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ABOUT
Rob Wooldridge
Arroyo Grande, CA
––––Work––––
Product Engineering Leader & Veteran
I bring a unique mix of hands-on technical chops and significant leadership experience, as a expert engineering leader and former Brigadier General. With 25 years of designing, building, and supporting full-stack, mission-critical products in production, I have successfully led high-performing teams in cloud computing, data engineering, and software development; in the private sector & the military.
I’m adept at engaging customers, driving operational efficiency and delivering cost savings. Transformed a key Space Force app, leading a seamless migration to Google Cloud. Demonstrated ability to operate at C-suite level while leveraging decades of hands-on engineering experience to get the product right. I work hard to build trust with my teammates so we can solve complex problems and align technology solutions with strategic business goals.
Media links:
• General Officer Biography
• Korean War Memorial Dedication
• Urban Operations Planner Course
• Podcast - Urban Training: Division and Above,
––––Personal––––
Dad of 3, Husband of 1, backpacker, hammock camper, gamer, lego assembler, and infrequent skydiver (D22612)I was a Navy brat, bouncing around the country in my childhood, and ended up in California for high school and college. After I graduated from Cal Poly San Luis Obispo, I served on active duty as a Field Artillery officer for six years, most of which was as a paratrooper in the 82nd Airborne Division. In my last job on active duty, I returned to Cal Poly as a Captain to teach cadets how to become an Army officer and get my master's degree at night. I left active duty to join the civilian technology sector and transitioned my military career to the National Guard. For more than 20 years, I held two careers at the same time: one as a part-time Army officer leading hundreds or thousands of people during no-fail missions and another as a hands-on Information Technology leader writing code everyday. Serving for over 31 years was a dream come true for a boy who grew up in a military family as the son and grandson of navy officers. I am grateful for my family, friends, and teammates who supported my long career. Best job I ever had.
experience
Head of Product Engineering

SAIC – Head of Product Engineering, 2011-Present
• Leads the sole Agile DevSecOps team supporting U.S. Space Force’s premier, cloud-based spaceflight safety product, providing 24/7 mission support and Space Domain Awareness for global clients, including spacecraft owner/operators who manage $billions in on-orbit assets.
Tech Details: Google Cloud(FedRAMP), RESTful API, GitOps, Infrastructure as Code(Terraform/Ansible), CI/CD, Linux, MySQL, Redis, BigQuery, Pentaho ETL
• Scaled the product to over 100x data volume, as well as 10x supported users, organizations, and managed objects on orbit.
• Leverages deep data engineering expertise to design and deploy scalable, secure data pipelines and databases in the cloud.
• Writes elegant code and engages directly with stakeholders to deliver targeted solutions.
• Directed and contributed to numerous upgrades and site improvements, including P2V & infrastructure as code, while maintaining 99.95% uptime SLA for 13+ years.
• Revitalized a faltering customer relationship by introducing Agile/Scrum methodologies; results significantly boosted efficiency and generated over $1.2M (5 FTE) in additional revenue.
• Individually recognized by government clients for exceptional leadership and technical support to the U.S. Strategic Command while providing an “invaluable [service] for maintaining and improving spaceflight safety.”
• Led the team that consistently earned ""Exceptional"" ratings on Contractor Performance Assessment Reports (CPARs) due to our focus on delivering superior customer service."
Advisor

Onebrief – Advisor 2025 - Present
• Leverage my strategic and operational planning experience for Series C defense tech startup.• Leverage my strategic and operational planning experience for Series C defense tech startup.
Urban Warfare Institute – Executive Chairman 2024 - Present
• Lead a 501(c)(3) nonprofit organization dedicated to advancing the study of urban environments, urban operations, and urban warfare.
• I provide strategic oversight and foster collaboration between military, academic, and policy communities to enhance understanding of complex urban operations.
• Advised the Center for Naval Analyses how US Marine Corps should plan, train, and equip Marines for the complexities of large-scale combat in future urban environments.
• Spearhead partnerships and thought leadership efforts to expand the organization’s reach and impact.
• Oversee the organization's urban warfare training, ensuring relevant Urban Operations courses are informed by the latest research, operational best practices, and real-world lessons learned.
Brigadier General


