VP Of Engineering

The Role

We are seeking an experienced and entrepreneurial engineering executive to lead our technology organization through its next stage of growth. This role is pivotal to Sydecar's success: you will define and execute the technical vision, scale a high-performing engineering culture, and partner closely with the CEO, COO, Product, and business leaders to deliver outcomes that accelerate both growth and efficiency.

The ideal candidate excels at translating strategy into scalable architecture and execution, while mentoring leaders and inspiring teams. You will join Sydecar's executive team as a trusted partner, shaping the future of our platform and industry.

This position is VP of Engineering or SVP of Engineering. Compensation and title will be determined based on seniority and confirmed during the process.

Responsibilities

Technology Strategy & Vision

• Define and own the long-term technical vision aligned to Sydecar's business strategy.
• Balance investment in new architecture with continuous improvement of existing systems and reduction of technical debt.
• Leverage emerging technologies, including AI/ML, to create efficiencies and competitive advantage.
• Develop independent hypotheses about business strategy and engage at the leadership level, demonstrating strong business context and the ability to connect technical decisions to Sydecar's goals.
• Ensure systems are scalable, extensible, and resilient to support evolving customer needs and future business scale.

Execution & Delivery

• Drive consistent, predictable delivery of complex projects, improving engineering estimation, velocity, and quality.
• Champion engineering excellence in development, testing, deployment, observability, and security.
• Own success metrics by defining what success looks like for engineering, setting measurable goals, and ensuring progress and outcomes are transparent and reportable to senior leadership.

Leadership & Culture

• Build and scale Sydecar's engineering organization with a bias for fewer, highly productive, collaborative engineers.
• Mentor and develop engineering managers and ICs, fostering growth and accountability.
• Serve as a visible culture carrier, exemplifying Sydecar's values of ownership, excellence, humility, and winning together.
• Challenge senior leadership constructively and defend technical strategy with conviction, ensuring the engineering perspective is represented in key company decisions.

Cross-functional Partnership

• Partner with Product, CX, and Design to deliver business-critical outcomes.
• Represent engineering at the board and with investors, translating technical strategy into business impact.
• Drive alignment across distributed teams while maintaining urgency, high ownership, and focus on outcomes.

Qualifications

• 15+ years of software engineering experience with 8+ years in senior engineering leadership roles (Team Lead, Head of Eng, VP, CTO, etc.).
• Proven success leading and scaling teams of 20–50+ engineers in high-growth, resource-constrained startup environments.
• Track record of delivering scalable systems and complex products on time and with quality.
• Strong technical background with the ability to dive deep and challenge assumptions while empowering engineering teams.
• Experience partnering with C-Suite leaders to define technology roadmap with ability to lead execution & strategy.
• Board-level communication skills and executive presence; ability to inspire confidence across internal and external stakeholders.
• Comfort operating in hybrid/distributed teams and evolving, ambiguous environments.

Preferred

• Series A/B stage leadership experience in fintech, B2B SaaS, or highly regulated industries.
• Experience modernizing legacy systems and balancing technical debt with new development.
• Exposure to both startup scrappiness and larger-company best practices, with ability to translate appropriately to Sydecar's stage.

Sydecar's Values

Our values are important to the way we live and work at Sydecar. They guide our priorities, behaviors and interactions.

Ownership: We are committed to and proud of our work and growth. We hold ourselves accountable for achieving our goals.

Excellence: We set and exceed ambitious goals through ownership, data-driven decisions, and rigorous execution.

Humility: We value feedback and recognize that growth comes from learning from each other and our experiences.

Win Together: We are driven by a passion for winning and we champion the success of our team members, our customers, and our partners.

Sydecar is committed to the principle of equal employment opportunity for all employees and to providing employees with a work environment free of discrimination and harassment. All employment decisions at Sydecar are based on business needs, job requirements and individual qualifications, without regard to race, color, religion or belief, national, social or ethnic origin, sex (including pregnancy), age, physical, mental or sensory disability, HIV Status, sexual orientation, gender identity and/or expression, marital, civil union or domestic partnership status, past or present military service, family medical history or genetic information, family or parental status, or any other status protected by the laws or regulations in the locations where we operate. Sydecar will not tolerate discrimination or harassment based on any of these characteristics. Sydecar encourages applicants of all ages.