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Senior Director, PLG User Experiences

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: DocuSign
Full Time position
Listed on 2026-06-19
Job specializations:
  • Design & Architecture
    Product Designer
Salary/Wage Range or Industry Benchmark: 250000 USD Yearly USD 250000.00 YEAR
Job Description & How to Apply Below

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

As the Senior Director of the PLG User Experiences Team, you’ll be the primary architect and strategic visionary for Product‑Led Growth experiences  will lead a team of Product Designers, Content Designers, and Researchers to transform complex customer and business problems into seamless, intuitive growth engines that bridge the gap between product adoption and high‑converting revenue channels. You will own the end‑to‑end experience strategy for high‑impact flows such as trial sign‑up, checkout, self‑cancellation, product onboarding and adoption.

Your mission is to move beyond simple feature delivery to systemic value creation, mapping complex workflows to eliminate friction while ensuring all designs remain usable, accessible, aesthetically pleasing, and on brand. You will operate as a change agent, revolutionizing internal ways of working by infusing AI tools and methodologies into the design process to accelerate prototyping, research synthesis, and content generation.

In this high‑impact role, you will act as a strategic peer to creative leadership in Brand and Product Experience Design (XD) and work closely with Product Management and Engineering leadership across multiple organizations. Beyond day‑to‑day execution, you will champion a culture of diversity, innovation, and creative excellence, recruiting and mentoring a world‑class team across multiple locations.

Responsibilities
  • Develop and communicate the long‑term product design vision.
  • Align design decisions with Docusign’s overall objectives, brand identity, and revenue targets.
  • Coordinate efforts with senior leadership across the company.
  • Identify and capitalize on innovation opportunities by staying abreast of industry trends, emerging technologies, GenAI, and evolving user needs.
  • Architect the UX for end‑to‑end growth experiences including conversion, expansion, retention, product onboarding, activation, and engagement loops.
  • Recruit, mentor, and inspire a high‑performing team of UX Designers, UX Content Strategists, and Researchers.
  • Foster a collaborative culture where designers feel empowered to experiment and grow.
  • Revolutionize internal workflows by integrating AI tools into the design process.
  • Implement and optimize design systems and processes to ensure high‑quality output and timely delivery.
  • Establish and enforce creative standards, design systems, and content guidelines across all PLG funnels.
  • Actively lead design reviews to ensure consistency, craft, and execution detail.
  • Act as a strategic bridge between design, product management, and engineering.
  • Effectively communicate design rationale to executive leadership to influence decision‑making and ensure technical feasibility.
  • Oversee the integration of qualitative and quantitative user research into the design lifecycle.
  • Ensure that user insights and usability testing directly inform iterations and systemic improvements.
What You Bring
  • 15+ years of experience in UX Design or Product Design leadership, with a significant portion dedicated to SaaS and high‑growth environments.
  • Experience leading large‑scale design organizations through complex digital transformations.
  • Experience in e‑commerce UX, particularly in subscription‑based models and complex billing or pricing ecosystems.
  • Experience managing multi‑disciplinary creative teams including product design, content strategy and design, and customer research.
  • Visionary Leadership: A strong record of building and scaling diverse design teams, with a focus on…
Position Requirements
10+ Years work experience
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