Founding Product Manager

ABOUT HYPERSCALE Hyperscale is building the AI-native intelligence layer for physical operations, starting with trucking carriers. We are a team of ex-Samsara engineers and fleet operators automating the highest-volume back-office workflows (load coordination, scheduling, driver support, and more) with agentic AI. Our product is deployed with some of the largest fleets in the US, autonomously handling ~70% of tasks with strong customer satisfaction. We are small, moving fast, and backed by top investors. THE ROLE We are looking for a Founding Product Manager to own product discovery, roadmap, and customer implementation for Hyperscale. You will be part of the pod we send to customer sites: sitting alongside the Sales Engineer and Account Executive, running discovery sessions, converting customer insights into product direction, and managing ongoing implementation relationships through go-live and beyond. This is not a spec-writing role at a large company. The person who thrives here is low-ego, high-agency, and genuinely excited to be in the room with customers figuring things out in real time. Much of this role involves thinking critically about how to use AI to automate what a traditional PM does: discovery synthesis, spec writing, implementation tracking, and beyond. That requires real depth in both product and engineering, which is why we are looking specifically for engineers who have made the transition into product. You will report directly to the CTO and be one of the most important hires we make this year. WHAT YOU'LL DO Product Discovery and Roadmap - Travel on-site with the customer pod to conduct workflow discovery with dispatchers, drivers, and operations teams - Mine customer conversations for product insights and unmet needs - Convert field learnings into a clear, prioritized roadmap that engineering can build against - Advocate for the roadmap internally and make the case for what to build next and why - Write product specs that give engineers exactly what they need without over-engineering the process Customer Engagement and Implementation - Run ongoing meetings with customers to update them on implementation progress and product developments - Iterate directly with customers on specific features: scope, validate, and refine in real time - Manage the customer relationship from post-sale through go-live and expansion - Identify gaps between what customers need and what the product currently does, and close them quickly - Work closely with the Sales Engineer and Account Executive as part of a coordinated customer pod - Partner with engineering to scope builds, set timelines, and unblock delivery Scaling the Function - Bring the voice of the customer into every product and engineering discussion - Help define the go-to-market motion as we scale from a handful of marquee customers to a repeatable sales process - Build the AI workflows that automate and scale the PM function WHAT SUCCESS LOOKS LIKE (FIRST 90 DAYS) - A working roadmap that reflects real customer needs and has buy-in from engineering - Running customer implementation meetings independently with minimal founder involvement - At least one feature shipped that came directly from something you heard in the field - Engineering and sales both trust you as the connective tissue between them and the customer WHO YOU ARE - Started as a software engineer and transitioned into product: you bring real engineering depth, not just technical familiarity - Actively thinks about how to use AI to automate the PM function itself, not just the products you build - 5+ years of experience across engineering and product, including 2+ in a product management role, ideally including time at an early-stage company - Founding PM mentality: you write specs AND take customer calls AND figure out what nobody told you to do - Highly comfortable talking to customers, including non-technical operators and executives - Strong product intuition: you can walk out of a customer conversation with a clear point of view on what to build - Technical enough to work credibly with engineers and understand integration complexity - Low ego and high adaptability: you do not need a defined process to be effective - Willing and excited to travel on-site to customer locations - Ready to reshape what you do and how you do it as AI redefines what's possible NICE TO HAVE - Background in logistics, trucking, fleet management, or supply chain software (Samsara, Motive, Flexport, or similar) - Familiarity with TMS platforms (McLeod, TMW, Omnitracs), ELD systems, or dispatch software - Prior experience with AI/ML products, e specially conversational AI or agent-based systems - Experience in professional services, implementation, or customer success engineering WHY HYPERSCALE - Real product in production with major US fleets, not a prototype - Clear ROI and strong metrics already proven in the field - Direct access to the engineering team and real influence over product direction - Opportunity to define the product management function from scratch - Path to leadership as we scale - Work on genuinely hard AI problems in a massive, underserved industry