Hi, DocuSign. I’m Isaac Steiner a values-driven design leader currently in Chicago.


✔ Glad to be in conversation.




I’m interested in the challenges that DocuSign has of building an evolutionary agreements platform.

In order to scale design initiatives across various product teams and technology partners, there’s an opportunity for inspirational and pragmatic design strategy that reinforces the vision across tribal barriers.

Among other things, I shared a theme in person which may help with this…


Clear intent, valuable results

While I’m sensitive to context, constraints aren’t always the most important thing about great design. I’m driven by the ways an intention can be set into motion toward meaningful outcomes. Design leaders need to understand these two sides dynamically balanced in all people (especially end-users).


I strive for a compelling vision of the future, framed by clear insights.

This is focused on momentum and collaboration.

It’s grounded in the real lives of people (inside and outside the building).

I strive to build system of relationships that produce meaning (to stakeholder and shareholders).

This is focused on delivery and autonomy.

It’s grounded in processes that build trust.


Currently I’m leading product and user experience design strategy for a pre-seed, platform-based data startup in the alcohol and beverage ecosystem. In the meantime, I’m exploring where I can best contribute next.




Observations as I’ve grown in design


1. Start from insights :
History is discovery of (complex, storied) contexts.

I grew into design within the context of cross-disciplinary theory and practice. Effective work always starts from where people already are and moves outward.

2. Design for behavior :
Communication is what the listener does (behavior).

I honed craftsmanship extending brand language into interactive systems and grounded my understanding of goal-centered methodologies in human motivation and behavior.


3. Build as a team :
language is the grammar of good products.

I led engagements within complex platform ecosystems, witnessing the fragility of service delivery and interaction patterns when tribal affinities reign. Systems broke when the intent was lost.

4. Innovate for humans :
Models (business, revenue, platform) are structures for people.

The heart of an enterprise are the models that signal its health (unit economics, platform partnerships, operations, stakeholder return). If those models aren’t built to scale and adapt and invite disruption, they aren’t human enough to be of enduring value.








CUSTOMER DISCOVERY: Customer Modeling and Journey Mapping · Service Blueprinting · Jobs Mapping · Feature and Opportunity Roadmapping…

PRODUCT DISCOVERY & DESIGN: Design Research (Qualitative / Quantitative) Strategy, Execution, Analysis · Information Architecture, Ontologies · Process Flows and Concept Maps · Interaction Design and Pattern Libraries · Visual Design, Prototyping…

PRODUCT MANAGEMENT: Requirements Definition (TDD) · Pair Programming · Front-End Code QA · HTML/CSS using Bootstrap, Slim (Ruby on Rails)


BUSINESS MODELING: Market Research, Audits, Benchmarking · Pricing Model Research Analysis

FACILITATION & PRESENTING: Workshop Design and Facilitation · Sprint Coaching · Executive Presentation · Co-Design

MANAGEMENT LIAISON: Executive Team Liaison · Team One-on-ones · Small Team (3–8) Direct Delegation

STAKEHOLDER RELATIONS: Client Management · Conflict Resolution · Project Management · Project Debrief · Vendor Relation

TRAINING & GROWTH: Mentorship · Interpersonal Coaching · Tools / Skill Teaching


Hiring · Team Workshop Design · Internal Conference Creation

POSITIONING: Brand Discovery · Identity Definition (Visual, Verbal, Mood) · Brand Standards and Guidelines · Brand Extension · Collateral Design · Print and Environmental Design Production

CONTENT GENERATION: Content Strategy · Copywriting and Editing · Brand Voice Guidelines · Photography Art and Creative Direction

CUSTOMER ACQUISITION: Marketing Coordination · Social Media Strategy and Execution · Digital Media Design


(It’s hard to avoid jargon —Point is: In a new setting, I learn the skills needed for my strengths produce meaningful value in products, people, and an organizations reputation.)


Notable Experience

(A summary of recent roles, the scope of impact, and example accomplishments)


Head of Product & User Experience

May 2017 – Present
1 year, 6 months


Responsible for guiding the product vision of this pre-seed, platform-based data startup. Managed design strategy, operations, and output for a remote team of ten including content experts, contractors and stakeholders.

Initially asked to consult with the founders to refine the business model into a pitch for investors. Quickly became a lead, focusing the business case on user-centered (goal-centered) methods. I also worked alongside our head engineer acting as product manager and principal designer for our platform.

SCOPE: Business Modeling (Platform Network Effects Models, Quantitative Pricing Research, Platform Pricing Model, Market Sizing) · Product Discovery & Design (Contextual Observation, Task Analysis, Customer Segmentation, Distributed Co-Design, Behavioral User Archetypes, Service Blueprints, Journey Mapping, Interaction Models, Prototype/Fakedoor Split-testing, Innovation Pipeline, New Technology Experimentation) · Product Management ((Feature Definition, Engineering Coordination, Feature Testing, API Planning, Rails Development, Release Planning, Deployment Support) · Training & Growth, Culture Development (Contractor Hiring and Coaching, Team Training, Internal Conference) · Positioning (Brand Brief, Design System Governance, Product Marketing Coordination) · Product Design

NOTABLE ACCOMPLISHMENTS: Customer Discovery: Created behavioral-based service journey for hypotheses testing developed from task analysis, contextual user insights, quantitative studies and partner/market research. · Product Discovery: Scoped and executed design and coordination for alpha, closed beta and public release features from conception to launch while overseeing design system quality using slim/git. · Scaling Insights: Aligned disparate skill levels by leading market research, revenue study/analysis and opportunity mapping to produce living platform innovation roadmap and network effect I.P.


