VP of Engineering – Chief Technology Officer

Role Overview

• The VP of Engineering will serve as a strategic technology leader and visionary for Northwoods, driving the engineering organization’s architecture, product roadmap, and operational excellence.
• This role requires deep technical leadership across various domains including AWS cloud infrastructure, Ruby and React-based SaaS development, and the application of emerging AI technologies — coupled with an understanding of the complex data and compliance requirements of U.S. State Health and Human Services systems.
• The VP of Engineering will be responsible for defining and executing a multi-year strategy focused on:
• Define a unifying engineering strategy and roadmap for managing the success of customers, leveraging Compass and Traverse while designing our next-generation offerings with an AI first mindset.
• Establish clear architectural governance and set consistent technical direction across the entire product portfolio.
• Drive the evaluation and standardization of CI/CD practices and modern DevOps pipelines to enable scalable, efficient SaaS delivery.
• Lead the adoption and institutionalization of a GenAI-assisted approach to increase engineering throughput.
• Advance the use of GenAI and emerging technologies within the product to benefit customers and the next generation of innovation.
• Evaluate and refine the engineering organization to ensure an effective structure, strong leadership, and a culture that fosters innovation, continuous skill development, and scalable growth.
• Implement continuous improvement in AWS operations, monitoring, services, cost profiles and core engineering processes.
• Set measurable engineering goals that track output, identify improvement opportunities, and drive accountability.
• Implement continuous improvement in the Secure Development Lifecycle (SDLC) while supporting compliance and industry standard practices.
• Oversee incident response, vulnerability management, and security posture.
• Lead Business Continuity (BCP) and Disaster Recovery (DRP) readiness efforts.
• Align Northwoods products with state HHS regulations and case management needs.
• Lead interoperability efforts with systems like SACWIS, CCWIS, Medicaid, and SNAP/TANF.
• Maintain awareness of federal and state technology frameworks (ACF, CMS, NIEM, NC Child Welfare Data Framework).

Requirements

• Extensive experience (10+ years) in senior engineering leadership roles, such as VP of Engineering, Director of Engineering, or similar.
• Deep expertise in cloud-native architecture, particularly the AWS ecosystem: EKS, EC2, Lambda, PostgreSQL, S3, and so on.
• Proven technical depth in the current modern stack: Ruby on Rails, React/TypeScript, and modern CI/CD.
• Experience in managing, maintaining, and modernizing C# / .NET Framework applications and complex installer/deployment tooling (MSI, WiX).
• Prior experience with security compliance (SOC 2, HIPAA) and implementing preventative security controls (SAST, SCA).
• Demonstrated ability to drive cultural change, adopt new technologies, such as Generative AI.
• 3-5 years of experience managing offshore teams
• 2-3 years of experience leveraging AI to support the SDLC process to improve team efficiency with working examples
• Working experience using Cursor, Microsoft Co-Pilot, GitHub or similar AI tools in coding practice with measurable results.

Tech Stack

• AWS
• Cloud
• EC2
• Postgres
• React
• Ruby
• Ruby on Rails
• SDLC
• TypeScript
• .NET

Benefits

• Medical (includes H.S.A. option with employer contribution)
• dental, and vision insurance
• Short
• and long-term disability
• Company paid basic life insurance
• 401(k) with 4% company match and immediate vesting
• Free financial education and consultation
• Wellness program that helps you earn lower premiums
• Robust EAP program that includes free therapy sessions, lifestyle coaching, legal/ID theft services, and more
• 12 weeks fully paid parental leave
• Up to $5,000 adoption fee reimbursement
• $500 wellness reimbursement after 60 days of employment
• Generous PTO policy and 10 company paid holidays
• Company paid cell phone plan