California Army National Guard – Senior Leader 2000 - 2024
• Brigadier General / Deputy Commanding General – 40th Infantry Division
• Provided executive leadership of all operations, training, and exercises within the 40th Infantry Division, one of 18 divisions in the Army. Directed training for 12K+ soldiers spanning the West Coast and Hawaii; mentored 300+ senior leaders while in this role. I Significant strategy planning and public speaking responsibilities.
• Implemented enterprise strategies that optimized resource allocation, enhanced unit readiness, and achieved strategic objectives for California and the nation. Partnered with other senior-level leaders on implementing strategies that optimized resource allocation, enhanced unit readiness, and achieved strategic objectives for the state and nation.
• Managed 200+ security cooperation engagements, including 19 major exercises in the Middle East while deployed to Kuwait in 2023 and 2024; effectively doubled partnership activities while managing responses to adversarial attacks on U.S. forces and bases.
• Launched and directed a dedicated Urban Warfare Center; led specialized training courses for four years by enlisting assistance from global subject matter experts. Trained all U.S. branches and international students.
• Organized, trained, and led the division’s tactical command post during strenuous exercises; assumed leadership of division operations on multiple occasions and enhanced flexibility and adaptability.
• Commanded Joint Task Forces during two state emergencies spanning multiple weeks in 2020 and 2021; led over 1,000 soldiers in high-visibility, high-impact support of civil authorities.
• Served as senior trainer for a Brigade Combat Team during both an eXportable Combat Training Center (XCTC) rotation and a brigade Warfighter command post exercise; ensured that the brigade achieved its training objectives.
Chief of Staff/Operations Director (Colonel) — 40th Infantry Division,
• Led, directed, and trained 500+ people on the General Staff; coordinated and synchronized their activities during planning and mission execution
California Army National Guard,Brigade Commander (Colonel) — 100th Troop Command,
• Exercised trust-based leadership of 1.8K people spread throughout Central and Southern California while developing and mentoring 20+ subordinate leadership teams. Worked with the Indian Army on multiple exercises.
• Improved the brigade's composite ranking within the state of California on key performance indicators from 8 of 12 peer brigades to #1 of 12.
Battalion Commander (Lieutenant Colonel) — 1st Battalion, 143 Field Artillery Regiment
• Promoted ahead of peers to become the commander of a National Guard field artillery battalion composed of 400 soldiers in seven locations spread out over 17K square miles.
• Consistently ranked in the top three out of 27 executive managers throughout the state on leadership and important operational key performance indicators.
executive chairman

California Army National Guard – Senior Leader 2000 - 2024
• Brigadier General / Deputy Commanding General – 40th Infantry Division
• Provided executive leadership of all operations, training, and exercises within the 40th Infantry Division, one of 18 divisions in the Army. Directed training for 12K+ soldiers spanning the West Coast and Hawaii; mentored 300+ senior leaders while in this role. I Significant strategy planning and public speaking responsibilities.
• Implemented enterprise strategies that optimized resource allocation, enhanced unit readiness, and achieved strategic objectives for California and the nation. Partnered with other senior-level leaders on implementing strategies that optimized resource allocation, enhanced unit readiness, and achieved strategic objectives for the state and nation.
• Managed 200+ security cooperation engagements, including 19 major exercises in the Middle East while deployed to Kuwait in 2023 and 2024; effectively doubled partnership activities while managing responses to adversarial attacks on U.S. forces and bases.
• Launched and directed a dedicated Urban Warfare Center; led specialized training courses for four years by enlisting assistance from global subject matter experts. Trained all U.S. branches and international students.
• Organized, trained, and led the division’s tactical command post during strenuous exercises; assumed leadership of division operations on multiple occasions and enhanced flexibility and adaptability.
• Commanded Joint Task Forces during two state emergencies spanning multiple weeks in 2020 and 2021; led over 1,000 soldiers in high-visibility, high-impact support of civil authorities.
• Served as senior trainer for a Brigade Combat Team during both an eXportable Combat Training Center (XCTC) rotation and a brigade Warfighter command post exercise; ensured that the brigade achieved its training objectives.
Chief of Staff/Operations Director (Colonel) — 40th Infantry Division,
• Led, directed, and trained 500+ people on the General Staff; coordinated and synchronized their activities during planning and mission execution
California Army National Guard,Brigade Commander (Colonel) — 100th Troop Command,
• Exercised trust-based leadership of 1.8K people spread throughout Central and Southern California while developing and mentoring 20+ subordinate leadership teams. Worked with the Indian Army on multiple exercises.
• Improved the brigade's composite ranking within the state of California on key performance indicators from 8 of 12 peer brigades to #1 of 12.
Battalion Commander (Lieutenant Colonel) — 1st Battalion, 143 Field Artillery Regiment
• Promoted ahead of peers to become the commander of a National Guard field artillery battalion composed of 400 soldiers in seven locations spread out over 17K square miles.
• Consistently ranked in the top three out of 27 executive managers throughout the state on leadership and important operational key performance indicators.
Founder

