Every technology decision a retainer client faces gets a memo like this one: the options, our recommendation, what it costs, what could go wrong, and what has to be true for it to work. This sample is for a fictional contractor. The format is the one you would receive.
Illustrative sample. The company, people and figures are fictional. The format is what a Fractional CTO client receives.
Decision memo
To: Owner and General Manager, Cedar Basin Electric (fictional)
From: Ashlee, Fractional CTO, Sandcastle
Date: 25 September 2026
Decision needed by: 15 October 2026 (the current support contract renews 1 November)
Subject: Job-costing system: keep, upgrade or replace
Background
The job-costing system that runs the company’s 40 active projects is on a 2016 on-premise version that the vendor stops supporting next year, and the support renewal is due 1 November. The choice is whether to renew as is, move to the vendor’s current cloud edition, or replace the system.
Job costs, purchase orders and crew hours all pass through this system, but hours are keyed in from the field time-entry app by two coordinators (about 9 hours a week) and accounting re-enters vendor invoices from it (about 4 hours a week). The system has no export beyond a monthly report and no way for the accounting system or the field app to connect to it. The AI opportunities identified in the assessment (timesheet anomaly flags, automated invoice matching) are all blocked by this one gap.
Options considered
|
Option |
One-time cost |
Ongoing |
Notes |
| A |
Renew support on the current version for one more year and change nothing |
$0 |
$9,600 a year |
Keeps the 13 hours a week of re-keying. Support ends in 2027 regardless, so this defers the decision, it does not avoid it. Delivered by the vendor. |
| B |
Move to the vendor’s cloud edition, which has an API and an accounting connector |
$18,000 to $26,000 (vendor migration $12,000 to $15,000; connection to accounting and the field app $6,000 to $11,000) |
$14,400 a year |
Data migrates with history. Removes most of the re-keying. Unblocks the two AI features. Migration delivered by the vendor; the connections by Sandcastle or the vendor’s partner. |
| C |
Replace with a contractor-specific platform that includes job costing, time entry and purchasing |
$45,000 to $70,000 (licenses, migration, retraining) |
$22,000 to $30,000 a year |
Removes the field app and its subscription too. Twelve to eighteen months of disruption across the whole company for a gain the cloud edition mostly delivers. Delivered by the new vendor. |
| D |
Custom-build a replacement |
$120,000 or more |
Maintenance |
Sandcastle could build this. We recommend against it: job costing is a solved problem and the company’s needs are not unusual enough to justify owning the software. |
Recommendation
Option B. Move to the current cloud edition before the November renewal, and connect it to the accounting system and the field app in the same quarter. It is the only option that removes the re-keying, keeps the history, and unblocks the roadmap for under $30,000.
This memo does not decide whether to replace the field time-entry app. That question is worth revisiting in twelve months, once hours flow automatically; the case for replacing it gets weaker, not stronger.
What has to be true for this to work
- The vendor confirms in writing that project history and open purchase orders migrate intact (ask for a reference client who migrated in the last year).
- The field app’s vendor confirms the API access needed for hours to flow across (they have said yes by email; get it in the contract).
- Two coordinators are available for a week of parallel running in the migration month.
Risks and how we would handle them
- The migration slips past the renewal date: negotiate a three-month support extension on the old version as part of the cloud deal, before signing.
- The accounting connection needs custom work the connector does not cover: cap the connection budget at $11,000 and stage it, hours first, invoices second.
- Staff resist the new screens: the coordinators who do the re-keying today are the ones who gain the most; involve them in the parallel-running week.
Next steps
- Owner decides by 15 October.
- Sandcastle requests the migration quote and the reference client from the vendor this week, and reviews the statement of work before signature.
- Vendor migration November; connections December; parallel running the first two weeks of December; old version retired by 31 December.
Every memo lists at least one option that does not involve Sandcastle. Options A, B and C are delivered by outside vendors; Sandcastle’s role in Option B is limited to the connections and to reviewing what the vendor sends.