Executive Assistant to the CEO

Gumloop is the AI automation platform for the enterprise. We believe understanding a task should be the only prerequisite to automating it. We make it easy for any team to build and deploy AI agents that automate real work across hundreds of integrations, no engineering required. The platform has three pillars:

1. Agents — Conversational AI assistants that use tools (integrations, workflows, code sandbox, MCP servers) to accomplish open-ended tasks. Unlike workflows that follow fixed paths, agents decide which tools to use and when, adapting based on context. Users configure agents with a system prompt, a model, and a set of tools. Agents can be deployed to a chat UI, Slack, or Microsoft Teams, and can run autonomously via scheduled or event-based triggers.

2. Workflows — Visual, drag-and-drop automations composed of connected nodes on a canvas. Each node is a discrete operation (call an API, run AI, read a spreadsheet, send an email). Workflows are deterministic and repeatable. They can be triggered manually, on a schedule, via webhook, or by external events (new email, Slack message, etc.). Workflows can also be attached to agents as callable tools — the agent orchestrates, the workflow executes.

3. Gumstack — Enterprise-grade MCP hosting, observability, and AI governance. Organizations provision managed MCP servers, control which AI models are available, audit every tool call, and enforce security policies across all agents and workflows.

We're moving fast. Teams at Gusto, Ramp, Shopify, Samsara, Instacart, and Opendoor are already building and deploying AI agents on Gumloop to automate real work across their organizations. That's not a demo. That's production.

We've raised $70M from Benchmark, First Round Capital, Y Combinator, Nexus Ventures, Shopify Ventures, BoxGroup, and The Cannon Project to build a world class team.
Role Overview

This is a critical hire for Gumloop. As Executive Assistant to the CEO, you'll work directly with Max to keep him focused on the highest-leverage work and help the broader team move faster. You'll be the connective tissue of the company: organized, proactive, and comfortable operating in a fast-moving environment where things change quickly and no two days look the same.

This isn't a role for someone who needs a lot of hand-holding. We're looking for someone who takes ownership, figures things out, and makes things happen, because at a company this size, you're often the last line of defense.

What You'll Do

• Own Max's calendar, inbox, and scheduling, keeping him focused and on time

• Coordinate meetings, travel, and logistics across time zones

• Draft and manage internal and external communications on Max's behalf

• Help prepare materials for investor meetings, board updates, and key stakeholder conversations

• Take notes, track action items, and follow up to make sure nothing falls through the cracks

• Assist with company-wide events, offsites, and team coordination

• Handle ad hoc personal and professional tasks as needed

• Anticipate needs before they arise and solve problems before they become problems

• Find creative solutions to novel operational challenges, thinking beyond "how it's always been done"

What You Bring

• 2+ years of experience supporting a senior executive

• Exceptional organizational skills and attention to detail

• Strong written and verbal communication. You can draft a clear, professional email quickly.

• Comfortable with ambiguity and able to make good judgment calls without waiting for direction

• Discreet and trustworthy with sensitive information

• Proficiency with Google Workspace, Slack, and calendar tools

Bonus

• Experience at an early-stage startup or tech company

Our Values

• Relentless Resourcefulness. This is our most important value. Make things happen, especially when the path isn't obvious. When you hit a wall, run through it. There's no plan B most of the time. Treat every problem like you're the last line of defense, because at a company this size, you often are.

• Optimistic by Default. Be the type of person who looks for the reasons things will work, not the reasons they won't. There are always 100 reasons not to try. It's always those ambitious enough to try that succeed. You should be excited to tackle hard things because you actually believe you can do it.

• Creativity. As AI can do more and more of the technical work, the value comes from your ability to think about problems in novel ways. Most of the problems we're solving have never been solved before, so you'll be breaking new ground most of the time.

• Reliability. We need to know that we can trust you to execute on tasks as well as we would ourselves. When you say you'll do something, you do it.