Founder - Gibson
• Originals Online 2014 - 2017
• Founded and managed a direct-to-consumer e-commerce venture focused on novelty barbecue lighters.
It director & enterprise manager

United States Property & Fiscal Office - IT Director & Enterprise Applications Manager 2007-2011
• Directed enterprise software development, support, and strategy ensuring 16K employees statewide enjoyed high availability and performance for mission-critical financial, logistics, and personnel applications. Led geographically-distributed, cross-functional teams of customers, engineers, and leaders to develop scalable, secure, and integrated solutions that enhanced operational efficiency.
• Spearheaded the creation of a business intelligence scorecard that tracked 50+ KPIs; results improved data-driven decision making and delivered a $2.7M savings over the course of four months.
• Achieved a 95%+ customer satisfaction rating in surveys; earned recognition for exceptional responsiveness and deep technical acumen.
• Administered a $350K annual operations budget and drove significant costs savings while maintaining high service levels and operational efficiency.
Data Infrastructure lead

United States Property & Fiscal Office - Data Infrastructure Lead 2000 - 2007
• Oversaw the design, implementation, and maintenance of database systems. Managed a team of data infrastructure specialists and ensured optimal performance, security, and scalability of databases. Collaborated with cross-functional teams to support application development, monitor database performance, and troubleshoot complex issues. Held responsibility for database architecture, backups, disaster recovery plans, and introduction of best practices to ensure data integrity and availability in a 24/7 environment.
• Maintained 99.99% system uptime, safeguarded mission-critical financial, logistics, and HR databases with zero security breaches; successfully upheld 100% data integrity across all operations
skydiving instructor

Plummet Skydiving – Skydiving Instructor 2004 - 2008
• Strapped paying clients to my chest and jumped out of perfectly good airplanes over 250 times as an independent contractor. Also coached new skydivers and shot/mixed videos of jumps.
paratrooper
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US Army – Artillery Officer & Paratrooper 1993 - 1999
• Jumped out of planes and shot big guns.
• ROTC University Instructor and website manager - Recruited, taught, and supervised over 80 college students preparing to become US Army officers.
• Battalion Fire Support Officer - Led a small team of integration specialists who planned and conducted target acquisition to engage enemy positions in support of a battalion of attack helicopters.
• Battery Executive Officer - Supervised operations, training, promotions, and evaluations for 105 paratroopers. Managed a fleet of 22 vehicles, six howitzers, three trailers, and $5 million in equipment
• Battery Fire Direction Officer - Supervised a ten-person technical operations center that directed artillery fire in a high-pressure, zero-defects environment
• Company Fire Support Officer - Led a small team of integration specialists who planned and coordinated artillery, mortar, and aircraft support for a company of 14 air-dropped armored vehicles
• Deployed to Haiti on the first wave of Operation Uphold Democracy
• Earned Ranger Tab and Senior Parachutist Badge
certification

Certifications
• Google Certified Professional Cloud Architect (PCA) 05/2025 - 05/2027
• Google Certified Cloud Engineer (ACE) 09/2024 - 09/2027
• Red Hat Certified System Administrator (RHEL 6 and 7) 04/2012 - O 11/2018
• Oracle Certified Database Administrator (8i, 9i and 10g) 05/2001 - C 11/2011
• Certified Scrum Master (Scrum Alliance)
• Security+ & Previous DoD 8570.01M Certified
• United States Parachute Association D-22612, Tandem Instructor, 1K Wings - 6899, 12 Hours FF - 5217
about
Rob Wooldridge
Arroyo Grande, CA
––––Work––––
Product Engineering Leader & Veteran
I bring a unique mix of hands-on technical chops and significant leadership experience, as a expert engineering leader and former Brigadier General. With 25 years of designing, building, and supporting full-stack, mission-critical products in production, I have successfully led high-performing teams in cloud computing, data engineering, and software development; in the private sector & the military.
I’m adept at engaging customers, driving operational efficiency and delivering cost savings. Transformed a key Space Force app, leading a seamless migration to Google Cloud. Demonstrated ability to operate at C-suite level while leveraging decades of hands-on engineering experience to get the product right. I work hard to build trust with my teammates so we can solve complex problems and align technology solutions with strategic business goals.
Media links:
• General Officer Biography
• Korean War Memorial Dedication
• Urban Operations Planner Course
• Podcast - Urban Training: Division and Above,
––––Personal––––
Dad of 3, Husband of 1, backpacker, hammock camper, gamer, lego assembler, and infrequent skydiver (D22612)I was a Navy brat, bouncing around the country in my childhood, and ended up in California for high school and college. After I graduated from Cal Poly San Luis Obispo, I served on active duty as a Field Artillery officer for six years, most of which was as a paratrooper in the 82nd Airborne Division. In my last job on active duty, I returned to Cal Poly as a Captain to teach cadets how to become an Army officer and get my master's degree at night. I left active duty to join the civilian technology sector and transitioned my military career to the National Guard. For more than 20 years, I held two careers at the same time: one as a part-time Army officer leading hundreds or thousands of people during no-fail missions and another as a hands-on Information Technology leader writing code everyday. Serving for over 31 years was a dream come true for a boy who grew up in a military family as the son and grandson of navy officers. I am grateful for my family, friends, and teammates who supported my long career. Best job I ever had.
EXPERIENCE
Head of Product Engineering
Advisor
Brigadier General
executive chairman
Founder
It director & enterprise applications manager
Data Infrastructure lead
skydiving instructor
paratrooper
certification
DETAIL
detail
detail
detail
detail
detail
detail
detail
detail
detail

