Sr. Technical Learning Specialist

Location: Seattle, Washington

Department: People & Workplace Experience

Work Mode: Hybrid

About the Role

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 business processes and simplify lives through intelligent agreement management. Our platform unleashes business-critical data trapped in documents, integrating with systems of record to save time, money, and opportunity. As the #1 company in e-signature and contract lifecycle management (CLM), Docusign drives innovation in secure, digital agreement workflows. We are seeking a highly motivated Sr. Technical Learning Specialist in the People & Workplace Experience team to lead execution of critical Tech Learning initiatives like Engineering Onboarding, Cloud Edu, and Eng-Focused bootcamps. This individual contributor role, reporting to the Technical Learning Director, blends program management, technical acumen, and partnership expertise to deliver impactful learning across engineering teams fueling Docusign's e-signature and CLM innovations. In our hybrid designation (minimum 2 days/week in-office), you'll thrive in a collaborative, innovation-driven culture. Key responsibilities include partnering on skill gap analyses aligned with engineering OKRs, defining strategies for AI/ML and Cloud curricula, managing program delivery and vendors, evaluating impact via KPIs, and iterating based on insights to support Docusign's rapid technological evolution. You'll communicate complex concepts clearly to stakeholders, remove impediments, and ensure programs enhance engineering excellence in intelligent agreement management. The ideal candidate brings 5+ years of experience, a relevant Bachelor's degree, LMS proficiency, and a passion for tech enablement. Join Docusign's inclusive culture where diverse talent builds trust, fosters belonging, and transforms the world through agreeable agreements. This position requires U.S. work authorization without sponsorship and is not eligible in certain states.

Key Responsibilities

• Partner with engineering teams and stakeholders to conduct skill gap analyses and identify tech learning needs aligned with DocuSign's critical engineering programs and OKRs
• Define tech learning strategy and structure for complex technical curricula (e.g., AI/ML development, Cloud) including selecting delivery modalities like e-learning, instructor-led training, and bootcamps
• Manage end-to-end delivery and planning of tech learning programs such as Engineering Onboarding, Cloud Edu, and Eng-Focused bootcamps
• Act as primary owner for program execution, managing timelines, logistics, scheduling, and systems access to ensure all milestones are met
• Collaborate with Instructional Designers and Subject Matter Experts (SMEs) to create or curate high-quality, engaging technical content aligned with learner goals and DocuSign's intelligent agreement management innovations
• Evaluate program effectiveness through surveys, feedback, and data analysis, tracking KPIs like completion rates, engagement, and impact on job performance
• Select, onboard, and manage external training vendors to maintain quality and performance standards
• Serve as primary communication link, presenting updates, metrics, and translating complex technical concepts into actionable insights for engineering stakeholders
• Iterate on program content, delivery methods, and strategy based on data-driven insights to keep pace with rapid tech changes in e-signature and CLM
• Identify, address, and remove obstacles, while supporting risk and change management activities

Required Qualifications

• 5+ years of related experience in technical learning or training program management
• Bachelor's degree in Business, Computer Science, Engineering, or a related technical field
• Experience with technical competencies and leading complex, end-to-end tech learning programs, preferably in technology or AI/ML domains
• Proficiency with LMS/LXP platforms (e.g., Workday Learning), Google Workspace, Gemini, and ChatGPT
• Experience selecting, managing, and governing external vendors and partners for training delivery
• Demonstrated experience tracking engineering KPIs, conducting program audits or assessments to align with future-facing engineering OKRs and KPIs
• Proven ability to manage expectations and collaborate effectively across diverse, cross-functional engineering teams

Preferred Qualifications

• Familiarity with basic concepts of prompting, AI/Machine Learning (ML), Cloud, and Software Development life cycle
• Professional certification in Project Management (e.g., PMP, PgMP) or Agile/Scrum
• Experience collaborating with academic institutions and research labs
• Background in e-signature, contract lifecycle management (CLM), or intelligent agreement management technologies
• Hands-on experience scaling engineering onboarding and bootcamp programs in fast-paced tech environments

Required Skills

• Technical program management
• Skill gap analysis
• LMS/LXP administration (e.g., Workday Learning)
• AI/ML and Cloud curriculum design
• Vendor management and governance
• KPIs and OKRs tracking
• Cross-functional stakeholder collaboration
• Data-driven program evaluation
• Content curation with SMEs
• Risk and change management
• Google Workspace and Gemini proficiency
• ChatGPT and prompting techniques
• Agile/Scrum methodologies
• Engineering onboarding expertise
• Bootcamp program scaling
• Clear technical communication
• Obstacle resolution and improvisation

Benefits

• Competitive base salary range: $97,000 - $139,525 (Washington, Maryland, New Jersey, New York including NYC metro)
• Company bonus plan based on performance
• Paid Time Off including earned time off and company holidays
• Paid Parental Leave up to six months
• Comprehensive health benefits with 100% employer-paid options from day one
• Retirement plans with potential employer contributions
• Learning and Development including coaching, online courses, and education reimbursements
• Compassionate Care Leave for life-changing events

DocuSign is an Equal Opportunity Employer.