Chief of Staff, AI Automation

Tifin • Boulder, CO

6d • Onsite

About The Position

TIFIN builds the AI operating layer for wealth, delivering agentic workflows across the industry’s core personas. This role is for a highly capable, technically inclined operator to work directly with the Founder & Executive Chairman on high-priority initiatives. The position requires a blend of CEO Chief of Staff judgment and technical curiosity, with the ability to prototype AI workflows. The ideal candidate will be comfortable tackling complex problems with the CEO, driving cross-functional initiatives, and personally building AI prototypes.

Requirements

• Exceptional operator who is also genuinely technical, knowing how to use technology to build and solve problems.
• Hands-on experience building with modern AI tools, LLMs, agentic systems, automation platforms, or adjacent technologies.
• Ability to independently prototype workflows and solutions without relying entirely on engineering resources.
• Experience working closely with a founder, CEO, or senior executive.
• Strong judgment and ability to quickly understand unfamiliar businesses, products, and problems, form a point of view, and act on it.
• Ability to turn loosely defined objectives into concrete action while managing multiple high-priority workstreams.
• Clear communication skills and ability to engage credibly with executives, engineers, investors, partners, and other senior stakeholders.
• Background could include Chief of Staff, business operations, product, engineering, AI, consulting, founding or operating a startup, or a combination of these.
• Must be authorized to work in the US without sponsorship.

Nice To Haves

• Former founders and operators who have built technical products or businesses may be particularly well suited to this role.

Responsibilities

• Partner directly with the CEO to translate priorities and ideas into clear plans, owners, and execution.
• Own high-priority projects that span products, businesses, and functions across TIFIN.
• Rapidly get up to speed on new problems, develop a point of view, and move from ambiguity to action.
• Anticipate issues, dependencies, and opportunities to increase the speed and quality of CEO priorities.
• Personally build and prototype AI-powered and agentic workflows that improve TIFIN's operations.
• Identify work that can be redesigned using AI rather than simply layering AI onto existing processes.
• Translate loosely defined business problems into working AI prototypes and workflows, experimenting quickly.
• Partner with product and engineering teams when an initial prototype or workflow should become a more scalable solution.
• Take ownership of important initiatives that do not fit neatly within one existing function.
• Work across product, engineering, commercial, and operations to move complex work from idea through execution.
• Create structure around ambiguous problems, establish clear owners and timelines, and maintain accountability.
• Do the work required to move an initiative forward, including research, analysis, building workflows, preparing recommendations, or resolving operational blockers.

Benefits

• 90-100% medical, vision and dental coverage for you and your dependents
• Retirement benefits
• Flexible PTO
• Relocation assistance is available for exceptional candidates currently outside of the area.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed