13 - Guarding the Vault: Cybersecurity Strategies for Finance with Chithra Rajagopalan

5 to 50: Financial Strategies for Growing Companies

Is your finance department your company’s biggest security risk?

Join Jeff Rudner on this episode of 5 to 50: Financial Strategies for Growing Companies as he welcomes Chithra Rajagopalan, Head of Finance at Obsidian Security, to discuss how the convergence of finance and cybersecurity can either expose companies to billion-dollar breaches or unlock strategic resilience. From managing phishing threats to balancing AI innovation with secure financial practices, Chithra shares practical, cost-effective tactics for protecting sensitive data and strengthening internal operations. Whether you're a founder, CFO, or finance leader, this episode is packed with insights to help you scale securely in today’s digital-first world.

What you will learn:

• How to quantify cybersecurity risks and their potential financial impact
• Why separating finance and security departments is crucial for maintaining expertise
• The critical importance of proper user access management
• How to implement cost-effective security measures for early-stage companies
• Why multi-factor authentication and proper data hygiene are non-negotiable
• How to balance AI adoption in finance while maintaining security and data protection
• The framework for creating effective partnerships between CFOs and CISOs
• Why centralized data management must be balanced against security considerations
• How to protect against increasingly sophisticated phishing attacks
• The essential security protocols every finance department should implement

Chithra Rajagopalan is a seasoned finance leader with deep experience in high-growth SaaS companies. Currently Head of Finance at Obsidian Security, she has successfully led organizations through fundraises, acquisitions, international expansion, and IPO readiness. With prior roles at Deloitte and fast-paced startups, she’s known for her strategic insight, operational rigor, and strong executive partnership. Chithra also serves on the boards of two non-profits focused on nurse retention and social equity for underprivileged children, reflecting her commitment to impact beyond business.

• Chithra Rajagopalan on LinkedIn
• Obsidian Security Website
• Jeff Rudner on LinkedIn
• Proseer Website
• Book a Consultation Contact Us
• Download Our eBook Transforming Accounting Solutions

Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.
Check out our three most downloaded episodes:

• Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
  
• The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling

• Pivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon