Senior Director, Software Engineering

Pickle is on the hunt for a dynamic and driven Senior Director of Software Engineering to revolutionize the future of warehouse automation. The ideal candidate is an experienced engineering leader with deep expertise and a passion for robotics. They will actively collaborate across teams, partnering with key stakeholders in product, deployment, hardware, and sales to create customer-focused solutions.

The Senior Director of Software Engineering will oversee multiple engineering teams focused on developing cutting-edge solutions in autonomy, robot performance, and human-machine interfaces.

Responsibilities

• Lead, mentor, and manage multiple software engineering teams, including individual contributors and engineering managers.
• Negotiate the distribution of features across releases for all software teams, empowering engineers with the freedom and responsibility to own their work.
• Lead the overall software development process, diving in and out of the trenches to create processes that enable high levels of execution.
• Collaborate with other members of Pickle’s leadership team to shape the long‑term vision and direction of the company's software development efforts.
• Partner with Product & Program Management to track progress toward each release as well as any changes in deadlines or deliverables.
• Identify gaps within the software team, whether structural or skill‑based, and collaborate with People Operations to fill, upskill, or outsource as needed.
• Oversee the software engineering budget, making data‑driven decisions about investments in tools, technology, and personnel.
• Manage relationships with external vendors and service providers as necessary.

Skills & Experience

$225,000 - $275,000 a year

Pay Equity @ Pickle Robot

At Pickle Robot Company, we believe transparency builds trust. The salary range listed here is provided in accordance with Massachusetts law and reflects what we reasonably and in good faith expect to offer for this role. We often consider candidates at different levels of seniority, and final compensation will reflect the level at which a candidate is hired, along with factors like experience and location.

About Pickle Robot

Want to get in on the ground floor of a fast‑growing, VC‑backed robotics company? Join Pickle Robot! We build systems that companies and their teams love.

Pickle robots unload trucks. Every day, millions of trucks and containers are loaded and unloaded, often requiring manual labor—tough, dirty, dangerous, and hard to staff. Pickle automates this process using AI, machine learning, and robotics to deliver reliable products. Our Unload Systems work with teams on loading docks to make the job safer, faster, and more efficient.

Pickle provides best‑in‑class benefits including health, dental, & vision insurance; unlimited vacation, along with all federal and state holidays; 401(k) contributions of 5% on your salary; travel supplies, and other items to make your working life more fun, comfortable, and productive.

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