Salesforce Workstream Overview

Center of Excellence + Salesforce — scope, sequence, funding, capacity and ownership for 2027–2028

Leadership Team briefing · Outward Bound USA · September 2026

Executive Summary

What this document is

Outward Bound USA has several Salesforce efforts underway or proposed for 2027 and 2028. They are currently discussed as separate projects with separate budget lines, which makes them look more expensive, more numerous and less connected than they are. This brief pulls them into a single view so the Leadership Team can see what each project is, how they depend on one another, what they cost, who would own them, and what changes for Schools as a result.

It is a decision document, not a status report. Section 17 lists the choices that need to be made. Everything before it exists to support those choices.

The problem we are trying to solve

Each School runs its own Salesforce system, built and customized independently over roughly a decade. That independence is not the problem in itself. The problem is that the Schools and the national office cannot reliably answer shared questions — how many students come back for a second course, where group sales are stalling, how enrollment is tracking across the network — because the underlying data is structured differently in every system, and in some cases is not collected at all. We have also committed to funders, specifically through the Character Compass grant, that we will be able to report on repeat participation across the network.

The work breaks into three layers. Shared foundation is the plumbing: agreed data definitions, a governance agreement, and the Data Pipeline that moves information between School systems and the national office. Business capabilities is where value shows up: better group sales processes, a shared enrollment capability, and recovering revenue currently lost to cancellations. Use and deployment is what happens inside Schools, including bringing every School to a workable minimum standard.

$560K
Identified funding across AAO and Lilly for 2027–28
11
Salesforce systems — nine Schools plus two national orgs
3 of 9
Schools that cannot currently connect a student across programs
$15K–$65K
Annual licensing the pipeline could retire — Nintex now, potentially the CDP later
What is new since the last discussion

Two Schools have already spent, or are about to spend, their own money on Salesforce work that overlaps with what is proposed here, and both have asked whether OBUSA can help pay for it. A third has deferred its own Salesforce investment while waiting for clarity from us. Section 07 lays this out. It is not a recommendation to reimburse anyone; it is a live dynamic the Leadership Team should decide how to handle before it is decided for us.

The five things worth knowing before the discussion:

  1. These are not independent projects. Four of them require the same conversations with the same people at the same Schools. Running them separately means asking overworked School staff the same questions four times.
  2. The money is already identified, but split across two grants in ways that do not yet match the work. Resolving which grant pays for what is a decision, not a budget increase.
  3. Schools are not at a common starting point. Some can already track a student across multiple programs; others are working from spreadsheets and paper forms. Network-level reporting will only ever be as good as the weakest inputs.
  4. The Data Pipeline is infrastructure, not a product. Judged on its own savings it looks modest. Judged on what it makes possible — dashboards, faster technology changes, marketing tools for Schools without marketing staff — it has the widest reach of anything here.
  5. Capacity is the real risk. As currently drawn, one Center of Excellence role would absorb most of this work while also being responsible for sales enablement. Section 14 offers structural options.

How to read this if you have ten minutes: Section 03 defines each project in plain terms. Section 11 shows the money. Section 12 shows a proposed order of work. Section 17 lists the decisions.

01 · The Map

One portfolio with three layers

These efforts are usually listed side by side, as if they were equivalent. They are not. One layer is shared infrastructure, one is where revenue and mission value appear, and one is what happens inside Schools. Reading them as layers makes both the order of work and the budget questions clearer.

Layer 1 — Shared foundation (the plumbing)

Data Standards & Baseline

Agreement on the minimum fields, names and definitions every School uses, what moves between systems and what stays local. A standard model already exists as a starting point.

Prerequisite for everything else

Data Pipeline

The mechanism that moves course, application, contact and program data between School systems and the national system. Turned on one data type at a time. Replaces Nintex.

Restart · partly built already

Data Governance

A written agreement on how shared data may be used — reporting and operations now, no fundraising prospecting without a separate network decision.

Unresolved · affects School trust
▼   powers   ▼
Layer 2 — Business capabilities (where value appears)

Sales Activation

Common approach to handling inquiries and leads for group programs, so Schools can see where deals stall and compare performance meaningfully.

Underway · CoE-led

Enrollment Platform

A shared enrollment capability, starting with group programs. Open enrollment already runs on the same underlying mechanism. The name Schools and EDs will recognize.

Largest build · 2027

Waitlist & Cancellation Recovery

Recapturing open enrollment revenue currently lost when students cancel for reasons we can influence, and working waitlists more systematically.

Small · quick payback
▼   enables   ▼
Layer 3 — Use and deployment (what happens in Schools)

Repeat Participation (Lilly)

Being able to see when a student returns — a day program, then an expedition, then something longer. Mostly a reporting and data-completeness question once group data flows.

Grant commitment

School Baseline Parity

Bringing Schools without program tracking up to a workable minimum, and reusing what advanced Schools have already built instead of rebuilding it.

Gates the value of everything above

Development / Donor Data

Fundraising systems and donor records. Genuine demand from School development leaders, and the most sensitive subject in the portfolio.

