CTO

About Postal:

Postal offers a modern virtual mailbox and registered agent for businesses. Postal provides an official address for government, IRS, checks, and vendor communications so companies don't have to use an apartment / shared office address. Postal's AI summarizes mail and recommends compliance actions, and its marketplace of service providers are ready to perform the mundane compliance work that otherwise falls through the cracks. It's time to stop touching paper, worrying about lost forms, and changing your mailing address. Postal's pitch is simple: physical mail is the start of the workflow, and AI can help you finish it.

Postal differentiates with both software and services:

• Postal’s AI triages customer mail, generating summaries, extracting deadlines, and telling you what actions to take via reports.
• Postal Compliance Services provides a marketplace of human service providers that can actually handle these compliance tasks for you.

Physical mail is a greenfield use case for businesses to integrate AI into core operations. Mail remains the system of record for all major corporate compliance, finance and legal issues - particularly in highly regulated industries. Mail is also a uniquely good fit for AI/LLM workflows - highly consequential, painful for humans to process, but short and structured enough for models to do exceptionally useful work.

We have built a system of record for corporate compliance that lets our customers focus on their core business and outsource everything else. Our pitch (mail is the start of the workflow, and AI can help you finish it) is resonating strongly with customers, and we are growing rapidly. We’re looking for a CTO to double down on AI-driven compliance workflows and lead full-stack technical development.

What You Will Own:

• The full-stack development and maintenance of the Postal platform;
• Postal’s overall technical strategy and architecture;
• The exercise of technical decision making judgment around security, reliability, scalability, and compliance;
• Collaborative execution with product, operations, and compliance; and
• Technical project planning, prioritization, and delivery timelines.

What You Will Build:

• Improvements to a system that is in production use by hundreds of customers
• New tools that test our hypotheses about how AI can be leveraged to solve compliance problems at lower cost and greater speed for American businesses.

Helpful Skills: Claude Code / Cursor / etc, TypeScript, Next.js, Express + Prisma, React, and LLM API integration

What We Are Look For:

• Technical:
  • 6+ years of professional software experience
  • Prior experience as a senior engineering leader (CTO, VP Engineering, Head of Engineering)
  • Strong systems thinking and comfort making high impact architectural decisions
  • Highly proficient with both AI dev tools and AI API integration
  • Experience owning product features across both backend and frontend technologies.
• Non-technical:
  • Extremely strong organization skills.
  • Extremely strong oral written communication skills, with the ability to convey complex technical concepts to both technical and non-technical stakeholders.
  • A healthy sense of curiosity about the world, the AI compliance and mail spaces, and the startup ecosystem.
  • Previous exposure to early stage startups or fast-paced environments is a plus.

What We Offer:

• The opportunity to own real outcomes and meaningfully shape our technical direction and culture.
• Competitive salary and equity options, aligning your success with the company's growth.
• Comprehensive medical, dental, and vision insurance and a 401k.
• A flexible hybrid work culture with days in the office to work closely with the team and remote days to have focused work time.
• Ongoing opportunities for learning and skill development to keep you at the forefront of your field.

Diversity:

• Prioritizing diversity, multiculturalism, and inclusion is hugely important to us. Postal welcomes and encourages applicants from diverse backgrounds and abilities to apply.

Interview Process

TLDR: Meet with the founders —> three day work trial —> decision.

At Postal, the final step in the interview process is a paid, in-person "work trial." It's designed so candidates can feel the culture, collaborate with future teammates, and deliver outcomes to customers. During the work trial, candidates take a real customer problem (there are plenty), build a solution, and implement it.

What our work trial looks like:

• 3 days in person in Manhattan
• paid hourly
• all expenses covered (flights, hotels, meals)
• clear outcome: candidates leave knowing whether or not they've got a full-time offer.