Chief Technology Officer

Arlington, VA /
Technology /
/ Hybrid
At StraighterLine we are on a mission to help students succeed!

About Us
StraighterLine is the leading provider of high-quality, affordable, online courses that help learners earn college credit and meet their professional goals. Each year, 150,000 learners take one of StraighterLine’s 215 courses to upskill into new careers or earn credit from over 2,000 colleges and universities worldwide. StraighterLine works with institutions and corporate partners to provide their students and employees with flexible education options that allow them to work and learn at their own pace. Visit for more information.

Working at StraighterLine
StraighterLine team members work every day knowing that they are helping learners on their path to employability and career success. We're an inclusive team that fosters collaboration, that trusts and communicates openly. Like our students, we are lifelong learners and strive for excellence in our work. We are committed to bringing innovative solutions to the field - your ideas will never go unheard. And, best of all, we love to celebrate each other's contributions and wins.

We also know how important a life outside of work is, and the support that employers can contribute.
See the end of this posting to learn more about our great benefits.

We are recruiting a Chief Technology Officer to help achieve our vision of a tech-enabled platform of courses, credentials and services that offers flexible and accessible pathways to careers in high-demand fields. Our strong preference is for candidates who are local to the DC/Baltimore area. The CTO will work closely with the executive leadership based out of Washington, DC. We are looking for candidates based in the Washington, DC/Baltimore metro area who are able to come into our Arlington, VA office twice a month.


The CTO has accountability and responsibility over engineering and enterprise IT functions. Reporting directly to the CEO, they represent the technology team on the Executive Leadership Team, communicate direction and data-driven insights to leadership peers, and facilitate cross-functional collaboration. They develop our technology strategy, aligning engineering resources, capital and infrastructure to meet short- and long-term business goals.  They partner closely with the Chief Product Officer to align technology strategy and roadmap with product strategy and roadmap. A key focus is to decrease time to value for new features, functionality and content. The CTO takes the initiative in thought leadership, innovation and creativity for our technology strategy.


    • Build, support, and mentor a best-in-class engineering team of 15+ people
    • Strengthen the information security environment and systems with the goal of reducing vulnerabilities
    • Track, analyze and monitor technology performance metrics, use insights to drive efficient feature delivery and functionality
    • Identify, compare, select and implement technology solutions to meet current and future needs
    • Develop, track and control the development of the department budget
    • Create overall technology standards and practices and ensure adherence
    • Keep abreast of new trends and best practices in the technology landscape
    • Work closely with product, growth and content teams to define and deliver new products and enhancements
    • Work with the leadership team to set clear priorities and goals for technology management and production, balancing the long-term and immediate needs
    • Oversee data security, management, and governance
    • Manage strategic vendor and technology partner relationships, including our two offshore vendors
    • Manage Engineering and IT resource allocation, goal/KPI setting, and performance metrics
    • Make infrastructure decisions, ensuring technical excellence, versatility, safety and soundness, resiliency and scalability in the architecting and engineering of product solutions, as well as managing all technical delivery
    • Facilitate the development and implementation of disaster recovery and IT security failure plans
    • Ensure compliance with SOC, PCI and other technical standards
    • Manage IT support team including helpdesk, network, server, and application support
    • Create and optimize processes for user support, ensuring top-tier, responsive helpdesk support for day-to-day IT needs
    • Be accountable for the operability and health of all IT systems at StraighterLine, including troubleshooting, upgrades, backup and system optimization for business sustainability and growth
    • Create strategic plans and set timelines for evaluation, development, and deployment of all technical, web, and mobile services
    • Complete due diligence for any future acquisitions into StraighterLine and integrate future technology for consistency within StraighterLine’s technology roadmap


    • Bachelor’s degree in computer science, engineering, information systems or related field (master’s degree preferred).
    • Previous experience as a CTO, VP, director, or similar leadership role
    • Prior experience as a senior engineering leader overseeing architecture and engineering for enterprise-wide technology platforms and leading SaaS technology platforms
    • Broad knowledge of software engineering: languages, frameworks, techniques, and industry trends
    • Experience leading complex, major changes and initiatives; demonstrated skills in change management on an organizational and interpersonal level; experience with integrating teams across multiple business units and managing a geographically dispersed workforce
    • Experience designing and managing an effective IT governance framework across the spectrum of IT service delivery
    • At least 15 years of progressively responsible experience in the engineering field, including hands-on experience in several different technology functions (e.g., software development, cloud-based technical architecture, and information security)
    • At least five years in a senior leadership role leading a medium-sized technology team that includes engineering, enterprise systems and security functions
    • Experience leading and motivating software engineering teams and managing complex software projects
    • Track record of establishing, building and leveraging cross functional relationships

Core Competencies

    • Strong department leader with skills in strategic planning, goal setting, processes development, budgeting, and creating opportunities for professional development within technology teams
    • Excellent communication, leadership, and strategic thinking abilities with a problem-solving aptitude
    • Solid understanding of broad technology trends and the ability to align innovation with business goals
    • Strong communication with ability to convey technical topics in easy-to-understand business terms and work collaboratively with cross-functional teams and external partners
    • Strategic smarts, including the ability to identify new opportunities, drive clarity, create focus, and make tough decisions in complex and dynamic contexts
    • Ability to track and identify new technologies to solve complex business issues
Our Benefits:

Unlimited PTO
Medical, Dental, and Vision Insurance Coverage (*one option full funded by StraighterLine) 
401K Safe Harbor plan: StraighterLine contributes 3% of your total salary whether you contribute or not
Six weeks paid parental leave
Free StraighterLine courses for you and your family members

We are an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law.