Founding Account Executive

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're hiring a Founding Account Executive who will own and close foundational deals with trucking carriers. You'll work directly with the founders to build Hyperscale's sales motion from the ground up - defining our sales process, refining our value proposition, and establishing us as the category leader in AI for carrier operations.

You'll be selling at the frontier of AI adoption in operations: engaging C-suite and operations leaders about autonomous agentic systems that fundamentally transform how carriers run their business. This means understanding both the cutting-edge technology and the operational realities carriers face, then navigating complex sales cycles to close transformative deals.

This is a high-impact, hands-on role where you'll shape the sales playbook and have direct influence on product, pricing, and go-to-market strategy. If you like building from zero, owning the full sales cycle, and working closely with founders in a startup environment, this role is for you.

Sales and deal execution

• Own the full sales cycle from discovery to close for enterprise and strategic mid-market accounts

• Navigate complex, multi-stakeholder sales processes involving operations, IT, procurement, and C-suite buyers

• Run compelling demos and ROI conversations that tie our agentic AI platform to concrete business outcomes

• Negotiate commercial terms, manage procurement processes, and close six- and seven-figure deals

• Build and manage a healthy pipeline to consistently hit and exceed quota

Sales strategy and process building

• Help define our sales methodology, qualification criteria, and deal progression framework

• Refine our pitch, value propositions, and competitive positioning based on frontline conversations

• Experiment with pricing models, packaging, and contract structures to optimize for win rate and expansion

• Build sales collateral including decks, ROI calculators, case studies, and security/compliance materials

• Establish repeatable motions that will scale as we grow the sales team

Market development and partnerships

• Identify and pursue strategic accounts that represent high-value opportunities or reference potential

• Build relationships with key industry players, partners, and influencers in the trucking ecosystem

• Represent Hyperscale at industry conferences, customer events, and trade shows

• Provide market intelligence and competitive insights to inform product roadmap and positioning

Cross-functional collaboration

• Work closely with product and engineering teams to communicate customer needs and influence roadmap

• Partner with forward deployed engineers and customer success on seamless hand-offs and deployment planning

• Collaborate with marketing on demand generation, content, and field programs

• Contribute to hiring and mentoring future AEs as the sales team scales

• 3-6+ years of mid-market or enterprise sales experience, with a track record of consistently meeting or exceeding quota

• Demonstrated success selling complex technical products (ideally B2B SaaS) into enterprise accounts

• Experience managing full sales cycles with deal sizes of $100K+ ARR

• Strong technical aptitude and ability to understand and articulate sophisticated product capabilities

• Excellent storyteller who can translate technical features into business value and ROI

• Skilled at navigating complex organizations and building relationships with diverse stakeholders

• Self-starter with high ownership - you build process, don't just follow it. Cold calling, generating outreach, building relationships excites you.

• Comfortable with ambiguity and rapid iteration in a fast-moving startup

• Experience selling AI/ML products or other emerging, category-defining technologies

• Background in logistics, trucking, fleet operations, supply chain, or adjacent industries

• Prior work at an early-stage startup or as a founding sales hire

• Experience selling into operations-heavy or field service organizations

• Network or relationships within the trucking/logistics industry

• Track record of building sales processes and playbooks from scratch

• Awards for top achievement (President’s club, Winner’s circle, Top 10%)

• Experience public speaking in front of executive level personas

• Passion in closing large, complex deals

San Francisco preferred (in-person). We move quickly and value tight feedback loops across sales, product, engineering, and customers.

• Real product in production with major US fleets

• Clear ROI and strong metrics already working in the wild

• Sell cutting-edge agentic AI technology that's delivering transformative impact for customers

• Define the sales motion and playbook for a category-defining product

• Build the sales team and culture from day one, with a clear path to sales leadership as we scale

• Direct access to founders, product, and customers with immediate impact on strategy

• Backed by top VCs and growing quickly - doubling the team this year

To apply: Send a note with your LinkedIn and 1-2 examples of work you're proud of (a deal you closed, a sales process you built, a market you opened, or anything that shows how you think and sell).