Founding Sales Engineer

Hyperscale•San Francisco, CA

27d•Onsite

About The Position

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 (driver support, load coordination, scheduling) with agentic AI. Our product is deployed with some of the largest fleets in the US, autonomously handling ~70% of inbound calls 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.

Requirements

3 to 6 years as a forward deployed engineer, sales engineer, solutions engineer, or technical account manager in B2B SaaS
Strong technical foundation: comfortable discussing APIs, webhooks, data integrations, and system architecture
Excellent communicator who can translate technical details into business outcomes for non-technical buyers
Experience running pilots, POCs, or technical evaluations with enterprise customers
High agency: you proactively identify blockers, pull in resources, and drive deals forward
Comfortable with ambiguity: you can demo half-built features and prototype solutions on the fly
Willing and excited to travel on-site to customer locations

Nice To Haves

Experience deploying AI/ML products or other complex technical systems in production
Background in logistics, trucking, fleet operations, or adjacent industries
Prior work as a solutions engineer, implementation engineer, or forward deployed engineer
Experience with enterprise integrations, ETL pipelines, or middleware platforms
Startup experience or comfort operating in fast-moving, high-autonomy environments
Scripting and automation skills (Python, SQL, etc.)

Responsibilities

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