Strategy Meeting
Artifact info
Title:

Iris Cocreative — Operational Strategy & Team Expansion Intro

Engagement:

Iris Website Redesign

Client:

Iris Cocreative

Meeting Date:
April 22, 2026
Next Meeting Date:
No items found.
People
Ashle Gilreath
James Redenbaugh
Artifact Image
Meeting Summary

🧭 Context & Quick Technical Items

This introductory session between James Redenbaugh and Ashle Bailey-Gilreath (of Pro Social World) began with a few housekeeping items before moving into a substantive conversation about Iris Cocreative's operational challenges and the possibility of Ashle stepping into a project management and operations role.

On the technical side, James confirmed a cookie consent error had been resolved — an issue that had been particularly persistent for Apple users and had generated repeated complaints from at least one partner (01:01). The fix included added redundancy to ensure cross-browser reliability. Ashle also asked about safely removing a QA staging site on Webflow [tag="webflow"] to reduce hosting costs; James confirmed the staging site appeared to already be on the free tier, so there was no immediate cost concern. She also confirmed that removing James as a Mailchimp user would not break any API tokens or Zapier integrations (05:08).

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🏗️ Where Iris Cocreative Stands

James gave an honest, high-level picture of where Iris is right now. The recent departure of Iván Lopez has been a catalyst for rethinking how the team operates (06:47). While Iván was affordable and a long-term asset, inconsistencies in quality and task ownership had been ongoing. The contractors Iris works with now tend to have stronger attention to detail and a better sense of completion — but they cost more, which means profit margins need to improve to sustain the team.

The current project mix ranges from $5,000 smaller builds up to larger, more complex app-development engagements like the Hollow Movement platform. James described himself clearly as the bottleneck — the most limited resource in the company, most trusted by clients, and most involved in every project. The challenge is finding ways to get more out of his time while delegating effectively to capable team members.

James also shared some personal context: he got married in September and he and his wife are planning to start a family soon (34:37). His wife is transitioning careers toward art therapy, which means James needs to create more financial stability and breathing room — both for their life together and to ensure Iris can operate without him being indispensable to every decision.

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💡 The Hollow Movement App — A Window Into Iris's Direction

To give Ashle a sense of what Iris is building, James walked through the Hollow Movement app — currently in beta (17:24). The platform is built on Webflow [tag="webflow"] with significant custom code, and includes:

  • AI-assisted profile generation based on user responses, including auto-generated tags, categories, and banner images
  • global directory and map of members
  • Holon profiles — group/organization profile types with wall-sharing functionality
  • Built-in member-to-member messaging
  • Assessment systems that plot responses on archetype graphs
  • Intelligent matching — launching imminently — that generates compatibility analyses between any two directory members
  • Sliding-scale membership payments and subscription management [tag="stripe"]
  • A planned learning management system as a future addition

[technology="Custom Membership System"]

[technology="Assessment Systems"]

[technology="Intelligent Matching Algorithms"]

[technology="Directory Systems"]

[technology="Online Learning Platforms"]

What makes this particularly significant for Iris is that everything is being built modularly (21:45). The goal is a reusable, interconnected ecosystem — so once assessments are built for Hollow Movement, they can be deployed for another client with much less effort. More ambitiously, James envisions profiles and content that travel across client platforms, so a user on Hollow Movement could bring their profile into a Pro Social environment or access a course running simultaneously across multiple sites. The downstream potential is significant, and Hollow Movement — launching at The Wave event — is the first proof of concept.

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📈 Sustainability, Pricing & Structural Possibilities

Ashle and James had a candid conversation about Iris's financial reality (37:28). Iris has operated in a mission-first mode for years — charging enough to get by while prioritizing client relationships and ecosystem growth. That approach made sense while building the portfolio and processes. Now, with a strong track record and increasingly sophisticated capabilities, Iris is well-positioned to charge significantly more and structure projects to protect margins.

Ashle offered a direct framing: it's not about profit for its own sake — it's about sustainability. That means being able to pay the team well, take on the right projects, and have enough flexibility that James isn't personally derailed every time life happens.

One structural idea that came up: if Iris continues building open-source tools and public goods, it could potentially pursue 501(c)(3) nonprofit registration (40:50). This would allow Iris to receive tax-deductible donations, apply for technology-focused grants, and maintain service-based revenue alongside a public benefit mission. James found this genuinely interesting and worth exploring further.

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🛠️ Project Management Systems & What Needs to Change

James walked Ashle through the current state of Iris's internal tooling (43:20). The team moved away from ClickUp after James began building a custom project management system — one that has some genuinely impressive pieces, including auto-generated meeting artifacts, Airtable [tag="airtable"]-synced project data, and custom views by team member. But the build stalled under the pressure of client work, and it currently lacks a reliable global task view, consistent timeline use, and time tracking.

[technology="Collaboration Management Tools"]

The result is a system that's more complex than it needs to be but not yet complete enough to fully rely on. James acknowledged the pattern himself — and Ashle offered a grounded observation: a functional project management foundation is the prerequisite for everything else (45:21). Whether that means finishing the custom build or committing to an existing tool like ClickUp, the decision needs to be made and followed through.

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🤝 Exploring a Role for Ashle

Ashle's background is in operations and general management — financial projections, project management, people management, contracts, internal procedures, and delegation frameworks — across roughly 15 years, primarily in the nonprofit sector (13:05). She's also deeply embedded in the same client ecosystem Iris serves, having worked closely with Hollow Movement and being familiar with organizations like Jan's (who James just confirmed is moving forward as a new client).

The conversation stayed exploratory rather than defining a specific role, but the areas of potential overlap are clear:

  • Project costing and financial projections — modeling out different engagement types by hours and rates to build reliable pricing
  • Hour tracking frameworks — establishing lightweight tracking that gives James actual data without feeling like surveillance
  • Internal procedures and delegation structure — helping the team operate more independently
  • Project management system decision — either completing the custom build or migrating to a reliable tool
  • Scenario planning — mapping out what different growth paths (freelancer, scale, nonprofit, funding) would look like operationally

Ashle is currently wrapping up a separate project and would have more availability in about two weeks. She's available on a contractor basis, not full-time — which James noted is consistent with how everyone else at Iris works and actually aligns with the culture he prefers.

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Action Items

James Redenbaugh

  • Draft an initial outline of the responsibilities and role Ashle might play at Iris (42:28)
  • Share an overview of current systems, tools, and active projects for Ashle's review (42:55)
  • Schedule a follow-up meeting for Wednesday or Thursday of next week (48:12)

Ashle Bailey-Gilreath

  • Book a follow-up session on James's calendar for mid-next week (48:12)
  • After reviewing James's materials, sketch out initial thoughts on how she'd approach the role and any early solutions (48:59)
Relevant Initiatives

Iris Portal

Priority: 
Very High
Size: 
XXL
Planning Stage

Talent Access

Priority: 
High
Size: 
M
Holding

Iris Studio Design

Priority: 
Very High
Size: 
L
Planning Stage

Operations & Financial Structure

Priority: 
Very High
Size: 
L
Planning Stage

Modular Platform Ecosystem

Priority: 
High
Size: 
XXL
Creation Stage
Transcript