Decision gate, not a 2027 build
Each project carries the same four fields: business outcome  ·  Salesforce deliverable  ·  School value measure  ·  estimated annual value
The portfolio in one sentence: a shared enrollment capability built on shared data plumbing, using group sales as the first real test case, which addresses the Lilly repeat-participation commitment and the sales enablement mandate at the same time — with donor data deliberately held behind a decision gate.

02 · The Projects, Defined

What each project is, what it is meant to achieve, and what changes when it is done

The short descriptions above are deliberately compressed. This section gives each project a fuller definition so there is no ambiguity about what is being proposed, what it excludes, and what a School would actually notice.

1 · Data Standards & Baseline

Layer 1 · Low complexity · Medium School effort
What it is
A negotiated agreement across the network on the minimum set of information every School records the same way: field names, stage definitions, how a lead is recorded, what a completed application looks like, and which pieces of information move between School and national systems. An existing standard model, developed over the last decade and tested across the network, is the starting point rather than a blank page.
What it is not
It does not require Schools to work the same way, use the same processes, or give up customization. It sets a floor, not a ceiling.
Goal
A documented minimum standard that every School has agreed to and can meet, so that data collected in nine places can be read as one picture.
Outcome when complete
  • Network reporting stops carrying caveats about non-comparable data
  • New Salesforce work at any School is built once, correctly, rather than reworked later
  • Schools currently building — and there are several — align now rather than after their systems harden

2 · Data Governance Agreement

Layer 1 · Medium complexity · Low School effort
What it is
A written agreement setting out how shared data may and may not be used. The operative distinction is between using data for reporting and operations, which is the current intent, and using it for fundraising prospecting, which would require a separate network decision. A data governance section was drafted for the National Operating Standards and subsequently removed, so a mechanism outside that process is needed.
What it is not
It does not reopen the National Operating Standards or the Charter.
Goal
An agreement Schools trust enough that sharing group program data no longer feels like a risk to their donor relationships.
Outcome when complete
  • The most common objection to data sharing has a written answer
  • Schools can participate without a standing concern that participants become national prospects
  • Later decisions about donor data start from an agreed framework rather than from scratch

3 · Data Pipeline

Layer 1 · High complexity · Medium School effort
What it is
The mechanism that moves agreed data between School Salesforce systems and the national system, in both directions. It already operates for open enrollment. The work is to restart a paused implementation, add group program data, build a repeatable template so it can be rolled out School by School, and connect the national system to the website and the Customer Engagement Platform (Segment, Snowflake and Braze).
What it is not
It is not a single switch that exposes everything. Data types are turned on one at a time, by decision. Donor data is not in scope.
Goal
Group program data moving reliably between Schools and the national office on a template that can be deployed repeatedly, with Nintex retired.
Outcome when complete
  • One connection point to network data instead of eleven separate ones
  • The $15,000 annual Nintex fee ends
  • Opens a later option to retire the CDP layer, currently around $50,000 a year, once the pipeline carries that function
  • Dashboards, marketing tools and future systems connect once rather than per School
  • Improvements built once can be deployed to other Schools rather than rebuilt

4 · Sales Activation

Layer 2 · Medium complexity · High School effort · Underway
What it is
Center of Excellence work to map how group program inquiries are handled today, define a common set of pipeline stages and practices, identify where automation genuinely helps, and give each School a roadmap to get there. A phased roadmap already exists running from September 2026 through December 2027, covering journey discovery, shared pipeline stages, automation improvements, platform design and network reporting.
What it is not
It is not a simultaneous network-wide rollout, and it does not cover individual participant sales or multi-week programs.
Goal
Schools operating a common approach to group sales, adapted locally, with visible pipeline and conversion data.
Outcome when complete
  • Faster response to group inquiries, which is itself a conversion factor
  • Schools can see where prospects stall instead of guessing
  • Staff spend less time on manual tracking and follow-up
  • Directly serves the sales enablement mandate the AAO grant funds

5 · Enrollment Platform

Layer 2 · High complexity · High School effort · Largest build
What it is
A shared enrollment capability covering group programs, built on the pipeline and extending components that already exist from the open enrollment build. Rather than designing from theory, the approach is to identify the strongest existing School build, harden it, and make it deployable to others.
What it is not
It is not a new CRM, and it is not a replacement for School systems. It is a capability deployed into them.
Goal
A working model other Schools can adopt at a fraction of the cost of building their own.
Outcome when complete
  • Schools avoid the cost of independent builds — recent School estimates for comparable work have run $30,000–$40,000
  • A consistent enrollment experience for groups and partners
  • The infrastructure becomes something EDs can recognize and describe
  • Open enrollment and group enrollment eventually share one foundation

6 · Waitlist & Cancellation Recovery

Layer 2 · Low complexity · Low School effort
What it is
Capturing why students cancel, building a workflow to move waitlisted students into vacated places, and reducing attrition that falls within our control. This was already included in the prior pipeline scope of work rather than being a new idea.
What it is not
It does not address course inventory decisions or pricing.
Goal
A measurable reduction in cancellations we can influence, and faster backfill of places that do open up.
Outcome when complete
  • Revenue already won is retained rather than lost late in the cycle
  • Higher fill rates without additional marketing spend
  • Clear data on why students leave, which informs everything upstream

