We’re pleased to announce our latest investment out of ASV III: Thoughtly, based in New York City, builds AI phone agents for high-consideration consumer categories like insurance, mortgage, and education. Thoughtly’s agents call every new lead in seconds to qualify and schedule, then hand off to licensed reps. By closing the speed-to-lead gap and orchestrating follow-ups across voice, SMS, and email—integrated with Salesforce and HubSpot—Thoughtly lifts conversion and show rates while lowering CAC without adding headcount.

We’ll have more to share about the company in an upcoming post, but for now, a hearty congratulations to founder/CEO Torrey Leonard and his team on this tremendous milestone.

This September, our event season wrapped up with a flourish up in Skaneateles, with our second annual CEO Summit followed by our Annual Meeting. At the CEO Summit, Neenah Jain and Laura Kinder guided us through enlightening conversations with founders/operators such as Ray Bohac, Prabhdeep Singh, and Chedy Hampson. Next, Joann Maria Yarrow of Syracuse Stage joined us to facilitate a workshop on pitching/storytelling, delivering unexpected insights and pro tips for maximizing body language and nonverbal cues.

Finally, Anthony Santaro interviewed special guests from the Syracuse Men’s Basketball Program: Head Coach Adrian “Red” Autry, who played pro basketball with Team USA and in various leagues overseas; Assistant Coach Allen Griffin, himself a former Syracuse hoops standout; and General Manager Alex Kline, who previously served in scouting roles for the Knicks and the New Orleans Pelicans.

The next day, at our Annual Meeting, we had the pleasure of introducing the founders of ASV III portfolio companies Motive, Tiga AI, and Qumis to our investors. We capped off the afternoon with a keynote featuring Shirzad Chamine, the bestselling author and visionary behind the Positive Intelligence (PQ) framework. Shirzad offered our audience a crash course on PQ’s ten saboteurs, which undermine performance, well-being, and relationships, while also sharing practical exercises to prevent said saboteurs from exerting undue influence.

Earlier this summer, we partnered with 43North for our Summer Soirée, held once again at the Mandana Barn in Skaneateles; the following day, we hosted a Founder Wellness Retreat facilitated by TalentRise and Sky Yoga Studios, which gave founders an opportunity to decompress and practice mindfulness techniques. Further south, we welcomed Mike and Kass Lazerow of Buddy Media and Golf.com for a book launch event during New York Tech Week, as part of our Cereal Founders Breakfast Series. We look forward to announcing the next installment in that series soon. Prior to that, we cohosted a Vertical AI Summit along with our friends at nvp capital, H/L Ventures, and Lynx Collective. In addition to several other in-house events, we’ve been busy hunting for deals not only across New York State but also in promising markets such as Nashville, Detroit, Toronto, and others.

Our increased event activity compared to prior years has corresponded to an overall surge in our pipeline, one driven as much by the Cambrian explosion of AI startups as by our own technical retooling, which has allowed us to apply our rigorous sourcing process to an ever-growing cross section of opportunities. We’ve also been able to continually iterate on that process to incorporate new learnings about the ways in which the venture landscape has evolved, and the ways in which it hasn’t.

For all generative AI’s reality-warping effects, the essential recipe of what constitutes a venture-scale business hasn’t changed. Enduring companies are built by founders who deeply understand the problems afflicting their end users; who can rally exceptional teams around their mission; who are agile enough to pivot without losing balance; and who know how to balance capital efficiency with the appropriate dose of aggressive opportunism. The businesses in ASV III, while diverse in their focus areas, are united in that they embody these characteristics.

Guests digging into the Goan buffet at ASV’s Summer Soirée at the Mandana Barn.

Whats New at ASV

After graduating from Cornell, Jin Kwon officially joined ASV as an Analyst. Jin originally proved his mettle last summer as a Venture Fellow, and we’re thrilled to welcome him to the team full time. Around the same time, we welcomed Ayham Boucher into the fold as a Senior AI Advisor. Ayham serves as Head of AI Innovations at Cornell, overseeing a slew of AI implementations across various faculties and functions within the university.

In addition to helping the team vet the technical capabilities of AI startups, Ayham has proved instrumental in instilling a culture of continuous dialogue and learning amid a constantly-evolving AI landscape. Recently, Ayham and managing partner Somak Chattopadhyay traveled to Tbilisi, Georgia, for the AI Innovate Conference. The gathering brought together researchers, founders, and investors at the forefront of the field, offering a unique vantage point on both the promise and practical hurdles of deploying AI at scale. Their participation reflects our commitment to deepening expertise, contributing to the global conversation, and ensuring that ASV remains a trusted partner to entrepreneurs navigating this transformative era.

We are still early in deploying ASV III, with the majority of the fund yet to be invested. In addition to Thoughtly, we have another investment at the term sheet stage that we hope to announce soon.

Company Updates

• Compyl raised $12M in Series A funding amid a year of rapid growth as it continues to redefine the GRC space.

• Motive announced its certification with Nissan USA in July. This is the Company’s first volume brand, and Motive’s largest certification to date. This will allow Motive to better serve Nissan’s over 1,000 dealerships. With Nissan USA, this brings the Company’s OEM partnerships to 10.

• Multiplayer launched Full Stack Session Recordings, enabling developers to condense debugging and feature development timeframes from hours to minutes.

• Tiga AI raised a $2M pre-seed round led by Bull City Ventures, which Armory participated in.

Jobs

• Compyl is looking to fill several sales and engineering openings, primarily remote and based around the New York and Boston metros.

• Heretto is hiring an Implementation Manager & Custom Solutions Developer, along with a Senior Full Stack Developer.

• Motive is hiring across a range of sales, engineering, product, and customer success roles, predominantly in Seattle and Oklahoma City.

• Thought.ly is hiring a CFO/COO and a Head of Sales.

• Qumis is hiring a Founding Operations & Automation Lead, as well as a Founding Staff AI Engineer.

About ASV

Armory Square Ventures (ASV) is a venture capital firm based in the Finger Lakes region of New York State, with offices in NYC and Indianapolis. The firm was an early investor in ACV Auctions (NASDAQ:ACVA), Bentobox (acquired by Fiserv), and numerous other high-growth B2B Software companies.

We lead seed and early-stage rounds in B2B SaaS, marketplace, and vertical AI companies and play an active role recruiting talent, customers, and follow-on capital to help our companies scale.

We like to say we are an optimism engine for secondary cities and a community catalyst for regions outside Silicon Valley. As a firm, we are also enriched and nourished by individuals from a range of backgrounds, who are all passionate about uplifting and inspiring growth in cities across the Northeast and Midwest.

• Stage: Seed & Series A

• Location: Management based in New York State and/or other emerging cities across the US

• Check Size: $500k - $3M in the first round with plenty of reserves for follow-on capital

• Business Profile & Model: Software, mobile, or technology-enabled services (emphasis on B2B) with repeatable, recurring, or transaction-based revenue models

• Market: Addressable markets of at least $1B+

• Team: Full-time technical/product leader and sales/marketing leader

• Traction & Unit Economics: Prototype of product deployed with a small sample size of customers; capital efficient

We’re hard at work scouting new investments. If you or someone you know has startup questions, reach out to either Anthony, Jin, or Preston (emails below). We are actively investing out of our third fund and look forward to sharing more on it as it continues to take shape.

Best wishes in the meantime.

The Armory Square Ventures Team