Enterprise scale transformation

From team-focused tool to enterprise-grade cloud platform

Background & context

BUSINESS CHALLENGE

This established scale-up identified a specific business limitation: they were declining business from both existing customers and prospects who required enterprise-scale capabilities in their cloud solution. While the product earned high satisfaction ratings from individual engineers and small teams, the company lacked confidence in meeting enterprise-scale metrics requested by CTOs and leadership teams. This gap resulted in missed revenue opportunities, particularly from organizations requiring cloud deployment capabilities at scale.

TEAM STRUCTURE

The company operated on a trio/triad model, establishing co-ownership between design, engineering, and product across all hierarchy levels. To address the scale challenge, they formed a leadership trio:

Design Lead (my role)
Engineering Lead
Product Lead

My responsibilities spanned:

Strategic planning with the trio
Direct involvement with a delivery team
Design team management for embedded team members

STRATEGIC VISION

The team's mandate focused on developing and executing a strategy to scale our solution for enterprise markets while transitioning from on-premise to cloud deployment. The broader objective positioned the company as a trusted enterprise-level cloud solutions provider in the deployment space, measured through new enterprise client acquisition and successful migration of existing clients to cloud platforms.

Approach

This transformation represented a complex, multi-year effort spanning product development, organizational change, and go-to-market strategy. For brevity, this section focuses on four key aspects of our approach that were fundamental to the project's success: understanding the nature of enterprise transformation, defining our target audience through research, developing our organizational persona, and creating a structured capability framework.

1. Understanding enterprise transformation

The team understood that enterprise transformation extended beyond simply scaling up existing capabilities. It required fundamental changes to internal operations, product capabilities, and customer touchpoints.

Example: Administrative impact analysis

Hands-on users (in this case engineers) care about onboarding, efficient workflow, and troubleshooting. Admins, on the other hand, care about optimization, through tailored configuration, standardized practice, policy compliance, etc.

As part of enterprise transformation, embedding high-quality admin capabilities into the product (analytics, reporting, configuration, reporting, etc.) enables:

Effective response to policy and audit regulations.
Giving the right access for people in the organisation.
Continuously optimising the deployment workflow through automation and checkpoints.

2. Understanding the audience

The first challenge for the team was defining “enterprise” customers at the level of detail needed to define their needs, and the capabilities we needed to invest in to respond to those needs. I led the research effort, and had ownership of the “key customers” deliverable.

Example: Internal quantitative research

Initial quantitative research focused on understanding patterns for existing customers with enterprise potential, and using these patterns to narrow the definition of “enterprise” from 1000s to 100s of clients.

Combined data sources:

Amplitude product analytics
Snowflake SQL query analysis
Collaboration with data science team
Internal data gathering tools

Identified 50 key product usage indicators e.g.:

Number of tenants
Deployment frequency
User count
Median deployment duration

Example: External qualitative research

Starting with the hundred customers identified through quantitative analysis, I conducted an in-depth review of existing customer feedback recordings. This analysis revealed which customers didn't align with our cloud transformation strategy - some were committed to on-premise deployments, while others had unique use cases that wouldn't generalize across the enterprise segment.

The review exposed specific knowledge gaps about enterprise characteristics, particularly around:

How different teams within these organizations coordinated deployments
Their internal compliance and governance requirements
Their cloud migration readiness and barriers

We designed targeted interviews to fill these gaps. These conversations served a dual purpose - gathering missing information and identifying potential transformation partners. Through this process, we narrowed our pilot audience to five customers who had both the strategic alignment and organizational bandwidth to partner with us.

SAMPLE
INSIGHT

Enterprise teams were bypassing our UI entirely for scaled operations, writing custom scripts to handle bulk deployments and configurations - a stark difference between on-premise and cloud usage patterns that would need to be addressed.

SAMPLE
INSIGHT

Organizations had created informal "deployment councils" - cross-functional groups that met weekly to coordinate releases across teams. These councils needed visibility and governance tools that didn't exist in our single-team-focused product.

SAMPLE
INSIGHT

Many companies maintained parallel deployment processes - a "fast lane" for smaller teams using our UI directly, and a "governance lane" for larger, coordinated releases using custom tooling. This dual approach was creating efficiency and compliance challenges they wanted to eliminate.