7 · Repeat Participation (Lilly)

Layer 3 · Medium complexity · Medium School effort · Grant commitment
What it is
The ability to see a student's full history with Outward Bound — a day program in the autumn, an expedition in the spring, a teacher program alongside it — and report on it. Schools increasingly design deliberate progressions, but the records are currently disconnected. Two evaluation questions sit under this, developed with RYTE at Montclair State: what helps or hinders building a good tracking system, and whether data quality improves as tracking improves.
What it is not
It is not new survey instruments or new evaluation methodology.
Goal
Reporting on repeat participation to Lilly without caveats about missing or incomparable data.
Outcome when complete
  • A grant commitment is met with evidence rather than estimates
  • Schools can see which progressions actually work
  • Alumni and re-engagement become addressable rather than theoretical
  • Future funders can be shown network-level outcome data

8 · School Baseline Parity

Layer 3 · Medium complexity · High School effort
What it is
Targeted help for Schools that cannot currently record program participation in Salesforce, so they reach a workable minimum. It also covers taking what advanced Schools have already built and making it portable, rather than commissioning the same work repeatedly.
What it is not
It is not rebuilding systems Schools already have, and it is not a uniform implementation.
Goal
Every School able to record and report program participation to a common minimum standard.
Outcome when complete
  • Network reporting stops inheriting the weakest inputs
  • The Schools furthest behind stop falling further behind
  • Investment already made by advanced Schools benefits the whole network
  • Every other project in this portfolio delivers its full value rather than a partial one

9 · Dashboards & Network Reporting

Layer 3 · Low complexity · Low School effort
What it is
Reporting drawn automatically from governed data rather than assembled by hand: open enrollment progress, group pipeline health, demographics, and potentially course outcome data. Includes response time to group inquiries, inquiry-to-booking conversion, and forecasting views.
What it is not
It does not add reporting burden for Schools; it draws on data already being captured.
Goal
Boards, the Leadership Team and School leadership able to see network performance without asking someone to build it.
Outcome when complete
  • Network data no longer depends on one person or team being available
  • Board and ED conversations start from shared numbers
  • Staff hours currently spent assembling reports are returned to other work

10 · Development / Donor Data

Layer 3 · High complexity · High School effort · Held
What it is
Fundraising systems, donor records, and the question of whether donor data is ever shared across the network. Demand is real: School development leaders have asked for support, and at least two Schools are actively moving fundraising data into Salesforce. It is also the subject most likely to generate resistance, and has been an open conversation for more than a decade.
What it is not
It is not proposed as a 2027 build, and no network donor data sharing is contemplated in this period.
Goal
A clear recommendation and a published decision point, so Schools know when and how the question will be addressed.
Outcome when complete
  • The most contentious topic is removed from the 2027 conversation without being hidden
  • Schools investing in fundraising systems now do so against known standards
  • A decision gate exists rather than an indefinite silence

03 · At a Glance

The same ten projects, compared side by side

Project Layer Complexity School effort Status Single-sentence goal
Data Standards & Baseline1LowMediumNot started Agree the minimum every School records the same way
Data Governance1MediumLowUnresolved Put permitted use of shared data in writing
Data Pipeline1HighMediumPaused, partly built Move group data between Schools and national on a repeatable template
Sales Activation2MediumHighUnderway Common group sales approach with visible pipeline
Enrollment Platform2HighHighScoping A shared enrollment capability Schools adopt rather than rebuild
Waitlist & Cancellation2LowLowIn prior scope Retain enrollment revenue currently lost to cancellation
Repeat Participation3MediumMediumNot started Report repeat participation to Lilly without caveats
School Baseline Parity3MediumHighNot started Bring every School to a workable minimum
Dashboards & Reporting3LowLowNot started Network performance visible without manual assembly
Development / Donor3HighHighHeld A recommendation and a decision gate, not a build

Complexity and School effort are planning estimates based on the August scoping session and prior platform experience, not figures stated in a source document.

04 · Where They Overlap

The overlap is the reason to sequence them together

Several projects need the same conversations, the same Schools, the same consultant and much of the same build. Budgeting them separately counts shared costs more than once and makes the total look larger than it is.

Shared elementProjects that depend on itWhat happens if built separately
School discovery conversations Sales Activation · Enrollment Platform · Data Pipeline · Repeat Participation · Parity Five separate requests reach the same one or two technical people at each School
Minimum field and stage definitions Sales Activation · Enrollment Platform · Data Pipeline · Reporting Rework, and data that cannot be combined across Schools
Group program data capture Repeat Participation · Enrollment Platform · Reporting · Parity Lilly reporting carries permanent caveats
The pipeline mechanism Enrollment Platform · Repeat Participation · Reporting · Dashboards · future Donor Continued Nintex spend on a tool that is not a long-term answer
Consultant and engineer availability All technical projects Scheduling collisions and paid-for capacity sitting idle
Change management with Schools Sales Activation · Enrollment Platform · Governance · Parity Change fatigue, and a sense that scope is expanding without consent
The practical consequence: one discovery process across Schools, run through the Center of Excellence and serving every project, replaces five parallel efforts. This is the single largest capacity protection available in the portfolio.

