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. 

Arms Cyber

In a startup environment, it’s imperative to break down barriers — to be a Swiss Army Knife, of sorts, and get things done. It’s really that simple.

I can be found directly participating in the following:

New Business Development
• Lead Generation
• Lead Qualification 
• Lead Nurturing

Sales
• Inside Sales 
• Direct Cold Outreach
• Sales Methodology Development & Implementation

Product
• Product Pricing Strategy
• Product Feature Roadmaps
• Sprint Planning

Sales Development Representative

RevGenius

RevGenius is a group of revenue-generating sales and marketing professionals brought together to learn, share, support, and grow with each other.

Member

Experian

*Led three distinct Procurement projects, collaborating cross-functionally to integrate new account management software, to engage with a consulting firm to drive improved Return on Investment (ROI) impact, and to incorporate an innovative Sales methodology used by over 50% of Fortune 100 companies
*Formalized new cross-functional and holistic process for the calculation and presentation of ROI for nearly one dozen Revenue Cycle Management solutions, including development of new ROI calculators, Key Performance Indicator (KPI) benchmarking at Go-Live and annual comparisons for ROI model improvement.
*Delivered tailored ROI calculations for >100 Clients, closing deals of more than $10m Annual Contract Value
*Spearheaded the development and maintenance of revamped whitespace opportunity calculator informed by internal customer relationship management (CRM) data & detailed interviews with internal stakeholders.

Director, Client Success & Sales Enablement

*Successfully drove cross-functional Sales process improvement, accelerating the sales cycle by 67% 
Gained buy-in for overhaul of Support case routing, reducing average case resolution time in 3 months
*Meticulously crafted an improved Go-Live Date (GLD) forecast model through usage of advanced statistical modeling tools, achieving provable GLD variance of +/- 30% 
*Proactively developed sensitivity analysis model, leading to labor savings of $500,000 over five years
*Effectively led Contracting process change initiative for Machine Learning technology; collaborated across departments to gain consensus to onboard transformational technology, reducing time on manual processes by nearly 90%

Rotational Leadership Development Program Manager (Internal Consultant)

Hashed Health

*Highlighted significant information gap on company website, spearheaded 48-hour resolution plan leading to significant Google Adwords and Search Engine Optimization (SEO) improvements within a 30-day period
*Methodically aggregated key datapoints, crafting survey and designing report for 500+ conference attendees

Healthcare Blockchain Strategy & Operations Intern

BreakLine Education

BreakLine is an education and hiring initiative designed to prepare top veterans for careers in technology. The program combines intensive, graduate-level classroom instruction with hands-on workshops and professional networking.

BreakLine Tech Program

GreenLight Medical

GreenLight Medical Marketing/Strategy Intern

Acclaim Technical Services

Senior Linguist | Project Manager

BAE Systems, Inc.

Nangwik Services LLC

Contract Linguist | Project Manager

Mission Essential

I am a Cybersecurity Growth Partner at Arms Cyber. 

I joined Arms Cyber in March 2024, after four years of successful experience as a Director of Client Success and Sales Enablement at Experian, where I led cross-functional projects to develop and refine ROI methodologies, sales processes including Challenger Sale, and go-to-market strategies for various healthcare solutions, contributing to more than $100m in closed deals.

I am a fully certified Challenger Sale trainer, and as of March 2024, I hold current CRCR and CSBI certifications from HFMA.

Chris Hunter-Salas

I’m excited to share that I’m starting as a Corporate Account Executive at Glean! This has been a milestone I’ve been working toward since I first moved into sales, and I’m really grateful for the chance to take on this next chapter here.

Like a lot of people making this kind of transition, there were plenty of moments of doubt and imposter syndrome along the way. I definitely didn’t get here alone.

Huge shoutout to Sudhir Mazumdar, Reed Covington, and Patrick Gill for the coaching, feedback, and belief over the past few months, and for making sure I was truly ready for this step. And a big thank you to the entire SDR team for sharing ideas, role-playing, and being in the trenches with me every day.

I also want to thank Jacob Scheff and 🤿 Steven Broudy for opening doors, challenging me in the right ways, and investing in my growth. There are way too many people to thank by name, but if you’ve ever taken time to answer a question, let me shadow a call, or just checked in when things were tough, please know it made a real difference to me.

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The Battle

Robert Wood

Chris Hunter-Salas

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The Battle

Robert Wood

Chris Hunter-Salas

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