Director of Product Management, Managed File Transfer

Kiteworks•San Mateo, CA

3h•Hybrid

About The Position

This role is about transforming Managed File Transfer (MFT) from a file-movement category into a governed data-exchange substrate for agentic work, driven by the increasing regulation of data access by AI agents and autonomous workflows. The Director will inherit a robust product line including Kiteworks MFT on Apache Airflow, numerous connectors, FIPS 140-3 validated crypto, ABAC, AI Data Gateway, Secure MCP Server, Kiteworks Compliant AI, and Governed Agent Assists. The objective is to make Kiteworks MFT the decisive product in the category by reimagining it as intelligent, agentic, policy-enforced data exchange between humans, systems, and AI, surpassing competitors like Progress MoveIT, Fortra GoAnywhere, Cleo, IBM Sterling, and Axway. The role emphasizes being a builder first, shipping products, prototyping with AI tools, and focusing on measurable model quality and category share.

Requirements

You've shipped a 0→1 AI-powered product to production and watched it fail, learn, and get good.
You've written at least one eval suite that changed how your team made decisions.
You've built something worth shipping, yourself, with AI in the loop — even if it was small, even if it was a side project.
You have an opinion about agent UX, and you can defend it with artifacts.
You've either owned, shipped to, or lived inside a regulated environment — financial services, healthcare, federal, critical infrastructure — deeply enough to know what a real compliance buyer actually asks.
You've carried a P&L or a major product line with meaningful revenue.

Nice To Haves

Fluency in the stack: Prompting, context engineering, RAG, embeddings, fine-tuning decisions, MCP, agent SDKs, eval infra (Braintrust, LangSmith, or equivalent).
Taste: The ability to look at an agent response, a UI, a workflow, and know in two seconds whether it's good.
Comfort at the edge of the model frontier: Knowing when a capability is 80% there and you can prompt the last 20%, versus when it's 10% there and you should come back in a quarter; building anyway, when the target is moving.
Builder energy: High agency, high urgency, slope over intercept; shipping v1s fast and making them great in public.
A protocol-level understanding of SFTP, AS2, FTPS, and HTTPS file-exchange patterns.

Responsibilities

Own the agentic MFT roadmap, extending Kiteworks MFT beyond scheduled SFTP/AS2/PGP jobs into autonomous, policy-enforced data exchange for humans and agents.
Decide what ships in the next 90 days, 9 months, and 3 years, holding the roadmap loosely and rewriting it when new models drop.
Ship AI-native MFT capabilities end-to-end, including natural-language workflow authoring (plain English → Airflow DAG → AS2 endpoint), LLM-driven content classification and DLP beyond regex, agentic partner onboarding that collapses weeks of AS2/SFTP config into a supervised 20-minute conversation, predictive anomaly detection and behavioral baselining, and intelligent error triage that resolves incidents before the customer files a ticket.
Define and own the eval suite for every AI-touching feature, including golden datasets, LLM-as-judge rubrics, regression thresholds, abstention rates, faithfulness scores, and calibration curves.
Write behavior specs, not feature specs, covering refusal categories, no-fly topics, escalation triggers, and action boundaries for every Governed Agent Assist.
Set the autonomy dial per workflow (human-in-the-loop, human-on-the-loop, or fully autonomous) and defend choices to security, compliance, and the customer.
Orchestrate agents in your own workflow, run Claude Code on your own backlog, maintain the CLAUDE.md that your team codes against, and automate the parts of your job that should be automated.
Own the model strategy (primary, fallback, cost-optimized), deciding when to prompt, when to RAG, when to fine-tune, when to wait three months for the next Claude.
Monitor provider drift and price changes, pick your fights with frontier vs. open-weights, and know your cost per classification, per routing decision, per compliance check — down to the cent.
Translate regulation (NIS2 Article 21, DORA's 24-hour reporting clock, EU AI Act Annex III, FIPS 140-3, CMMC 2.0, GDPR, SOC 2, the DHS M-25-21 mandate for continuous-authorization AI gateways) into a specific product requirement, a specific audit artifact, and a specific salesroom proof point.
Partner with research (Kiteworks' growing AI/ML team) to embed, co-design retrieval pipelines, and influence post-training.
Dogfood ruthlessly, shipping every feature through internal Governed Assists first, watching real users hit real edges, and feeding those edges straight into the next eval.
Position the category, owning the narrative that Kiteworks MFT is the governed data layer for humans and AI agents.
Sit in the customer advisory board and outflank MoveIT and GoAnywhere on security story and Cleo/Axway on agent story.
Present to the executive team.
Travel occasionally.
Write and listen.
Be held to business outcomes: revenue, retention, category position, NPS, and measurable AI quality.