Chief of Staff, Office of CTO

Beacon Software•San Francisco, CA

About The Position

Beacon is unlike most product companies. Where others start with a single core product and expand into adjacencies over time, portfolio diversity is a Day 0 reality for the organization. Every product and team across the portfolio operates differently. The CTO’s internal "customers" range from portfolio company (portco) engineering teams and pod leaders to the deal team. Because of this multi-faceted structure, there is a constant stream of deeply technical, high-impact work that no single pod or portco owns. The complexity lies in the sheer heterogeneity: no two problems are the same, and they compound rapidly as new businesses are acquired and integrated. Today, this work either lands directly on the CTO or does not happen. A technical Chief of Staff who can jump seamlessly in and out of unfamiliar codebases, architectures, and cross-functional teams closes that gap. The right candidate will increase overall leverage by an order of magnitude which is the baseline expectation for this role. 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. 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.

Requirements

Ideally a former founder (3–4 years out of school, YC or equivalent accelerator background preferred).
Must have experience working as a Chief of Staff at the Office of the CTO.
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.
Exceptional written and verbal communication skills; capable of writing technical blogs and communicating complex systems to non-technical stakeholders.
Extreme hustle, high adaptability, and strong systems thinking.
This is an elite technical execution role, not a project management or administrative EA position.

Responsibilities

Work directly with the CTO and embed with portcos during critical inflection points.
Serve as the eyes, ears, and hands on the ground to ensure critical launches and migrations land smoothly.
Scale modern AI workflows across 30+ small, lean engineering teams.
Help evaluate which portfolio products are durable vs. exposed to AI disruption.
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).
Carry diligence findings post-close to ensure remediation actually happens.
Act as the connective tissue between engineering and deal, ops, finance, and pod leaders.
Serve as a face for Beacon in the San Francisco tech and founder scene through technical blog posts, architectural deep dives, and meetup talks.
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.