Tech Learning & Enablement Specialist

WEX•Boston, MA

2d•$124,900 - $146,100•Remote

About The Position

As a Tech Learning & Enablement Specialist, you are the "Systems Architect" of our people ecosystem. Your mission is to ensure that our leadership capabilities, collective awareness of critical skills, and internal culture evolve as fast as our technology. This role is a strategic bridge between leadership’s vision and the technical execution of our engineering and product teams. You will ensure our tech talent is not only highly skilled but also deeply aligned with our long-term roadmap. You will act as an internal consultant, using data-driven insights to diagnose friction points and design interventions that scale our most valuable asset: our people.

Requirements

4+ years in Organizational Development, Technical Enablement, or a related role within a SaaS or high-growth tech environment.
Ability to translate "soft" qualitative data into "hard" quantitative insights that resonate with technical leaders.
A strong understanding of the Software Development Life Cycle (SDLC), cloud infrastructure, and modern engineering culture.
A proven ability to see how a change in one department (e.g., Engineering) impacts others (e.g., Product or Sales).
Exceptional ability to "speak engineer" while also being able to present clearly to non-technical stakeholders.

Responsibilities

Lead the "people side" of technical pivots, re-orgs, or process shifts (e.g., migrating to new AI-driven workflows).
Support gap analyses to identify the difference between our current state and the future-ready organization we need to become.
Work with the CTO and VPs of Engineering to translate high-level business goals into actionable internal communications and team-level objectives.
Ensure that the "why" behind technical shifts (e.g., migrating to a new tool) is clearly understood across all teams, and that individuals have the tools to stay informed on tooling and processes.
Partner with DevOps and Engineering Leads to support the standardization of best practices (e.g., CI/CD protocols, security-first coding, agile ceremonies).
Create opportunities for staff to learn about and lean into those best practices.
Lead the rollout of new developer tools and platforms, ensuring high adoption rates and minimal friction through targeted change management plans.
Partner with subject matter experts to create continuous learning paths that keep our technical talent at the cutting edge of the industry.
Identify emerging skill requirements (e.g., AI/ML integration, Rust, cloud-native patterns) and assess current team competencies.
Create or curate high-impact learning paths, workshops, and "Lunch & Learns" that keep the team on the cutting edge.
Manage external vendor relationships for specialized certifications and technical bootcamps.
Protect and evolve the company’s "innovator" DNA, ensuring that core values are reflected in how we work and make decisions.
Design learning campaigns alongside our partners to ensure that these improvements are made with the Product Operating Model in mind.
Build out recognition programs as an additional way to reinforce and uplift champions for our desired culture and skills.
Create or support opportunities to hear from employees regarding pain points and needs to inform strategy on how to best support.
Utilize organizational health surveys as another feedback mechanism.
Build programs designed to help high-performing engineers transition into effective people managers.
Partner with leadership to design off-sites and strategic planning sessions.