Rachana

Kumar

Founder

Stealth Startup

New York,

New York

2026 Cohort

Industry

Technology

Area of Expertise

Artificial Intelligence

Immediately Qualified to Serve

Compensation

Previous Board Experience

Nonprofit, Private

Rachana Kumar is a public company technology executive and AI governance leader who served as Chief Technology Officer of Etsy, Inc. (NASDAQ: ETSY), where she owned a $1B+ P&L and led 1,200 people across engineering, security, data, machine learning, cloud infrastructure, and IT. Over her decade at Etsy, the marketplace scaled from roughly $1 billion to $13 billion in annual gross merchandise sales and the active buyer base expanded from 46 million to more than 90 million customers across 200+ countries and territories. She is now Founder and CEO of an AI-native venture, building applied AI systems in production, a current, working vantage point on the technology boards are being asked to govern.

She presented quarterly to Etsy’s board of directors on technology and product strategy and AI developments, and reviewed and approved the CISO’s reporting to the board’s risk committee. She oversaw the enterprise cybersecurity function, SOX compliance controls, and global data privacy obligations, and led executive compensation planning and succession for her senior leadership team. Her organization was central not only to revenue but to profitability, driving the operating efficiency behind Etsy’s adjusted EBITDA margins of approximately 27%.

Rachana built and executed Etsy’s AI strategy, scaling generative AI from 3 to more than 30 production applications spanning search, discovery, customer support, marketing, and logistics. She established Etsy’s Responsible AI group to address bias, transparency, and emerging regulatory requirements, and created an internal platform enabling engineers to integrate external LLMs without infrastructure complexity. That work maps directly to the questions boards now face on AI oversight, model risk, third-party dependency, and disclosure.

Her M&A experience spans technology due diligence and post-merger integration across multiple acquisitions, including Depop, DaWanda, A Little Market, and Canasta Rosa. As VP of Engineering and Managing Director of Etsy Mexico, she launched and scaled the company’s Mexico operations to approximately 200 employees. During the COVID-19 demand surge, she scaled infrastructure and customer experience through 200% sales growth without compromising platform stability.

She currently serves as an Advisory Board Member of HALO, the TPG-backed global leader in branded merchandise, recognition, and incentive solutions, with more than 1,800 employees across 42 offices, advising the board and senior management on product and technology strategy, AI transformation, and organizational change. She is a Strategic Advisor to Suno AI, a Board Member of Liberty Science Center, and a member of the Advisory Technology Council at Lincoln Center for the Performing Arts.

A frequent keynote speaker at Microsoft Build, Google Cloud Next, and the WSJ CIO Network Summit, Rachana has been featured in The Wall Street Journal and recognized among Technology Magazine’s Top 100 Leaders in Tech and the Top 50 Most Powerful Women in Tech. She holds a Master of Public Administration from Columbia University and a Bachelor of Engineering from RV College of Engineering.

Code of Conduct: Governing Data & Emerging Tech

Boards are no longer observers of emerging technology; they are stewards of how it’s governed. This panel goes beyond awareness to examine how directors can structure oversight, define accountability, and measure governance effectiveness in AI, data use, and digital innovation. Panelists will share practical strategies for building governance systems that ensure transparency, ethical decision-making, and responsible innovation at scale.

Speakers include: Sita Lowman, Nithya Das, Suresh Sharma, Byron Loflin

Your First Board Meeting: A Director’s Playbook

Designed for aspiring and newly appointed directors, this session offers practical guidance on how to step confidently into your first boardroom. Learn what to expect in early meetings, how to contribute with purpose, and how to quickly build credibility and trust among seasoned peers. Gain insight into board dynamics, unspoken protocols, and the critical questions new directors should be ready to ask and answer.

Tactics that Work: Case Studies in Navigating Shareholder Activism

In this tactical, director-focused session, participants will engage in case-based exercises to dissect real campaigns and pressure scenarios. From activist letters to proxy fights, explore how boards can craft strategic responses that reinforce governance integrity, protect corporate reputation, and align with long-term priorities. Walk away with actionable tactics and frameworks to strengthen board preparedness in the face of growing investor scrutiny.

Inside the Boardroom: Resilience Planning in Action

This interactive session places directors inside the boardroom during moments of disruption. Through tabletop exercises and real-world scenarios, participants will explore how boards can apply structured frameworks to assess geopolitical risk, anticipate threats, and make decisive decisions under pressure. Designed as a classroom-style session, this breakout provides practical tools to strengthen oversight and build a proactive board response strategy in an increasingly uncertain world.

Reputation & Response: How Boards Navigate Shareholder Activism

As shareholder activism intensifies, boards face mounting pressure to defend strategy, protect corporate reputation, and engage stakeholders with clarity. This panel brings together seasoned directors to explore how boards can respond effectively while maintaining credibility, board alignment, and stakeholder trust. Hear real-world insights on navigating activism in today’s high-stakes, high-visibility environment.

Speakers include: Gaby Sulzberger, David Cahoy, Rachael Coffey, Eduardo Gallego

Navigating Global Markets: Trade, Tariffs, and Supply Chain Strategy

As global disruptions reshape business models, this panel will explore how boards can navigate the practical complexities of trade, tariffs, and supply chain shifts across regions. Panelists will share how directors are guiding companies through regulatory changes, sourcing challenges, and new market risks, while seizing opportunities for growth and operational agility.

Speakers include: Titi Cole, Mia Mends

Strengthening Oversight: Risk Management and Board Resilience

This keynote will equip directors to think globally about risk through the lens of geopolitical foresight, cross-border tensions, and long-term instability. Learn how boards can strengthen oversight and guide enterprise-wide resilience by anticipating disruption and embedding a proactive risk culture in a changing world.

Speakers include: Rodger Baker