Sierra Ventures: Our Early-Stage Investment in Cimulate

Announcing Our Seed + Series A Investment in Cimulate: Redefining Commerce Starting with Search

At Sierra Ventures, we are excited to announce our investment in Cimulate, a groundbreaking company at the forefront of enterprise AI for commerce. Sierra led Cimulate’s 5M Seed round in Fall 2023, and today, the company announced a $28M Series A led by Spark Capital.

Right Team, Ground Breaking Technology, Right Market 

Cimulate’s founders, John Andrews and Vivek Farias, bring unmatched expertise in AI-powered retail innovation:

• Vivek Farias, a professor at MIT, is a renowned expert in reinforcement learning and applied probability, contributing the groundbreaking research that underpins Cimulate’s technology.
• John Andrews, a veteran in retail technology from Endeca / Oracle, delivers the strategic vision and operational leadership to scale a world-class company.

Their complementary expertise and shared vision lay the foundation for Cimulate’s success in shaping the future of AI-driven commerce.

I first met the founders in 2016 when they founded Celect, an inventory optimization company.  I really liked them with John’s great product management and go-to-market chops from Endeca/ Oracle and Vivek's “lights out” brilliance from Stanford/ MIT, but I could not see the “big company” vision.  We decided to remain friends and stay in touch. They continued to sell Celect to Nike and remained there till they founded Cimulate in 2023, as they saw the technology shift to LLM and Generative AI.  Fast forward to the Fall of 2023 when my phone rang, and they walked me through their vision to go from customer intent to order using a blazing-fast LLM custom-built for commerce. Ie, no dependence on 30 years of old search techniques that rely on indexes, logs and click streams!  And they had a prototype working and the lab results were mind-blowing. We immediately decided to partner and lead their Seed round!

Seed to Series A Journey:  What OpenAI did for text data, Cimulate has done for commerce data.

Their Seed to Series A journey has been amazing to watch.  They assembled a world-class team of PhD’s and practitioners in Boston, signed up design partners, and got to work.  As they took their first 3 customers live, the results were transformational for their customers: > 20 % plus Click per Visit and Add to Cart and > 10% purchase rate!  How? Cimulate has reimagined legacy commerce search with an industry-first, generative AI-based approach to deliver faster, smarter, and conversion-focused shopping experiences. Drawing on groundbreaking MIT research and led by seasoned founders with a proven track record, they built their invention’s first Commerce Experience Server Powered by CustomerGPT.

The Solution: The World’s First Commerce Experience Server Powered by CustomerGPT

At the core of Cimulate’s innovation is the Commerce Experience Server, the world’s first platform designed to deliver hyper-optimized, content- and context-aware search and discovery experiences. This breakthrough is powered by CustomerGPT, Cimulate’s proprietary Large Language Model (LLM)-based operating system, an achievement on par with OpenAI’s ChatGPT—bringing the transformative power of AI to commerce data.  The LLM is pre-trained but gets added context from the customer's data (like product catalog), is easy to deploy, and is blazing fast.

Legacy Search Technologies Fall Short as they have been based on "incremental” architectures

Traditional search technologies from Adobe, Salesforce.com, Elastic, and Algolia are all based on index/ customer log analysis-based techniques, which are incremental at best.

These traditional search technologies fail to meet modern consumer expectations in today's fast-paced commerce landscape. Retailers lose an estimated $234 billion annually to search abandonment, driven by outdated systems that cannot deliver relevant, engaging, and conversion-focused results.

Cimulate tackles this challenge head-on by merging deep AI expertise with practical solutions that unlock the full potential of retailers’ data.  Consequently, customers are ripping out the old technologies and putting them in Cimulate.

In this $2B Market, a new leader is going to emerge

Cimulate’s focus on scalable personalization and actionable insights positions it as a leader in the $2 billion commerce search and broader commerce experience markets. Its groundbreaking integration of content, context, and customer data allows retailers to deliver highly tailored shopping experiences at scale without compromising speed or reliability.

John Andrews, CEO and Co-Founder of Cimulate, highlights the transformative impact of their technology:

“Today’s commerce ecosystem is at a crossroads, with traditional search technologies failing to meet the expectations of modern consumers. CustomerGPT combines the power of LLMs with actionable insights to optimize every touchpoint in the customer journey, driving measurable outcomes for retailers.”

The Road Ahead

Cimulate’s funding comes at a pivotal moment for commerce. As generative AI reshapes industries, Cimulate’s world-first approach positions it as a leader in redefining customer experiences. By addressing critical pain points like search abandonment and providing scalable, data-driven solutions, Cimulate is unlocking significant value for retailers and their customers.  For example, if you are a 1 billion GMV merchant, without too much additional work, you could add 100M plus to your GMV, and this is the first module Cimulate has released!

Sierra is proud to partner with John and Vivek as we reshape this market.  For us at Sierra, it reminds us that supporting entrepreneurs who are revolutionizing industries is a labor of love mutual trust and respect.  Sometimes, it takes waiting out an inning to win the long game.  We are thrilled that a friendship that started in 2016 ultimately resulted in us partnering.

I look forward to building an iconic company together.

 To learn more about Cimulate, visit www.cimulate.ai and schedule a demo.