A quick orientation to your stewardship picture

• To start, tell me which role on your team owns major donor stewardship day to day Options: VP of Advancement, Stewardship Director, Major Gift Officer, Development Operations Manager, Shared responsibility, Other
• How many active major donors, five-figure-plus, does your organization manage right now Options: Fewer than 50, 50 to 150, 151 to 500, More than 500, Unsure
• Walk me through a typical stewardship plan you create for a five-figure donor, step by step
• When was the last time a major donor downgraded or lapsed and stewardship execution was a clear factor, what happened
• Which system currently stores your authoritative gift and contact records Options: Your primary donor CRM, Fund accounting system, Separate stewardship spreadsheet, A ticketing or task system, Other

Where donors most often fall out of the plan

• What single missed stewardship moment would most likely cause a major donor to reduce or stop giving Options: Delayed acknowledgment, No impact report, Lack of personal outreach, Incorrect attribution or gift details, Other
• How often do acknowledgment or impact reporting deadlines slip for your top 50 donors Options: Almost always, Often, Occasionally, Rarely, Never
• Name the role that usually first notices an unacknowledged gift and how long it typically takes to resolve that issue Options: Gift officer, Development operations, Finance, Stewardship manager, It is not noticed
• Tell me about the last time an impact report arrived late or with errors, what did the donor say and how did your team respond
• Which donor segments do you think are most at risk today because stewardship is inconsistent Options: Major donors (5-figure+), Principal donors (6-figure+), New major donors, Recurring mid-level donors, All segments equally

How these gaps show up for fundraising and reputation

• If you could quantify it, how much annual revenue would a 5 percent drop in retention of your major donors cost you Options: Under $100k, $100k to $500k, $500k to $2M, More than $2M, Unknown
• In a typical year, about how many donors downgrade or go silent after a stewardship lapse Options: None, 1-5, 6-20, 21-50, More than 50, Unsure
• What downstream processes fail when stewardship tasks are not completed, for example in renewals, campaign planning, or donor reports
• Which stakeholders outside development, for example finance or communications, raise concerns when stewardship falters Options: Finance/CFO, Communications/Marketing, President/CEO, Board members, None regularly
• When a high-value donor expresses dissatisfaction, what response time and owner does your leadership expect Options: Same day, senior leader, 48 hours, stewardship director, One week, gift officer, Varies case by case

If stewardship reliably worked for every major donor

• Imagine every major donor received a timely acknowledgment and a clear impact update, what would retention and re-engagement look like in 12 months
• Which measurable signals would you use to prove stewardship is working, select up to three Options: Retention rate among 5-figure donors, Average gift size change, Time to acknowledgment, Re-solicitation conversion rate, Donor satisfaction or NPS, Number of personalized reports delivered
• How would predictable stewardship rhythms change a gift officer's priorities, and what would make adoption feel less like extra admin
• What would have to change in your donor-facing communications to make impact reports more compelling and timely
• If a pilot shows a clear retention lift, what internal barrier would most likely stop you from moving to full rollout Options: Budget constraints, Lack of leadership buy-in, Technical integration failure, Staff capacity, Nothing would stop us

Obstacles, risks, and timeline killers

• Which single implementation risk would force you to halt a pilot or delay deployment Options: Data migration errors, Integration failures with CRM, Gift officer resistance, Legal or compliance gating, Other
• Do you have a recent audit or report documenting data quality in donor records Options: Yes, within 6 months, Yes, within 12 months, No formal audit, Not sure
• Identify the team or role that controls API or integration access to your donor CRM and whether they can approve work windows
• How many dedicated technical hours per month could your organization commit to migration and testing during a pilot quarter Options: Under 20 hours, 20-40 hours, 40-80 hours, More than 80 hours, Unsure
• What compliance or approval steps, for example gift committee review or legal sign-off, could add weeks to your timeline

