Instructional Design Lead

Files.com•Austin, TX

7d•$95,000 - $175,000•Onsite

About The Position

Most company training fails for one simple reason: it confuses documentation with learning. At Files.com, we’ve already done the hard part that most organizations never do—we’ve written down the truth. We have an internal reference library that captures how our platform works, how our teams operate, and the standards we expect. Now we need the person who can turn that depth into real competence. We’re hiring an Instructional Design Lead to transform existing reference material into role-based training and assessments that employees can actually absorb, retain, and apply on the job. This isn’t “make it pretty” work. It’s systems work: building structured curricula, chunking complex material into learnable lessons, creating practice and evaluation, and producing training that measurably improves onboarding speed and performance. This is a builder role for someone who cares about clarity, craft, and outcomes. Who We Are We’re Files.com, a profitable, founder-led SaaS company powering secure file transfer and automation for 4,000+ brands you know: Marc Jacobs, GrubHub, Michelin, Hot Topic, Stamps.com, Planet Fitness, KFC, and more. We’ve built a $35M+ business with just 70 people by hiring smart, disciplined, and high-output teammates who act fast and own outcomes. Backed by $46.5M from Riverwood Capital, we’re scaling intentionally — and this role is a critical piece of that growth. Our offices are located in the best parts of two amazing cities: Scottsdale, AZ (Old Town): A bright, modern office with huge windows ☀️, craft coffee ☕️, free drinks, and free catered breakfast every day 🍳🥓. Step outside and you’re surrounded by some of the best lunch and happy hour spots in Arizona. Austin, TX (Downtown): A brand-new space in the heart of downtown, surrounded by energy, culture, and some of the best food and nightlife in Texas. Free breakfast daily, plenty of room to collaborate, and the vibrancy of Austin right outside the door. Twice a year, we bring the whole team together for energizing off-sites in cities like New Orleans, Nashville, and Miami. Bottom Line: This isn’t a content factory role, and it’s not a “make training look nice” job. This is a core, high-impact position where you’ll build the learning systems that determine how quickly and effectively Files.com scales its talent. You’ll turn deep, technical reference material into structured training that produces real competence, faster onboarding, and higher performance across the company. If you care about adult learning, clarity, and building durable systems that actually work in the real world, this is a rare opportunity to do your best work.

Requirements

You love turning complexity into clarity
You build structured learning—not just content
You care about adult learning, practice, and measurement
You’re fast, organized, and quality-obsessed
You’re AI-enabled and systems-minded
You prefer shipping real output over brainstorming

Responsibilities

Turn reference into learning: Convert existing written material into structured courses, modules, and lessons built for retention and real-world application.
Design learning paths: Create role-based curricula for onboarding, enablement, and ongoing development—with clear progression and prerequisites.
Build assessments that prove competence: Write quizzes, scenarios, and practical evaluations that measure job readiness (not just recall).
Chunk and sequence effectively: Break complex concepts into digestible steps with reinforcement, repetition, and checkpoints.
Run an AI-assisted production pipeline: Use AI tools to accelerate drafting, question generation, and formatting—while applying rigorous human review for accuracy and tone.
Create consistency at scale: Establish templates, rubrics, and review processes so courses are cohesive, “Files.com-grade,” and repeatable across teams.
Improve over time: Use feedback and performance signals to iterate on course clarity, structure, and assessment reliability.