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Sr. Technical Learning Specialist

DocuSign
parental leave, paid time off, remote work
United States, Washington, Seattle
999 3rd Avenue (Show on map)
Nov 20, 2025
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).


What you'll do

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-Focussed 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.

Responsibility

  • 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


Job Designation

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.


What you bring

Basic

  • 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, and conducting program audits or assessments to align with future-facing engineering OKRs and KPIs

  • Experience managing expectations and working effectively across diverse, cross-functional engineering teams

Preferred

  • Familiarity with the 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


Wage Transparency

Pay for this position is based on a number of factors including geographic location and may vary depending on job-related knowledge, skills, and experience.

Based on applicable legislation, the below details pay ranges in the following locations:

Washington, Maryland, New Jersey and New York (including NYC metro area): $97,000.00 - $139,525.00 base salary

This role is also eligible for the following:

  • Bonus: Sales personnel are eligible for variable incentive pay dependent on their achievement of pre-established sales goals. Non-Sales roles are eligible for a company bonus plan, which is calculated as a percentage of eligible wages and dependent on company performance.

Global benefits provide options for the following:

  • Paid Time Off: earned time off, as well as paid company holidays based on region
  • Paid Parental Leave: take up to six months off with your child after birth, adoption or foster care placement
  • Full Health Benefits Plans: options for 100% employer paid and minimum employee contribution health plans from day one of employment
  • Retirement Plans: select retirement and pension programs with potential for employer contributions
  • Learning and Development: options for coaching, online courses and education reimbursements
  • Compassionate Care Leave: paid time off following the loss of a loved one and other life-changing events

Work Authorization Notice: Please note that we do not provide visa sponsorship or immigration support for this position. Applicants must already be authorized to work in the United States on a full-time, permanent basis without the need for current or future sponsorship.


Life at Docusign

Working here

Docusign is committed to building trust and making the world more agreeable for our employees, customers and the communities in which we live and work. You can count on us to listen, be honest, and try our best to do what's right, every day. At Docusign, everything is equal.

We each have a responsibility to ensure every team member has an equal opportunity to succeed, to be heard, to exchange ideas openly, to build lasting relationships, and to do the work of their life. Best of all, you will be able to feel deep pride in the work you do, because your contribution helps us make the world better than we found it. And for that, you'll be loved by us, our customers, and the world in which we live.

Accommodation

Docusign is committed to providing reasonable accommodations for qualified individuals with disabilities in our job application procedures. If you need such an accommodation, or a religious accommodation, during the application process, please contact us at accommodations@docusign.com.

If you experience any issues, concerns, or technical difficulties during the application process please get in touch with our Talent organization at taops@docusign.com for assistance.

Applicant and Candidate Privacy Notice


States Not Eligible for Employment

This position is not eligible for employment in the following states: Alaska, Hawaii, Maine, Mississippi, North Dakota, South Dakota, Vermont, West Virginia and Wyoming.


Equal Opportunity Employer

It's important to us that we build a talented team that is as diverse as our customers and where all employees feel a deep sense of belonging and thrive. We encourage great talent who bring a range of perspectives to apply for our open positions. Docusign is an Equal Opportunity Employer and makes hiring decisions based on experience, skill, aptitude and a can-do approach. We will not discriminate based on race, ethnicity, color, age, sex, religion, national origin, ancestry, pregnancy, sexual orientation, gender identity, gender expression, genetic information, physical or mental disability, registered domestic partner status, caregiver status, marital status, veteran or military status, or any other legally protected category.

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