Chief Technology Officer (CTO)

About Bookkeeper360:
Bookkeeper360 is a fintech company helping small businesses manage their finances through cloud-based accounting, payroll, tax, and advisory services, powered by AI-driven insights. Since 2012, we’ve been a trusted partner to thousands of business owners and have earned recognition from NerdWallet, Forbes, and Entrepreneur as a top bookkeeping solution.

We’re proud to be named one of Accounting Today’s 2024 Best Firms to Work For and a Fastest Growing Company by Inc. 5000. With a 4.8-star Google rating from 1,000+ clients, we’re growing fast and expanding our team to meet demand.

Want to learn how it all started? Check out the story of our founder and CEO.

About the Role:
We are seeking a visionary Chief Technology Officer (CTO) to lead our product development and engineering organization. In this role, you’ll set the technology strategy, scale and mentor a growing engineering team, and ensure our platform’s security, scalability, and performance. As both a strategic leader and hands-on contributor, you’ll shape the long-term roadmap, dive into architecture and development when needed, and partner with leadership to align technology with business goals while driving innovative solutions for small business owners.

• Set the technology vision and roadmap to align with company strategy and growth goals
• Oversee all engineering functions, including front-end, back-end, DevOps, infrastructure, and security
• Lead development of the Bookkeeper360 App, ensuring a world-class, scalable SaaS product
• Establish best practices in software development, code quality, testing, and deployment
• Direct, evaluate, and approve product architecture and technical design decisions
• Drive innovation, evaluating new technologies and tools to improve product and team performance
• Build and scale the engineering team through hiring, mentorship, and professional development
• Partner with product, operations, and leadership teams to bring new features from ideation to launch
• Monitor system reliability, performance, and data security, ensuring compliance with industry standards
• Manage technical budgets, vendor relationships, and resources to maximize ROI
• Serve as a thought leader representing Bookkeeper360’s technology vision internally and externally

• Strategic leadership: You can see the big picture and align technology with business goals, while executing in a fast-paced, growth environment.
• Hands-on expertise: You’re comfortable rolling up your sleeves to write code, review architecture, and guide technical decisions.
• People-first leader: You inspire, mentor, and grow high-performing engineering teams.
• Execution-focused: You thrive on setting ambitious goals, meeting deadlines, and delivering measurable outcomes.
• Tech-forward mindset: You’re passionate about using technology to solve real-world problems and drive innovation.

• 10+ years of progressive engineering leadership experience, with 3–5 years in a senior leadership role (VP/CTO/Director) at a SaaS company
• Deep technical expertise with Ruby on Rails (5+ years full-stack) and modern web technologies
• Strong knowledge of system architecture, security, scalability, and cloud infrastructure
• Proven success leading product development from ideation through execution
• Track record of hiring, building, and scaling engineering teams
• Excellent communication skills, with the ability to explain complex technical concepts to non-technical stakeholders
• Experience in fintech, data, or analytics platforms is a strong plus

• Salary range from $175,000–$225,000/year + performance bonus
• Equity / Stock Options 
• Comprehensive benefits package including medical, dental, and vision
• 401K with employer match after the first year
• Paid parental leave for all parents (biological, adoptive, and foster)
• Fully remote work environment
• Unlimited PTO after your first year
• Company-paid holidays
• Team-building events and virtual activities
• Career development and internal promotion opportunities

At Bookkeeper360, we are committed to hiring diverse talent of different backgrounds and as such, it is important to us to provide an inclusive work environment for all. We do not discriminate on the basis of race, gender identity, age, religion, sexual orientation, veteran or disability status, or any other protected class. As an equal opportunity employer, we encourage and welcome people of all backgrounds to apply.