MGMT Boston - W1, Q1 25 - Cimulate / Jeremy Aubin, TireTutor

Cimulate / Jeremy Aubin, TireTutor / Last Week on The Lantern

Jan 08, 2025

Welcome to MGMT Boston where we try to help 1,100+ of you manage your awareness of top Boston startups and local up & coming operators putting in the work. Glad to have you here!

TLDR:

Cimulate - building a generative AI platform for commerce, peering into the future and redefining the customer experience for a Gen-AI and LLM-driven era
- Thanks to Jeff Boehm for the intro
Jeremy Aubin, Head of Enablement @ TireTutor - an engineer and early stage startup operator who fulfilled his childhood goal of living & working in Boston, building his career where the rubber meets the road, friction and all
- Thanks to Ries McQuillan for the intro
Last Week on The Lantern: Brad McNamara, Morrissey Market / Joe Sawyer, CMO @ Flashpoint

Other Resources:

MGMT Boston Operators Club - a community and opportunity engine for 100+ Boston based up & coming venture backed operators
The Lantern Short Form Video Series (YT)
2025 Boston Tech Big Board - 2025 First Draft is live!
Trusted Partners - top local partners we’ve worked with directly at MGMT Boston or would trust with our own resources
The Endeca Effect: Overview / Markets / People / Products / Conclusion / Bonus - Steve Papa Alumni Learnings
2023 1H Recap / 2023 2H Recap / 2024 1H Recap / 2024 1H Recap

Cimulate

Founders: John Andrews, Vivek Farias
Founding: 2023
Mission: Optimizing every pixel of the Commerce customer experience, from intent to purchase
Employees: 13 & 70% Local
Workplace: Hybrid (Downtown Boston HQ)
Stage & Capital Raised: Series A & $33M raised
Investors: Spark Capital, Sierra Ventures, Pillar VC, LFX Venture Partners, Commerce Ventures
Key Customers: PacSun, Tillys, Acelab
Glassdoor Rating: N/A
Valuation (estimated): $100M - $200M (assuming average equity dilution in the $28M Series A fundraise)
^ this is a useless number from MGMT Boston. There is no tangible valuation until the business is sold or goes public. Don’t forget it!

Cimulate is building a generative AI platform for commerce, peering into the future and redefining the customer experience for a gen-AI and LLM-driven era. This team is leveraging AI to reimagine the commerce customer experience starting with search and enable brands to help people find products they love.

John Andrews & Vivek Farias were introduced in 2014 by Steve Papa, the Founder of Endeca. John was an Endeca veteran of 8+ years who stayed on after their successful $1B+ acquisition to run Oracle’s Commerce product. Vivek is an MIT professor who has been leading AI initiatives for over a decade and doesn’t even have a LinkedIn profile for chrissake (he doesn’t need one)! John & Vivek teamed initially at Celect, a successful retail analytics startup, which was acquired by Nike in 2019 just 6 years after founding. TLDR? These are commerce veterans.

The duo kept in touch. John continued to work at Nike full time and Vivek consulted while continuing his research & teaching at MIT. Vivek was early to the world of Generative AI and kept John up to speed on transformer models and Google’s groundbreaking research with large language models long before the arrival of ChatGPT from his seat in Cambridge.

When GPT 3.5 was released, it became clear there was a real opportunity to leverage AI in new ways for commerce. Large language models predict the next best word in a sequence or sentence. Perhaps this transformer driven sequencing logic could also be used to predict the “next best action” for a customer. If someone could build an engine for customer behavior to help surface & optimize more relevant content for consumers, on behalf of brands, that would be pretty valuable.

U.S. e-commerce sales are due to exceed $1T in 2024 for the third consecutive year (src). Generative AI will disrupt legacy players with platforms built on keyword & vector search optimization. What took the Endeca team years to build (a truly innovative generational technology) can be deployed in months with next generation AI tooling. This is a unique moment in time to leverage new technology to deliver a better search experience for commerce.

The shopping experience is about to undergo a massive transformation. To start? It will become more conversational.

