The team

New company.
Established team.

Decades in cybersecurity, digital forensics, cloud infrastructure, and regulatory compliance – working alongside consultants, lawyers, and regulators in the rooms where the work actually gets done.

Now we are building the AI-accelerated product version of what regulated markets always needed.

Founding Team

Evan Jennings

Co-founder & CEO
Ex-PwC Cybersecurity Risk & Regulatory

Evan Jennings is Octosight’s Co-founder and Chief Executive Officer. He spent his career working inside the regulated markets the company now serves and started Octosight to build the AI-accelerated solution his consulting teams and his clients always needed but never had.

His early career in investment banking and asset management, followed by fourteen years as a consultant with PwC, built the foundation for Octosight’s investment, operational, and deals diligence capabilities. At PwC, Evan created and led a skunk-works engineering team to solve data-risk and regulatory challenges that commercial tools could not address, delivering cloud-native solutions used in multi-billion-dollar transactions, national-security matters, breach response, and global compliance programs. He presented one of these innovations, a CFIUS data-risk mitigation solution, to the U.S. Department of the Treasury at their request.

Evan and Brent have worked together since 2016, and members of Evan’s team now form the backbone of Octosight.

Brent Botta

Co-founder & CTO
Ex-FBI CART, Digital Forensics

Brent Botta is Octosight’s Co-founder and Chief Technology Officer. He spent his career building digital forensics and data risk mitigation systems in the markets Octosight now serves, which led him to start the company to build a cloud-native, AI-accelerated version of these technologies.

Brent began his career as a Special Agent for the Georgia Secretary of State and later as a member of the FBI’s Computer Analysis Response Team (CART) and the FBI’s West Coast Cyber Team. He supported major investigations, responded to national incidents including Y2K and 9/11, and executed more than 825 federal and state search warrants.

After leaving federal service, Brent spent eighteen years in executive leadership roles, building eDiscovery technologies and delivering complex client implementations. His work established core patterns used across the modern eDiscovery landscape, and he is a named inventor on multiple patents in the field.

Brent and Evan started working together in 2016, and Brent has worked with members of Octosight’s founding team dating back to 2004.

Scott Telle

Founding Software Engineer
Ex-PwC Cloud Engineering

Scott Telle is a Founding Software Engineer at Octosight. His career has focused on building secure, scalable cloud-native systems on AWS and delivering them inside regulated, enterprise environments – experience that now underpins Octosight’s architecture.

Scott is a rare engineer who can take a whiteboard concept, spoken direction, or ambiguous problem statement and ask the questions needed to drive it all the way to production.

Before joining PwC through its 2020 acquisition of EagleDream Technologies, an AWS Premier Consulting Partner, Scott spent six years at EagleDream building cloud-native applications, leading engineering teams, and delivering large-scale modernization and transformation programs.

Scott is a highly adaptable engineer and a true startup force multiplier – the kind of builder who improves every system he touches and can rapidly pivot when priorities or constraints change. He and Evan began working together at PwC following EagleDream’s acquisition.

Kairi Wright

Founding AI Researcher & AI Engineer

Kairi Wright is a Founding AI Researcher and AI Engineer at Octosight. A mathematician, he has been working hands-on with language models since 2015 – long before LLMs entered the mainstream – applying them to real-world problems in regulated environments for large enterprises.

Kairi is a data-focused applied researcher who understands how AI performs in production, not just in demos, and can turn his research into enterprise-quality production code. His experience spans model development, large-scale token processing, and building AI systems that meet enterprise expectations around reliability, accuracy, and operational control.

At Octosight, Kairi is the driving force behind how our platform will process hundreds of millions of tokens efficiently across both commercial models and the internal domain-specific models we are developing from the ground up.

Mekalyn Carroll

Founding Designer

Mekalyn Carroll is a Founding Designer at Octosight, where she blends user interface (UI) and user experience (UX) product design to create intuitive enterprise workflows. She is a master of Figma design and prototyping, enabling the team to experience and validate product ideas long before code is written.

Mekalyn has a rare ability to translate loose conversations, sketches, and evolving requirements into clear wireframes and polished designs that developers can implement without friction. Her background in both design and copywriting gives her an edge – she shapes not only how the product looks, but how it communicates, ensuring clarity and cohesion across every interaction.

She works hand-in-hand with engineering, designing within the realities of toolkits, components, and platform constraints, and refining features toward clarity and usability. Her adaptability, attention to detail, and end-to-end design approach make her a core contributor to how Octosight builds software used in regulated markets.

Advisory Board05 advisors

The people the team turns to.

Executive leaders, investors, and operators who have navigated the markets Octosight serves – regulatory risk, cybersecurity, deal diligence, and enterprise scale. They help us see around corners.

Scott Dillman

Retired PwC Partner who served as the firm’s Risk Management Technology Leader and COO for the U.S. Cybersecurity practice, and previously served as an MD at Dreamit Ventures.

Kevin Kreb

Retired PwC Partner who served as a Forensics practice partner, Risk Management Partner responsible for the Forensics and Cybersecurity practices, and Deputy CFIUS Compliance Officer.

Eric Minnick

Investor and entrepreneur, currently the General Partner at Versus Ventures and formerly the Chief Investment Officer at Andover Ventures and a Principal at Cerity Partners.

Jacqueline Olynyk

Retired PwC Partner and former PwC Board Member who served as Advisory Risk and Quality Leader, Products Data and Accelerations Leader, Advisory NY Regional Leader, and CFIUS Compliance Officer.

Rowan Paul, M.D.

Sports Medicine and Interventional Regenerative Orthobiologics physician and founder of RegenCore Medical, TOBI Networks, and Launch Biosciences, with multiple exits. EHR/HIPAA expert who sits on several global scientific and medical advisory boards, serves as Head Physician for the San Francisco Ballet, and previously served as a Sports Medicine physician for the Oakland Athletics.

Now boarding