Sr. Technical Learning Specialist

Company Overview

Docusign brings agreements to life. Over 1.5 million customers and more than a billion people in over 180 countries use Docusign solutions to accelerate the process of doing business and simplify people’s lives. With intelligent agreement management, Docusign unleashes business-critical data that is trapped inside of documents. Until now, these were disconnected from business systems of record, costing businesses time, money, and opportunity.

Using Docusign’s Intelligent Agreement Management platform, companies can create, commit, and manage agreements with solutions created by the #1 company in e-signature and contract lifecycle management (CLM).

We are seeking a highly motivated and experienced Sr. Technical Learning Specialist to lead the successful execution of our critical Tech Learning initiatives aligned with our business goals and enablement strategy to build and scale several critical investments on Engineering Onboarding, Cloud Edu, Eng‑Focused bootcamps. This role requires a blend of strong program management skills, technical acumen for clear communication, and expertise in managing external partnerships to deliver high‑quality, impactful technical learning experience across our engineering teams.

This position is an individual contributor role reporting to the Technical Learning Director.

• Partner with engineering teams and stakeholders to conduct skill gap analyses, identify tech learning needs aligned with critical engineering programs and OKRs
• Define tech learning strategy and structure for complex technical curricula (e.g., AI/ML development, Cloud) including selecting appropriate delivery modalities (e.g., e‑learning, instructor‑led training, bootcamps) aligned with right tech enablement plans
• Manage delivery and planning of tech learning programs
• Act as the primary owner for program execution, managing timelines, coordinating logistics—scheduling, systems access—ensuring all milestones are met
• Collaborate with Instructional Designers and Subject Matter Experts (SMEs) to create or curate high‑quality, relevant, and engaging technical learning content aligned with learner goals
• Evaluate the effectiveness and relevance of learning programs through surveys, feedback collection, and data analysis
• Select, onboard, and manage external training vendors, ensuring quality and performance standards are maintained
• Define and track key performance indicators (KPIs) and metrics, such as course completion rates, learner engagement and experience, and long‑term impact on job performance and retention
• Serve as the primary communication link, effectively presenting project updates, results, and performance metrics to engineering stakeholders and translate complex technical concepts into clear, actionable information
• Iterate on program content, delivery methods, and overall tech learning strategy based on data‑driven insights to ensure programs remain current with rapid technological changes
• Identify, address, and remove obstacles and impediments hindering program progress
• Support risk and change management activities for the program

Hybrid: Employee divides their time between in‑office and remote work. Access to an office location is required. (Frequency: Minimum 2 days per week; may vary by team but will be weekly in‑office expectation)

Positions at Docusign are assigned a job designation of either In Office, Hybrid or Remote and are specific to the role/job. Preferred job designations are not guaranteed when changing positions within Docusign. Docusign reserves the right to change a position's job designation depending on business needs and as permitted by local law.

• 5+ years of related experience
• Bachelor's degree in Business, Computer Science, Engineering, or a related technical field
• Experience with technical competencies
• Experience with LMS/LXP (e.g., Workday Learning) Google Workspace, Gemini, ChatGPT
• Experience leading complex, end‑to‑end tech learning programs, preferably in a technology or AI/ML domain
• Experience in selecting, managing, and governing external vendors and partners
• Experience with tracking engineering KPIs,…