Innovation Lead, Office of the CEO

Crescendo•San Francisco, CA

1d•Hybrid

About The Position

We are looking for an Innovation Lead, Office of the CEO to work closely with the Office of the CEO to turn AI capability into real, measurable business outcomes. This role is for someone who is deeply hands-on with AI and comfortable operating as both a builder and an operator. You will design and deploy mini assistants, task-specific copilots, reusable AI personas, and AI-powered workflows (including Gemini Gems or equivalent) that embed AI directly into business processes. Your mandate is to operationalize AI across the company, translating AI insight into executable work—across the tools and systems the business uses—and embedding AI directly into how the company operates.

Requirements

2–5 years of experience in business operations, consulting, product ops, automation, or similar roles
Deep, practical experience applying AI in real business workflows
Hands-on experience building mini assistants, task-specific copilots, reusable AI personas, or Gemini Gems (or equivalent)
Experience conducting competitive analysis and market research to inform AI strategy and tooling decisions
Proven ability to evaluate and recommend buy vs. build approaches for AI solutions
Proven ability to design and implement AI-driven automation
Experience translating complex initiatives into executable work using modern project management tools (Asana, Jira, or similar)
Strong process thinking, ownership mindset, and results orientation

Nice To Haves

Experience in an AI-native or high-growth startup
Familiarity with SaaS, product, or GTM operations
Experience supporting executive teams or Chief of Staff–led initiatives
Experience evaluating AI vendors, platforms, or emerging technologies in fast-moving markets

Responsibilities

Design, build, and maintain mini assistants, task-specific copilots, reusable AI personas, and AI workflows that support core business processes
Create Gemini Gems or equivalent AI agents embedded directly into day-to-day operations
Ensure AI solutions are reusable, scalable, and aligned to real business needs
Continuously iterate based on adoption, performance, and impact
Identify high-leverage opportunities to automate workflows using AI
Implement AI-driven automation across operational, project, and execution workflows
Reduce manual effort while improving speed, consistency, and quality
Conduct competitive and market analysis to understand how peers and competitors are applying AI
Evaluate third-party tools, platforms, and vendors to inform buy vs. build decisions
Partner with leadership to recommend pragmatic, outcome-driven AI investments
Balance speed, cost, scalability, and differentiation when determining build vs. buy paths
Translate AI outputs into clear, executable work items using the company’s project management tools (e.g., Asana, Jira, or equivalent)
Break AI-enabled initiatives into actionable workstreams with clear owners and outcomes
Partner with teams to ensure AI-driven work is delivered, adopted, and measured
Work closely with the Chief of Staff to support CEO priorities
Use AI to increase leverage across planning, communication, and follow-through
Act as a trusted AI operator for high-impact, cross-functional initiatives
Integrate AI into recurring operating cadences (planning, reviews, standups, retros)
Enable teams to use AI naturally in daily work and project execution
Develop prompts, templates, and lightweight playbooks