3. Target client profile

In addition to user personas, organizational personas emerged from synthesis of research findings, alignment with marketing strategy, and coordination with the go-to-market team. This profile is core to the transformation, but it also served to raise organizational awareness of key customers and their needs.

Scale metrics

Quantitative metrics that indicate enterprise-level product adoption

Monthly active users exceeding 1000
Over 10,000 deployments monthly
Multiple deployment pipelines per team

Operational model

How teams organize and execute deployment activities

Cross-functional release councils
Standardized deployment practices
Centralized governance model

Operational model

How teams organize and execute deployment activities

Cross-functional release councils
Standardized deployment practices
Centralized governance model

Technical maturity

Assessment of technology adoption and modernization progress

Cloud-native architecture adoption
Container orchestration expertise
Early majority adoption position

Technical maturity

Assessment of technology adoption and modernization progress

Cloud-native architecture adoption
Container orchestration expertise
Early majority adoption position

Technical maturity

Assessment of technology adoption and modernization progress

Cloud-native architecture adoption
Container orchestration expertise
Early majority adoption position

Note: Since this profile was initially based on existing customers who were using our solution primarily at team or department level rather than enterprise-wide, we extrapolated many quantitative metrics. We analyzed usage patterns from our most scaled deployments and combined these with customer interviews about their total organizational scope to project enterprise-level requirements.

4. Capability framework

The transformation from team-focused to enterprise-grade platform required a clear definition of required capabilities and their maturity levels. We developed a framework that defined core platform qualities and features needed for enterprise adoption, based on pilot customer needs, market expectations, and technical requirements for operating at scale. Each capability was assessed against three maturity levels - Workable (minimum viable functionality), Marketable (competitive differentiator), and Delightful (industry-leading capability) - allowing us to prioritize our investments and track progress in a structured way. This framework guided both our technical roadmap and our customer communications throughout the transformation.

Implementation strategy & execution

The implementation of our enterprise transformation strategy required careful orchestration of multiple parallel tracks while maintaining momentum with pilot customers. Rather than attempting a "big bang" transformation, we structured our approach to deliver incremental value through parallel workstreams, each focused on specific aspects of the enterprise capability set.

Transformation timeline & tracks

The transformation journey was structured to maintain momentum while building deep understanding. The timeline reveals several strategic elements:

RESEARCH & ANALYSIS PHASE

Our research efforts focused on three key objectives:

Identifying capability gaps in our enterprise offering
Defining target market segments and their characteristics
Testing assumptions about where to invest development resources

This phase included both "Big Fish" enterprise customer research and capability ranking surveys, synthesized into reference documentation for alignment across teams.

PRIORITY IMPLEMENTATION TRACKS

Based on research findings and resource availability, we established dedicated tracks for:

Core platform capabilities
Performance optimization
Feature development

Each track operated independently but coordinated through regular checkpoints to ensure coherent delivery of enterprise capabilities.

ENTERPRISE EXPERIENCE FOUNDATION

We established a dedicated experience track to develop foundational elements needed across all enterprise features, such as:

Workflow patterns for administrative and deployment tasks
Page typology to define reusable patterns that ensure consistency in how various pages scale
Component library suitable for high-volume management
A common grid framework for complex data display

This foundation work was crucial groundwork before detailed design could begin on specific product functions, ensuring consistency and scalability across the platform.

Experience scope framework

The experience strategy implementation required balancing two distinct types of work:

Remediation
Existing capabilities were enhanced to support enterprise scale and non-engineer personas. We approached this through tiered customer segments:

Enterprise customers (broad segment)
Key accounts (priority subset)
"Pilot-like" accounts (similar journey patterns)
Pilot-specific (pilot customer)
Tactical improvements (quick wins)

Creation
New capabilities were developed to support non-deployment work such as:

Administrative functions
Monitoring dashboards
Configuration management
Cross-team coordination

This segmented approach allowed us to test and validate improvements with our pilot customer while ensuring the solutions would scale to the broader enterprise segment. Benefits from pilot customer work flowed upward, informing solutions for larger customer segments.