What alternatives and internal options you are weighing

• What vendors, incumbent processes, or internal projects are you actively considering instead of engaging an external stewardship platform Options: Staying with current CRM processes, Building an internal tool, Another vendor solution, Engaging a consultant, Not decided
• What would have to be demonstrably true about your current approach for you to decide to keep it rather than switch
• Has anyone on your team proposed building stewardship workflows internally and who would lead that effort Options: Yes, technical team, Yes, development operations, Yes, fundraising leadership, No formal proposal, Not sure
• If you stay with the incumbent approach, how quickly could missing features like scheduled impact reports and acknowledgment tracking be delivered Options: Already available, 4-8 weeks, 2-6 months, Longer than 6 months, Not available
• Which evaluation criteria will matter most when you choose, select up to three Options: Total cost, Speed of deployment, Ease of use for gift officers, Integration risk, Reporting and analytics, Support and training, Data ownership

Operational readiness: can this actually roll out here

• Which systems must connect for a successful rollout and are API credentials already available Options: Your primary donor CRM, Gift processing/payment gateway, Fund accounting system, Email and communications platform, Reporting or data warehouse, Other
• Please identify the day-to-day owner for migration and testing in your organization and confirm whether they have release authority
• How would you rate the cleanliness of stewardship-related fields in your donor data, such as acknowledgment dates, gift designations, and donor interests Options: Mostly clean, Some gaps, Significant issues, Unknown
• How many donor records would need migration for a pilot covering one to two gift officers' portfolios Options: Fewer than 1,000, 1,000 to 5,000, 5,001 to 20,000, More than 20,000, Unsure
• Are there regulatory, donor privacy, or legal approvals required before moving donor data to a new system Options: Yes, internal legal approval, Yes, external regulator filing, No approvals needed, Unsure
• If the CRM team cannot provide access within your target window, what happens to the project and who makes that call

Decision triggers and next steps

• If the pilot achieves the retention lift you expect, what approvals, budget steps, or governance milestones are required to move to full deployment
• Which timeline best matches your preference for pilot and full rollout Options: Pilot in 4 to 6 weeks, full in 3 months, Pilot in 6 to 8 weeks, full in 4 to 6 months, Pilot next quarter, full in 6 to 9 months, Unsure
• List the people in your organization who must sign off on acceptance criteria and who must attend go or no-go checkpoints
• What single metric or outcome, if met by the pilot, would make you comfortable recommending purchase to leadership Options: Improved retention percentage, Reduced time to acknowledgment, Higher donor satisfaction, Increased re-solicitation success, Other
• Would you like to schedule a technical readiness call with your CRM owner and which part of the week works best Options: Yes, mornings on weekdays, Yes, afternoons on weekdays, Prefer next week, Not right now

• Solution Experience Session

• Confirm the current state and its cost
• Customer confirms the demonstrated workflow eliminates the missed acknowledgment and impact-report gaps they described.
• Provide a sample portfolio of 8-12 donors and recent stewardship notes to use in the pilot scenario.
• Customer agrees that the migration approach will surface legacy stewardship records and prevent donor omissions.
• End-to-end donor scenario walkthrough
• Provide read-only access to a CRM sandbox or export of donor, gift, and stewardship note records for migration validation.
• Customer identifies the remaining evidence and timeline required to approve a pilot covering one gift officer's portfolio.
• Migration and integration proof steps
• Run a migration validation on the provided sample portfolio and deliver a migration report that identifies missing or unmapped stewardship records within five business days.
• Validate the future state
• Draft pilot acceptance criteria based on the validated future state and share it before the pilot start.
• Evidence checklist and next decision items

• Solution Experience Session
• Solution Experience Deck
• Solution Brief

• meeting
• slides
• document

• Migrate Donor Contacts and Gift History
• Migrate Legacy Stewardship Records and Acknowledgments
• Configure Stewardship Plan Templates
• Automate Gift Acknowledgment Workflows
• Configure Impact Report Templates and Delivery
• Set Up Personalized Communication Sequences
• Integrate and Sync with Source CRM
• Run Integration QA and Data Reconciliation
• Deploy Pilot Portfolio for One Gift Officer
• Train Gift Officers on Platform Workflows
• Configure Endowment Performance Update Feed
• Configure Reminder and Escalation Rules
• Build Stewardship and Retention Dashboards
• Enable Role-Based Access and Permissions

