Founding Sales Engineer

Founding Sales Engineer (SF In-Person Preferred)
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.

We are looking for a Founding Sales Engineer to own the technical side of our enterprise sales process. You will work directly with the founders, Head of BD, and engineering team: running technical discovery, designing POCs, traveling on-site to customer locations, and supporting implementation through go-live. This role blends pre‑sales and post‑sales, and the ideal person can flex across product, engineering, and sales depending on what the moment requires.

If you like solving complex integration challenges, translating technical capabilities into business value, and shaping product direction from the field, this role is for you.

You’ll be working on the frontier of applied AI deployment: taking sophisticated agentic systems from demo to production in complex operational environments. This means understanding customer workflows deeply, configuring AI agents to handle their specific use cases, and solving technical integration challenges in real‑time – all while the technology itself is rapidly evolving.

This is a highly technical, customer‑facing role where you'll split time between customer sites and working with our product team. If you like being in the field, solving hard problems on the fly, and seeing immediate impact from your work, this role is for you.

• Lead technical discovery calls with carrier IT, operations, and executive teams

• Understand customer workflows, systems (TMS, ELD, dispatch software), and integration requirements

• Design proof-of-concept configurations that map our AI agents to specific customer use cases

• Document edge cases and requirements to inform the product roadmap

• Run tailored product demos tied to each prospect’s workflows and pain points

• Scope and execute pilot programs with clear success metrics (call resolution rate, time savings, CSAT)

• Build ROI models showing cost savings and efficiency gains

• Troubleshoot issues during pilots and coordinate with engineering to resolve them quickly

• Travel to customer sites roughly once a month for one to two days at a time (up to 25% travel in steady state)

• Embed with customer operations teams to conduct workflow discovery and scope integrations

• Write code or prototype solutions on‑site when needed to unblock deals or accelerate implementation

• Answer RFPs, security questionnaires, and compliance documentation (SOC 2, data handling, etc.)

• Lead technical deep‑dives with buyer IT and security teams on architecture, data flows, and integrations

• Build proposals, integration plans, and implementation timelines

• Address technical objections early and build internal champions

• Scope integrations (APIs, webhooks, data pipelines) with engineering for new customers

• Support initial deployment: data mapping, workflow configuration, testing, and go‑live

• Train customer teams on configuration, agent tuning, and performance monitoring

• 3+ pilots launched with clear metrics showing product value

• Technical close plan established for every active enterprise opportunity

• Core sales collateral built: demo script, ROI calculator, integration overview, security FAQ

• Strong working relationship with engineering and a clear process for escalating customer needs

• At least 2 deals closed where your technical work was critical to winning

• 2 to 5 years of experience as a software engineer or full stack engineer, ideally at a high‑growth B2B company

• You have built and shipped real products end to end, not just scripts or…