Tola Capital

Tola Capital is a Seattle-based venture firm founded in 2010 by former Microsoft executives Sheila Gulati and Stacey Giard. The firm has grown to manage $688 million across multiple funds, backing 57 companies with 12 notable exits including Auth0's $6.5 billion acquisition by Okta and Clipchamp's acquisition by Microsoft. With a current Fund III of $230 million deployed in late 2023, Tola is among the most active institutional investors in AI-enabled enterprise software at the seed through Series B stages. Understanding NRR and why top quartile exceeds 120% is valuable for any founder.

Tola's investment approach is hypothesis-driven—the team identifies structural shifts in how enterprises buy and use software, then seeks founders building specifically into those transitions. The firm is particularly known for backing operators who have lived the problem they are solving, often bringing deep domain expertise from prior roles at Microsoft, AWS, or other enterprise software leaders.

Unlike generalist VCs who spread across sectors, Tola has maintained a consistent focus on enterprise transformation enabled by AI. This narrow focus has allowed the firm to build deep pattern recognition and a reputation that draws strong deal flow in its target categories.

The firm's portfolio includes two unicorns—Glia, a digital customer communication platform, and OneTrust, a privacy and data governance platform—as well as numerous other category leaders across DevOps, data infrastructure, security, and operations software.

Tola Capital invests in companies building the next generation of enterprise software, with AI as the core enabling technology. The firm's hypothesis-based approach means they identify macro-level shifts in enterprise buying behavior and seek founders building specifically into those transitions—whether that is AI governance, compliance automation, or domain-specific intelligence layers. Understanding unit economics and LTV:CAC is valuable for any founder.

Current focus areas include domain-specific foundation models, AI/ML tooling for enterprise teams, AI SaaS applications, AI compliance and governance platforms, AI security tools, and what Tola calls 'Enterprise of the Future'—companies redefining how large organizations buy, deploy, and manage software.

Tola invests from seed through Series B, with primary deployment at seed and Series A. Check sizes range from $1 million for early checks to $15 million at Series A, with up to $40 million available for Series B and growth rounds when warranted. The firm prefers to lead or co-lead rounds, though they participate alongside other investors when conviction is high.

The firm takes a long-term view on product-market fit. Tola has backed companies that took several years to achieve enterprise scale, providing follow-on capital and operational support through inflection points. This patience is a hallmark of their operator-first philosophy.

Tola's team brings direct operating experience from Microsoft, Amazon, and other major enterprise software companies. This background shows up in how the firm thinks about enterprise sales cycles, pricing architecture, and customer success—dimensions that matter enormously when evaluating early-stage bets.

Fund III, a $230 million vehicle closed in November 2023, is currently the primary deployment vehicle. The fund is concentrated on AI-enabled enterprise software companies, reflecting the team's view that AI is the most significant structural shift in enterprise software since the move to cloud-native architectures. Understanding EBITDA multiples in growth-stage valuation is valuable for any founder.

Recent portfolio additions include Palosade (AI agents for DevSecOps), DBtune (AI-powered PostgreSQL optimizer), Maxinsights (data solutions for robotics foundation model companies), and Tana (AI-native workspace combining knowledge graphs and AI agents). These investments reflect Tola's continued conviction in AI tooling and application-layer opportunities.

The firm has also backed companies in the AI compliance and governance space—including Holistic AI, which helps enterprises manage the full AI lifecycle from discovery through risk assessment and monitoring, and TrustCloud, a compliance automation platform with predictive intelligence for enterprise governance commitments.

On the developer tools front, Tola continues to support companies like SpecStory, which is building the system of record for human intent in AI-driven software development, capturing the decisions that drive product changes. This sits at the intersection of developer tooling and AI—a space Tola knows well from its earlier bets on Pulumi and other DevOps platforms.

Tola's track record includes 12 notable exits, several of which represent category-defining outcomes. Auth0, the identity platform acquired by Okta for $6.5 billion in 2021, is among the most celebrated outcomes in Pacific Northwest venture history—and Tola was an early backer.

OneTrust, a platform operationalizing trust across privacy, security, data governance, GRC, and ESG programs, reached unicorn status under Tola's ownership. Kabir Barday leads the company as CEO.

Glia, which provides a digital customer communication and CoBrowsing platform, is another portfolio unicorn. The company's platform has become essential for financial services and insurance companies looking to modernize customer interactions.

Pulumi, the cloud engineering platform enabling teams to build, deploy, and manage modern cloud applications using any language and any cloud, remains an active portfolio company under CEO Joe Duffy. Tola invested in 2017, and Pulumi has grown into a significant player in the infrastructure-as-code space.

Smartsheet and Highspot are also part of the portfolio—both leading their respective categories in enterprise project management and sales intelligence. ExtraHop, a cybersecurity platform, is another notable holding that has scaled significantly.

