---
title: 'Founding Software Engineer (Customer Experience) at Hyperscale'
canonical: 'https://feeny.ai/job/founding-software-engineer-customer-experience-hyperscale-san-francisco-mexdvsta057z'
type: 'job'
last_seen: '2026-09-10'
---

# Founding Software Engineer (Customer Experience) at Hyperscale

- **Company:** Hyperscale
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-03-26
- **Last confirmed live:** 2026-09-10
- **Apply:** https://jobs.ashbyhq.com/hyperscale/950c982f-5fb9-481b-a6ad-808feba76757

## Job description

Founding Software Engineer (Customer Experience)

## About Hyperscale

Hyperscale is building AGI for physical operations. We're a team of ex-Samsara engineers and operators deploying frontier agentic systems in the real world. The result is a superagent that autonomously handles the highest-volume, most complex back-office workflows physical operations depend on: load coordination, scheduling, support, finance and billing, and more. We're live with some of the largest fleets in the US, running millions of autonomous tasks each week, with strong customer satisfaction. We're backed by top investors and moving fast.

## The Role

We are looking for a Founding Software Engineer to own the technical side of our customer lifecycle. You will work directly with the founders, GTM, and engineering teams: 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.

## What You'll Do

Technical Discovery and Solution Design

- 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

Demos, Pilots, and Proof of Value

- 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

On-Site Customer Engagement

- Travel to customer sites roughly once a month for one to two days at a time (up to 10% 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

Technical Sales Support

- 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

Onboarding and Post-Sales

- 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

What Success Looks Like (First 90 Days)

- 3+ pilots launched with clear metrics showing product value
- Technical close plan established for every active 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

## Who You Are

- 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 one-off integrations
- Strong foundation in full stack development, APIs, webhooks, and system architecture
- You are an engineer who actually wants to talk to customers and are curious about sales and product, excited to flex into those areas over time
- High agency, you proactively identify problems and figure out solutions without being told how
- Comfortable with ambiguity and moving fast in an environment where the playbook does not exist yet
- Willing to experiment with new ways of working as AI rapidly changes how companies operate, you do not cling to a fixed process
- Excited about traveling on-site to customer locations and being embedded in their world
- Scrappy and gritty, you have had to figure things out from scratch before and thrived doing it

## Nice to Have

- 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 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.)

Location San Francisco preferred (in-person when not traveling). We move quickly and value tight feedback loops across deployment, product, engineering, and customers.

## Why Hyperscale

- Real product in production with major US fleets
- Clear ROI and strong metrics already working in the wild
- Work hands-on with cutting-edge agentic AI technology in high-stakes production environments
- Direct customer exposure and immediate feedback loops - see your work drive real operational outcomes
- Build the deployment playbook and forward deployed function from day one, with a path to leadership as we scale
- Backed by top VCs and growing quickly - doubling the team in the first half of the year

## About Hyperscale

## Company Overview
- **One-liner**: Hyperscale provides a voice-first AI command center that automates complex trucking workflows, from driver check-ins and breakdown triage to maintenance scheduling and compliance, enabling fleet operations teams to scale their frontline work.
- **Entity Type**: Private (Seed stage)
- **Headquarters**: San Francisco, California, United States
- **Founded**: 2024
- **Founders**: Oliver Song and Bo DellaMaria

## Core Business
- **Primary industry/industries**: Logistics & Supply Chain; Enterprise AI / Agentic AI for Physical Operations
- **Target customers**: B2B, mid-to-large size trucking carriers and fleet operators (e.g., PS Logistics)
- **Mission or purpose statement**: To improve the efficiency and safety of carrier operations, making sure no one gets left behind in the age of AI [runhyperscale.com](https://www.runhyperscale.com/about/)

## Products & Services
- **VIC (Virtual Intelligent Companion)**: A voice-first, always-on AI agent that handles driver calls 24/7. VIC can triage breakdowns, schedule maintenance, interpret fault codes, check hours of service, confirm deliveries, collect proof of delivery, and escalate issues to human dispatchers only when necessary. It functions as an inbound/outbound voice interface that replaces routine dispatcher-driver communications.
- **Hyperscale Platform (The AI Command Center)**: An integrated suite of AI-powered modules for Fleet Operations, Maintenance, Safety, and Planning. Key capabilities include:
    - **Proactive AI**: Uses data from TMS, driver preferences, HOS, and location to simulate the best driver-load match.
    - **Maintenance at Scale**: Schedules and notifies drivers of needed maintenance before breakdowns occur.
    - **Safety Coaching**: Delivers targeted, contextual coaching to drivers after safety violations or in inclement weather.
    - **Customer Communication**: Proactively reaches out to customers with ETAs and appointment scheduling.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (Seed stage)
- **Key Metric**: Total funding not disclosed; company has publicly shared ROI case studies (e.g., $1.4M+/year in operational savings for a 1,000-1,500 truck carrier) [hsys.ai](https://www.hsys.ai/)
- **Notable Investors/Partners**: Backed by "industry veterans and top institutional funds" [runhyperscale.com](https://www.runhyperscale.com/about/). Key customer partnership: **PS Logistics** (one of the nation's largest carriers). Recognized on the **2026 FreightWaves FreightTech 100** list, alongside Samsara, McLeod, and Uber Freight [hsys.ai](https://www.hsys.ai/post/hyperscale-systems-named-to-freightwaves-freighttech-100).
- **Growth Signals**:
    - Founded in 2024 and has already deployed a production-grade AI agent with major carriers.
    - Reported 6.2% monthly employee growth (LinkedIn, reaching 9 employees) and a growing LinkedIn follower base (+4.7% monthly to 265 followers).
    - Expanding globally with team presence in the US, Philippines, Spain, and Australia [linkedin.com](https://www.linkedin.com/company/hyperscalesystems).
    - 3 active job postings for founding-level roles (Software Engineer, Forward Deployed Engineer, Product Manager).
    - Reported a 40% increase in dispatcher productivity in a 6-week pilot [hsys.ai](https://www.hsys.ai/).

