Madison-Davis, LLC · 1 month ago
Deputy Chief Technology Officer
United States
Full-time
Remote
Director/Executive
10+ years expMadison-Davis, LLC is seeking a Deputy Chief Technology Officer to act as the primary execution arm of the CIO/CTO, translating technology strategy into measurable outcomes. The role involves overseeing technology delivery across engineering, infrastructure, and operations while driving modernization initiatives and ensuring alignment across global teams.
Human ResourcesInformation TechnologyStaffing Agency
Responsibilities
Act as the primary execution arm of the CIO/CTO, translating technology strategy into clear, scalable, and measurable outcomes across engineering, infrastructure, and operations
Own cross-organizational technology delivery, ensuring alignment between application engineering, infrastructure, cloud platforms, and operations engineering
Drive simplification of architectures, platforms, and delivery models to reduce complexity, improve reliability, and accelerate time-to-market
Ensure technology decisions support an open-source-first philosophy while maintaining enterprise-grade reliability, security, and compliance
Oversee large global organizations, with multiple layers of leadership and globally distributed teams (US, UK, India)
Create a culture of accountability, ownership, and execution, ensuring leaders are empowered but held to clear outcomes
Partner with senior leaders on headcount planning, org design, succession planning, and leadership development
Drive consistency and standards without stifling innovation across diverse teams
Identify and remove systemic bottlenecks in how software and infrastructure are designed, built, tested, and deployed
Improve delivery velocity, quality, and predictability while operating in a regulated financial environment
Lead large-scale modernization and transformation initiatives, including legacy modernization, cloud adoption, and platform rationalization
Establish clear metrics around delivery, reliability, cost efficiency, and engineering productivity
Serve as a trusted advisor to the CIO/CTO and executive leadership, providing clear visibility into execution, risks, and trade-offs
Communicate complex technical topics clearly to non-technical executives and business stakeholders
Represent technology leadership in C-suite forums, steering committees, and global leadership discussions
Qualification
Required
10+ years of progressive technology leadership experience in financial services, fintech, or enterprise software environments
Proven experience leading large, multi-layered global technology organizations (300+ engineers)
Strong background across both software engineering and infrastructure/platform engineering
Demonstrated success driving large-scale transformation, modernization, or operational improvement initiatives
Deep understanding of enterprise systems, hybrid cloud environments, and modern software architectures
Strong technical foundation in one or more of: Software engineering (Java, C#, Python, Node), Infrastructure platforms (Windows, AD, Citrix, virtualization, mainframe a plus), Cloud platforms (AWS, Azure, private cloud)
Hands-on understanding of: Distributed systems and scalability, CI/CD pipelines and automation, DevOps and SRE principles, Open-source ecosystems
Ability to challenge architectural decisions and guide senior engineers without micromanaging
Executive presence with the ability to influence at the C-suite and Board-adjacent level
Comfortable operating in controlled chaos, legacy environments, and transformation scenarios
Pragmatic, delivery-focused leader who balances speed with stability
Strong communicator who can align diverse teams around a shared vision
Naturally collaborative but willing to make hard decisions when needed
Engineering and infrastructure leaders are aligned, empowered, and executing against a clear strategy
Delivery is faster, more predictable, and less complex than before
Technology platforms are modernizing without disrupting critical financial systems
Company
Madison-Davis, LLC
Madison-Davis is a staffing and recruiting company offering financial services.
51-200 employees
H1B Sponsorship
Madison-Davis, LLC has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
15%
Represents job field similar to this job
Management and Executive
Engineering and Development
Accounting and Finance
Legal and Compliance
Customer Service and Support
Human Resources
Trends of Total Sponsorships
*2026 (3)
2025 (22)
2024 (15)
2023 (8)
2022 (3)
2021 (1)
Funding
Current Stage
Growth StageLeadership Team
Jesse Siegal
Managing Partner, Chief Revenue Officer & Chief Operating Officer
I
Ian Stewart
Founder and Advisor
Recent News
2026-06-09
Company data provided by crunchbase