Migrate Donor Contacts and Gift History

• How many donor contact records need to be migrated from your current CRM? Options: Less than 1,000, 1,000-5,000, 5,000-25,000, More than 25,000
• Specify which gift date ranges should be included (for example: last fiscal year, last 3 fiscal years, all history) Options: Last fiscal year, Last 3 fiscal years, Last 5 fiscal years, All available history
• Provide the CRM exports or objects that will supply gift-level data (for example: Gifts table export, Payments export, Pledges export)
• Do you need historical tax receipts and PDF acknowledgment letters attached to donor records during migration? Options: Yes, No
• Define the acceptance criteria that will confirm data migration completeness for contacts and gifts (for example: 99% donor records present, 100% gifts for last 3 fiscal years, <1% duplicate rate)
• Identify who on your team will own validation of migrated gift amounts, donor IDs, and duplicate remediation Options: Development operations, Gift officer, Stewardship director, Other

Migrate Legacy Stewardship Records and Acknowledgments

• List the legacy stewardship artifacts to migrate (acknowledgment letters, stewardship plans, impact report PDFs, activity notes) Options: Acknowledgment letters, Stewardship plans, Impact report PDFs, Activity notes, Other
• Indicate whether legacy stewardship files are stored in the CRM, a shared network drive, or a fundraising database Options: CRM, Shared network drive or cloud storage, Fundraising database, Other
• Identify any legacy acknowledgment templates that contain donor-specific impact paragraphs that must be parsed and mapped rather than attached as a PDF Options: Yes, No
• Are legacy stewardship statuses required to be mapped to platform statuses (for example: 'acknowledged', 'impact delivered', 're-solicitation paused')? Options: Yes, No
• State the acceptable tolerance for missing legacy acknowledgment documents at cutover (for example: none, <1%, <5%) Options: None, <1%, <5%, Other

Configure Stewardship Plan Templates

• Select the stewardship plan templates you need (for example: standard acknowledgment plan, impact reporting schedule, re-solicitation cadence, gift-specific plan) Options: Acknowledgment plan, Impact reporting schedule, Re-solicitation cadence, Gift-specific plan, Other
• Provide the default touchpoints and timing each template should include (for example: immediate acknowledgment within 48 hours, impact report at 6 months)
• Will you require template variables that pull from CRM fields such as gift purpose, gift amount, fund name, or campaign code? Options: Yes, No
• Name who in your organization should be able to create and edit stewardship templates (for example: development operations, gift officers, stewardship director) Options: Development operations, Gift officers, Stewardship director, Other
• Provide a sample acknowledgment or stewardship template we should mirror for configuration

Automate Gift Acknowledgment Workflows

• Choose the acknowledgment channels you use: postal letter, personalized email, phone call, or donor portal message Options: Postal letter, Personalized email, Phone call, Donor portal message
• Confirm your target SLA for initial acknowledgment after receipt of funds (for example: within 48 hours, 7 days, 30 days) Options: Within 48 hours, Within 7 days, Within 30 days, Custom
• Specify the CRM field or event that should trigger automatic acknowledgment creation (for example: 'Gift Received Date', 'Payment Processed')
• Do you require a human approval step for acknowledgments above a dollar threshold and if so which threshold applies? Options: No, Yes — gifts ≥ $5,000, Yes — gifts ≥ $25,000, Yes — custom threshold
• If you selected a custom approval threshold, specify the dollar amount and the approver role
• Indicate whether acknowledgment workflows should create tasks or calendar reminders for gift officers when a personalized touch is required Options: Yes, No

Configure Impact Report Templates and Delivery

• Select the types of impact reports you deliver: project updates, endowment performance summaries, donor-restricted use reports, annual reports Options: Project updates, Endowment performance summaries, Donor-restricted use reports, Annual reports, Other
• Provide the delivery cadence you use for major donor impact reports (for example: 6-month, annual, campaign milestone) Options: 6-month, Annual, Campaign milestone, Custom
• Indicate whether impact reports must include financial performance data from the endowment accounting system or donor-restricted fund reports Options: Yes, No
• Specify allowed file formats and maximum sizes for report attachments (for example: PDF up to 10MB, web link only) Options: PDF up to 5MB, PDF up to 10MB, Web link only, Other
• Who will own sign-off on impact reports before delivery and what evidence will validate sign-off (for example: signed PDF, recorded email approval)
• Should delivery of impact reports be automated to donor-preferred channels captured in the CRM? Options: Yes, No

