Robert Wood

CISO | Servant Leader | Advisor | Lifelong Student (posts here are my own opinions and musings)

I have built, scaled, and run security programs as a CISO at 4 different organizations ranging from small tech startups to trillion dollar government organizations. The early part of my career was spent working in application security and red teaming. Cybersecurity is a passion of mine; using it to do amazing things is something that gets me fired up.

That’s why I founded Sidekick Security. To help organizations achieve security-led growth and digital transformations. In an age of trust as currency in so many industries, I believe this is the time when security truly can be an enabler. 

Beyond that, I am a lifelong learner. I love studying outside of my field and finding ways to expand the mental models I have to solve problems differently, more effectively, or to think about them in altogether new and fresh ways. 

Founder and CEO

Helping to connect SMBs and startups with exceptional security talent. A fresh, blue ocean strategy on the cyber security services market for organizations that really need it. 

Sean Doherty

What does GovDash do?

GovDash is the AI platform for winning government contracts. Produce high-quality proposals, run capture, organize your data, and a whole lot more. All in one place. Replace multiple broken tools with GovDash, the platform designed to make your business development team more effective—and happier.

We are supported by top investors such as:

▹ Y combinator
▹ Northzone
▹ Craft Ventures
▹ Soma Capital
▹ Global Founders Capital
▹ Olive Tree Capital

How To Get In Touch?

▹ Book a meeting on our website: https://govdash.com/

Co-Founder & CEO

We've all experienced frustration when working with data tools - 74% of employees feel unhappy or overwhelmed when working with data. We founded Olli.ai to reimagine the way that teams work with data, leveraging state-of-the-art AI models to help people get their data questions answered in seconds.

Announcing GovDash’s $30M Series B.

One of America’s core advantages is that we can pull cutting-edge capability from the private sector and put it to work fast. Yet we make it far harder than necessary to do so.

Great companies struggle to find, win, and deliver government contracts not from lack of capability, but from dense, unforgiving processes: lengthy solicitations, compliance traps, amendments, brittle tools, and admin that steals time from delivery.

The first wave of AI was supposed to fix this, however, GovCon workflows are too long and regulated for prompt wrappers to automate reliably. Most "AI for GovCon" tools shifted the burden back to teams.

We chose a different path at GovDash.

Since launching ~2 years ago, we've built AI-native infrastructure: a workflow engine that executes full lifecycles end-to-end, and we started with proposals.

We focused on fundamentals: advanced document parsing, structured solicitation understanding, company knowledge organization, and compliance-first UX.

& we went multi-product early because proposals depend on capture, past performance, pricing, and contracts. Real leverage comes from unifying the lifecycle so context compounds across teams.

The results:

- $5B+ in customer contract awards in 2025 alone
- 16× revenue & customer growth since Series A
- 70% of teams using 2+ modules
- 501% YoY growth in daily Dash usage

Hundreds of contractors across defense, civilian, state/local, and education now win faster and deliver better.

This $30M Series B accelerates our roadmap in 2026: deepening GovDash Discover, Capture, Proposal, Pricing, and Contract; expanding into Delivery & beyond; pushing Dash’s agent capabilities into more workflows; and adding sharing for teaming/partners.

At GovDash we’re building the rails for doing business with government; vertically integrating procurement workflows so contractors focus less on bureaucracy and more on their capabilities and how they further American interests.

We're hiring. If you're ready to build the execution layer for government work, join us: https://lnkd.in/eJQmY2VN (or DM me).

Grateful to our customers, team, and investors. Onward in 2026. 🇺🇸

CEO at GovDash - AI platform for winning government contracts

Office pup is tuckered out after a series of big announcements (FedRAMP & Series B).

Thank you to our customers, investors and teammates for so much support over the past few weeks. 🇺🇸

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Super excited to once again partner with Y Combinator in this round.

Special thanks to Brad Flora & Jon Xu who have supported us from day 1!

GovDash raised a $30M Series B to build AI-native infrastructure for government contracting. It vertically integrates the full procurement lifecycle, from opportunity discovery to delivery and recompete, so contractors win faster and focus on mission-critical work instead of paperwork and bureaucracy.

Since its Series A, revenue and customer base have grown 16x, and GovDash now powers hundreds of businesses serving the government across federal, state/local, and education sectors.

Joey Foster recently joined GovDash as an Account Executive.

Joey has deep experience in government contracting, having spent ~7 years at Tribal Health moving from Account Manager → Senior Account Manager → Director of Business Development, and he ran his own GovCon consulting business for the last 5 years.

Welcome Joey!

We're very excited to announce Joey Foster joining us on the sales team!

Joey received his Bachelor of Arts in Psychology from Harvard University, and has nearly 8 years of GovCon experience overseeing Business Development and Client Services in healthcare staffing. 

He has spent the majority of his career thus far scaling Federal contractors and small businesses through strategic thinking and a client-focused approach.

Welcome to the team Joey!

#govcom #govcon #federal #govtech

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Robert Wood

Sean Doherty

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The Battle

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