CHIEF TECHNOLOGY OFFICER (CTO)

Beneration has helped transform the employee benefits industry with cutting-edge financial technology solutions. We digest thousands of data points from insurance carriers, invoices, and benefit administration systems to give employers and brokers much-needed clarity and risk mitigation related to their monthly insurance spend. In a nutshell, we make sure that when companies are paying for employee benefits, they are paying the correct amount, to the correct carriers, for the correct people.

As Chief Technology Officer (CTO), you will be Beneration’s initial in-house senior engineering leader. You will oversee outsourced tech partners in the near term while building and scaling an internal engineering team. You will define and execute Beneration’s overall technology strategy and architecture, and drive the transformation of our processes through automation and modern AI technologies. This role reports directly to the CEO.

RESPONSIBILITIES

  • Define and drive Beneration’s overall technology vision, strategy, and architecture.
  • Manage outsourced development vendors to ensure quality, secure, and efficient software delivery.
  • Recruit, build, and lead an internal engineering team, setting culture, standards, and practices.
  • Collaborate with Product Management to deliver impactful software solutions, including VerifiaBill and Salesforce integrations.
  • Architect automation-first systems, leveraging modern AI technologies (LLMs, agents, intelligent workflow automation).
  • Oversee infrastructure, cloud, and security practices to ensure enterprise-grade reliability.
  • Communicate effectively with senior leadership and cross-functional teams to align technology with business goals.
  • Apply industry-leading AI technology to drive innovation at Beneration.

QUALIFICATIONS

  • 8+ years of experience in software engineering, including leadership roles (Head of Engineering, CTO, Lead Architect, etc.).
  • Proven experience managing outsourced teams and building high-performing internal engineering teams.
  • Deep knowledge of SaaS/web app technologies, cloud infrastructure (Azure preferred), and enterprise integrations (e.g., Salesforce).
  • Hands-on experience with AI and automation technologies, including practical application of LLMs.
  • Strong understanding of Agile methodologies and product development practices.
  • Excellent communication skills, with the ability to partner with business leaders and translate technical concepts to diverse audiences.
  • Startup or early-stage company experience strongly preferred.

ABOUT YOU

  • You believe in the business value of creating exceptional customer experiences.
  • You are customer-obsessed and driven to solve complex needs through technology.
  • You bring a strong foundation in software engineering and systems design.
  • You thrive in dynamic, fast-paced environments and enjoy building from the ground up.
  • You are inquisitive, creative, and forward-thinking, always bringing new ideas and challenging the status quo.

WORKING AT BENERATION

Beneration has a completely remote workforce. Our company headquarters is in Philadelphia, PA and our team is largely located on the east coast of the USA.

We offer a competitive benefits package, including:

  • Discounted health, dental, and vision insurance with a wide variety of coverage options.
  • Company-paid short-term disability, long-term disability, life insurance, and AD&D coverage.
  • Employee-paid voluntary benefits, including accident, critical illness, hospital indemnity, pet insurance, home & auto insurance, personal liability, identity theft protection, and legal aid.
  • 401(k) with company match up to 4% after six months.
  • This position offers a competitive salary and equity, giving you a real stake in the company’s success.
  • A collaborative and growth-focused environment with frequent promotions and role customization.
  • An inclusive team culture that values innovation and employee growth.

We are an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status.