SAIC – Head of Product Engineering, 2011-Present
• Leads the sole Agile DevSecOps team supporting U.S. Space Force’s premier, cloud-based spaceflight safety product, providing 24/7 mission support and Space Domain Awareness for global clients, including spacecraft owner/operators who manage $billions in on-orbit assets.
• Tech Details: Google Cloud(FedRAMP), RESTful API, GitOps, Infrastructure as Code(Terraform/Ansible), CI/CD, Linux, MySQL, Redis, BigQuery, Pentaho ETL
• Scaled the product to over 100x data volume, as well as 10x supported users, organizations, and managed objects on orbit.
• Leverages deep data engineering expertise to design and deploy scalable, secure data pipelines and databases in the cloud.
• Writes elegant code and engages directly with stakeholders to deliver targeted solutions.
• Directed and contributed to numerous upgrades and site improvements, including P2V & infrastructure as code, while maintaining 99.95% uptime SLA for 13+ years.
• Revitalized a faltering customer relationship by introducing Agile/Scrum methodologies; results significantly boosted efficiency and generated over $1.2M (5 FTE) in additional revenue.
• Individually recognized by government clients for exceptional leadership and technical support to the U.S. Strategic Command while providing an “invaluable [service] for maintaining and improving spaceflight safety.”
• Led the team that consistently earned ""Exceptional"" ratings on Contractor Performance Assessment Reports (CPARs) due to our focus on delivering superior customer service."

Onebrief – Advisor 2025 - Present
• Leverage my strategic and operational planning experience for Series C defense tech startup.• Leverage my strategic and operational planning experience for Series C defense tech startup.


California Army National Guard – Senior Leader 2000 - 2024
• Brigadier General / Deputy Commanding General – 40th Infantry Division
• Provided executive leadership of all operations, training, and exercises within the 40th Infantry Division, one of 18 divisions in the Army. Directed training for 12K+ soldiers spanning the West Coast and Hawaii; mentored 300+ senior leaders while in this role. I Significant strategy planning and public speaking responsibilities.
• Implemented enterprise strategies that optimized resource allocation, enhanced unit readiness, and achieved strategic objectives for California and the nation. Partnered with other senior-level leaders on implementing strategies that optimized resource allocation, enhanced unit readiness, and achieved strategic objectives for the state and nation.
• Managed 200+ security cooperation engagements, including 19 major exercises in the Middle East while deployed to Kuwait in 2023 and 2024; effectively doubled partnership activities while managing responses to adversarial attacks on U.S. forces and bases.
• Launched and directed a dedicated Urban Warfare Center; led specialized training courses for four years by enlisting assistance from global subject matter experts. Trained all U.S. branches and international students.
• Organized, trained, and led the division’s tactical command post during strenuous exercises; assumed leadership of division operations on multiple occasions and enhanced flexibility and adaptability.
• Commanded Joint Task Forces during two state emergencies spanning multiple weeks in 2020 and 2021; led over 1,000 soldiers in high-visibility, high-impact support of civil authorities.
• Served as senior trainer for a Brigade Combat Team during both an eXportable Combat Training Center (XCTC) rotation and a brigade Warfighter command post exercise; ensured that the brigade achieved its training objectives.
Chief of Staff/Operations Director (Colonel) — 40th Infantry Division,
• Led, directed, and trained 500+ people on the General Staff; coordinated and synchronized their activities during planning and mission execution
California Army National Guard,Brigade Commander (Colonel) — 100th Troop Command,
• Exercised trust-based leadership of 1.8K people spread throughout Central and Southern California while developing and mentoring 20+ subordinate leadership teams. Worked with the Indian Army on multiple exercises.
• Improved the brigade's composite ranking within the state of California on key performance indicators from 8 of 12 peer brigades to #1 of 12.
Battalion Commander (Lieutenant Colonel) — 1st Battalion, 143 Field Artillery Regiment
• Promoted ahead of peers to become the commander of a National Guard field artillery battalion composed of 400 soldiers in seven locations spread out over 17K square miles.
• Consistently ranked in the top three out of 27 executive managers throughout the state on leadership and important operational key performance indicators.

