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Executive Director, Application Development – Investment Services

March 2, 2026

About the position

At USAA, our mission is to empower our members to achieve financial security through highly competitive products, exceptional service and trusted advice. We seek to be the #1 choice for the military community and their families. Embrace a fulfilling career at USAA, where our core values – honesty, integrity, loyalty and service – define how we treat each other and our members. Be part of what truly makes us special and impactful. The Opportunity USAA is seeking an Executive Director, Application Development – Investment Services to lead teams responsible for the end‑to‑end buildout of the Investment experience ecosystem for both members and service representatives. This leader will deliver secure, scalable, member‑centric technology within a product‑aligned Agile model, partnering closely with business stakeholders to accelerate value. Leveraging deep domain expertise, the role develops capabilities that expand access, enhance the member experience, and drive sustainable growth. The Executive Director also oversees the technology strategy and execution for Investment Services, ensuring integrated solutions that improve operational efficiency and elevate experiences for both members and employees. We offer a flexible work environment that requires an individual to be in the office 4 days per week. This position is based in San Antonio, TX Relocation assistance is available for this position

Responsibilities

Performs workload management and prioritization duties in support of operations for the functional area assigned.
Applies subject-matter-expert functional knowledge to lead subordinate workers in producing work deliverables in support of departmental initiatives.
Develops functional policies, procedures and guidelines.
Identifies opportunities and facilitates major improvements to processes and systems.
Ensures that the assigned application group develops processes and tools that contribute to the company business objectives.
Ensures that all application processes developed internally or by external service providers are conducted in line with corporate social responsibility, environmental and technical policies and applicable standards and legislation.
Oversees the assessment of the technical and business fitness of the application portfolio and their associated costs and risks
In partnership with CTO, Infrastructure and IT Security, ensures that the organization's applications are effectively secured and that risks are mitigated and comply with legal and corporate privacy and confidentiality rules.
Establishes management routines to ensure appropriate oversight of the organization’s software development and maintenance activities.
Serves as financial steward for the organization and manages relationships with major vendors and service providers to ensure they cost-effectively meet the needs of the organization.
Evaluates and selects third party vendors to provide value added services.
Facilitates the contracting process through the Third-Party Risk Management (TPRM) enterprise process.
Responsible for contract company/service performance providing timely feedback to ensure the best value for USAA.
Collaborates with CTO to ensure that solutions are consistent with technology standards.
Works across IT and business partners to reduce technical debt.
Collaborates with other leaders and/or stakeholders and develop an application development strategy that aligns with business strategy, adds value and is within budget constraints.
Responsible for team’s adherence to SDLC and applicable controls.
Works to ensure teams have appropriate, development plans consistent with domain of expertise.
Mentors across the technical community.
Provides oversight to the engagement with the business DPO and ensures deliverables adhere to Agile practices/methodologies.
Ensures risks associated with business activities are effectively identified, measured, monitored, and controlled in accordance with risk and compliance policies and procedures.

Requirements

Bachelor's degree in computer science, computer information systems or related field of study; OR 4 years of related experience (in addition to the minimum years of experience required) may be substituted in lieu of degree.
10 years of experience in general IT management competencies.
4 years of people leadership experience in building, managing and/or developing high-performing teams required.
Strong technical background of web-based application architecture, system and database architecture, security application integration and object-oriented languages in a large enterprise environment.
Extensive experience in all stages of the software development life cycle: requirements gathering, design, development, testing, and implementation.
Demonstrated ability to communicate technical information to a non-technical audience.
Experience collaborating with key resources and stakeholders, influencing decisions and managing work to achieve strategic goals required.
Demonstrated experience in vendor contract management and management of distributed development teams and resources.
Demonstrated financial acumen involving budgets, forecasting, and executing on the budgets for applicable technology support function.
Understanding of relevant industry frameworks, i.e. COBIT, ITIL, SAFe, etc.
Understanding of Legislative and Regulatory Compliance Requirements.
Experience overseeing the technology life cycle from requirements analysis, feasibility estimates, design, code, documentation, testing, implementation, and support.
Technical knowledge and understanding of technical domains that reside within Infrastructure Services, Security, Data or Application Development.
Experience conducting cost benefit analyses and leveraging results to drive technology support solutions.
Demonstrated thought leadership in embedding intuitive story telling of technology support functions including concise presentation of complex technical details.
Experience and ability to drive a culture of quality and personal accountability through technology support teams.

Nice-to-haves

Prior experience leading the design and build of institutional-grade investment technologies from the ground up, including integration with market data provider technologies
A robust background in modern technology stacks with the ability to navigate complex systems and drive innovation
Deep technical experience within the Investment Services industry, specifically focused on Broker Account Services, Customer Relations Management and Financial Planning & Advice
Strong architectural foundation paired with an intimate understanding of the Investment Services industry… to align technical solutions with organizational goals
A positive, \"team-first\" builder mindset with a passion for solving complex problems and fostering a collaborative, high-performance environment

Benefits

comprehensive medical, dental and vision plans
401(k)
pension
life insurance
parental benefits
adoption assistance
paid time off program with paid holidays plus 16 paid volunteer hours
various wellness programs
career path planning and continuing education

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...