified her position as an influential, trusted source for in-house counsel, it has become a self-generating source for new paying customers.?

The classes have been a perfect segue to buying software - she has taught 507 students in paid classes through Sept. 30, 2024 and has led to 2,000+ companies to the pipeline to buy GC AI.?

In less than a year, Cecilia has single-handedly closed hundreds of paying customers ranging from high-profile tech companies to highly regulated industries such as healthcare, manufacturing, and industries that are not only skeptical of AI but face uphill battles internally to implement new tools.?

On our Friday afternoon calls, I am consistently blown away by a pre-seed stage company’s ability to close 20+ seat deals.?

They are not partnering with a handful of design partners for free more are they selling to YC batchmates where a large % of those companies will not be around in the next five years.?

Here’s a small snapshot of their current customers:?

GC.AI is a prime example of building for the expert, you. When a trusted source and deeply knowledgeable expert teams up with an experienced engineer, you have a unique ability to close larger deals than expected because your company is not an experiment, it’s a legitimate business.?

As a PLG investor, I’m reminded of the many similarities between Figma and GC AI, not only from a product perspective with an intuitive, specialized tool that users not only use daily but throughout the entire work day, and from a go-to-market perspective where education, community, and high NPS organically fuel growth and drive adoption across legal teams of all sizes.?

A unique insight in the early days of Figma was the designer to engineer ratio has increased dramatically over the last decade. Design is not a nice to have, it’s a core function of the business for brand, UX/UI, and has proven impact on the bottom line.?

The same is true for in-house counsel. Companies who are cutting back on outside counsel and bringing legal in-house to ensure their company is prepared for the new climate of increased government protection, risks across the business in light of artificial intelligence, and the ever changing needs of businesses of all sizes in periods of economic uncertainty. Cecilia at GC AI saw this - having been part of the Amazon legal team (1,000s of lawyers) and teams at Cruise and other regulatory-heavy companies.?

For startups, this will come as a surprise as we often see in-house counsel as a role that’s created in later growth stages of a company.?

For more established companies, we frequently see companies with 5,000 employees have an in-house counsel team of 150+ people.?

As GC AI continues to build a much-loved tool for a team historically underserved by software, we’re proud to be hands-on investors and actively building out the sales team to support Cecilia in her efforts across education, customer onboarding, customer success & seat expansion, and closing the over 2,500 companies currently in the pipeline.?

If you’re a lawyer with sales experience and want to have a significant impact on how in-house counsel uses AI or an engineer looking to work on the hardest problems in LLMs in the pinnacle vertical for AI, please apply here.?

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