Tola Capital

Tola Capital — Research Document Overview Tola Capital is a Seattle-based venture capital firm founded in 2010 by Sheila Gulati and Stacey Giard, both former Microsoft executives. The firm is singularly focused on investing in software companies that power business transformation across industries. With $688M raised across multiple funds—including Fund III at $230M closed in November 2023—Tola Capital is widely recognized as the largest venture fund headquartered in Seattle that many outside the Pacific Northwest may not know. The firm brings deep operational expertise from decades inside the software industry, creating a distinctive partnership model that goes beyond capital to actively engage in product roadmaps, positioning, and go-to-market strategy. Investment Thesis Tola Capital practices hypothesis-based investing—the team forms a view about which needs and solutions will drive transformational change in large markets, then seeks founders building precisely in those spaces. The firm believes every industry will eventually be transformed by software, and that the most defensible companies are built at the intersection of deep domain knowledge and emerging technology. For the current fund cycle, Tola's focus has shifted decisively toward AI-enabled enterprise software, specifically targeting what Sheila Gulati calls the "enterprise scaffolding" of AI: the layer above foundational models that makes AI trustworthy, measurable, and deployable at enterprise scale. Priority thesis areas include: Domain-specific Foundation Models — AI trained on proprietary industry data AI/ML Tooling — Infrastructure that accelerates model adoption and deployment AI SaaS Applications — Applications integrating frontier AI into enterprise workflows AI Compliance and Governance — Responsible AI, policy, and audit tools AI Security Tools — Securing AI systems and AI-native attack surfaces Enterprise of the Future — Workflow automation, employee experience, and productivity The firm explicitly avoids consumer applications, hardware-only plays, and foundational model development (e.g., LLM pretraining infrastructure). Stage and Check Size Tola invests at Seed through Series B: Seed: $1M–$4M, targeting first institutional check Series A & B: $5M–$15M, scaling into product-market fit Fund III targets 25–30 portfolio companies globally. The firm takes meaningful ownership positions and is structured to lead rounds, though they will co-lead and participate selectively in strong syndicates. Lead Tendency Tola Capital typically leads or co-leads rounds, particularly at the Seed stage. Their operational depth—direct involvement in product roadmap, positioning, competitive strategy, and enterprise sales—makes them most effective as lead investors or board members, not passive followers. Portfolio Highlights Tola has an active portfolio of 38+ companies and 18+ exits. Notable current investments include: OneTrust — Enterprise trust, privacy, and compliance platform (rumored unicorn) Pulumi — Cloud engineering and infrastructure as code (backed since 2017; launched AI agent "Neo" in 2025) Nooks — AI-native tools for phone sales teams Simpplr — AI-powered employee experience platform TrustCloud — Compliance and GRC automation platform (raised $15M, May 2025) Tracera — ESG data collection and sustainability reporting ($12M Series A, April 2025) Tana — AI-native knowledge workspace ($25M Series A, February 2025) Crogl — Cybersecurity AI for security analysts ($30M, March 2025) Pay-i — FinOps platform measuring generative AI cost and ROI (Seed, May 2025) Palosade — AI agents for DevSecOps (Seed, December 2024) Notable exits include: Clipchamp — Acquired by Microsoft (2021) Hybris — Acquired by SAP (2012) OSIsoft — Acquired by AVEVA/Schneider Electric (2012) Zilla Security — Acquired by CyberArk for $165M (February 2025) Arcus — Acquired by Addepar (May 2025) IntSights — Acquired by Rapid7 (2018) ProtectWise — Acquired by Verizon (2015) Team Sheila Gulati, Managing Director and Founder: A second-generation software entrepreneur, Sheila spent over a decade at Microsoft where she led enterprise IT strategy and launched Microsoft Azure. She served in the Developer business unit and on Corporate Development overseeing acquisitions. Before Microsoft, she worked at Robertson Stephens supporting tech IPOs including Juniper Networks and F5. She is on the National Board of Pratham (education NGO). Stacey Giard, Venture Partner (Co-Founder): Co-founded Tola Capital in 2010 with Sheila; brings extensive operational background in enterprise software. Aaron Fleishman, Partner: Former Strategy Manager at Microsoft and eCommerce startup founder; Georgetown and Wharton-educated; focuses on identifying enterprise AI investment opportunities. Akshay Bhushan, Partner: Former Associate at L.E.K. Consulting advising Fortune 500 clients in software, aviation, and healthcare; applies product management experience to enterprise software investment. Vahé Torossian, Venture Partner (joined July 2025): Brings decades of technology and go-to-market leadership; supports portfolio companies on commercial scaling. Phil Sorgen, Venture Partner: Additional venture partner with enterprise software expertise. Karolin Beck, Venture Partner: Additional venture partner focused on European portfolio. Tashi Schmidt, CFO and Partner: Manages fund finance and operations. Geographic Focus Primarily US with global reach. The firm has made investments across the United States (Seattle, San Francisco, New York, Chicago, Boston), Europe (London, Germany, Sweden, Israel), Canada (Montreal), and Southeast Asia (Singapore). Decision Process Tola operates as a partnership with an investment committee. Sheila Gulati leads sourcing and strategy, with partners Aaron Fleishman and Akshay Bhushan active in deal evaluation. Venture partners contribute domain expertise and support portfolio engagement. The firm is described as selective—they typically invest in 8–10 companies per fund before deployment accelerates. Founder Preferences Tola seeks founders with "real invention"—deep domain expertise, technical differentiation, and genuine insight into a specific industry's transformation. They favor founders with enterprise experience (large company or scale-up backgrounds) who understand how to sell into complex organizations. The firm places high value on culture, ambition to build multibillion-dollar companies, and willingness to collaborate closely on product and go-to-market strategy. Anti-Thesis Tola does not invest in: foundational AI/LLM infrastructure (pretraining, GPU clouds), consumer apps, hardware-only businesses, or companies without a clear enterprise customer and revenue path. Recent Thesis Essays "As Enterprise AI Adoption Accelerates, Pricing is Still the Wild West" (Aaron Fleishman, April 2025) — analyzes AI agent pricing models from consumption-based to value-based. "More Power, New Problems: Where Software Composers Get Stuck" (February 2025) — examines friction in AI-assisted software development. "My Productivity Quest and Tana's Series A" (February 2025) — thesis piece accompanying Tana investment.