## Competitive Advantages
- **Deep Logistics & AI Expertise**: Founded by Oliver Song and Bo DellaMaria, who previously helped scale Samsara through its IPO. The team includes talent from Samsara, Uber Freight, and other logistics/AI leaders, giving them both operational credibility and technical depth.
- **Voice-First Agentic AI**: Unlike traditional text-based chatbots or simple IVR systems, Hyperscale’s VIC is a true agentic AI capable of holding complex, contextual conversations. It listens, understands driver intent, and takes actions (e.g., scheduling a repair, providing securement protocols) without human intervention—achieving 50%+ call resolution without escalation [hsys.ai](https://www.hsys.ai/post/hyperscale-systems-named-to-freightwaves-freighttech-100).
- **Modular, Scalable Platform**: The platform is designed as a suite of flexible modules (Operations, Maintenance, Safety, Planning) that carriers can adopt incrementally. This reduces implementation friction and allows for a "land and expand" strategy.
- **Proven Enterprise Adoption**: Secured a partnership with PS Logistics (a top 100 carrier) and is already in production, providing verifiable ROI ($1.4M+/yr savings for a mid-size carrier). This validates strong product-market fit in a notoriously difficult-to-penetrate industry.

## Strategic Focus
- **Scaling Deployments**: Moving from pilot projects (e.g., P&S Transportation) to broader adoption across the partner carrier's fleets.
- **Deepening Agent Capabilities**: Expanding VIC’s role from call handling to more complex autonomous tasks, including proactive outbound customer communication, optimized driver-load matching, and predictive maintenance.
- **Becoming the Standard**: Leveraging the 2026 FreightTech 100 recognition to build credibility and become the default "AI Command Center" for fleet operations.
- **Building the Team**: Actively hiring founding engineers and product managers to accelerate product development and customer delivery.

## Why Work Here
- **High-Impact Founding Team**: As a seed-stage company, you’d be a **founding team member**, working directly with experienced founders who have a track record of scaling a company to an IPO (Samsara). This offers significant ownership, autonomy, and career growth.
- **Massive Market with Clear Product-Market Fit**: The company is solving a real, painful problem in a multi-billion dollar industry (trucking/logistics). They have paying customers and proven ROI, reducing the typical "startup risk" and giving employees a sense of building something that truly matters.
- **Engineering & AI at the Core**: The culture emphasizes "extreme velocity & customer obsession" and "rapid iteration" [runhyperscale.com](https://www.runhyperscale.com/about/). The tech stack includes Python, and the core work involves building advanced AI agents that interact in real-time with drivers.
- **Culture**: Described as "customer-first," "operational superhumans," and "extreme velocity." The founders are hands-on and work closely with customers. The tone is ambitious but grounded in real-world operational understanding.
- **Location/Work Style**: Headquartered in San Francisco, with a distributed team (Philippines, Spain, Australia). The exact remote/hybrid policy is not explicitly stated for all roles, but given the small team size and global presence, significant flexibility is likely.
- **Notable Perks**: The chance to work on cutting-edge agentic AI; roles have high visibility with the founders; potential for a liquidity event given the founders' IPO experience.

## Sources
1. [hsys.ai - Company Homepage](https://www.hsys.ai/)
2. [runhyperscale.com - About Page](https://www.runhyperscale.com/about/)
3. [LinkedIn - Hyperscale Company Page](https://www.linkedin.com/company/hyperscalesystems)
4. [f4.fund - Company Profile](https://f4.fund/startups/hsys)
5. [hsys.ai - FreightTech 100 Announcement](https://www.hsys.ai/post/hyperscale-systems-named-to-freightwaves-freighttech-100)
6. [jobs.ashbyhq.com - Careers Page](https://jobs.ashbyhq.com/hyperscale)

## Other roles at Hyperscale

- [Founding Customer Success Manager](https://feeny.ai/job/founding-customer-success-manager-hyperscale-san-francisco-fax9gn1r8rgn) — San Francisco, CA
- [Founding Product Manager](https://feeny.ai/job/founding-product-manager-hyperscale-san-francisco-557tmak263rb) — San Francisco, CA
- [Founding Senior Software Engineer](https://feeny.ai/job/founding-senior-software-engineer-hyperscale-san-francisco-22cbvvpbmvf4) — San Francisco, CA