Head of AI Initiatives

Head of AI Initiatives at Files.com

At Files.com, our mission is to accelerate the world's success by building and distributing technology that makes data integration and movement effortless. We build mission-critical infrastructure that powers complex, high-stakes digital supply chains for thousands of organizations.

We're creating a completely new role at Files.com: Head of AI Initiatives.

This isn't a research job. It isn't an internal 'AI strategy' role. And it definitely isn't an innovation lab that ships demos.

This is a builder–operator seat for someone who wants to embed AI into the operating system of a serious SaaS business — across sales, marketing, support, engineering, and operations — and ship real, margin-positive AI systems that people use every day.

AI at Files.com: From Hype to Real Tools

We're building real, operational AI infrastructure that's live today — powering both customer-facing features and internal workflows.

Customer-Facing AI Initiatives

• MCP Integration (Live Now): We released our initial MCP (Model Context Protocol) integration last year. Customers can execute agentic tasks — automated sequences of actions — through their preferred AI stack.
• In-App Agentic AI Experience (Coming Soon): We're building an in-app version of the above, where customers can trigger agentic workflows directly inside Files.com. In this version, we'll manage the AI infrastructure behind the scenes, dramatically reducing time-to-value.
• AI-Powered ETL Infrastructure (In Development): We're expanding customer-facing AI into AI-powered Extract/Transform/Load inside the Files.com UI: summarizing files, extracting data, transforming documents, and enabling enterprise customers to run highly customized workflows using their own data within Files.com.

Internal AI Tools (All Live and In Use Today)

We're aggressively deploying AI inside our business to learn what works firsthand — and to build credibility, training data, and internal reference architectures that fuel the external roadmap.

Already launched:

• Transcription + Contextual Wrapping: Every Zoom and phone call across key teams is transcribed automatically — but unlike commodity transcription, we feed Files.com-specific context (product names, acronyms, terminology) to materially improve recognition accuracy. We own the ingestion pipeline end-to-end: upload, batching, retries, metadata tagging, and permissioning.
• Transcription Refinement Engine: A second tool strips fluff (greetings, 'ums,' connection issues) and shrinks transcripts ~80% with no meaningful loss — lowering AI costs and improving downstream accuracy.
• Sales Brief Generator: A tool that digests every prospect conversation and generates a complete internal deal brief for weekly pipeline review — cutting AE prep time by 50%+ and helping scale sales without scaling headcount.
• Coaching & Gap Analysis Engine: Custom evaluation prompts/models flag missed follow-ups, incomplete answers, tone issues, and process adherence gaps across onboarding, support, and sales transcripts. Managers jump directly to high-signal coaching moments. And unlike Gong-style black boxes, we control the prompts and inject our training philosophy into the system.

Next in Development: AI-Powered Upsell Detection

We're building what may become our highest-impact internal AI tool: identify every expansion opportunity across customer communications (calls + email). The hard part isn't 'use GPT-4.' It's building the specialized ETL pipeline to normalize, structure, and index messy comms data from Gmail, Zoom, CRM, and archives — then layering AI on top. This also becomes a reference architecture we can productize as part of an ELT + AI bundle.

The Role and Its Impact

Today we have roughly 10 production AI initiatives. Our goal is to build 50–100.

'Production' means persistent, systematized, observable, and teachable — not ad hoc prompting.

You will own the outcome: turning AI into repeatable leverage across the company, through a portfolio of high-ROI initiatives — and building the standards, libraries, infrastructure, and enablement needed for that to compound.

This role is for someone who wants to be the internal AI founder/operator — shipping constantly, teaching constantly, and raising the company's baseline capability permanently.

What You'll Do

You'll act as the owner of the company's AI operating system — and you'll ship.

• Build and Scale a Portfolio of AI Initiatives: 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.
• Ship End-to-End Systems (Hands-On): 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.
• Own the AI Stack and Model Strategy: 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.
• Build Prompt + Workflow Libraries (Company IP): Create reusable templates, chains, and role-based playbooks; Version and maintain them like real software; Make the 'best way' easy and repeatable.
• Build Knowledge/Context Systems: 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.
• Teach and Enable the Whole Company: 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.
• Create Governance Without Bureaucracy: 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.

What Success Looks Like (Outcomes)

Within 6–12 months, you've:

• Increased the number of production AI initiatives meaningfully (with adoption and impact).
• Built a repeatable intake → build → deploy → measure pipeline.
• Shipped internal AI systems that teams use daily.
• Established prompt/workflow libraries that represent real company IP.
• Raised baseline AI competence across the org through training and systems.
• Created clear standards so initiatives are durable and maintainable.

Within 12–24 months:

• The company runs 50–100 production AI initiatives.
• AI becomes a default layer of how work gets done.
• The organization compounds faster with the same headcount.
• The systems keep working even if any one person leaves.

Characteristics of the Ideal Candidate

We're looking for a rare mix: AI expert + hands-on operator + teacher.

• You have strong, practical AI depth: You understand the current model landscape and how to evaluate tradeoffs; You've deployed AI in real environments where reliability, costs, and governance matter; You know what actually drives adoption inside companies.
• You're a doer, not a delegator: You can build: prompts, workflows, tooling, lightweight platforms; You can move from ambiguity to shipping without needing perfect requirements; You enjoy iterating based on real feedback and metrics.
• You think in systems and compounding leverage: You love turning chaos into repeatable workflows; You build libraries, playbooks, and 'default paths' that reduce variance; You care about durability, maintainability, and upgrade paths.
• You're a teacher and multiplier: You can train and coach people with very different skill levels; You make advanced concepts practical and approachable; You leave behind capability, not dependence.
• You have high standards for production: You care about observability, security, data handling, and lifecycle management; You don't confuse 'cool' with 'useful'; You know how to balance speed with correctness.

Why Files.com

• Founder-led, engineering-first DNA: We build like engineers. We care about systems, quality, and operational excellence — and we want AI built the same way.
• Massive surface area for impact: At our size, you can touch every function and see immediate results. This role can change how the entire company operates.
• High production bar, real-world stakes: We serve serious customers with mission-critical needs. That culture translates internally: we ship things that work.
• Freedom to build the AI platform intentionally: You won't be trapped in committee decisions or locked-in messes. You'll have real authority and real accountability.
• Career-defining seat: This is a rare opportunity to define what 'Head of AI' actually means in a serious SaaS company — with scope, trust, and hands-on ownership.

Perks & 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

Bottom Line: We're looking for someone who wants to build the AI foundation of a company — not advise, not experiment, but actually build. You'll turn AI into leverage across every team, create systems that last, and shape the future operating model of Files.com. If you want a seat where your work changes how an entire SaaS company runs, this is it.

Key skills/competency

• AI Strategy
• Prompt Engineering
• Data Integration
• Machine Learning Operations (MLOps)
• SaaS Operations
• Product Development
• System Design
• Change Management
• Stakeholder Communication
• Executive Leadership