05 · Where Schools Actually Are

The starting points are further apart than generally assumed

The September 2026 Character Compass subgrant reports asked each School directly about tracking students across multiple program experiences. The answers fall into three groups. Network capabilities cannot produce felt impact until the lower group reaches a workable baseline, because combined reporting inherits the weakest inputs.

GroupSchoolStated positionWhat it means for the portfolio
AdvancedCSIOBS
Cathleen Stone Island
A Salesforce-based Participant Management Database tracks individual students across programs and years, including repeat participation and progression through pathways; focus is now on refining reporting Strongest candidate source model for progression tracking
AdvancedOBCA
Outward Bound California
Salesforce reporting tracks participation across OBCA programs and progressive touchpoints; explicitly lacks visibility beyond its own School and has asked for a shared tracking tool Clear demand signal for the network layer; extend rather than replace
BuildingNYCOBS
NYC Outward Bound Schools
Salesforce restructure underway and being integrated with sales process work; still using spreadsheets for multiple touchpoints; has asked to see models from other Schools Align now, while the build is still in progress
BuildingPOBS
Philadelphia
Working with RYTE and OBUSA on more efficient tracking; current process is a manual count Local instance that another School has already built upon
BuildingVOBS
Voyageur
Students identified in spreadsheets; no Salesforce tracking system yet; a task force is meeting monthly through year end to determine whether contract help is needed Remediation candidate with internal momentum already formed
BlockedCOBS
Colorado
Tracking students across their engagement journey is not currently possible; has deferred its own Salesforce and advertising investments pending clarity on Center of Excellence scope Our delay is directly suppressing School investment
BlockedNCOBS
North Carolina
No significant progress beyond returning cohorts; states the primary need is the ability to connect student experiences in Salesforce, which it does not have Direct dependency on the shared capability
BlockedHIOBS
Hurricane Island
No analysis performed to date; expresses confidence in tracking within its own programs, with work planned for the autumn Stated confidence may understate the work required
BlockedCBOBS
Chesapeake Bay
Response centred on a research partnership rather than CRM capability; Salesforce position not established Discovery needed before scoping

Positions are drawn from the September 2026 subgrant reports covering all nine Schools. Group labels are an interpretive grouping for planning purposes. The two national Salesforce systems — OBUSA and OBSG — complete the count of eleven.

What has already been built and could be reused

Several Schools have constructed versions of what the network needs. Philadelphia built a local Salesforce instance that Outward Bound California subsequently built upon. Hurricane Island has built sales pipeline functionality with support from the network engineer. Cathleen Stone Island built participant tracking that already answers the progression question. The practical question for 2027 is not whether to build an enrollment capability from nothing, but which existing build to harden, template and deploy.

The Hurricane Island attribution derives from a meeting transcript and is worth confirming directly before it is presented externally.

06 · School Investment Already in Motion

Two Schools are spending their own money on overlapping work, and both have asked for help

This is the part of the picture least visible in budget conversations. While the network-level work has been in planning, individual Schools have moved ahead on their own, at their own cost, on work that overlaps directly with what is proposed here. Two have asked whether OBUSA can contribute. A third has done the opposite and paused its spending while waiting for us.

SchoolWhat they have done or are doingCost and funding positionWhat it means for this portfolio
CSIOBS Runs group programs only, with no open enrollment. Uses Raiser's Edge for donor data and has been evaluating a migration to Salesforce, partly driven by the network move to a common donation platform. New development leadership is motivated to move fundraising into Salesforce. Already operates advanced participant tracking on the program side. Estimated the migration at $30,000–$40,000 and formally asked whether OBUSA could assist with what it described as an unbudgeted expense An explicit, documented funding request already on record. Also the strongest existing progression-tracking model in the network.
NYCOBS Only overnight programming at one site is recorded in Salesforce today. Other outdoor programs collect course outcome surveys but the data is not entered; some climbing program forms are still on paper. Previously used Salesforce for both sales and fundraising before moving to separate tools. Has now contracted an external developer to upgrade Salesforce so programme and fundraising data sit in one architecture. Separately engaged an IT consultant on privacy and security. Identified a developer at approximately $30,000 and proceeded after OBUSA indicated the School would be responsible for costs Considerable further work is still needed on capturing all programme data, courses, enrollment and lead tracking. Alignment now avoids rework later.
COBS Deferred planned Salesforce enhancements and related advertising investment while awaiting clarity on Center of Excellence scope Spending withheld rather than committed Demonstrates the cost of ambiguity: our planning delay is suppressing School investment
Why the Leadership Team needs to address this deliberately. Funding sits in the Lilly budget that was originally conceived partly to help Schools make exactly these transitions. Internal correspondence has already raised the questions directly: how much is available to support Schools, how much is needed specifically for the two Schools furthest from the standard, and whether any could help those Schools move fundraising data into Salesforce. Those questions are unresolved. Meanwhile Schools are making decisions and spending money.
The choice is not whether to reimburse. It is whether we set a consistent, explainable position — before individual conversations set it for us. Options range from no retrospective support, to support conditional on alignment with network standards, to counting School spend as a contribution toward future fees. Each has different implications for fairness across the nine Schools, several of which have not spent anything and may reasonably ask why others were funded.