Set Up Personalized Communication Sequences

• Identify which donor attributes should drive personalization (for example: giving history, fund interest, last contact method)
• Select the channels sequences should span: email, printed mail, phone task, SMS, donor portal Options: Email, Printed mail, Phone task, SMS, Donor portal
• Indicate the desired drip cadence for re-engagement sequences for lapsed major donors (for example: 30/60/90 days) Options: 30/60/90 days, Custom cadence, Event-driven only
• Will you require merge tokens for gift officer names, fund impact statistics, or campaign milestones in sequence content? Options: Yes, No
• Describe how sequences should pause when a high-touch interaction is logged (for example: pause on logged call or personalized meeting)
• Who approves donor-facing sequence templates prior to go-live? Options: Development operations, Stewardship director, Gift officers, Other

Integrate and Sync with Source CRM

• Identify the type of donor CRM connection available: hosted CRM with API, CSV/flat-file exports, or on-premise database export Options: Hosted CRM with API, CSV/flat-file exports, On-premise database export, Other
• Specify which CRM objects and fields must be synchronized (for example: Contact email, Gift ID, Gift Date, Gift Purpose)
• Confirm the synchronization cadence you require: real-time webhook, hourly batch, nightly batch, or weekly Options: Real-time/webhook, Hourly batch, Nightly batch, Weekly
• Who will provide API credentials and a test integration account for the source CRM? Options: Your technical lead, Third-party integrator, We will need assistance obtaining them, Other
• Estimate the expected volume of daily changes (new gifts and contact updates) to size API calls and sync windows Options: <50, 50-200, 200-1,000, 1,000+
• Are there custom field mappings or picklist values that must be transformed during sync (for example: custom fund codes, gift purpose values)? Options: Yes, No

Run Integration QA and Data Reconciliation

• List the reconciliation reports you need after integration (for example: gift count by date, gifts by donor, unmatched gifts, duplicate detection) Options: Gift count by date, Gifts by donor, Unmatched gifts, Duplicate detection, Other
• Provide the automated tests required in QA: field mapping checks, duplicate detection, foreign currency conversion checks, and tax receipt generation tests
• Describe the acceptance metrics that will validate successful integration QA and data reconciliation (for example: gift counts match within 0.5% for last fiscal year, zero critical mismatches, API error rates <1%)
• Who will own reconciliation exception triage and what SLA do you expect for remediation of critical mismatches?
• Do you require a sandbox-to-production dry-run reconciliation as part of the cutover plan? Options: Yes, No

Deploy Pilot Portfolio for One Gift Officer

• Confirm the pilot scope: one named gift officer's active portfolio for one quarter Options: Yes — one gift officer one quarter, No — modify pilot scope (describe)
• Describe the pilot acceptance criteria that will determine success (for example: 80% adoption by portfolio, zero missed acknowledgments for pilot gifts, feedback from the gift officer captured)
• Indicate how many active donors will be included in the pilot by count or segment (for example: <50, 50-150, 150-300) Options: <50, 50-150, 150-300, Other
• Select which workflows the pilot will exercise: acknowledgment only, full stewardship plan execution, impact report delivery Options: Acknowledgment only, Full stewardship plan, Impact report delivery, Other
• Who will provide pilot training and what follow-up coaching cadence do you require (for example: weekly coaching for 4 weeks) Options: We will train internally, Vendor-led training session, Hybrid train-the-trainer

Train Gift Officers on Platform Workflows

• How many gift officers require initial training during rollout? Options: 1-5, 6-15, 16-50, 50+
• Choose the training formats you prefer: live webinars, on-site workshops, recorded videos, or train-the-trainer Options: Live webinars, On-site workshops, Recorded videos, Train-the-trainer
• Will you need role-based training materials for gift officers versus development operations and managers? Options: Yes, No
• Select the success thresholds that will define training completion for a gift officer (for example: complete checklist, pass assessment, manager sign-off) Options: Complete checklist, Pass assessment, Manager sign-off, Other
• Who will be your internal training coordinator and what is their primary contact for scheduling sessions?

