Head of AI Initiatives

Location: Downtown Austin TX (In-Office)

Type: Full-time Executive Leadership

Compensation: World-class executive pay equity premium benefits

At our mission is to accelerate the worlds 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.

Were creating a completely new role at : Head of AI Initiatives.

This isnt a research job. It isnt an internal AI strategy role. And it definitely isnt an innovation lab that ships demos.

This is a builderoperator 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 : From Hype to Real Tools

Were building real operational AI infrastructure thats 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): Were building an in-app version of the above where customers can trigger agentic workflows directly this version well manage the AI infrastructure behind the scenes dramatically reducing time-to-value.
• AI-Powered ETL Infrastructure (In Development): Were expanding customer-facing AI into AI-powered Extract/Transform/Load inside the UI: summarizing files extracting data transforming documents and enabling enterprise customers to run highly customized workflows using their own data within .

Internal AI Tools (All Live and In Use Today)

Were 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 -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

Were building what may become our highest-impact internal AI tool: identify every expansion opportunity across customer communications (calls email). The hard part isnt use GPT-4. Its 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 50100.

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 companys baseline capability permanently.

What Youll Do

Youll act as the owner of the companys AI operating system and youll 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 612 months youve:

• 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 1224 months:

• The company runs 50100 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

Were 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
• Youve deployed AI in real environments where reliability costs and governance matter
• You know what actually drives adoption inside companies

Youre 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

Youre 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 dont confuse cool with useful
• You know how to balance speed with correctness

Why

• 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 wont be trapped in committee decisions or locked-in messes. Youll 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: Were looking for someone who wants to build the AI foundation of a company not advise not experiment but actually build. Youll turn AI into leverage across every team create systems that last and shape the future operating model of . If you want a seat where your work changes how an entire SaaS company runs this is it.