Armory Square Ventures

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Introducing PromptPath


We’re pleased to announce that Armory co-led a $12 million Series A round in PromptPath, an Austin-based automotive technology company whose AI-enabled platform turns dealership conversations into real-time operational execution and at-your-fingertips customer context.

We are co-leading alongside our friends at FM Capital, with participation from Automotive Ventures, Holman Ventures, Assurant Ventures, and leading dealer groups. As part of the financing, ASV Managing Partner Somak Chattopadhyay and industry veteran Keith Jezek (former CEO of Open Lending and co-founder of vAuto) are joining the Board of Directors.

At a modern dealership, the customer journey moves with real horsepower. A single transaction touches inbound and outbound phone inquiries, conversations on the physical showroom floor, financing discussions, and more. Yet across these transitions, critical customer context often falls between the cracks. Notes taken on phone calls are left incomplete, sales reps are forced to juggle disconnected systems while on the line, and managers lack real-time visibility into whether dealership best practices are being faithfully observed.

The tools built to address this communication gap have historically fallen into two categories: reactive call tracking that scores calls days after the fact, or generic voice bots that attempt to automate away the human salesperson. In automotive retail, where high-ticket transactions rely on trust, nuanced negotiation, and personal rapport, neither approach solves the core issue.

PromptPath was built to bridge this divide. Rather than replacing human sales reps, PromptPath’s platform acts as an in-the-moment copilot. By integrating directly into existing dealership phone and operational workflows, the platform delivers live context to staff during conversations, automatically logs structured summaries into the CRM, and standardizes best practices across rooftops. From the first phone call through final delivery, PromptPath keeps customer context connected across every department.

PromptPath is led by seasoned AutoTech operators who have spent decades building core dealership infrastructure:

  • Amit Maheshwari (Chief Executive Officer): Proven industry executive who previously co-founded and scaled i-Vantage, served as SVP of Corporate Development and Enterprise Solutions across Dealertrack and Cox Automotive, co-founded Rollick, and served as EVP at Tekion.

  • Jason Barrie (Chief Operating Officer): A 20-year AutoTech veteran with deep expertise across operations, product, and go-to-market leadership. Barrie spent 16 years at Dealertrack and Cox Automotive before co-founding automotive startup Carmatic and serving as COO at DAS Technology.

  • Max Steckler (Co-Founder & CPTO): Veteran AutoTech product leader who helped scale Cobalt Group’s advertising business to $250M, led large digital portfolios at CDK Global, and held senior operating roles at DealerSocket and Podium.


Why We Invested

PromptPath builds directly on Armory’s long-standing thesis in vertical software and AutoTech, a playbook previously reflected in our investments in ACV Auctions (formerly NYSE: ACVA, acquired last month by Copart), Motive, and TireTutor.

  • Human-First AI Workflow: High-value purchases still require human relationships. PromptPath focuses on empowering dealership staff during live interactions rather than attempting to displace them, making the technology sticky and widely embraced across sales teams.

  • Measurable Customer Impact: Across early dealer deployments, PromptPath has driven significant, measurable gains in appointment setting rates, documented CRM activity, and process adherence. Customers don’t just see it as a reporting dashboard; they rely on it as a core operating habit.

  • Natural Multi-Department Expansion: Starting as a high-utility calling solution, PromptPath’s architectural foundation is engineered to extend across the entire dealership—from the phones to the physical showroom and the F&I department.

  • Deep Domain Credibility: In automotive retail, trust and industry familiarity dictate enterprise adoption. Amit, Max, Jason, and the PromptPath team bring decades of combined experience building and distributing mission-critical software for dealers.

We are thrilled to welcome the PromptPath team to the ASV portfolio, and we look forward to collaborating with FM Capital, Keith Jezek, and our syndicate partners to help support their next chapter of growth.

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If you are a founder building a transformative B2B company, we want to hear from you. We review every submission and appreciate you sharing your vision.

Ready to build the future?

If you are a founder building a transformative B2B company, we want to hear from you. We review every submission and appreciate you sharing your vision.

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If you are a founder building a transformative B2B company, we want to hear from you. We review every submission and appreciate you sharing your vision.

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© 2026 Armory Square Ventures

Syracuse

235 Harrison St.,
Syracuse, NY 13202

Skaneateles

42 E. Genesee Street,
Skaneateles, NY 13152

New York

26 Broadway,
New York, NY 10004

Indianapolis

6151 Central Avenue,
Indianapolis, IN 46220

© 2026 Armory Square Ventures

Syracuse

235 Harrison St.,
Syracuse, NY 13202

Skaneateles

42 E. Genesee Street,
Skaneateles, NY 13152

New York

26 Broadway,
New York, NY 10004

Indianapolis

6151 Central Avenue,
Indianapolis, IN 46220

© 2026 Armory Square Ventures

Syracuse

235 Harrison St.,
Syracuse, NY 13202

Skaneateles

42 E. Genesee Street,
Skaneateles, NY 13152

New York

26 Broadway,
New York, NY 10004

Indianapolis

6151 Central Avenue,
Indianapolis, IN 46220

© 2026 Armory Square Ventures