07 · Why the Data Pipeline Matters

Its biggest value is what it makes possible later, which is why it loses budget arguments

Judged as a standalone project, the pipeline produces a modest saving. Judged as infrastructure, it changes what the organisation can do next. Most of the capabilities below only become available once there is a single connection point to network data.

Connecting systems to each other today

55

Possible connections across 11 Salesforce systems — nine Schools plus two national orgs. Every new tool must be negotiated, built and maintained against each one separately. Processes become more error-prone and new technology gets slower to introduce.

Connecting through a hub

11

Each system connects once to the national system, which holds the shared view. The website and the Customer Engagement Platform connect to the hub rather than to every School individually.

Vendor documentation prepared before the Northwest school closed describes twelve Salesforce systems. Current planning should use eleven.

What it unlocksWhat becomes possibleWho benefits
One connection point for future technology New tools connect once to network data instead of being negotiated across every School. As technology changes, the cost of adopting or replacing a tool falls substantially. Some capabilities are only available to organisations that can offer a single connection point. OBUSA and Schools — cheaper, faster adoption of whatever comes next
Self-serve dashboards Enrollment, group, demographic and potentially course outcome reporting drawn from governed data rather than assembled by hand. Removes dependence on one person or team being available to produce network numbers. Boards, Leadership Team, School leadership
Marketing tools for non-marketers Salesforce flows and Campaign connections into Braze put basic marketing within reach of Schools that have no marketing staff, without specialist tooling at each location. Schools without dedicated marketing capacity
Richer School records A School's records can be enriched with network context — for example, a group student from one School who later enrolls in an open enrollment course elsewhere. Schools — better customer knowledge and re-engagement
Retiring legacy tooling Nintex is replaced rather than extended, ending its $15,000 annual fee. Once the pipeline is carrying data between systems directly, it also opens a path to retiring the CDP layer, currently around $50,000 a year. OBUSA — direct cost reduction, with a larger second step available later
Room to innovate in ways not yet defined Centralised, governed access is a precondition for capabilities the network has not yet identified. The value is real but cannot be estimated in advance. The network — future optionality
A second-order saving worth naming. Retiring Nintex is the immediate, contracted saving. The larger one sits behind it: once the pipeline is moving data between Salesforce systems directly, the CDP layer — roughly $50,000 a year — becomes a candidate for removal, because the pipeline would be performing much of the function we currently pay for. This is not a 2027 decision and it is not free: it would require re-instrumenting the Customer Engagement Platform, which carries its own cost and risk. It belongs in the picture as a future option rather than a budgeted saving.
How to weigh it: the pipeline should be assessed on what it enables, not on what it saves. Scored on its own savings it will always lose to a project with a visible revenue line. Scored on what it makes possible — including reducing what we spend to run the Customer Engagement Platform at network depth — it has the widest reach of anything in this portfolio.

08 · Technical Debt and a Single Source of Truth

Reducing accumulated technical debt has been an explicit goal since the first engagement

"Technical debt" here means the accumulated cost of systems that were built quickly, customized independently, and now have to be maintained separately. Retiring it was named in the original 2024 advisory objectives alongside consolidating and standardizing systems. Documentation from that work describes the architecture that addresses it, and records that substantial parts are already complete.

ComponentWhat it doesRecorded status
Centralized development Functionality used across School systems is managed from one central configuration rather than maintained separately in each Ready for deployment
Standard data model enforcement A shared data model held in place by configuration, requiring matching definitions while still letting Schools add their own customization above it Ready for deployment
Configurable collection and distribution The mechanism for gathering School data centrally and sending governed data back out Ready for deployment
Website integration with course data Course information surfaced through the public site Needs finalizing
CEP and Snowflake integration Braze connected through Snowflake rather than School by School Needs finalizing
Segment CDP receiving pipeline data Unified profile data flowing from the national system Needs finalizing

Why this matters for the 2027 decision

09 · Timeline

Discovery closes in 2026, building runs through 2027, the donor decision sits in 2028

ProjectQ4 2026Q1 2027Q2 2027Q3 2027Q4 20272028
Unified School discovery
Data Standards & Baseline
Data Governance
School Baseline Parity
Sales Activation
Data Pipeline restart
Enrollment Platform
Repeat Participation
Dashboards & Reporting
Waitlist & Cancellation
Development / Donor
Discovery and definition Build Deploy to Schools Operate and improve Held — conversation only, no build

Shaped by two anchors from the August scoping session: discovery completing through the end of 2026 with technical work sequenced across 2027, and an expectation that the group build takes roughly half the 14 months the original open enrollment platform required, because existing components are being extended rather than built from nothing. The Center of Excellence group sales roadmap runs on a compatible track, with network-wide reporting targeted for December 2027.

