Senior Staff Software Engineer

About the Role:

Wing is looking for a Sr. Staff Software Engineerto join our Technology Organization team. This role will be based remotely in the US and requires occasional presence in Wing offices for effective collaboration, primarily in our Palo Alto, CA office.

This is a unique, high-impact role for a senior technical architect who operates with a horizontal scope, acting as a force multiplier to elevate the entire software organization. Our engineering teams are developing a highly automated, reliable, and scalable drone delivery network, and we are seeking an expert to help us design, build and scale it.

This position is for a "benevolent meddler" and technical mentor who thrives on earning the trust of teams to solve complex, systemic problems that others may not see. You will leverage your deep expertise in areas like software architecture, production reliability, large-scale data analysis, and distributed systems to find and address unseen risks and opportunities for improvement, both process and technical, across Wing. They need to know how and when to instill the right level of rigor into our systems, policies and practices at the right times. This role requires someone who is intrinsically driven to teach, mentor, and grow the engineering organization's capabilities, ultimately helping us build the future of delivery. 

What You’ll Do: 

• Integrate deeply with our engineering teams by rolling up your sleeves to help debug complex issues, participate in design sessions, and understand our production systems firsthand. You will earn the trust and respect of the organization to effectively lead and influence change from within.
• Drive strategic initiatives and process development to increase the reliability, quality, and efficiency of the Wing delivery network, ensuring our software architecture can scale with the business.
• Analyze and review system designs, architecture, production systems, and team practices to uncover systemic issues and opportunities for improvement across Wing’s software.
• Synthesize these findings into a clear vision, creating and owning foundational Software Engineering Principles in addition to a strategic roadmap for increasing reliability, and observability.
• Educate and upskill the entire software organization by establishing formal curriculum and processes, developing new training materials, and personally mentoring engineers on software design and production excellence.
• Lead our post-incident reviews, acting as a key escalation point for major outages and driving the decisions and follow-through that prevent future failures.
• Advocate for the engineering organization by using your data-driven insights and hands-on findings to influence technical direction and investment at the leadership level.
• Champion a collaborative engineering culture where learning from one another is paramount, mentoring software engineering leaders and fostering an environment of continuous improvement.
• Represent Wing’s technical excellence both internally and externally through involvement in recruiting, industry outreach, conference presentations and standards organizations.

What You’ll Need: 

• 15+ years of professional experience, including significant work in Software Engineering, Site Reliability Engineering (SRE), and building large-scale distributed systems.
• Expertise in designing, analyzing, and troubleshooting complex, large-scale distributed systems.
• A deep and practical understanding of modern reliability principles, including incident management, post-mortem culture, SLO/SLI development.
• Demonstrated ability to drive strategic technical decisions across large organizations
• Proven experience as an educator and mentor, with a passion for teaching and developing processes and technical curriculum for other engineers.
• High emotional intelligence and empathy to earn the trust of engineering teams
• Mature data analysis skills to make informed decisions on technical strategy and investment.
• Exceptional communication and influencing skills, with the ability to earn trust and work horizontally across a large engineering organization to drive change.