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.

Base pay range

$225,000.00 / yr - $275,000.00 / yr

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

Engineer with 10+ years of experience in a software engineering role, with progressively increasing responsibility over time

Strategic people leader with 7+ years in a management role within software engineering

Talented roboticist with several years of experience in developing products, ideally in the warehouse automation and / or supply chain space

Experienced with modern programming languages such as C / C++, Python, JavaScript / TypeScript, Rust

Demonstrated experience applying AI / ML technologies to real‑world hardware and systems, with a focus on scalable, reliable solutions

Strong understanding of ML applications across devices, embedded software, robotics, and related domains, with an emphasis on feasibility and impact

Proven expertise in applying SOLID principles to create robust, maintainable, and adaptable software architectures within agile development environments

Skilled in integrating modern machine learning and AI technologies

World‑class coach, mentor and leader; you help engineers thrive and inspire teams to achieve impossible things

Ability to manage staff from diverse backgrounds and career paths, from experienced, expert‑level engineers to early‑career startup developers

Willing and able to work from our Charlestown, MA office at least three times per week

About Pickle Robot

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% of your salary, travel supplies, and other items to make your working life more fun, comfortable, and productive.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans.

Pay Equity

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.

Seniority level

Not Applicable

Employment type

Full‑time

Job function

Engineering and Information Technology

Industries

Transportation, Logistics, Supply Chain and Storage

#J-18808-Ljbffr