The Digital Jane × A Step to Freedom

Case Study  ·  2022–2026  ·  Los Angeles, CA

Three Years.
One Mission.
Built Together.

A Step to Freedom came to The Digital Jane as a 25-person organization running on legacy knowledge and goodwill. Over six engagements and three years, we built hundreds of systems, trained teams at every level, and stayed present as they grew to 150+ people strong. This is what it looks like when two mission-driven organizations do the work together.

6 Engagements
3+ Years
200+ Deliverables
25→150+ Team Growth
"This is 31 years of a company working how we were — and we've pulled it together, upgraded and up-leveled." — Kenya Croom, Executive Director, A Step to Freedom

A Step to Freedom is a Los Angeles-based nonprofit dedicated to ending homelessness through housing-focused case management and community services. When our partnership began in 2022, they had the mission, the momentum, and the people — but the systems hadn't kept pace. Together, we changed that.

The Partnership Story

Six Chapters. One Continuous Thread.

Each engagement built on the last. No one-off projects — a sustained commitment to building what ASF needed at every stage of their growth.

Era 01

Getting the Foundation Right

Audit to Execution

Before anything could be built, we needed to understand what existed. Our first engagement began with a deep 360° audit of ASF's workflows, tech stack, and shared drives — then immediately moved to implementation. We migrated their project management to Monday.com, built their first real filing architecture, created foundational SOPs, and mapped every tool in their tech ecosystem with automation recommendations.

This was the starting line. We weren't just consultants recommending change — we were hands-on partners executing it.

Monday.com Migration SOPs & Documentation Tech Stack Mapping Drive Architecture Automation Setup
01
Oct 2022
A Step to Freedom team
The ASF team that we were building infrastructure to support
ASF community outreach
ASF's direct community work — the programs we built systems to support
02
Sept 2023

Era 02

Building What Didn't Exist Yet

Infrastructure + Program Development

ASF was expanding into structured housing services — and they needed program infrastructure to match. This engagement went beyond operations into program design. We developed the full structure for their Housing Readiness Program, created case manager workflows, and built the accompanying Monday.com architecture to support program delivery.

We also overhauled their filing system and continued deepening their SOP library. This era was about building things that simply hadn't existed before — not improving what was broken, but creating what growth required.

Housing Readiness Program Case Manager Workflows Program Structure Design Filing System Overhaul

Era 03

Scaling the Team

HR Department Transformation

From 25 to 100+ employees. That kind of growth without infrastructure doesn't work — and ASF knew it. This engagement focused entirely on the Human Resources function: restructuring the department's roles and workflows, designing an end-to-end recruitment and onboarding process, and rebuilding Monday.com as a centralized HR management hub integrated with PayChex and Google Suite.

In April 2024, we facilitated ASF's leadership Vision Casting retreat — a milestone moment that brought the senior team together to align on goals and build shared ownership of what came next.

HR Process Design Recruitment Workflow Vision Casting Facilitation Onboarding Architecture Monday.com HR Build
03
Feb – Apr 2024
Vision casting session facilitated by TDJ
TDJ facilitated ASF's 2024 Vision Casting leadership retreat
Vision casting presentation
Setting organizational goals together — the work behind the work
04
Oct 2024

Era 04

Strengthening Leadership

Senior Team Clarity & Systems

A 100-person organization operates differently than a 25-person one — and leadership had to evolve with it. This engagement focused on the Executive Director and her senior team: clarifying decision rights, redefining contractor SOWs, building a 90-day check-in process, and removing the bottlenecks that had quietly accumulated at the top.

We also designed automated onboarding communications and developed frameworks for mandatory training management — creating the connective tissue between HR, programs, and operations that a scaling nonprofit requires.

ED Workflow Redesign SOW Development Onboarding Automation Leadership Role Clarity Contractor Management

Era 05

Built to Last

Training Governance & Knowledge Transfer

The goal of great consulting is to make itself unnecessary. This engagement was about exactly that — transferring full ownership of ASF's shared drive governance, documentation standards, and training architecture to their internal team. We delivered five live training sessions across five weeks, rebuilt their Drive User and Administrator Guides, and established audit and accountability cycles designed to sustain without us.

By the end, ASF's designated administrator was prepared to facilitate future trainings independently. That's what self-sufficiency looks like in practice.

5-Session Training Series Knowledge Transfer Drive Governance Administrator Handoff Sustainability Planning
05
Oct – Dec 2025
ASF community service
The mission that drives everything — ASF serving their community
Approval systems roadmap presentation
Facilitating the approval systems design sessions with ASF managers
06
Feb 2026 – Present

Era 06  ·  Active

Governance from the Ground Up

Approval Systems & Decision Architecture

When a December 2025 training session surfaced that coordinators were defaulting every decision to the Executive Director, we knew the next chapter had to address governance. This current engagement builds org-wide decision and approval frameworks — grounded in ASF's own bylaws — that clarify authority at every level: coordinator, manager, director, and ED.

Using a co-creation model across four departments, we're not designing top-down policy. We're facilitating managers to extract their own authority from governing documents and define what their teams can handle independently. The result: a Decision & Approval Matrix that ASF owns, maintains, and evolves long after this engagement closes.

Approval Framework Design Decision Matrix Governance Co-Creation 4-Department Rollout Active Engagement

What We Built Together

The Numbers Behind
the Transformation

These aren't deliverable counts. They're markers of an organization that outgrew its old self — and had the systems to prove it.

🏗️
200+
Deliverables Across All Engagements
Hundreds of SOPs, templates, process maps, workflows, and documented systems — built as collections, not one-offs, so the whole team could own them.
🎓
Dozens
Trainings Facilitated
Live training sessions across every engagement — not just delivery but adoption. From drive governance to Monday.com to program workflows, the team was taught, not just handed tools.
👥
25→150+
Team Growth Supported
Infrastructure built and continuously scaled as ASF grew from a 25-person organization to a 150+ person team operating across multiple sites and programs.
⚙️
6
Departments Strengthened
Programs, HR, Operations, Finance, Executive Office, and ASF Kitchen — every function touched with systems designed to grow with them, not just for the moment.
🤝
3+
Years of Sustained Partnership
Not a one-time engagement. A relationship built on trust, shared values, and a genuine commitment to ASF's mission — returning again and again as the organization evolved.
🏠
1
Housing Readiness Program Built from Scratch
Full program structure, case manager workflows, and Monday.com infrastructure — designed around the people ASF serves and the mission that drives everything.

The Work in Action

Alice facilitating Housing Readiness Roadmap
Presenting the Housing Readiness Roadmap — a program built from zero
Vision casting retreat setup
The 2024 Vision Casting retreat setup
2024 team vision casting
Leading the ASF team through organizational goal-setting
Leadership facilitation session
Facilitation in the room where strategy happens
Roadmap presentation to full team
Walking the full team through the roadmap

"This is 31 years of a company working how we were — that we've pulled together in this timeframe and upgraded and up-leveled. It has been a heavy lift, and I really applaud you guys. You have done an amazing job."

Kenya Croom  ·  Executive Director, A Step to Freedom

Tech Stack
Monday.com Google Shared Drive Slack Salesforce PayChex Flex Zapier 1Password Trainual Google Workspace

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