10 · The Money

More is identified than the conversation assumes, held in four places

SourceAmountYearCurrently associated with
Salesforce Improvement Support$200,0002027 Salesforce and sales journey work — automation, change management, School roadmaps
Sales & Salesforce consultant$50,0002027 Consultant to drive the work
Lilly / Character Compass technology$275,000Unspent Data pipeline and related technology; none drawn to date
Group sales data & reporting$35,0002027 Dashboards, pipeline visibility, forecasting
Total identified$560,000 2027–28Across AAO and Lilly

A split already proposed internally for the Lilly technology funds

Earlier planning correspondence proposed moving pipeline implementation to 2027, reducing it to roughly $150,000, and reserving the remainder — about $125,000 — for supporting Schools directly. That split has not been confirmed, but it is the closest thing to an existing position on how much could go to School-level work, and it bears directly on the investment question in Section 06.

What vendor work has actually cost

EngagementAmountDurationNote
Strategic advisory: foundational assessment$28,0008 weeks Negotiated down from $36,400. System health scans, consolidation roadmap, technical debt strategy
System improvements$164,20015 weeks Negotiated down from $189,400. Split across two fiscal years
Data pipeline and student experience — initial$200,000 Original proposal
Data pipeline and student experience — revised $171,00018 weeks Reduced by shortening the timeline, with Nintex retirement added to scope. $9,500 per week

Approximately $30,000 was subsequently carved out of the pipeline scope to make room for the network Salesforce engineer's time within the same grant funding.

Two patterns worth noting. Every engagement so far has been negotiated below its opening estimate, and the most recent reduction came from compressing the timeline rather than cutting deliverables. The weekly rate gives a reliable unit for sizing 2027 work against available funds, rather than negotiating a total in the abstract.
What remains unresolved: which grant carries which project; whether unspent Lilly personnel budget can be moved to technology; how much is reserved for School support; and whether some scope moves to 2028. Views in the September leadership check-in ranged from an expectation that more will be needed, to an observation that the net budget effect is close to zero because expense and grant revenue release together.

11 · A Proposed Order of Work

Sequencing based on dependency, offered for the Leadership Team to accept, amend or replace

The order below follows dependency logic rather than preference. Projects that prevent rework elsewhere come first, infrastructure follows, and the most sensitive work is deliberately held. Figures are planning allocations against identified funding, not approved budget lines.

TierProjectIndicativeLikely sourceWhy here
1Data Standards & Baseline $25,000AAO consultant Lowest cost, shortest duration, prevents rework everywhere else. A standard model already exists to build from
1Data Governance Staff time Precondition for Schools sharing group data. Without it every other project carries a trust cost
1Sales Activation $200,000AAO / SF Improvement Already underway, owned and budgeted; directly serves the sales enablement mandate
2Data Pipeline restart $175,000Lilly technology Infrastructure for group data, Lilly reporting, dashboards and Nintex retirement. Known scope, known vendor, partly complete
2School Baseline Parity $50,000Lilly technology Schools furthest behind cannot contribute usable data without help, which caps the value of everything above
2Enrollment Platform $75,000Lilly technology Makes the infrastructure legible to Schools and EDs. Extends existing builds rather than starting over
3Dashboards & Reporting $35,000Group sales line Low effort, high visibility. Produces the view that makes the whole portfolio legible to Boards and EDs
3Repeat Participation Within tier 2Lilly technology Rides on pipeline and parity work; remaining cost is fixing gaps at Schools with incomplete data
3Waitlist & Cancellation Within tier 2Lilly technology Already inside the prior pipeline scope; folding it in avoids a separate engagement
4Development / Donor $0 in 20272028 decision Highest complexity and sensitivity. Conversation continues, decision point is published, nothing is built

Indicative allocations total $560,000 against identified funding. They do not include any provision for the School investment question in Section 06, which would draw on the same pool.

12 · Capacity

Keeping the portfolio from landing on one person

The most likely failure here is not funding or technology. It is that one Center of Excellence role absorbs delivery, coordination, School engagement and vendor management at once, and the sales enablement mandate suffers. The consultant agreement adds to this by requiring a named internal lead committing at least half their time for the duration of the engagement. Five structural options are available, and they combine.

Option 1 · Highest leverage

Name a Product Owner who is not the Center of Excellence lead

The consultant requires a named Product Owner with final say over what gets built in what order, committing at least half-time. If that is also the person responsible for sales enablement, School engagement and go-to-market work, the mandate cannot hold. A dedicated hire, a contracted role, or an existing staff member whose portfolio is reshaped would convert a full-time overload into a defined contribution.

Effect: removes the single largest time commitment from the CoE portfolio. Cost: a partial role, potentially fundable from grant personnel underspend.

Option 2

Let the consultant carry project management, as the agreement already provides

The vendor model includes a delivery lead who manages schedule, anticipates risk, oversees resources and owns project communications, alongside a senior consultant providing oversight. Used as designed, internal coordination load drops substantially. The risk is paying for project management and then duplicating it internally out of habit.

Effect: moves sequencing and communications overhead outside the organisation. Cost: already included in engagement pricing.

Option 3

Split ownership by layer rather than by project

Assign the shared infrastructure layer to a technology owner, the School-facing capability layer to the Center of Excellence, grant reporting to Learning and Evaluation, and the open enrollment components to Program Sales. Each owner holds one coherent domain rather than slices of several, and nobody is accountable for both building a capability and persuading Schools to adopt it.