Principal, Design Strategist

Jun 2018 – Present
6 months, consulting, part-time

Product discovery and definition, including design and development coordination for stealth payments platform speeding to market with mobile native solution to residential construction project management.

Contracted with premium denim retailer for heuristic evaluation, information design and optimization of customer order flow, utilizing split-testing in production. Supported with key responsive component design to modernize the mobile web order experience.

SCOPE: Product Discovery & Design (Design Research Strategy, Information Architecture, Process Flows, Concept Maps, Mental Model definition, Interaction Design flows and patterns, Information Design, Visual Design) · Content Generation (Content Strategy, Lead Generation, Brand Voice) · Positioning (Identity Definition, Brand Standards, Collateral Design)


Senior Designer, Project Lead

Sep 2012 – May 2017
4 years, 9 months

Quickly rose as senior contributor responsible for leading project teams and client engagements after establishing the Visual Design discipline within this highly sought after enterprise UX design, strategy, and innovation firm.

Involved in proposing, planning and executing and training others to create effective interactive design systems that scale based on proven human-centered design methodologies.

NOTABLE ACCOMPLISHMENTS: Design Coordination: Led internal initiatives to review visual strategy and methods for higher quality output and stakeholder trust across broad range of client engagements involving complex touchpoint ecosystems. · Firm Innovation: Initiated and led monthly company-wide internal conference for working group initiatives and design challenges to help unify service offering and unite team day-to-day operational strategy. 


Visual Designer

Aug 2011 – Sep 2012
promoted 1 year, 1 month

Built new process intellectual property for firm while collaboratively designing in cross-disciplinary client teams to uncover and solve user experience challenges within complex platforms and enterprise service architectures.

SCOPE: Facilitation & Presenting (Workshop Design and Facilitation, Executive Presentation, Co-Design) · Management Liaison (Partner Sales Coordination, Executive Team Liaison, Team One-on-ones, Small Team Direct Delegation) · Stakeholder Relations (Client Management, Conflict Resolution, Project Management, Project Debrief, Vendor Relations) · Training & Growth (Mentorship, Interpersonal Coaching, Tools / Skill Teaching) · Culture Development (Role Definition, Interviews, Team Workshop Design, Monthly Internal Conference Strategy)

NOTABLE ACCOMPLISHMENTS: Design Systems: Translated and extended client brand objectives into robust interactive principles, interface deliverables and visual design systems and oversight of code review for front-end implementation. · Intellectual Property: Created innovative visual discovery workshops and methodologies to reduce cost of rework while training other designers to scaled processes across entire project portfolio.


Design Instructor

Jan 2015 – Sep 2015
8 months, part-time

Responsible for course structure, curriculum, in-person classroom facilitation, grading and feedback for a 16-session, project-based class teaching the foundation of visual design. Before this, designed an evening Fundamentals of Visual Design class, facilitated a Chicago UX professionals panel discussion and designed and lead a day-long UX Bootcamp

SCOPE: Training & Growth, Community Development (Design Research & Ideation · Foundational Organizing Principles in Typography, Color, Form & Composition Theory · Art Direction & Brand Guidelines · Responsive Design · Design Communication & Critiques · User Experience Design Theory & Methods)


Technical Lead

Mar 2007 – May 2011
4 years, 5 months

High-performing communication & digital designer in fast-paced studio environment, working for over 52 clients on more than 400 projects ranging from consultation and art direction to identity and brand systems, ad specialties and marketing collateral to publications and online experiences. Also responsible for advising and implementing new technology adoption across the firm.


Jr. Designer

Aug 2005 – Mar 2007
promoted 1 year, 6 months

Delivered exacting layouts for quick-turn production jobs with a focus on exceptional delivery to vendors. Responsible for 24 newsletters per year, 30-page events publication, and production for tradeshow booth, packaging and display graphics, ad media revisions, specialties, billboard design, and identity collateral while maintaining consistency to existing design guidelines.

SCOPE: Positioning (Brand Discovery, Visual Identity Definition, Communication Design Brand Standards and Guidelines, Brand Extension, Collateral Design) · Print Design & Production (Investor Reports, Newsletters, Ad Media, Direct-Sales, Brochures, Folders, Product Catalogues) · Digital Design (Custom Websites, Native iOS App Design, Brochure Websites, Email Campaigns) · Environmental Design & Production (Billboards, Truck-wrap, Specialties, Embroidery, Apparel, etc.)

NOTABLE ACCOMPLISHMENTS: Applications Guide: Won approval of largest website contract in company history after led redesign of 128-page printed guide, integrating 6,500 products from European & U.S. catalog into new design framework. · Agency Operations: Researched, proposed and guided marketing agency restructuring plan around key administrative solutions using new digital technology for better coordination across designers. · Statewide Identities: Defined visual messages of 4 separate hierarchical organizations within a complex, 12 initiative, $200M statewide framework.



Notable Organizations


Every enterprise is a unique context, but common across all is the orchestration of resources to create value.

Here are a sample of organizational contexts I’ve been exposed to through my work (plus a few sample engagements shown with cover images)

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+91 more organizations across various industries in complex consumer and enterprise ecosystems.

I’m ready for this new challenge at DocuSign.


Thank you. Let’s keep the conversation going.

– Warm regards, Isaac Steiner