If you were planning to go to the Taylor Swift concert you would traditionally start browsing online to pull together an outfit. Or perhaps call your friends. But wouldn’t it be much better (and pretty fun) to shop by asking your favorite retailer(s) for some ideas?

Or how about if you’re not much of a shopper but you have a dinner party coming up next weekend and you’re looking for something simple. Maybe it’s a thin crew neck sweater that’s not too baggy. Wouldn’t it be incredibly helpful if a couple different cashmere or merino wool sweaters were surfaced for you to choose from quickly by your favorite retailer?

Everyone from Amazon to thousands of Enterprise scale retailers will need to replatform their search offering in the coming years to compete for customers in this evolving market.

Cimulate is building the CustomerGPT to present users with an optimized set of content from their favorite retailer by more deeply understanding customer intent. This LLM-based customer behavior engine allows them to deliver the optimal assortment of products and interactions to drive more sales.

Cimulate believes that owning the search infrastructure paired with the LLM driven conversational piece is really important to delivering a high performance shopping experience.

There are significant technical hurdles to making all of this work at the speed, scale, and cost to deliver a compelling commerce solution. The early Cimulate team has spent the past 18 months solving this problem and building the technical moat to make their platform performant and cost effective.

From John and Vivek’s whiteboard sessions in the summer of 2023, to a Seed fundraise and recently announced Series A fundraise led by Spark Capital in Q4 2024, it’s game on for 2025!

Cimulate has some serious traction with their initial customers and are building out a case study library to reach full commercial scale in the coming year. It’s time to put the foot on the gas with an urgency to chase this large, emerging replatforming in commerce (and perhaps beyond!). More to come here through these case studies, but the Cimulate team is seeing upwards of 25% increase in engagement and 15% increase in purchase rates when compared to solutions that were considered state of the art just a couple of years ago.

With their credentials, John & Vivek have assembled an all-star team of former colleagues and up & coming researchers to build a large, important Boston based technology company. Over the past year they have been adding to their Engineering & Data Science resources and will continue to scale product management too.

The key initiative for 2025 is to scale GTM - building a pre-sales, post-sales & marketing team - acquiring dozens of customers as they build out their platform from Boston HQ. They will also bring on HR & Recruiting later in the year to more systematically scale their team.

Operators to Know:

Alinna Brown, Product Manager
Juan Manuel Chaneton, Head of Data Science
Yizhou Huang, Research Scientist
Mohamed Abdul Huq Ismail, Staff Software Engineer
John Roman, Staff Software Engineer
Evan Yao, Research Scientist
John Lazenby, Senior Data Scientist

My investigative powers continue to need work so apologies to the Cimulate team if I missed any up & coming operators internally

Key Roles To Be Hired:

More roles coming in 2025!

If I were interviewing here are some questions I’d ask:

Could you share some details about the key milestones for 1H 2025?
What are the biggest challenges as you position Cimulate versus legacy competition?
What is the long term vision for the company?
What are the most important roles you’ll be looking to add in 2025 // teams that need the most help?

We’re optimizing for readability here so to learn more about Cimulate you’ll have to D.Y.O.R. I’m excited to watch this team bring more commerce companies into the age of artificial intelligence. All consumers applaud your efforts. See you around town!

Jeremy Aubin, Head of Enablement @ TireTutor

Jeremy Aubin is an engineer and early stage startup operator who fulfilled his childhood goal of living & working in Boston, building his career where the rubber meets the road, friction and all. Today he is the Head of Enablement at Seed stage consumer marketplace & shop management platform TireTutor.

Growing up in No(rthern) Ware, New Hampshire..the location speaks a bit for itself. It’s a big, small town that takes 30 minutes to drive from one side to the other. Jeremy’s dad owned a construction company and built every house they ever lived in growing up. He preached a mindset that if something was broken, you should try and fix it yourself first. His mom worked at local skiing destination Pats Peak. Both parents gave Jeremy and his sister every opportunity they needed to succeed in life.

From an early age, Jeremy wanted to move to Boston. He remembers traveling to visit the Boston Aquarium and looking out the window to see TD Garden, pledging to live in the city one day. From that point on, he was maniacally focused on achieving his goal.

