Chief Technology Officer

Each year the US and Canadian governments give out billions of dollars in R&D tax credits to fund businesses, but the application process is cumbersome and time-consuming.

Boast.AI is building the future of tax credit recovery with artificial intelligence so companies can get more money, faster for less time and risk.

Boast’s mission is to help innovative companies become successful and we’ve built a community of 60k+ technology professionals called Traction to support that mission, bringing leaders from the fastest growing companies like Google, Shopify, Twilio, Slack, LinkedIn, Zoho, GitHub, Cloudflare, and many more to share advice via weekly webinars, monthly dinners, and an annual conference.

As the Chief Technology Officer (CTO), you will be a key member of the executive team and lead all strategy and execution of technology at Boast.AI. 


  • Retain, attract, and lead a diverse, inclusive, and increasingly distributed engineering team that can meet and exceed company goals in service of our mission
  • Work with the HR to set up a sustainable engineering hiring funnel
  • Ensure technical and career growth opportunities for team members
  • Troubleshoot personnel issues to ensure resolution inline with our values
  • Help plan and facilitate training and professional development activities
  • Manage and motivate the engineering team to deliver high-quality high-usability software on time and within budget
  • Direct and help the engineering team in pivotal decision making concerning infrastructure, architecture, security, and scalability
  • Develop and embed excellent communication practices with the engineering team and across the organization to ensure a high degree of alignment as we scale
  • Develop and embed a clear framework for productivity and velocity in order to ensure we’re scaling effectively
  • Maintain and scale the existing technologies and build on it
  • Keep abreast of the latest developments in fintech, artificial intelligence, machine learning, and software engineering
  • Ensure security standards and best practices are met
  • Review and optimize software development processes to ensure consistent and predictable delivery
  • Ensure proper performance monitoring of our tools and platforms
  • Serve as a part of the executive team to decide on strategies for short term and long term needs of the company and product roadmap
  • Participate in annual planning activities
  • Participate in activities to monitor the health of the business
  • Provide impactful insights into the company’s strategic direction
  • Lead the strategy, planning, and execution of the technology roadmap & OKR’s
  • Lead estimating and capacity planning activities
  • Track and report on process-related metrics
  • Strategize and execute on IP development and manage the company’s IP portfolio
  • Provide regular market insights to ensure our technology strategy stays current and contributes to our competitive advantage
  • Work closely with our Product team to collectively bring high-quality software to our customers in accordance with requirements, quality standards, and timelines
  • Work closely with our Customer Success team to help troubleshoot any technical roadblocks and assist with any technology-related client escalation.
  • Work closely with our Sales team to help expand our client base and develop partnerships
  • Attend and contribute to key business development meetings
  • Represent Boast.AI at technology conferences and at executive level customer engagements


  • 10+ years of experience as a SaaS technology or fintech leader, managing cross-functional technology resources in a geo-distributed environment
  • Undergrad or Masters degree in Computer Science, Engineering, or a related field required
  • Built and scaled large engineering teams 
  • Defined and managed OKRs
  • Architected complex platforms and developed enterprise-level technology roadmaps
  • Designed, implemented, and optimized processes for development, QA, security, and IT
  • Experience running a 24×7 high-availability platform
  • Experience with artificial intelligence, machine learning, and natural language processing
  • Experience with Python and Google Cloud Platform
  • Experience with public speaking a plus
  • Experience with taking a company through acquisition or public a plus


  • Competitive salary, bonus, and benefits
  • Flexible work environment

Please email your resume and cover letter in confidence to