The framework helped us balance immediate pilot customer needs with longer-term enterprise scalability requirements. It also provided clear scope boundaries for the UX at Scale initiative in 2023, ensuring we maintained focus on the most impactful improvements.

Enterprise experience - UX at scale

Mandate and scope

The experience strategy work stream was tasked with transforming our product experience from team-focused to enterprise-ready. This meant:

Making all enterprise-scale capabilities accessible through the UI
Supporting both administrative and deployment workflows
Creating scalable patterns for high-volume data management
Developing page templates and component libraries for enterprise use cases
Enabling cross-team coordination and governance
Supporting both "fast lane" (team) and "governance lane" (enterprise) workflows
Ensuring consistent experience across new and remediated features

My role spanned both strategic and hands-on implementation:

Led the strategic discovery and solution process
Worked directly with one delivery team implementing pilot solutions
Managed designers embedded in other delivery teams
Ensured consistent application of patterns across teams

Discovery and design process

Broadly following the Continuous Discovery methodology to systematically understand and address enterprise needs:

Journey Mapping

Created end-to-end journey maps across multiple enterprise personas
Included technical users, administrators, and governance roles
Mapped interactions between personas at each stage
Identified pain points and opportunities at key touchpoints

Pilot Focus

Narrowed scope to journey stages most critical for pilot customers
Concentrated on administrative workflows and scale challenges
Documented specific scenarios where current UI broke down at scale

Opportunity Mapping

Built opportunity trees linking user needs to business outcomes
Generated "How Might We" statements for key challenge areas
Grouped opportunities by theme (e.g., bulk operations, cross-team visibility)
Prioritized based on pilot customer impact and technical feasibility

Solution Discovery
Each theme went through a design sprint process:

Research synthesis and context setting
Ideation workshops with cross-functional teams
Concept development and rapid prototyping
Testing with pilot customers
Refinement based on feedback

Design delivery

Delivery teams leveraged established patterns in their features
Design system ensured consistency across teams
Regular reviews maintained coherence of enterprise experience
Iterative refinement based on implementation learnings

This structured approach ensured that both new capabilities and remediated features contributed to a cohesive enterprise experience, while maintaining the efficiency our technical users expected. The resulting design patterns and components continue to accelerate development of new enterprise features across the platform.

Transformation initiatives

The enterprise transformation catalyzed several strategic initiatives across the organization. Here are three key examples that demonstrate the project's broader impact:

Experience maturity framework

I developed a framework for evolving our product experience to support enterprise-scale usage. Each stage mapped to increasing levels of user and business value:

This framework served multiple purposes:

Guided product teams in evolving features from basic functionality to enterprise-grade capabilities
Helped us communicate our maturity journey to enterprise customers
Provided a way to assess whether features were ready for enterprise use
Supported prioritization decisions between different types of improvements

We identified two distinct value curves:
Approach 1: Incremental technical buildout delivering steady value improvements
Approach 2: "Big bang" improvements requiring longer incubation but delivering higher ultimate value

Customer Intelligence Pipeline

I was responsible for establishing a comprehensive system for gathering and synthesizing customer intelligence from multiple sources:

Analytics/Telemetry: Product usage data from tools like Amplitude
Qualitative Research: Customer feedback from tools like Zoom and Chorus
Sales Engagement: Direct customer interactions and feedback
Quantitative/NPS Research: Structured feedback collection

This pipeline fed into a centralized customer profile system in Salesforce, ensuring all teams had access to consistent, current customer intelligence. The system particularly focused on our key enterprise accounts, helping us track their needs and progress through transformation.

Organizational redesign

The transformation prompted a restructuring of our product development organization into three focused groups:

Experience Group: Focused on user-facing features and workflows, organized around key product areas like deployment, operations, monitoring, and administration
Platform Group: Responsible for core services and infrastructure
Enabling Group: Provided shared tools and systems supporting other teams

Each group contained multiple teams with their own focus areas, while design resources were organized into groups (DLG/DMG) that supported multiple teams. This structure helped balance specialized knowledge with cross-functional collaboration, particularly important for enterprise-scale features that touched multiple parts of the system.

This organizational model reflected our understanding that enterprise transformation required changes not just to our product, but to how we worked as a company.