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. 

Datadog

As agencies take on secure-by-design initiatives and scale under mandates like M-15-14, M-21-31, EO 14028, and FISMA, the pressure to move quickly, reduce risk, and prove readiness keeps growing.

I work with federal teams (and the FSIs that support them) to bring clarity across the stack, from infrastructure to applications, performance to posture. Most friction comes from legacy decisions, siloed teams, and blind spots across environments.

Here’s how I help cut through the noise:
- Unify observability across hybrid and multi-cloud platforms
- Reduce tool sprawl and operational overhead
- Connect ops, security, and modernization priorities
- Support faster troubleshooting and more resilient systems

Here’s how other agencies are approaching it:

Strategic Account Executive, Federal Civilian

Tanium

Supported Civilian agencies in advancing EO 14028, M-22-09, CDM, and FISMA priorities through real-time endpoint visibility and control. Focused on helping agencies shift from legacy tools to unified, modern platforms aligned with Zero Trust and risk-based initiatives.

Collaborated with FSIs and partners like ServiceNow to support integrated modernization strategies. Led long-view engagement in environments where Tanium was not previously considered, requiring trust, education, and mission alignment.

Generated $5M+ in new pipeline through strategic entry points (not expansions), laying the groundwork for durable, agency-wide transformation.

Director of Strategic Accounts, Federal Civilian

RSA Security

Archer is an eGRC platform that helps organizations identify, manage, and report risk across IT, business, and third-party environments while streamlining compliance and improving accountability.

Responsible for hunting new logos and driving growth across Federal and Enterprise markets in New England as part of a newly launched Business Development team.

• Won largest new business of 2022 (~$3.2M TCV) by helping a GSE modernize its GRC posture
• During the same period, tapped to cover an open territory and secured $6M in renewals and upsells in 6 months
• Delivered ~$9M in customer impact by aligning security investments with mission and regulatory goals
•Won 8 new enterprise logos by end of FY21

Business Development Manager, Archer

Retained and upsold ~$5M by aligning to agency GRC needs, and delivering maturity-based solutions mapped to FISMA and NIST RMF requirements.

Account Manager, Archer Federal

SecurID provides powerful identity and access management capabilities in authentication, access management, and identity governance – to fully protect organizations in a world without boundaries.

Retained ~$4M in federal accounts and drove new license growth by positioning SecurID as a foundational pillar of Zero Trust. Supported FedRAMP authorization to accelerate cloud adoption across the public sector.

Account Manager, SecurID Federal

Business Development Representative

Colette Phillips Communications

Promoted within a year to serve in dual roles: Account Executive, focused on driving revenue, and Chief of Staff, supporting strategic initiatives and executive alignment

Led high-impact diversity and inclusion initiatives across Boston, partnering with CEO Colette Phillips to develop strategic plans that drove meaningful change and elevated brand presence. Managed high-profile projects, secured widespread media coverage and engaged with C-level executives and political leaders.

Coordinated functional teams and ensured seamless execution of initiative designed to foster a more inclusive, equitable community, while balancing revenue-generating responsibilities on behalf of the firm.

Chief of Staff / Account Executive

minus5º ICEBAR

Photographer

Staff International

As a member of the North American Press & Communications team for Maison Martin Margiela, MM6, and Dsquared2, I managed sample logistics for top fashion outlets, red carpet events, and TV/film productions. I oversaw sample loan traffic, ensuring seamless send-outs and returns from celebrity stylists, fashion editors, and production teams at publications like Vogue, Elle, and WWD. I was also responsible for tracking and analyzing brand visibility—maintaining editorial and credit request charts, monitoring press coverage across daily, weekly, and monthly publications, and compiling detailed media reports to measure impact.

Press Communications Intern

✨  I grew up code-switching between Hiligaynon, Tagalog, and English, which meant paying close attention to what’s said and unsaid: tone, timing, subtext.

Somewhere along the way, it became the backbone of how I communicate. It taught me how to read between the lines, stay tuned into dynamics, and bring clarity into messy spaces. Skills that serve me well in FedIT where priorities are always shifting, mandates keep changing, and decisions are layered.

Over time, I’ve learned that in environments like these, clarity builds trust. It shows you’re listening, you understand the stakes, can help teams move with confidence, and make the complex feel doable.

This is the kind of work I get to be part of every day and it's why I love what I do. The problem-solving, the relationships that outlast a sales cycle, and the outcomes we build together.

Whether it’s CloudSmart, CDM, EO 14028, M-21-31, or whatever acronym lands next, I help agencies move the needle. Securely. Intentionally. Strategically.

If this sounds like the kind of partner you want in your corner, let’s connect! 

If not, no worries. We’ll probably cross paths 😏👀

#GovCon #FederalIT #Cybersecurity #ITModernization #Observability

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The Battle

Robert Wood

April P.

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