Principal Training & Enablement Specialist

About Checkr
Checkr is building the data platform to power safe and fair decisions. Established in 2014, Checkr’s innovative technology and robust data platform help customers assess risk and ensure safety and compliance to build trusted workplaces and communities. Checkr has over 100,000 customers including DoorDash, Coinbase, Lyft, Instacart, and Airtable.

We’re a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.

About the Role

Truework, recently acquired by Checkr, provides access to crucial employment, income information, and asset information needed for mortgage loans, apartment rentals, background checks, and more. We are disrupting a $5B+ industry, dominated by legacy incumbents and outdated processes, with a better product and intense customer focus. Within Checkr, Truework operates independently, allowing rapid iteration while also being able to leverage the strengths and assets from our core business. Think of it like joining a startup within a startup! 

As a Principal Training and Enablement Specialist, you will provide support across the Manual Verifications, Support, Sales, and RevOps teams within the Operations organization, focusing on the training, enablement, and content. This role is responsible for designing a scalable, global onboarding and continuous learning framework that drives faster ramp and consistency across a distributed workforce. In this role, you will be collaborating with both operations and go to market leadership to support a variety of teams, both directly customer facing and internal. You will be tasked with learning and distilling our product and integration systems into content that can be digestible for different audiences. 

Responsibilities:

• Lead the design and delivery of global training programs, partnering with SMEs, product managers, and stakeholders to ensure effective implementation and continuous feedback loops. 
• Update and implement onboarding and training frameworks that work across diverse regions and cultures, balancing classroom, digital, blended, and self-paced approaches. 
• Collaborate with stakeholders to ensure effective design and programmatic implementation of learning solutions that address workforce needs across different cultures and regions.
• Conduct a comprehensive global needs analysis and translate insights into instructional strategies that scale across teams as well as BPO sites. 
• Build processes for rapid iteration and continuous improvement in a fast-paced environment, setting standards for program quality and measurement.

What you bring:

• 3-5 years of instructional design experience.
• Experience in instructional technologies and Learning Management Systems.
• Experience with complex content and multiple delivery modalities: classroom, online, blended, and self-paced.
• Strong skills in multimedia design (video, micro-learning, job aids, responsive design, gamification, simulations) hands-on or through managing vendors.
• Ability to lead cross-functional stakeholders and own programs end-to-end from needs analysis to impact measurement.
• Thrives in a fast-paced, changing environment; self-motivated and able to work independently.
• Willingness to travel as needed. Both domestically and internationally.

What you get:

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive compensation and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to 25K reimbursement for fertility, adoption, and parental planning services
• Flexible PTO policy
• Monthly wellness stipend, home office stipend

At Checkr, we believe a hybrid work environment strengthens collaboration, drives innovation, and encourages connection. Our hub locations are Denver, CO, San Francisco, CA, and Santiago, Chile. Individuals are expected to work from the office 2 to 3 days a week. Starting January 2026, hub-based employees will be expected to work from the office 3 days per week. In-office perks are provided, such as lunch four times a week, a commuter stipend, and an abundance of snacks and beverages.

 One of Checkr’s core values is Transparency. To live by that value, we’ve made the decision to disclose salary ranges in all of our job postings. We use geographic cost of labor as an input to develop ranges for our roles