Head of Technical Programs

Parasail is redefining AI infrastructure by enabling seamless deployment across a distributed network of GPUs, optimizing for cost, performance, and flexibility. Our mission is to empower AI developers with a fast, cost-efficient, and scalable cloud experience—free from vendor lock-in and designed for the next generation of AI workloads.

Our flagship product is an inference platform harnessing a rapidly expanding global network of GPU providers, propelling us from $0 to $2M ARR in just four months. Inference is at the forefront of the AI revolution, presenting massive growth potential and substantial market opportunity. We’re seeking an entrepreneurial-minded leader to collaborate directly with our founder and CEO, driving revenue growth and securing pivotal early-stage customer partnerships. This role offers the unique chance to learn firsthand from a repeat founder, directly influencing our journey from $0 to $10M ARR.

The Head of Technical Programs will lead strategic customer engagements, manage critical deployments, and drive product adoption by bridging engineering, operations, and product strategy. Ideal for entrepreneurial technologists with early-stage startup experience, this role involves owning onboarding and proof-of-value projects, influencing product direction, and solving complex infrastructure challenges. You'll work closely with engineering teams and customers, gaining hands-on exposure to startup building, strategic decision-making, and scaling innovative technology. This role is perfectly suited for someone who wants to be a company founder or sharpen their founder skills for their next company.

Responsibilities

• Own technical engagements end-to-end: Lead discovery, scoping, technical validation, and successful implementation for new and existing customers
• Design and run proof-of-value projects: Define success criteria, orchestrate internal and external contributors, and deliver high-quality outcomes that drive conversion
• Deeply understand customer architecture: Translate complex infrastructure and ML workflows into actionable integrations and deployment plans
• Operate across disciplines: Collaborate closely with sales, product, and engineering to ensure customer needs are understood, prioritized, and acted on
• Build reusable playbooks and frameworks: This role will be key in helping the company transition from founder-led sales to a scalable sales organization.
• Be the voice of the customer: Proactively surface themes from the field to inform product strategy, influence roadmap, and close gaps in documentation or UX
• Get hands-on when needed: Whether building internal tools, writing example code, jumping on a debugging call, or authoring technical guides, you’re not afraid to dig into the details

What We’re Looking For

• 6–10+ years of experience in a technical role spanning customer-facing work and hands-on engineering
• Previous experience as a technical founder, early engineer, product owner, or solutions architect at a startup or high-growth company
• Strong fluency in AI, LLMs, and Python. Proficiency in cloud computing is a plus
• Proven track record of customer obsession—you build trust with technical users and know how to turn early proof points into long-term success
• Exceptional communication and problem-solving skills; you can move between strategic conversations with CTOs and technical working sessions with engineers
• Self-motivated, execution-focused, and energized by unstructured, high-impact workstreams

Bonus Experience

• Prior ownership of post-sales success, onboarding, or technical enablement functions
• Familiarity with developer platforms, model observability, or enterprise AI adoption cycles
• A history of creating technical content, training, or open-source contributions

Why Join Parasail

• Join a product-first company solving hard infrastructure problems in AI
• Partner directly with leading engineering and ML teams to build next-gen systems
• Help define how Parasail scales from early customer success to widespread adoption
• Fast-paced, high-trust culture with strong engineering values
• Competitive salary, meaningful seed-stage equity, and full benefits