As the first generation in his family to attend a university, Jeremy only applied to colleges in the Boston area. He had a mathematical mindset, taking college level engineering classes in high school and winning a national science award sponsored by Bausch & Loam. He even saved up money to buy himself a 3D printer, experimenting with CAD design, 3D photography, and DNA analysis.

Jeremy chose the Wentworth Institute of Technology to be surrounded by engineers and a strong technical culture. During his time at the university, he learned he didn’t just want to become a good engineer. Instead, he wanted to “talk the talk” and be able to communicate as a business leader in addition to having a strong technical background. Though he maintains he can still give any engineer a good run for their money on CAD design!

During his freshman year, Jeremy’s “Intro to Business” professor encouraged the class to get dressed up and attend an alumni event where Jason Abrahams, the Founder of TireTutor, was pitching his new startup. Jeremy thought the pitch was awesome and went up to introduce himself after the event. He even sent a follow up note afterward! Crickets.

During Jeremy’s junior year, Jason was back at Wentworth to teach a class called Entrepreneurial Marketing. Jeremy enrolled, got an A, and jumped at the opportunity to intern for Jason’s startup as part of Wentworth’s co-op program.

Jason’s generosity in giving back to Wentworth with his time and insights turbocharged the start of Jeremy’s career and he’ll forever be thankful. During the co-op, Jeremy did a bit of everything. He cold called prospects, sometimes got yelled at, and helped lay the groundwork for TireTutor’s emerging platform.

TireTutor was the first software platform to do true e-commerce for independent tire and service dealers across the U.S. They built an ordering platform connecting tire suppliers to process online orders from tire dealers and repair shops.

In those early days, Jeremy helped take online orders manually to help better scope the initial system buildout. Jason gave him more responsibility as he paid his dues and he was practically working at the startup full time by his senior year.

Once he graduated, Jeremy joined TireTutor full time to lead their initial product development efforts from 0-1. It was a tremendous learning experience, where he quickly figured out what he was good and..not so good at. Jason was kind enough to give him the space to fail and Jeremy threw whatever ego he previously had out the window.

The first big project they tackled after Jeremy joined the team full time was to launch their wholesale enterprise software platform. He worked closely with TireTutor’s Head of Engineering, Gizmo, navigating critical early decisions and accelerating the product development process by gathering customer feedback and advice. Alongside their early engineering team, Jeremy helped build the product from the ground up to become a platform and grow to handle millions of dollars of GMV (gross merchandise volume).

The wholesale enterprise buildout was a truly humbling experience. The quality level needed to be incredibly high and there wasn’t a lot of customer patience for screw ups. It was the first software in the vertical and they were able to integrate into their customers’ workflow via an Oracle/NetSuite API integration.

After testing with some initial customers over the first few months, the team built a plan to roll out their new platform gradually to the remaining customer base. But best laid plans quickly go out the window in startups.. A couple weeks before their planned launch, one of their largest customers had their old platform go down and asked to switchover early. Luckily, the TireTutor team was ready! They flipped the “on” switch to the new platform early. Working through the night, they began calling 800 customers across New England in <5 days to facilitate the migration across their customer base. That’s ripping a bandaid off!

Eventually, TireTutor hired a new Head of Product with more extensive experience. Jeremy gained an affinity for data and invaluable experience learning the inner workings of their application technology stack. He even helped bring on Sigma (like Tableau but on steroids) which was one of the best strategic decisions they’ve made from a software vendor standpoint to date.

Jeremy stepped up into a Head of Data role next to build out internal dealer reporting. This helped TireTutor better qualify their customers and understand their ongoing performance through a combination of analytics & marketing tools. He helped build an enrichment process so TireTutor had a fully fledged competitive market database and better sense of their various growth opportunities. He leveraged Google Cloud to lay the foundation for a data platform with customer & partnership insights to better inform the roadmap for tools & processes they should be using.

Once this project was completed, Jeremy became the Head of Revenue Enablement. In this role he owns technical partnerships and is responsible for setting the strategy for how they go to market as a team. He helps set the operating budgets, working closely with Jason and their investors. Jeremy also owns operations & enablement in terms of how their GTM team sells, packages their offerings, and how they deliver their service for customers from strategy to content to better achieve their goals.

