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RÉSUMÉ

Robert Dawson

VP of Engineering

Westminster, MDme@bobbydawson.com(410) 818-4847
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Executive summary

Transformational VP and engineering leader with 10+ years building, scaling, and leading high-impact software organizations across SaaS, data platforms, integrations, and consumer-facing products. Proven success managing 70+ engineers across product, data, AI/ML, DevOps, and security — delivering scalable architectures and driving a performance culture through metrics, accountability, and mentorship.

A builder at heart who thrives on operational excellence, rapid iteration, and empowering teams to ship meaningful products. Deeply experienced in cloud infrastructure, distributed systems, and data-driven product strategy. I specialize in ROI-driven prioritization and AI-first ADLC strategies that significantly multiply team performance and operational outcomes.

Selected impact

$1M → $100M
Valuation to acquisition
70+
Engineers led
14B+
Documents in production
$800K
Cloud spend removed
40%
MTTR reduction
5
Products shipped solo

Experience

EverTrue

·VP of Engineering

Sep 2025 — Present · Remote

Leading full organizational and technical transformation — restructuring and auditing the business, owning all technology strategy and architectural decisions, and implementing AI-driven initiatives to accelerate delivery and optimize operations.

  • Audited the department structure and filled weak positions with key players, driving immediate change and lifting morale
  • Pioneered migration strategy and team prioritization, multiplying productivity and direction
  • Set a repeatable cadence for growth across key initiatives

DonorSearch

·VP of IT & Security

Jan 2020 — Sep 2025 · Remote

Led all technology strategy, architecture, and execution for a high-volume SaaS data intelligence platform supporting billions of records across donor, business, and executive datasets. Oversaw key development through growth from $1MM business valuation to $100MM acquisition.

  • Scaled engineering from a small startup team to a multi-department organization of 20+ engineers across Product, Data, ML/AI, DevOps, Security, and UI/UX
  • Drove modernization from legacy monoliths to microservice-based distributed systems on AWS and Docker
  • Oversaw multi-cloud migration (Azure → AWS), container orchestration, and pipeline optimization handling 14B+ documents in Elasticsearch, reducing cloud spend by $800K
  • Built and led cross-functional squads across front-end (Laravel, React, Python), AI, and infrastructure
  • Directed integration strategy with Salesforce, Blackbaud, Microsoft Dynamics, EveryAction, and Monday.com
  • Championed AI and automation initiatives — ML model integration, AI-assisted development, and ChatGPT-powered data intelligence workflows
  • Elevated DevOps maturity through observability, CI/CD automation, and incident response improvements, reducing MTTR by over 40%

DonorSearch

·Lead Developer

Oct 2017 — Jan 2020 · Remote

Technical lead over core product development, architecture, and integrations across PHP, Python, and JavaScript stacks. Acted as the bridge between engineering and leadership — guiding architectural direction, mentoring junior developers, and ensuring the scalability and reliability of critical SaaS applications.

  • Played a pivotal role in modernizing legacy systems and establishing the foundation for future platform growth

Core competencies

Leadership

  • Engineering Strategy & Org Design
  • Performance Management
  • Mentorship & Leadership Development
  • Executive Stakeholder Management
  • Product & Platform Roadmapping

Platform

  • Large-Scale Cloud Infrastructure (AWS, GCP, Azure)
  • DevOps, CI/CD, Observability
  • Scalable Integrations & API Architecture
  • Distributed Systems & Microservices

Data & AI

  • AI/ML and Data Platform Leadership
  • AI-first ADLC strategy
  • Elasticsearch at scale
  • Data pipeline optimization

Governance

  • Enterprise Security
  • Compliance
  • Incident Response

Education

University of Maryland, Baltimore County

B.S. Computer Science

2005 – 2009

The short version: I scale the platform and the people at the same time.

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