Effect: reduces any one portfolio to roughly two or three projects. Cost: none, but requires deliberate assignment rather than default.

Option 4

Sequence so only one active build touches the Center of Excellence at a time

Standards and governance in the first half of 2027, group capability in the second, parity work running alongside as School-facing rather than build-facing activity. The roadmap already implies this; making it an explicit constraint stops scope arriving in parallel.

Effect: smooths peak load rather than reducing total load. Cost: a slower schedule, potentially extending into 2028.

Option 5

Distribute School engagement through a group of School-side champions

Schools with advanced systems have offered to share what they built, and Schools building now have asked to see it. A small group of School-side power users, convened through the Center of Excellence and the business development forum, can carry peer coaching and much of the feedback gathering. This turns nine individual relationships into a facilitated group.

Effect: reduces one-to-one engagement load and improves adoption. Cost: modest convening and facilitation time.

What applying options 1, 3 and 5 would look like

RoleWithout structural changeWith options applied
Center of Excellence Product Owner, Sales Activation, Enrollment Platform, standards, reporting, School engagement, parity Sales Activation and School-facing adoption, supported by a champion group
Dedicated Product Owner Not assigned; responsibility defaults to the CoE Named role holding backlog prioritization and the vendor relationship at half-time or more
Technology owner Shared informally across several people Pipeline, standards, architecture, dashboards, vendor scope
Learning & Evaluation Consulted on Lilly requirements Owns repeat participation reporting and the evaluation questions outright
Program Sales Consulted Owns waitlist and cancellation work; contributes prior platform knowledge
Consultant Build execution Build execution plus project management, sequencing and decision capture

13 · MOCHA Ownership

One owner per project, one manager across the portfolio

Manager Assigns, supports and reviews the owner
Owner One person accountable for the outcome
Consulted Input required before decisions land
Helper Does defined pieces of the work
Approver Signs off before it goes live
ProjectManagerOwnerConsultedHelperApprover
Portfolio and roadmapMike PiggBen Worden Theresa, Meg, Katie, MycahDX FoundationLT
Product Owner (vendor interface)Ben WordenTo be named Theresa, Meg, KatieDX Foundation delivery leadLT
Data Standards & BaselineBen WordenBen Worden Theresa, Meg, Katie, School technical leadsKaren Zelevinsky, DX FoundationLT
Data GovernanceMike PiggBen Worden Meg, Katie, EDs, Lach ZempOperations teamLT / Charter body
Sales ActivationBen WordenTheresa Salus Meg, Sales, MarketingCoE working group, champion groupTheresa Salus
Data PipelineBen WordenBen Worden Theresa, Katie, School technical leadsDX Foundation, Karen ZelevinskyLT
School Baseline ParityBen WordenKatie Dalbey Theresa, Julia, School data leadsKaren Zelevinsky, RYTEKatie Dalbey
Enrollment PlatformBen WordenTheresa Salus Meg, KatieDX Foundation, Karen ZelevinskyBen Worden
Repeat ParticipationMike PiggKatie Dalbey Ben, Theresa, RYTEDX Foundation, School data leadsKatie Dalbey
Dashboards & ReportingBen WordenBen Worden Theresa, Meg, Katie, FinanceMarketing analytics, Karen ZelevinskyLT
Waitlist & CancellationBen WordenMeg Peterson Program Sales, customer success teamDX Foundation, Karen ZelevinskyMeg Peterson
Development / DonorMike PiggJulia Farmer Ben, School development leadsKaren Zelevinsky, DonatelyLT
School investment positionMike PiggMycah Berryman Ben, Katie, Julia, EDsFinanceLT

MOCHA ownership is distributed across six people rather than concentrated in one, consistent with the capacity options above. This is a starting proposal for the Leadership Team to confirm or revise.

14 · Who Leads Which Side

School insight, technical build, strategy and vendor management are four different jobs

A lesson from the earlier engagement: vendors should not enter School conversations before internal decisions are settled. Schools hear from OBUSA. The vendor receives a defined scope.

School feedback, insight and change management

Center of Excellence — Theresa Salus, with the CoE working group, business development forum and School champions

Owns the discovery questions, the School conversations, sales journey facilitation, change management and School-specific roadmaps. Runs one unified discovery rather than several. Schools should experience a single coordinated request from OBUSA, not parallel asks from separate projects.

Technical build

Karen Zelevinsky — fractional Salesforce engineer

Implements defined requirements: automations, objects, integrations, reports. Has built and advanced Salesforce across most of the network and already holds access across systems, which makes execution faster and cheaper than routing everything through the consultancy. Does not decide the business model, so the quality of what we specify remains our responsibility. Named in the knowledge transfer documentation as an expert on the pipeline architecture, and already supporting individual Schools directly.

Business process strategy and project management

DX Foundation — consultant

The translation layer between business need and system design, which has been identified internally as a gap. Runs the delivery cycle, sequences work, maintains the decisions board and backlog, and hands suitable execution to the network engineer — a working relationship that already exists from prior engagements. Requires a named Product Owner committing at least half-time.

