You carry the weight of funders, boards, and communities that cannot afford more risk. At the same time, staff are tired of broken tools and last‑minute reporting scrambles. The first 90 days with a fractional CTO can feels like a big move, but you cannot wait a year to see change. The good news: the first 90 days with a fraction CTO do not need to be abstract or fuzzy. With the right plan, those three months can bring calmer systems, fewer fire drills, and clearer evidence that technology is finally starting to serve the work.
This playbook walks through how to use the fractional CTO first 90 days to get quick, visible wins while also setting up a real 1 to 3 year path forward.
Key takeaways for your fractional CTO first 90 days
- Treat the first 90 days as a focused project with clear outcomes, not open‑ended advice.
- Aim for three buckets of work: stabilize risk, free up staff time, and build a simple roadmap.
- Keep the work grounded in real cases, advocates, and reporting needs, not tools for their own sake.
- You, as CEO or executive leader, set the pace by choosing what “good enough for now” looks like.
The first 90 days with a fractional CTO: why they matter
Image created with AI: CEO and fractional CTO planning a 90‑day roadmap together.
Most justice-focused organizations grow faster than their systems. A new project here, a coalition there, a pilot tool that never quite got turned off. Before long, no one can see the whole picture.
The first 90 days with a fractional CTO are your chance to step back without slowing down. Done well, this period:
- Surfaces hidden risk in case data, youth records, or immigration files.
- Gives you one clear story you can share with funders and boards.
- Starts fixing problems staff feel every day, like duplicate data entry or manual reports.
Think of those 90 days as a structured breathing space. You are not pausing the work, you are clearing a path so it can move with less friction.
Days 1‑30: See the mess clearly and make it safe
Image created with AI: Fractional CTO reviewing systems and risks in the first 30 days.
The first month is about calm, structured discovery and basic stabilization. No big rebuilds yet.
What your fractional CTO should do in Days 1‑30
- Listen to the work. Short interviews with program leads, data people, operations, and that one staff member everyone calls when a system breaks.
- Map the ecosystem. Case tools, spreadsheets, survey platforms, grant portals, email, document storage, texting tools. A simple “system map” that shows how data moves, or does not.
- Assess risk. Where are the weak points for privacy and security, especially for people in detention, on supervision, or at risk of deportation?
- Triage incidents. If there are active fires, like access problems or repeated outages, they get quick, practical fixes.
By the end of Day 30, you want three things in hand:
- A one‑page picture of your systems and data flows.
- A ranked list of key risks and pain points.
- A short “first fixes” list that is already in motion.
Perfection is not the goal here. Shared clarity is.
Days 31‑60: Design quick wins that staff can feel
Once the picture is clear, the second month shifts into action that people actually notice. Staff do not care about an “architecture diagram”. They care about that Saturday night export that always fails.
Good targets for Days 31‑60
- Reporting fire drills. Automate one or two recurring reports for grants or boards so they take hours, not days.
- Duplicate entry. Remove at least one double data entry flow between a case tool and a spreadsheet.
- Access and permissions. Tighten who can see sensitive data, while making sure frontline folks are not blocked.
- Simple playbooks. Write 1‑page guides for common issues like onboarding new staff into systems or closing user accounts safely.
You and your fractional CTO should pick quick wins that:
- Match real complaints staff already raise.
- Reduce risk in areas that keep you up at night.
- Are small enough to finish in a few weeks, not months.
By the end of Day 60, staff should be able to say, “something is different”. Fewer brittle spreadsheets. Less fear of touching the wrong system. A report that just runs.
Days 61‑90: Lock in progress and set a real roadmap
Image created with AI: Team reviewing progress and quick wins at the 90‑day mark.
The third month connects short‑term wins to a longer story. This is where your board, finance team, and funders start to see shape.
Core work in Days 61‑90
- Document what changed. Before and after snapshots for key pain points, like time to pull a grant report or time to onboard a new partner site.
- Draft a 1 to 3 year roadmap. Plain language, broken into phases. Stabilize, then connect, then improve. Each phase tied to real outcomes, like “less staff time on manual reporting” or “safer handling of youth data”.
- Define roles. Clarify what the fractional CTO will own, what in‑house staff will own, and what might move to vendors.
- Build habits. Set up a simple tech steering group with program, data, and operations leaders who meet on a steady rhythm.
By Day 90, you want three clear deliverables:
- A short memo you can share with your board.
- A living roadmap that you can adjust without starting over.
- A stable cadence with your fractional CTO, so ongoing work does not slide back into chaos.
Metrics and signals to watch each month
You do not need fancy dashboards to tell if your fractional CTO first 90 days are working. Start with simple signals your staff already feel.
By Day 30
- Fewer surprise outages.
- Clearer understanding of where sensitive data lives.
By Day 60
- At least one key report faster and more reliable.
- Noticeable drop in “can you pull this for me” requests to your data person.
By Day 90
- A shared roadmap everyone can explain in a sentence.
- Less dread when someone mentions auditors, new grants, or board packets.
If these signals are not moving, it is a prompt for a direct conversation, not a reason to give up on the model.
FAQs about working with a fractional CTO in the first 90 days
Is a fractional CTO worth it if we already have an IT vendor?
Yes, if your main problems are about alignment, not just outages. IT vendors keep the lights on. A fractional CTO helps you decide which lights you actually need and how they should connect to the work.
What if our systems are “too messy” to untangle in 90 days?
Most organizations feel this way. The goal is not to fix everything. The goal is to name the mess in plain language, reduce the highest risks, and pick the first few moves that will actually hold.
Who should the fractional CTO report to?
For the first 90 days, they should sit close to the CEO, executive director, or a senior deputy. The work cuts across programs, operations, finance, and data. It needs clear sponsorship, not just an IT lane.
How CTO Input can help you run a calm, confident first 90 days
If you recognize your own organization in this picture, you are not alone. Many justice-focused networks, clinics, and hubs have grown on top of fragile tools and heroic staff effort.
CTO Input steps in as that steady, senior technology partner who starts from your mission, not from a product list. In the first 90 days, we focus on the same pattern laid out here: listen hard, make data safer, free up staff time, and give you a roadmap you can defend to funders and boards.
If you are ready to turn technology from a quiet source of stress into a reliable backbone for your advocates, set yourself a challenge: pick a date 90 days from now and decide that your relationship to tech will feel different by then. Reach out to CTO Input to start that conversation and put your own first 90‑day plan in motion.