Chief Technology Officer

Arlington, VA, United States

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At Hobsons, education is more than just our business; it’s our passion. Since 1974, we have been helping educators, administrators, students, and families maximize success through every stage of the learning lifecycle. Our mission is to maximize students’ chances of life success by connecting them to the best-fit education opportunities.


Chief Technology Officer


Job Summary

Hobsons is seeking a talented and visionary Chief Technology Officer to drive our technology operation and strategy. This role will report directly to the CEO of Hobsons and will oversee a team of 100 consisting of developers, engineers, architects, operations staff and agile coaches.

This position requires a unique combination of startup-like resourcefulness, top-flight technical expertise coupled with Software-as-a-Service (SaaS) and an information services background.

We need an individual with demonstrated proven success, in a SaaS, B2B and/or information services environment who has strategic experience in; leading and building development teams; creating, delivering and measuring high-impact technology strategies, plans and programs; guiding technology strategy; as well as directing technology infrastructure and development efforts.

The role focuses on product development throughput, technology strategy and implementation and moving the organization forward in skills, maturity, and scale.

You should be comfortable in an open, fluid, fast-growth environment and bring an energetic and creative approach to your work, spanning high-level strategy as well as in-the-trenches execution.


This position will be located in: Arlington, VA (Clarendon Metro)


Essential Functions/Responsibilities

Technology Strategy and Commercial Focus:

  • Drive Hobsons' technical vision and technology development with a commercial mindset and perspective
  • Be the technical voice of the business and, as necessary, meet with customers and partners
  • Seek to understand the business and customer so that product and engineering are effectively aligned to deliver excellent and scalable commercial products
  • Help to effectively resolve technology debt and advise the business on technology strategy
  • Drive technology strategy and direction in a way to make Hobsons more competitive in the marketplace – both from a product (external) and a talent acquisition (internal) perspective


  • Work collaboratively with the leadership team and CEO on technology strategy
  • Create a strong commercial and product mindset amongst the technology team
  • Drive technical innovation to ensure best architectural decisions are made across the business
  • Attract and develop top technology talent
  • Provide visibility into the development roadmap, sprints, throughput, expected timelines, etc.
  • Develop deep and strong working relationships with both internal and external stakeholders


Minimum Qualifications

  • The CTO will have a proven track record of successfully leading and driving commercial product development, architecture, and infrastructure activities that provide best in class product offerings and support
  • Ability to attract and develop exceptional technology talent
  • Experience interacting with clients or customers at a senior executive level
  • You must be an excellent leader and communicator, passionate about building world-class engineering organizations and be able to use technology as a key leverage point for the business
  • 15+ years of experience leading and managing technology teams and commercial software required
  • Be a leader who can rollup sleeves as needed to dig into problems and create solutions
  • Prior experience developing a successful, multi-tenant SaaS product
  • Knowledge of Data Security, Secure Coding, Encryption, Multi-tenancy, Scalability, and High Availability
  • Experience modernizing and centralizing legacy systems
  • Proven successful experience in and implementation of an Agile/Post-Agile development environment
  • Ability to actively communicate, inspire, and motivate
  • Experience with a mix of large enterprise customers as well as small, high-value customers
  • Experience and proven decision-making capabilities in real-world business problems – personnel, financial, business strategy, etc.
  • Experience with and knowledgeable in organizational development philosophies and approaches related to building high functioning teams and organizations

Hobsons recognizes the importance of taking care of our most valuable assets – our employees. That’s why we not only offer a comprehensive total rewards package but also continuously evaluate our offerings to meet the evolving needs of our workforce.

Benefits Include (but may vary depending on location)

  • Affordable and Competitive Medical, Dental and Vision Insurance Plans
  • 401(k) Plan with Match
  • Flexible PTO offering for all Exempt roles
  • Substantial time off for all Non-Exempt roles, including Floating Holidays and Premium Days for Volunteering, Personal Wellness and/or School Conferences/Visits
  • Education/Tuition Reimbursement
  • Life, AD&D, Short-term and Long-term Disability Insurance
  • Flexible Spending Accounts (FSA)
  • Voluntary Employee Programs: Legal Services, ID Theft & Credit Monitoring

Work-Life Balance & Culture

  • Company Closes December 24th through January 1st as a Paid Holiday
  • Generous Holiday Schedule
  • Employee Referral Bonus Program
  • Casual Dress Environment
  • Flexible Work Arrangement Opportunities
  • Global Fitness Program Membership Discounts
  • Hobsons Annual Achievement Awards Event
  • Employee Funded International Charity Programs
  • Adopt A Class - Local Community Involvement
  • Work Perks Discount Program



To view our comprehensive list of total rewards benefits, please visit  To learn more about Hobsons, and our products: Naviance, Intersect, Starfish, visit our corporate web site at and follow us on LinkedIn, Facebook and Twitter.

Ability to document identity and employment eligibility within three (3) days of original appointment as a condition of employment in compliance with Immigration Reform and Control Act requirements.


Note: U.S. Citizens and those authorized to work in the U.S. are encouraged to apply. We are unable to sponsor at this time.


Hobsons is an Equal Employment Opportunity (EEO) employer and welcomes all qualified applicants. Applicants will receive fair and impartial consideration without regard to race, sex, sexual orientation, gender identity, color, religion, national origin, age, disability, veteran status, or other legally protected status.

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