Strategy, sponsorship and vendor relationships

Ben Worden — executive sponsor

Holds the roadmap, the vendor relationships, the scope handed to the consultant, the cross-grant budget conversation and the governance question. Keeps vendors out of unstructured School conversations, and holds the value model, which spans enrollment, fundraising, technology cost and grant compliance.

Grant compliance and evaluation

Katie Dalbey — with RYTE (Jen Urban and team, Montclair State University)

Owns the Character Compass evaluation questions: what helps or hinders building a high-quality participant tracking system, and whether data quality improves as tracking improves. Confirms the build meets grant commitments and flags where School data gaps would undermine reporting. RYTE provides capacity-building support for the internally led evaluation.

Risk, privacy and data protection

Lach Zemp — risk management counsel

Student data privacy has already been raised as a concern by at least one School, specifically around third-party access and obligations under its own agreements with a public school district. Any governance agreement and any third-party access arrangement needs this review built in rather than added afterwards.

Prior-build knowledge

Meg Peterson

Holds the earlier platform scope of work and discovery materials. The contribution is compressing the learning curve — the original build ran 14 months from a standing start, and the value is in not rediscovering what has already been paid for.

15 · The Value Model

Every project needs a number an Executive Director would recognize

This is what moves the conversation from defending a budget line to weighing a portfolio against the revenue, capacity and savings it unlocks. The measures below are proposed methods; the baselines still need to be built.

ProjectHow value is createdHow to calculate itWhere it lands
Sales ActivationBetter group conversion Additional conversions × average group program valueSchool earned revenue
Enrollment Platform — groupsStaff time and conversion Hours saved × loaded staff cost, plus additional bookingsSchool capacity and revenue
Enrollment Platform — OEHigher fill rates Additional filled places × average net revenue per studentSchools and OBUSA
Repeat ParticipationStudents returning Additional repeat participants × average value of a subsequent enrollmentSchool revenue and grant compliance
Development / DonorDonor retention and reactivation Improvement in retention rate × average donor valueSchool contributed revenue
Data Pipeline — directTechnology and labour saving Retired licensing, starting with $15,000 annually for Nintex and potentially a further $50,000 for the CDP layer, less the cost of re-instrumenting, plus avoided integration and support hoursOBUSA and School technology cost
Data Pipeline — enablingCheaper future integration Cost of connecting a tool once versus across every system, multiplied by expected future integrationsNetwork technology capacity
Dashboards & ReportingLess manual reporting, less key-person risk Staff hours currently spent assembling network reporting × loaded costOBUSA, Boards, School leadership
Marketing for non-marketersCapability without headcount Campaign activity enabled at Schools with no marketing staffSchools with limited capacity
Data Standards & BaselineAvoided build cost Cost of independent School builds − cost of shared deployment. Recent School estimates for comparable work have run $30,000–$40,000School capital avoidance
School Baseline ParityUnlocks value elsewhere Share of network value currently unreachable because inputs are incompleteThe whole portfolio
Aligned programme and impact dataAccess to funding Grant dollars enabled or protected by shared reporting capabilityNetwork funding
Keep direct and enabling value separate. Direct value is created by the project itself. Enabling value is created elsewhere but depends on it. The pipeline has modest direct value and substantial enabling value, which is exactly why it is disadvantaged whenever it is judged in isolation against something with a visible revenue line.

16 · What the Leadership Team Needs to Decide

Eight decisions, each with a consequence

1

Do we adopt the layered portfolio model, or keep funding Salesforce as separate projects?

If adopted: one roadmap, one discovery, one consultant engagement, one story for EDs.
If not: parallel requests reach the same School staff, and totals keep looking inflated because shared costs are counted repeatedly.
2

Which grant pays for which layer?

One option on the table: AAO funds Sales Activation and standards; Lilly funds pipeline, parity, Enrollment Platform and repeat participation.
Effect: resolves the current budget overlap and keeps Lilly commitments demonstrably funded by Lilly money.
3

What is our position on Schools that have already invested their own funds?

If we set one now: we answer two live requests consistently and can explain the position to the other seven Schools.
If we do not: the position gets set case by case, in individual conversations, with fairness questions following later.
4

Do we name a Product Owner who is not the Center of Excellence lead?

If yes: the half-time commitment is absorbed without displacing sales enablement.
If no: Salesforce plausibly consumes that role for 2027 and crowds out the go-to-market work the AAO grant funds.
5

Do we fund School baseline parity as a named project?

If yes: the Schools furthest behind reach a usable standard and network reporting becomes credible.
If no: combined reporting inherits the weakest inputs, and Schools currently waiting continue to wait.
6

Do we commit to a data governance agreement outside the National Operating Standards?

If yes: Schools get written limits on how shared data may be used, which is the precondition for sharing group data.
If no: hesitancy persists, particularly where Schools see group participants as future donors.
7

Do we formally defer development and donor work to a 2028 decision point?

If yes: the most contentious topic leaves the 2027 conversation while the roadmap stays honest about where it leads.
If no: the hardest conversation in the network becomes a gate on everything else.
8

Do we require a quantified School value estimate before each project proceeds?

If yes: ED conversations shift from cost to return, and fee discussions get materially easier.
If no: we keep defending line items without evidence of what they are worth to the Schools funding them.