Urban Warfare Institute – Executive Chairman 2024 - Present
• Lead a 501(c)(3) nonprofit organization dedicated to advancing the study of urban environments, urban operations, and urban warfare.
• I provide strategic oversight and foster collaboration between military, academic, and policy communities to enhance understanding of complex urban operations.
• Advised the Center for Naval Analyses how US Marine Corps should plan, train, and equip Marines for the complexities of large-scale combat in future urban environments.
• Spearhead partnerships and thought leadership efforts to expand the organization’s reach and impact.
• Oversee the organization's urban warfare training, ensuring relevant Urban Operations courses are informed by the latest research, operational best practices, and real-world lessons learned.

Founder - Gibson Originals Online 2014 - 2017
• Founded and managed a direct-to-consumer e-commerce venture focused on novelty barbecue lighters.

United States Property & Fiscal Office - IT Director & Enterprise Applications Manager 2007-2011
• Directed enterprise software development, support, and strategy ensuring 16K employees statewide enjoyed high availability and performance for mission-critical financial, logistics, and personnel applications. Led geographically-distributed, cross-functional teams of customers, engineers, and leaders to develop scalable, secure, and integrated solutions that enhanced operational efficiency.
• Spearheaded the creation of a business intelligence scorecard that tracked 50+ KPIs; results improved data-driven decision making and delivered a $2.7M savings over the course of four months.
• Achieved a 95%+ customer satisfaction rating in surveys; earned recognition for exceptional responsiveness and deep technical acumen.
• Administered a $350K annual operations budget and drove significant costs savings while maintaining high service levels and operational efficiency.

United States Property & Fiscal Office - Data Infrastructure Lead 2000 - 2007
• Oversaw the design, implementation, and maintenance of database systems. Managed a team of data infrastructure specialists and ensured optimal performance, security, and scalability of databases. Collaborated with cross-functional teams to support application development, monitor database performance, and troubleshoot complex issues. Held responsibility for database architecture, backups, disaster recovery plans, and introduction of best practices to ensure data integrity and availability in a 24/7 environment.
• Maintained 99.99% system uptime, safeguarded mission-critical financial, logistics, and HR databases with zero security breaches; successfully upheld 100% data integrity across all operations

Plummet Skydiving – Skydiving Instructor 2004 - 2008
• Strapped paying clients to my chest and jumped out of perfectly good airplanes over 250 times as an independent contractor. Also coached new skydivers and shot/mixed videos of jumps.
.png)
US Army – Artillery Officer & Paratrooper 1993 - 1999
• Jumped out of planes and shot big guns.
• ROTC University Instructor and website manager - Recruited, taught, and supervised over 80 college students preparing to become US Army officers.
• Battalion Fire Support Officer - Led a small team of integration specialists who planned and conducted target acquisition to engage enemy positions in support of a battalion of attack helicopters.
• Battery Executive Officer - Supervised operations, training, promotions, and evaluations for 105 paratroopers. Managed a fleet of 22 vehicles, six howitzers, three trailers, and $5 million in equipment
• Battery Fire Direction Officer - Supervised a ten-person technical operations center that directed artillery fire in a high-pressure, zero-defects environment
• Company Fire Support Officer - Led a small team of integration specialists who planned and coordinated artillery, mortar, and aircraft support for a company of 14 air-dropped armored vehicles
• Deployed to Haiti on the first wave of Operation Uphold Democracy
• Earned Ranger Tab and Senior Parachutist Badge

Certifications
• Google Certified Professional Cloud Architect (PCA) 05/2025 - 05/2027
• Google Certified Cloud Engineer (ACE) 09/2024 - 09/2027
• Red Hat Certified System Administrator (RHEL 6 and 7) 04/2012 - O 11/2018
• Oracle Certified Database Administrator (8i, 9i and 10g) 05/2001 - C 11/2011
• Certified Scrum Master (Scrum Alliance)
• Security+ & Previous DoD 8570.01M Certified
• United States Parachute Association D-22612, Tandem Instructor, 1K Wings - 6899, 12 Hours FF - 5217