From Insight to Impact: Scaling the Venn Platform at Two Sigma | Anna E. Molosky

Institutional investors operate in a world where small decisions can have outsized consequences. When data is complex and markets move fast, insight—not information—is the differentiator.

At Two Sigma Investments, LP, Anna E. Molosky led the product strategy behind Venn by Two Sigma, a portfolio analytics and risk management platform designed to help institutional investors assess performance, understand risk factors, and make confident, data-driven investment decisions using quantitative models.

But delivering analytical power was only the starting point. The real challenge was transforming that value into a scalable, profitable platform—without compromising the rigor our users demanded.

Designing Growth Around the Customer

As head of Strategic Product Management and Product Design, my approach was grounded in one principle: growth must be earned through measurable customer value.

To achieve this, I introduced AI-enabled product frameworks that allowed us to move beyond intuition and into evidence. By programmatically analyzing feature usage at the individual user level, we uncovered which capabilities users relied on most, which features they were willing to pay for, and how pricing could reflect true perceived value.

This shift fundamentally changed how we approached monetization. Instead of imposing a pricing model, we allowed user behavior to inform it.

Turning a Free Platform into a Profitable Business

The results validated the approach.

Within two quarters of launching a new, data-driven pricing strategy, Venn evolved from a platform with no paying customers to one where 55% of users subscribed to the paid offering. In its first year, the platform generated $7.2 million in annual recurring revenue, supported by a 95% paid customer retention rate.

These outcomes were not the result of aggressive sales tactics, but of aligning product value, pricing, and customer needs through continuous learning and iteration.

A Smarter Way to Prioritize Product Investment

Sustainable growth requires disciplined prioritization. To that end, I designed an automated Product Prioritization Framework that consolidated multiple signals into a single decision-making system:

• In-app engagement and usage analytics

• Direct client feedback and feature requests

• Market dynamics and competitive intelligence

By leveraging AI to synthesize these inputs, the framework accelerated how quickly we identified high-impact opportunities and reduced bias in roadmap decisions. The result was a faster, more customer-centric path from insight to execution.

Leading Through Influence and Execution

Behind the platform was a highly capable team. I led an agile group of Product Managers and UX Designers, fostering a culture of accountability, collaboration, and data-driven decision-making. Much of this leadership required influencing across functions and stakeholders without formal authority—a skill essential in complex, matrixed organizations.

Together, we delivered new platform capabilities iteratively while maintaining a relentless focus on customer outcomes and business impact.

What This Experience Reinforced

Building and scaling Venn reinforced a conviction that continues to guide my work: AI and analytics are only powerful when paired with thoughtful product strategy and strong leadership.

When teams listen deeply to users, rigorously quantify value, and act decisively, they can turn sophisticated technology into durable growth. Venn’s evolution stands as a case study in how insight—when operationalized effectively—becomes impact.