Chief of Staff, Office of CTO

Beacon Software

• $160K — $200K *
Information Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • Former founder or experience with Y Combinator or similar accelerator preferred.
  • Expertise in building with modern AI tools and technologies.
  • Proven experience in delivering full-stack products end-to-end.
  • Exceptional communication skills for technical and non-technical audiences.
  • Strong adaptability and systems thinking in complex environments.

Responsibilities

  • Collaborate with CTO and portcos on critical launches and migrations.
  • Scale AI workflows across multiple small engineering teams.
  • Manage technical diligence for acquisitions post-LOI, ensuring actionable findings.
  • Facilitate cross-functional communication between tech and business teams.
  • Address urgent technical challenges, including stalled migrations and outages.

Benefits

  • Opportunity to work closely with industry leaders and 60+ software businesses.
  • Gain hands-on experience in diverse tech environments.
  • Access to professional development through elite apprenticeship.
  • Network within the San Francisco tech scene through events and talks.
  • Engagement in high-impact, visible projects.
Full Job Description
  • On-the-Ground Execution: Work directly with the CTO and embed with portcos during critical inflection points. First priority: Solid Starts as they onboard Cortex and Arc. You will serve as the eyes, ears, and hands on the ground to ensure critical launches and migrations land smoothly.
  • Portfolio-Wide AI Leverage: Scale modern AI workflows (agentic coding, support deflection, inline AI features) across 30+ small, lean engineering teams that lack the bandwidth to figure it out independently. Help evaluate which portfolio products are durable vs. exposed to AI disruption.
  • End-to-End Tech M&A Diligence: Own the technical workstream post-LOI. Run tech overview sessions, audit target architectures, review codebases, analyze infrastructure costs, and write the technical debt POV for Deal Previews and the Investment Committee (IC). Crucially, you won't just write reports, you will carry diligence findings post-close to ensure remediation actually happens.
  • Cross-Functional & External Glue: Act as the connective tissue between engineering and deal, ops, finance, and pod leaders so technology never feels like a black box. Externally, serve as a face for Beacon in the San Francisco tech and founder scene through technical blog posts, architectural deep dives, and meetup talks to drive deal and talent top-of-funnel.
  • Technical Firefighting & Operations: Parachute into stalled migrations, outages, unexpected departures, or vendor renegotiations. Keep the CTO's operating cadence tight: prep and follow-through for pod tech reviews, IC materials, key tech KPIs (uptime, infra costs, velocity), and senior hiring loops.


What You'll Do:

Beacon is looking for a high-slope, high-agency individual who views this role as an elite apprenticeship-a chance to look inside 60+ software businesses from the ground floor before starting or running their next major venture.

What Beacon Is Looking For:
  • Background: Ideally a former founder (3-4 years out of school, YC or equivalent accelerator background preferred).
  • AI-Native Builder: Builds with agents and modern AI-assisted tools by default, not as an afterthought.
  • Hands-On & Versatile: Proven track record of building and shipping full-stack products end-to-end. Comfortable diving into unfamiliar stacks and reading code quickly.
  • Communication: Exceptional written and verbal communication skills; capable of writing technical blogs and communicating complex systems to non-technical stakeholders.
  • Mindset: Extreme hustle, high adaptability, and strong systems thinking. (Note: This is an elite technical execution role, not a project management or administrative EA position.)

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