Files.com · 1 month ago
Head of AI Initiatives
Austin, TX
Full-time
Onsite
Director/ExecutiveFiles.com is on a mission to accelerate the world’s success by building technology for data integration and movement. They are seeking a Head of AI Initiatives to build and embed AI into the core operations of the company, driving high-impact AI systems across various functions.
Enterprise SoftwareFile SharingSaaS
Responsibilities
Identify high-leverage opportunities across every function
Prioritize ruthlessly for ROI, speed-to-production, and durability
Deliver dozens of initiatives that save time, reduce cognitive load, and increase quality
Prototype quickly, then productionize what works
Integrate AI into the tools we already use (CRM, support tooling, docs, repos, analytics, internal systems)
Instrument usage and outcomes; iterate relentlessly
Evaluate frontier vs cost-efficient models and tools
Make smart decisions about where we pay for premium capability
Avoid lock-in by designing swap-ready abstractions and clean interfaces
Create reusable templates, chains, and role-based playbooks
Version and maintain them like real software
Implement RAG systems that respect permissions and source-of-truth hygiene
Improve internal documentation discipline by making knowledge usable
Ensure context is accurate, fresh, and governed
Run workshops, office hours, and hands-on training
Produce a high volume of practical internal content
Build internal champions so capability becomes distributed, not centralized
Establish practical rules for safe/approved AI usage
Prevent tool sprawl, data leaks, and chaos — while enabling 'fast yes'
Partner with engineering/security to ensure reliability and compliance
Qualification
Required
Strong, practical AI depth
Understanding of the current model landscape and how to evaluate tradeoffs
Experience deploying AI in real environments where reliability, costs, and governance matter
Knowledge of what drives adoption inside companies
Ability to build prompts, workflows, tooling, and lightweight platforms
Capability to move from ambiguity to shipping without needing perfect requirements
Enjoyment of iterating based on real feedback and metrics
Thinking in systems and compounding leverage
Ability to turn chaos into repeatable workflows
Experience building libraries, playbooks, and 'default paths' that reduce variance
Concern for durability, maintainability, and upgrade paths
Ability to train and coach people with varying skill levels
Making advanced concepts practical and approachable
Leaving behind capability, not dependence
High standards for production
Concern for observability, security, data handling, and lifecycle management
Ability to balance speed with correctness
Benefits
100% Paid Health, Dental & Vision (75% for family)
401(k) with 4% Company Match
Equity Grants for Every Employee
Paid Parental Leave
20 PTO Days + 11 Holidays + Full Company Winter Break
Signing Bonus + Modern Apple Laptop (Mac-only environment) + Anniversary Gifts
Team Travel to NYC, Austin, Nashville, San Diego, and more
Company
Files.com
Files.com is a SaaS file transfer platform that helps organizations securely transfer & share files between users, teams, and organizations.
Founded in 2008
51-200 employees
Funding
Current Stage
Growth StageTotal Funding
$46.5MKey Investors
Riverwood Capital
2021-02-01Series A· $46.5M
Leadership Team
Kevin Bombino
CEO / Founder
Recent News
2025-12-18
2025-07-24
Company data provided by crunchbase