On the exit side, StackRox (container security, acquired by Red Hat), Clipchamp (browser-based video editing platform, acquired by Microsoft), and multiple Oracle acquisitions (Wercker, hybris, 3scale) demonstrate Tola's ability to identify infrastructure winners across multiple eras of enterprise software.

Tola evaluates investments through two lenses: the macro thesis and the founder. On the macro side, they want to see that a company is addressing a genuine structural shift in how enterprises buy or use software—not a marginal improvement on an existing category.

Founder quality is the most weighted variable. Tola prefers founders who have direct, lived experience with the problem they are solving. This means former practitioners who spent years inside the enterprises they now serve and who can speak fluently about the buyer, the workflow, and the competitive alternatives.

Product traction among developers or enterprise buyers is another key signal. Tola looks at usage metrics, customer concentration, and expansion rates. A company that can show evidence of developer love combined with early enterprise adoption is in the sweet spot for a Tola check.

Business model clarity matters. Tola prefers companies with identifiable enterprise sales motion,清晰的 pricing architecture, and a credible path to $10M+ ARR benchmarks before scaling go-to-market investment. The firm is skeptical of companies that require massive burn to acquire users in categories with long sales cycles.

Competitive positioning must be defensible. Tola looks for companies with proprietary data advantages, integration depth, or switching costs that compound over time. A company that can articulate a specific moat—and explain how it widens—stands out in the review process.

Tola also evaluates the team's ability to attract talent. A startup's most important product is its culture and leadership, and Tola spends real time understanding founder dynamics, team composition, and how the company has hired through earlier growth phases.

Warm introductions remain the primary signal source for Tola. The firm sees the best deal flow through referrals from portfolio CEOs, other founders in the Seattle and Bay Area ecosystems, and investors who co-invest regularly with Tola. A referral from someone who has worked with Sheila or Stacey directly carries significant weight.

Cold outreach through the website is viable but must be tightly written. Tola's team reads every submission, but the volume is high. A compelling cold submission should open with a one-line description of what the company does, followed immediately by evidence of traction (ARR benchmarks, user count, notable customers). The connection to Tola's thesis should be explicit—not implied.

For founders targeting a Tola check, the firm's website and blog are worth studying. Tola publishes extensively on AI trends, enterprise transformation, and their portfolio perspectives. Demonstrating familiarity with the firm's published thinking—and showing how your company fits into a thesis they have already articulated—differentiates you from founders who send generic pitch decks.

Tola's Seattle roots give the firm strong access to the Pacific Northwest engineering community. Founders building in the region should take advantage of local events and ecosystem touchpoints where Tola partners are present. The firm is also known for its operating support—Tola partners can be deeply engaged on product strategy, hiring plans, and follow-on fundraising coordination.

Follow-up discipline matters. Tola typically takes 3–5 weeks from first meeting to investment decision. Founders should send brief progress updates if there are meaningful milestones between initial meeting and decision time—not a weekly check-in, but material news (new enterprise signings, product launches, key hires).

Tola invests at early stages, but they expect founders to have a commanding grip on their financials. This means knowing your burn rate, runway, unit economics, and path to either profitability or the next priced round—not as aspirational projections but as operational facts you can defend in detail.

For AI-enabled enterprise software companies, investors want to see specific metrics: ARR benchmarks growth, net revenue retention, gross margin, and the ratio of customer acquisition cost to lifetime value. Tola will push founders on these numbers and expect crisp answers grounded in real data.

Financial models should be scenario-based. Tola wants to understand how your business behaves under different growth assumptions—what changes in hiring plans, where you draw the line on burn, and what the bridge to breakeven looks like. Founders who present a single best-case projection signal a lack of rigorous thinking.

Working with a fractional CFO is particularly valuable for AI infrastructure and developer tools companies. Professional financial guidance helps you build investor-ready materials, accurately project enterprise sales cycle impacts on cash flow management, and confidently answer the due diligence questions that arise in venture review.

Understanding your KPIs is not optional when pitching to Tola. The firm will want to understand which metrics you track obsessively, why those metrics are the right proxies for business health, and what you have done with the data to improve them. Founders who have instrumented their businesses well stand out.

If your current round does not result in a Tola investment, financial preparedness still matters—strong financials position you for future rounds with Tola or other enterprise-focused investors who see the same market.

Exploring other venture capital firms that focus on enterprise software and developer tools? Our collection of VC firm guides provides detailed information on investment criteria, portfolio companies, and strategies for securing funding from top-tier investors.

Each review is written with founder-specific context—real investment theses, actual portfolio companies, and answers to the questions that matter most when you are preparing to raise. Whether you are at the seed stage or raising a growth round, these guides help you target the right investors efficiently.

Finding the right investor fit is one of the highest-leverage decisions in a fundraise. A firm with deep category expertise can provide more than capital—it can open customer relationships, support hiring, and help navigate the operational challenges specific to your segment.