Configure Endowment Performance Update Feed

• Identify the system that will provide endowment performance data: investment accounting export, custodian feed, or manual reports Options: Investment accounting export, Custodian feed (CSV/API), Manual reports, Other
• Specify which performance metrics must appear in donor-facing updates (for example: year-to-date return, market value, distributions, spending rate) Options: YTD return, Market value, Distributions, Spending rate, Other
• Confirm the feed cadence required for endowment updates: monthly, quarterly, or on-demand Options: Monthly, Quarterly, On-demand
• Do you require mapping between institutional endowment fund codes and platform fund IDs for donor-facing reports? Options: Yes, No
• Who will approve endowment performance content prior to delivery to donors (for example: CFO, investment committee, stewardship director)? Options: CFO, Investment committee, Stewardship director, Other

• Non-Disclosure Agreement (NDA)
• Master Services Agreement (MSA)
• Order Form / Subscription Agreement
• Statement of Work (SOW)
• Data Processing Agreement (DPA)
• HIPAA Business Associate Addendum (BAA)
• Change Order Agreement
• Acceptance & Go/No‑Go Criteria

• Go-live Health Check (weeks 1-4)
• First Outcomes Measurement (weeks 4-10)
• Acceptance Gate Review (around day 90)
• Quarterly Success Review (ongoing)

• Log agreed configuration adjustments with delivery timelines and verification steps.
• Update the training materials or workflow scripts identified during root-cause analysis.
• Restate acceptance criteria and targets
• Produce a documented acceptance decision for each numeric criterion recorded in Solution Scope.
• Confirm the legacy stewardship system is decommissioned or formally retained read-only and that fallback usage is closed.
• Agree remediation actions, retest dates, and the signatory for final acceptance if required.
• Publish the acceptance record showing pass/fail per criterion and the signed acceptance artifact or documented buyer approval.
• If applicable, schedule the acceptance retest and list the artifacts required for verification.
• Execute the incumbent decommission checklist, archive data as agreed, and publish confirmation of contract/renewal disposition.
• KPI trend review
• Validate that major donor retention rate and impact report delivery remain on track or identify trend reversals requiring action.
• Ensure the open-ticket backlog is decreasing and that any recurring defects have remediation plans.
• Confirm that no team is operating in the legacy system and that any remaining access is read-only.
• Publish the quarterly KPI dashboard with data sources and calculation notes for transparency.
• Close or reprioritize the top five operational tickets and document expected resolution dates.
• Reconfirm success criteria and owners
• Confirm data migration completeness and that integrations are accepting transactions without critical errors.
• Verify initial gift officer adoption signals are present and identify any immediate training or configuration needs.
• Document remediation actions and resolution dates for all high-priority blockers.
• Publish the migration validation report showing record counts, error rows, and reconciliation status.
• Log and prioritize defects in the shared issue tracker with expected resolution dates.
• Schedule short targeted training sessions for gift officers covering any missing workflow steps.
• Present first-period outcome data
• Determine whether major donor retention rate and acknowledgement timeliness are trending toward the Solution Scope targets or require remediation.
• Identify root causes for any metric shortfalls and agree a prioritized remediation plan with dates.
• Confirm the data sources and calculations used to report each metric so everyone agrees on measurement provenance.
• Deliver a reconciled metrics package showing raw data extracts, calculation logic, and the period-over-period comparison.
• Execute the top three corrective actions with completion dates and verification steps ahead of the acceptance meeting.
• Present outcome data against each criterion
• Open issues and ticket burn-down
• Migration and integration validation
• Diagnose root causes for gaps
• Document acceptance decision
• Early adoption and usage signals
• Enhancement and configuration changes
• Prioritize corrective actions
• Blockers and open issues triage
• Confirm timeline to acceptance gate
• Incumbent residual usage check
• Incumbent system decommission status
• Agree immediate remediation actions
• Agree remediation items and resolution timeline
• Confirm next quarter objectives and checkpoints