Jack Wood

AI & Technology Leader | Engineering and Product Executive

New England area (Remote)• 20+ years experience, engineer first

Trusted by Leading Organizations

About

I'm an engineering, data, and AI leader focused on building intelligent platforms that drive measurable business value at enterprise scale. As SVP, Head of Engineering & Data at Symetra, I lead technology and AI initiatives that are reshaping the insurance and financial services landscape. With a background spanning engineering leadership, data strategy, and product innovation at organizations such as Symetra, Capital One, AppFolio, Wayfair, and Akamai, I bring a deep understanding of how to align technology investments with business outcomes.

My work centers on digital transformation through modern data architectures, AI/ML, and cloud-native engineering. I specialize in guiding large, distributed teams through technological change—building scalable systems that enable smarter decisions, streamline operations, and elevate customer experiences. From AI-driven underwriting and fraud detection to predictive analytics and intelligent automation, I’m passionate about transforming complex problems into elegant, data-informed solutions. I believe the future of enterprise innovation lies in cross-functional teams that blend product thinking, engineering excellence, and responsible AI.

Experience

Symetra

SVP, Head of Engineering & Data

2025 - Present • Bellevue, WA (Remote)

VP of Engineering

2023 - 2025 • Bellevue, WA (Remote)

Symetra Logo

Tasked with leading enterprise-wide transformation uniting engineering, data, and AI capabilities under a cohesive operating model.

Key Achievements:

  • Partnered with executive leadership to evolve Symetra's digital operating model, aligning product, data, and engineering toward shared outcomes
  • Established an AI-first engineering culture through capability development, governance, and enterprise enablement
  • Consolidated multiple engineering domains into a unified platform organization improving consistency, velocity, and resilience
  • Served as strategic advisor to the C-suite on modernization, workforce alignment, and AI adoption strategy
Digital Transformation AI-First Culture Platform Engineering Executive Leadership Strategic Advisory

Capital One / BlueTarp Financial

Head of Commercial Trade Credit Engineering

2019 - 2023 • Portland, ME

Head of Engineering, BlueTarp

2018 - 2019 • Portland, ME

Capital One Logo

Unified post-acquisition engineering organizations and re-architected legacy systems into modular, cloud-native platforms.

Key Achievements:

  • Modernized credit and underwriting infrastructure to support AI-based decisioning and advanced analytics
  • Scaled DevSecOps and observability practices, institutionalizing metrics-driven delivery across 200+ engineers
  • Partnered with Product and Data Science leaders to embed LLM-powered automation into customer workflows
  • Aligned technology and talent strategies to support rapid integration and platform scalability
M&A Integration Cloud-Native Architecture DevSecOps AI Decisioning LLM Integration

AppFolio / WegoWise

Head of Analytics & Engineering

2017 - 2018 • Boston, MA

Led technology strategy to position WegoWise for acquisition and post-merger integration into AppFolio's SaaS portfolio.

Key Achievements:

  • Built next-generation property analytics platform supporting benchmarking and sustainability insights for 500K+ properties
  • Directed integration and operational alignment post-acquisition, embedding AI-driven insights into SaaS workflows
  • Established standardized analytics architecture and governance framework improving data quality and reusability
M&A Strategy Property Analytics SaaS Integration AI-Driven Insights

Wayfair

Chief Information Officer / Chief Architect

2013 - 2017 • Boston, MA

Wayfair Logo

Drove enterprise-scale technology modernization supporting hypergrowth and operational scalability.

Key Achievements:

  • Consolidated global engineering teams and platforms enabling 5× faster feature deployment
  • Transitioned from monolithic to service-based architecture improving resilience and delivery cadence
  • Established data engineering practice supporting personalization, logistics optimization, and early ML adoption
Hypergrowth Engineering Service Architecture Data Engineering ML Adoption

Akamai Technologies

Principal Architect / Engineering Leader

2004 - 2012 • Cambridge, MA

Akamai Logo

Directed large-scale distributed systems design for Akamai's global CDN and application acceleration platforms.

Key Achievements:

  • Delivered fault-tolerant systems supporting billions of daily transactions across 100+ data centers
  • Contributed to early advancements in cloud acceleration and edge computing models
Distributed Systems CDN Architecture Edge Computing Global Scale

Earlier Roles

1995 - 2004

Built foundational expertise across diverse technical domains including hardware engineering, telecommunications, aerospace software systems, strategic consulting, and defense intelligence.

Roles:

  • Mindspeed Technologies – Hardware Engineer (Startup acquired by Conexant)
  • Lucent Technologies / Bell Labs – Distinguished Member of Technical Staff
  • NASA Jet Propulsion Laboratory – Software Engineer
  • Consulting – Senior Consultant
  • United States Air Force – Analyst (Top Secret/SCI clearance)
Hardware Engineering Telecommunications Aerospace Systems Defense & Intelligence Technical Consulting

Expertise & Skills

Leadership & Strategy

  • Remote Team Leadership & Management
  • AI Product Strategy & Roadmapping
  • Cross-functional Collaboration
  • Technical Mentorship & Coaching
  • Stakeholder Management
  • Agile & Lean Methodologies
  • Business Impact Analysis & ROI

Technical Skills

  • Python, Java, Scala, SQL
  • Spark, Hadoop, Kafka for Big Data
  • PostgreSQL, MongoDB, Redis
  • REST APIs & Microservices
  • Git, CI/CD, DevOps Practices
  • Data Visualization (Tableau, Looker)
  • Statistical Analysis & Experimentation

AI & Machine Learning

  • Deep Learning & Neural Networks (TensorFlow, PyTorch)
  • Natural Language Processing (NLP)
  • Computer Vision & Image Recognition
  • Recommendation Systems & Personalization
  • Time Series Forecasting & Predictive Analytics
  • Reinforcement Learning
  • Model Optimization & Hyperparameter Tuning

MLOps & Infrastructure

  • ML Pipeline Development & Automation
  • Model Deployment & Monitoring
  • Feature Engineering & Data Pipelines
  • A/B Testing & Experimentation Frameworks
  • Cloud Platforms (AWS, GCP, Azure)
  • Kubernetes & Docker for ML
  • Real-time Inference Systems

Cybersecurity

  • Zero-Trust Architecture & Network Security
  • Security Operations Center (SOC) Development
  • Threat Detection & Response Systems
  • SOC 2, PCI DSS, & Compliance Frameworks
  • Security Governance & Risk Management
  • DDoS Mitigation & Web Application Security
  • Identity & Access Management (IAM)

What I Value

Great Teams

I believe the best results come from working with exceptional people who are passionate about what they do.

Engineering Excellence

The discipline that ensures innovation doesn’t compromise reliability or security.

Constant Learner

Fuels curiosity, sharpens judgment, and keeps innovation grounded in relevance, allowing me to adapt, connect emerging ideas, and lead teams confidently through change.

Projects & Open Source

InternetGravity

View on GitHub →

Python-based project exploring network dynamics and data flow patterns across the internet, using graph theory and network analysis techniques.

Python Network Analysis Graph Theory

CSS framework and component library for building beautiful, consistent user interfaces with modern design patterns and accessibility features.

CSS UI Framework Design Systems

Explore more of my work and contributions on GitHub

Visit My GitHub Profile

Let's Connect

I'm always interested in connecting with fellow AI and technology leaders, exploring opportunities in machine learning and artificial intelligence, and discussing how we can work together to build intelligent systems that make a difference.