Chief Technology Officer, Conversational AI

Engineering · New York, New York
Department Engineering
Employment Type Full-Time

About the Role:

RAIN is a leader in Voice and Conversational AI. We are looking for a Chief Technology Officer (CTO) to lead our technology team, not only to lead and manage technical aspects of our agency work but to help shape the evolution of our department and company.


We are looking for a highly passionate and hands-on leader to work with our currently-remote team. You will report directly into RAIN’s CEO and serve as a key member of the RAIN Executive Leadership Team. You will set and execute the company’s engineering strategy and collaborate with company leadership and cross-functional team members on both strategic and development projects for our clients.


A successful candidate will be able to quickly and effectively envision and enact the “how” of bringing to life a given use case or set of requirements, with a strong working knowledge of the full stack of conversational AI, from ASR to NLU to TTS/STT.  


This position requires exceptional experience in both hands-on development and technical architecture, an ability to strategize around and execute on bespoke voice experiences (including custom software development, leveraging a range of available tools/SDKs, and deploying voice applications on a range of devices), strong engineering management experience and the ability to make smart technical decisions in a fast-paced environment. It also requires an ability to talk with clients – both technical and non-technical - and break down complex topics in a clear fashion. 


 What You’ll Do:

  • Complete hands-on development work and remove roadblocks as part of the client engagements
  • Write clean, structured code with change and reuse in mind
  • Architect solutions, based on customer-specific requirements and use cases, and own their implementation; evaluate the merits of various design patterns, libraries, frameworks, and processes
  • Partner with RAIN’s strategy, UX/VX, and creative teams as RAIN’s senior-most technical team member to interact with prospects and clients, exploring and advising technological possibilities, discovering solutions that fit their goals
  • Manage a team of engineers and systems architects and contribute to their professional growth and maturation, as well as that of the department as it grows with new talent
  • Bring expertise and passion for voice technology; understand the business side of voice technology and make cost-benefit technological recommendations
  • Break projects down into logical streams or sprints and be familiar with the merits and drawbacks of waterfall and agile development (both Kanban and SCRUM)
  • Discover and implement new technologies, emerging web development models, and major trends within the software development community that yield a competitive advantage


What You’ll Bring:


  • Bachelor’s degree (in Computer Science or Engineering preferred)
  • At least 6 years as a lead developer in a team setting, with at least 12 years of development experience overall
  • Full stack experience with an emphasis on NodeJS and Python necessary
  • Complex conversational AI experiences, solutions, or products in a team-leading role required
  • Understanding of architecture patterns such as Domain Driven Design or MVC architecture
  • Successful track record of developing quality software products and shipping production ready software
  • Understanding of ASR, TTS/STT services, Natural Language Processing and available Cloud APIs in conversational AI
  • Experience with containerized deployment and development environments across AWS and GCP with some Azure understanding
  • Experience with high scalability projects involving cloud-based infrastructure design and implementation
  • Understanding of how concepts like SLAs and contracts within software development teams work
  • Understanding of REST-ful API design patterns
  • Understanding of data models and an understanding for how data should be modeled for performance
  • Experience writing SQL queries for SQL Server or another Relational Database
  • Ability to design, develop and implement unit and scenario testing for existing code base and for new functionality under development
  • Excellent use of version control software such as GIT and patterns and practices around development workflow and branching strategy patterns
  • Ability to meet deadlines, define budgets and timetables, balance multiple priorities, and manage parallel projects to completion in a test-driven collaborative and iterative programming environment



  • An entrepreneurial and self-driven personality - you thrive in startup environments, and show persistence in the face of challenges. You maintain a strong bias for stepping up and taking action-yet demonstrate a willingness to learn and receive guidance. 
  • Strong communication, analytical, and problem-solving skills
  • A collaborative ethos, able to share your vision and work coherently, accept and operationalize feedback and enhance the vision and work of others on the team. 
  • Demonstrated ability to influence technical and non-technical audiences, including those at the senior leadership level.
  • Comfortable working with multi-location and distributed workforces.



Our office is located in NYC with remote team members across the country. Currently, we all are working remotely and will be flexible for the future.


*Salary will be evaluated commensurate with experience and location. This role will be eligible for a year-end discretionary incentive award.*



Who We Are:

RAIN is a leader in Voice and Conversational AI. We help businesses navigate voice technology.  We combine strategy, technology, and creativity to drive growth for our clients. We’re guided by the belief that technology is, by definition, an extension of humanity, and that great ideas come from a desire to enhance the lives of real people. 


At RAIN, we want to work with people of different backgrounds and walks of life. We want individuals who can bring diverse perspectives and experiences to our culture and company. We believe that transparency builds trust, so we default to disclosure in our communications. We believe in a safe, welcoming, and inclusive environment.


Restless & Ready. These are the two attributes that mark the talent thriving at RAIN. We look for people who don’t fit the traditional mold, with skill sets you don’t often see in traditional consulting. Said differently, we’re always keen to add more unicorns to the stable. We look for people motivated by big ideas and determined enough to make it a reality.


What We Offer:

We genuinely care about our employees’ happiness and engagement. 

  • Comprehensive Benefits Package: Health, Dental, Vision, and Health Savings Account 
  • Generous Paid Time Off that increases with tenure and seniority.
  • Mental Health/Wellness perks. Including 2 RAIN Check Days - for those days when you just need to take a rain check from work, we get it.
  • Volunteer Days.
  • 401k plan with employer contribution.
  • Short/Long Term Disability.
  • Fully stocked kitchen (when in the office).
  • Commuter subsidy.
  • Challenging problems to solve and an awesome team to collaborate with every single day.
  • Work culture focused on innovation and creation of lasting value for our clients and employees. 


* Note to Recruiters and Placement Agencies: We do not accept unsolicited agency resumes. *

RAIN is an Equal Opportunity Employer and is committed to fair and equitable hiring practices. All hiring decisions at RAIN are based on strategic business needs, job requirements, and individual qualifications. All candidates are considered without regard to race, color, religion, gender, sexuality, national origin, age, disability, genetics, or any other protected status.

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  • Location
    New York, New York
  • Department
  • Employment Type