Heading into 2025, the TireTutor team is highly focused on operations with launching the first true all-in-one POS at the end of 2024. This year is about focusing on the key metrics that drive their business as they become a growth stage company.

Navigating Tough Situations Drives Strategic Success
Navigating tough situations is a fundamental part of life in early stage startups. Jeremy’s hard won recipe for success? Get really close to customers, stay close to them, and live in your function.

When TireTutor set their early GTM strategy, it was critical for them to be able to “talk the talk” of their customer base. More generally known as “domain expertise”.

It was Jeremy’s experience, both by inexperience and logging all of those hours, that having a consistent “ground game” is what drives strategy. Not the other way around.

Strategy comes from talking to 100s of customers and properly segmenting your market successfully. Deeply understanding the customer segments pays huge dividends because not all prospects and customers are created equal.

TireTutor found that there were specific tire focused shops that fit their early platform really well. Then, over time, they also grew to serve shops who sold tires in addition to repair work. Both are great customers but each has a unique way of being prospected, closed, and serviced.

By staying close to all types of customers, Jeremy and TireTutor continue to provide solutions that they understand their customers want. That’s where the rubber meets the road!

3 Career Insights / Learnings

Leave Ego at the Door - “Leaving your ego at the door and being open to what it means to be good at something and not so good at something is an important first step to succeeding in a startup environment. It took me time to embrace that!”

Having Thick Skin - “Startups aren’t easy. You might get yelled at by your customers some days! Having thick skin is about being able to work through those challenges and around them each day to achieve your long term goals”

All Problems Aren’t Problems - “We all have problems that we deal with. But just because there are challenges, doesn’t mean it's the end of the world. Not all problems need to be or can be solved. But being honest about where things stand is really important to making progress”

Today, Jeremy is 100% focused on helping TireTutor and their team succeed. His greatest takeaway thus far is wanting to follow the theme of making a change in an industry in some way that he believes in. Going through this experience, there are hard days, so having the level of belief that what you’re doing is important helps him see through to the other side. Especially when you’re supporting people’s livelihoods and businesses!

If you want to learn more about Jeremy you can find him building GTM strategy at TireTutor, exploring Boston, or on LinkedIn. Thanks for sharing your hard fought insights. We’re excited to see your accomplishments continue to build in Boston in the coming years!

The Lantern Last Week - Brad McNamara @ Morrissey Market / Joe Sawyer, CMO @ Flashpoint

Brad McNamara, Founder & CEO @ Morrissey Market shares what he’s building connecting healthcare with food logistics and distribution:

Joe Sawyer, CMO at Flashpoint joins The Lantern to discuss how Flashpoint is closing out 2024, distilling the wins (and scars) from his career, navigating founder/advisor matches, and more:

The Lantern - a short form video series by MGMT Boston featuring the best startups (+founders), ecosystem leaders, and ferociously talented operators in Boston

W13: Matt Thoms, Baukunst / Pranav Kuber, Piction Health

W12: Andrew Smith, Swapt / Nemo Shi, Æthos

W11: Jehan Hamedi, Vizit / Drew Condon, BlueTrace

W10: Madeleine Smith, Civic Roundtable / Dana Wensberg, Paperless Parts

W9: Andrew Lau, Jellyfish / Will Lehmann, Step Function Ventures

W8: Palash Soni, Goldcast / Andy Palmer, Entrepreneur & Investor / The Market is Getting Better

W7: Daniel Pelaez, Cyvl / Sean Smith, Denim

W6: Jenni Goodman, Underscore / Jason Lavender, Electives / Productize Yourself

W5: Simon Taylor, HYCU / Nathan Rosenberg & Marc Printz, Farmblox

W4: Remen Okoruwa, Propexo / Amelia Van Camp, Mirakl

W3: Alex Ewing, OneScreen / Jess Lynch, FoundersEdge / What is MGMT Boston? And Why?

W2: Aniketh Mohanty, Wayfair / Amber Nigam, Basys.ai / W2 Summary (The Agents are Coming)