[Hiring] Director of Technology @Happy Howl

Role Description

This is a unique role at the intersection of technology leadership and AI-first operations. You'll be building an AI-powered force multiplier that makes every department at Happy Howl dramatically more effective. You'll own the entire technical infrastructure while deploying AI systems that automate, accelerate, and improve everything from product to marketing to fulfillment to finance.

What You'll Do

• AI & Automation:
  • Deploy AI-powered systems across every function of the business:
  • Customer service: intelligent ticket routing, automated response drafting, cancellation intervention workflows.
  • Marketing: automated ad performance reporting, creative asset tagging, campaign analytics pipelines.
  • Operations: inventory burn rate alerts, fulfillment SLA monitoring, co-manufacturer production tracking dashboards.
  • Finance: automated board reporting data pulls, cohort analysis refreshes, cash flow forecasting models.
  • Find the manual process, understand the business logic behind it, and replace it with something that runs itself.
• Technical Infrastructure:
  • Own the full technology stack — Shopify storefront, subscriptions, Klaviyo email/SMS, data pipelines, analytics, and every integration that connects them.
  • Be the single accountable owner for site uptime, page speed, checkout conversion, and data integrity.
• Cross-Functional Systems Building:
  • Participate in leadership meetings across departments to systematize strategic priorities.
  • Build intervention triggers, pipelines, and workflows based on departmental needs.
• Long-Term Team Building:
  • Hire and lead 1–2 AI Implementation Engineers who report to you.
  • Set standards, define the toolchain, and build the playbook for AI deployment.
• Emerging Technology:
  • Stay on the forefront of AI development and evaluate new models and tools.

Qualifications

• 5+ years of software development experience.
• Last 2–3 years focused on AI tools and real systems, not prototypes.

Requirements

• Own outcomes, not activity; measure success by what shipped and its impact.
• Move with urgency and judgment; provide recommendations when issues arise.
• Embrace the underdog spirit; leverage a small team effectively.
• Elevate everyone around you; solve problems collaboratively.
• Document everything; reject "good enough" when it threatens quality.
• Deliver work you're proud of, especially when no one is watching.
• Be locked in, not clocked in; focus on ownership, urgency, quality, and follow-through.
• Genuinely believe AI changes everything and have a track record of implementing it.

Nice to Have

• Experience in DTC, CPG, or subscription businesses.
• Familiarity with Shopify, Klaviyo, Stay.ai, Google Analytics, and Meta/TikTok ad platforms.
• Prior experience building AI-powered automations for customer service, marketing, or operations workflows.
• Data engineering background — ETL pipelines, warehousing, BI tools.
• Experience evaluating and deploying AI agents or multi-step AI workflows in production environments.

Benefits

• Competitive base salary ($160K–$180K) plus a meaningful annual bonus opportunity and equity.
• First technical leadership hire with full autonomy over technical decisions.
• Remote-friendly with flexibility to work from anywhere in the US.
• Opportunity to build an AI-first organization from the ground up.