About HappyRobot HappyRobot is the AI-native operating system for the real economy—a system that closes the circuit between intelligence and action. By combining real-time truth, specialized AI workers, and an orchestrating intelligence, we help enterprises run complex, mission-critical operations with true autonomy. Our AI OS compounds knowledge, optimizes at every level, and evolves over time. We’re starting with supply chain and industrial-scale operations, where resilience, speed, and continuous improvement matter most—freeing humans to focus on strategy, creativity, and other high-value tasks. You can learn more about our vision in our Manifesto. HappyRobot has raised $62M to date, including our most recent $44M Series B in September 2025. Our investors include Y Combinator (YC), Andreessen Horowitz (a16z), and Base10—partners who believe in our mission to redefine how enterprises operate. We’re channeling this investment into building a world-class team: people with relentless drive, sharp problem-solving skills, and the passion to push limits in a fast-paced, high-intensity environment. If this resonates, you belong at HappyRobot. About the Role We’re looking for a Lead Technical Support Engineer to be the bridge between our customers and our tech. You’ll be the first person users turn to when something breaks—or when they’re just a little confused. You’ll work closely with engineering, product, and ops to fix bugs, improve workflows, and make our AI workers smarter and more reliable. This is a high-trust, high-impact role. You’ll own customer-facing troubleshooting, root cause investigations, and escalations. You’ll turn noise into signal, helping the whole company learn faster from user pain. If you love solving puzzles, calming chaos, and making things just work , this one’s for you. Must-Have 3+ years of experience in a technical support, solutions engineering, or SRE-like role Comfort working with APIs, logs, databases, and modern web stacks (we use Python, JSON, Postgres, etc.) Clear, calm written communication — especially when customers are stuck or frustrated Curiosity and grit — you’ll go deep to figure out what’s actually going wrong High ownership mentality — if something is broken, you fix it or escalate it fast Comfort juggling a mix of tickets, tools, and ad hoc problem-solving every day Nice-to-Have Experience with support platforms like Intercom, Linear, or Zendesk Ability to write scripts or tooling (in Python, Bash, or similar) to automate repetitive workflows Exposure to observability tools like Sentry, Datadog, or Grafana Experience supporting AI/ML, data-intensive systems, or developer-facing tools Previous work in logistics, operations tech, or comms-heavy B2B platforms Why Join Us? Rapidly growing and backed by top investors including a16z, Y Combinator, and Base10. Top-Tier Compensation — Competitive salary + equity in a rocketship Ownership & Autonomy — You’ll own critical systems and shape user experience Real Impact — Every customer you help keeps freight moving and businesses running Work With the Best — Join a world-class team of builders, engineers, and operators Our Operating Principles Extreme Ownership We take full responsibility for our work, outcomes, and team success. No excuses, no blame-shifting — if something needs fixing, we own it and make it better. This means stepping up, even when it’s not “your job.” If a ball is dropped, we pick it up. If a customer is unhappy, we fix it. If a process is broken, we redesign it. We don’t wait for someone else to solve it — we lead with accountability and expect the same from those around us. Craftsmanship Putting care and intention into every task, striving for excellence, and taking deep ownership of the quality and outcome of your work. Craftsmanship means never settling for “just fine.” We sweat the details because details compound. Whether it’s a product feature, an internal doc, or a sales call — we treat it as a reflection of our standards. We aim to deliver jaw-dropping customer experiences by being curious, meticulous, and proud of what we build — even when nobody’s watching. We are “majos” Be friendly & have fun with your coworkers. Always be genuine & honest, but kind. “Majo” is our way of saying: be a good human. Be approachable, helpful, and warm. We’re building something ambitious, and it’s easier (and more fun) when we enjoy the ride together. We give feedback with kindness, challenge each other with respect, and celebrate wins together without ego. Urgency with Focus Create the highest impact in the shortest amount of time. Move fast, but in the right direction. We operate with speed because time is our most limited resource. But speed without focus is chaos. We prioritize ruthlessly, act decisively, and stay aligned. We aim for high leverage: the biggest results from the simplest, smartest actions. We’re running a high-speed marathon — not a sprint with no strategy. Talent Density and Meritocracy Hire only people who can raise the average; ‘exceptional performance is the passing grade.’ Ability trumps seniority. We believe the best teams are built on talent density — every hire should raise the bar. We reward contribution, not titles or tenure. We give ownership to those who earn it, and we all hold each other to a high standard. A-players want to work with other A-players — that’s how we win. First-Principles Thinking Strip a problem to physics-level facts, ignore industry dogma, rebuild the solution from scratch. We don’t copy-paste solutions. We go back to basics, ask why things are the way they are, and rebuild from the ground up if needed. This mindset pushes us to innovate, challenge stale assumptions, and move faster than incumbents. It’s how we build what others think is impossible.

• Provide technical support to customers experiencing database and platform issues • Translate complex technical concepts into clear, actionable guidance • Collaborate with customers to understand their use cases and optimise their implementations • Deeply understand customer pain points and challenges to deliver solutions that truly address their needs • Be a trusted advisor to customers and help them succeed • Manage customer cases from beginning to end. • Troubleshoot and optimise PostgreSQL and TimescaleDB performance issues • Help implement database solutions, including Timescaledb features like hypertables, compression strategies, and continuous aggregates • Analyse complex query execution plans and resolve performance bottlenecks • Test new database features related to TimescaleDB or Agentic PostgreSQL to stay ahead of customers and proactively help them leverage new capabilities • Investigate issues across the full stack — from application layer to database internals • Integrate and troubleshoot platform features

• Investigate, analyze, and resolve complex technical issues across Echosystem modules and third-party integrations • Act as a trusted technical advisor to customers • Solve problems and collaborate with the Customer Success team • Identify root causes and document repeatable solutions • Communicate insights to Product and Engineering teams for improvements • Participate in 24/7 support coverage under a Follow the Sun model • Provide backup coverage during high-priority events

• The Technical Support Engineer (TSE) is a strategic customer advisor and the internal voice for our customer base. • Provide outstanding technical support for the Docusign Intelligent Agreement Management (IAM) and associated services. • Handle incoming support channels to troubleshoot customer inquiries, including but not limited to API integrations, embedded systems issues, network and security-related impediments, 3rd party integrations, and multi-product workflows. • Use broad technical product expertise within IAM areas to help customers increase adoption. • Use support tools and resources vital to solve the customer issue, including Salesforce, Jira, Docusign proprietary logging systems, SharePoint, browser developer tools, internal admin console, SQL, and text analysis tooling. • Promote Docusign products and services to customers and prospective customers via consultative discussion and evaluation of their service and support needs.