Senior Associate, AI

About the role

The Senior Associate, AI will own the firm's AI-focused investment thesis from first contact through to conviction, acting as the primary technical and analytical lead for deals in the pipeline. This role requires deep due diligence on AI-native companies, translating complex model architectures and training approaches into clear investment theses that withstand rigorous partner scrutiny. You will be responsible for running point on all deal analysis that reaches investment committee, building and stress-testing financial models that reflect the realities of AI cost structures and scaling dynamics. The position demands active contribution to the expansion and refinement of internal AI tools and workflows, ensuring the team operates at the forefront of both strategy and execution. You will serve as the key interface with technical founders, helping portfolio companies navigate AI-specific build-vs-buy and hiring challenges. This role offers a clear trajectory toward Principal for an operator who thrives in a hands-on, high-ownership environment. You will be embedded full-time with the investment team at 22 Vanderbilt, working closely with partners to source, assess, and champion AI companies from day one. The position is central to scaling the firm's expertise in data and application-layer AI across healthcare, fintech, and business software.

Key facts

What you'll do

Run point on deal analysis for all deals nearing investment committee consideration, owning the narrative, numbers, and risk factors.

Initiate and execute end-to-end diligence for AI-native opportunities, constructing detailed financial models and rigorously stress-testing scenarios around growth, margin, and compute-cost assumptions.

Pressure-test technical claims made by founders, identifying gaps that generalist investors might overlook and articulating how those gaps materially alter the shape of potential returns.

Build and maintain the firm's point of view on the evolution of the AI stack, converting technical trends into concrete, actionable investment theses for the partnership.

Source AI-native investment opportunities directly, proactively identifying founders and technical operators before they enter broader market pipelines.

Represent Company Ventures within technical communities, labs, and specialized events where AI-native founders and operators are most active, establishing the firm as a visible and trusted participant.

Support portfolio companies as they navigate critical AI build-vs-buy decisions and technical hiring strategies, aligning their capabilities with long-term product roadmaps.

Engage as a co-owner of the firm's Residency program, attending all key sessions and driving execution alongside the Associate responsible for day-to-day operations.

Bring hands-on, current fluency to internal operations by evaluating and integrating the latest models and agentic tools that can enhance how the firm sources, diligences, and invests.

Articulate a technically grounded read on emerging capabilities, clearly explaining what is real today versus what is speculative and how that distinction shapes investment timing.

Champion the thesis that AI infrastructure and tooling will increasingly determine competitive advantage at the application layer, influencing product and market selection.

Assess founder-market fit within the AI context, placing particular weight on technical credibility, execution history, and adaptability in a fast-moving field.

Maintain a rigorous and up-to-date view of model performance, tooling releases, and deployment patterns to ensure investment decisions are based on current reality rather than historical benchmarks.

Translate complex technical and business information into concise materials that allow partners to make swift, well-informed decisions under tight deadlines.

Requirements

3-5 years of investing or directly relevant analytical experience, including time as an analyst or associate at a bank, a private equity firm, or another venture firm where you built real financial models under real scrutiny.

Modeling Competency demonstrated by the ability to construct a model from a cap table, growth curve, and set of assumptions, showing how a deal returns capital across multiple scenarios and identifying which assumptions drive outcomes.

Investment judgment proven by the ability to take a clear position on a deal in a partner meeting and defend it under genuine pushback and rigorous questioning.

AI-native behavior shown through daily use of frontier models and coding agents, with a track record of contributing to internal tooling or workflows that improve team efficiency.

Commitment to in-person collaboration based in the firm's offices at 22 Vanderbilt, with regular attendance and active participation in all-team meetings and off-sites.

Strong written and verbal communication skills, enabling you to present detailed analysis, challenge peers, and convey nuanced technical concepts to non-technical partners.

Intellectual curiosity and discipline, with the ability to rapidly assimate new technical information, challenge assumptions, and iterate on models and theses as new data emerges.

Ownership mindset, comfortable making decisions within a clear framework while also escalating appropriately and taking responsibility for the outcomes of your analyses.

Nice to have

Experience working directly with AI startups or technical founders in a builder, operator, or investor capacity.

Background in healthcare, fintech, or business software verticals where AI is a transformational force.

Contributions to open-source projects or public technical writing that demonstrate deep understanding of model architectures and deployment patterns.

Practical notes

This role is full-time based in New York City at 22 Vanderbilt.

The position is eligible for career progression to Principal for the right candidate.