Weekday (YC W21)

Founding Head of AI Products – Products & Automation Vertical

Weekday (YC W21)

full-time

Posted on:

Location Type: Remote

Location: Remote • 🇮🇳 India

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Job Level

Lead

Tech Stack

Cloud

About the role

  • Define and own the AI product vision, roadmap, and product catalog focused on automation and measurable ROI
  • Identify repeatable, high-value AI product opportunities emerging from client and internal workflows
  • Build end-to-end MVPs using modern AI stacks including LLMs, RAG pipelines, and agent-based workflows
  • Design production-ready foundations such as authentication, role-based access, logging, monitoring, analytics, and cost controls
  • Integrate AI solutions with common business tools like CRMs, spreadsheets, communication platforms, analytics, and ad systems
  • Lead pilot programs with early customers, including discovery, onboarding, success metrics definition, and feedback loops
  • Convert pilots into paid offerings by demonstrating ROI, documenting outcomes, and creating case studies
  • Define pricing, packaging, and monetization models including pilots, tiers, and usage-based plans
  • Create GTM assets such as demos, pitch decks, one-pagers, ROI calculators, and sales enablement material
  • Collaborate closely with consulting, delivery, and sales teams to productize repeatable wins
  • Establish lightweight delivery, support, and SLA models to ensure reliability and customer success
  • After initial traction, design the hiring plan and build a lean pod of engineers or analysts to scale delivery
  • Set standards for quality, security, evaluation, and continuous improvement of AI outputs

Requirements

  • 5–10+ years of experience with a strong track record of building and shipping products, ideally in 0→1 environments
  • Hands-on expertise with Generative AI, LLMs, prompt engineering, RAG systems, and AI-driven automation
  • Strong engineering foundation covering APIs, databases, integrations, cloud deployments, and observability
  • Proven ability to scope MVPs, prioritize effectively, and iterate quickly based on user feedback and data
  • Experience delivering production systems with monitoring, logging, and basic security best practices
  • Comfort working directly with customers—running discovery calls, pilots, enablement, and iterations
  • Strong product intuition with the ability to translate ambiguous problems into clear solutions and ROI narratives
  • Bias toward action, ownership, and fast execution in high-autonomy environments
  • Entrepreneurial mindset with the ability to balance strategy, hands-on building, and go-to-market execution
  • Clear communication skills to collaborate across technical, consulting, and commercial teams

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
Generative AILLMsprompt engineeringRAG systemsAI-driven automationAPIsdatabasescloud deploymentsmonitoringlogging
Soft skills
product intuitionclear communicationownershipfast executionentrepreneurial mindsetcollaborationprioritizationiterationcustomer engagementproblem-solving