The TrailMark Technology Assessment
See what your technology is and isn’t doing for your business, and get a clear plan to make it work for your goals.
Start with a free 30-minute callThe Short Answer
A TrailMark Technology Assessment is a fixed-price review of a business’s systems, vendors, spend, security and workflows, tied to its business goals. It delivers a current-state snapshot, a costed 90-day roadmap and a 60-minute leadership readout. Standard assessments cost $7,500.
Who it’s for
You run a business you know inside and out. Technology is a different story.
The assessment fits owners and leaders of growing small and mid-sized businesses, especially where:
- The business has real operational complexity: multiple locations, field crews, regulated data, or a major system change coming up.
- No one on the leadership team owns technology strategy and how it ties to the business.
- You have an IT person, an outside provider, a dev team, or none of these. It works either way.
Sound familiar?
Symptoms we see every week
- Growth has stalled and you can’t pin down why.
- Work takes longer than it should, and workarounds are everywhere.
- Software spend keeps rising and its value is unclear.
- A big technology decision is coming, and you want a straight answer before you commit.
- AI keeps coming up, and you want to know where it fits, if at all.
What you get
A clear picture and a plan
A candid current-state snapshot
Your systems, vendors, spend and security, with plain-language findings on how well each supports your goals. AI is one lens, not the whole story.
Your next 90 days, in order.
Prioritized and costed, tied to your business goals, with one owner for every item. It covers the next 90 days in detail and the bigger moves beyond them.
A 60-minute leadership readout
We walk through the findings and the plan with you, your leadership team, and your IT or dev lead if you have one.
What’s working
The systems and habits worth keeping and building on.
What’s costing you
Where time, money and risk are leaking, and what it costs the business.
What to do first
The first moves, in order, with costs and who should own them.
No readiness score. No 80-page binder. A clear picture and a plan.
Proof
What this looks like in practice
“They spent a few days with us, interviewed our management team, and turned a long list of technology needs into a real plan — a sequenced roadmap and a 90-day plan with one owner per item — instead of a pile of open issues.”
— Kyle Shirley, President, KWS Erectors
Read the story →Process
From free call to readout
Full assessments run 4–6 weeks and include on-site visits as scoped.
| Step | What happens | Timing* |
|---|---|---|
| 1. Free 30-minute call | We talk through your business, goals and what’s frustrating you. If it’s a fit, you get a written proposal. | Proposal within 2 business days |
| 2. Kickoff and interviews | We agree what success looks like over the next 12 months, then talk with you, key leaders and whoever runs your technology today. | Week 1 |
| 3. Inventory and findings | Systems & Applications, Data & Reporting, Spend & Vendors, Security & Risk, People & Process, and AI & Automation — and how each supports your goals. | Weeks 1–2 |
| 4. Roadmap | The prioritized, costed plan for 90 days and beyond. | Weeks 2–3 |
| 5. Readout | 60-minute session to walk through findings and the plan. | End of week 3 |
*Demonstrates typical timing, dependent on availability of stakeholders and access to relevant systems.
Price
You know the cost before we start
Standard
$7,500
fixed
- Best fit
- One business, up to 2 locations
- Timeline
- 2–3 weeks typically
Full
From $15,000
quoted after the free call
- Best fit
- Multiple sites or states, a system change underway, or complex scope
- Timeline
- 4–6 weeks
If you continue with TrailMark within 30 days of the readout, $2,500 of a Standard assessment fee is credited toward that engagement.
FAQ
Common questions
What does it cost?
How is this different from the free assessment my IT provider offers?
Do I need an IT department for this to be useful?
We have an IT person (or a dev team). Is this an audit of them?
Is this an AI readiness assessment?
What do you need from me?
What happens after the readout?
Will my information stay confidential?
You know your business. Let’s make your technology work for it.
Start with a free 30-minute callGet In Touch
Talk Through the Problem Before You Commit
Start with a free 30-minute call. We’ll learn about your business and recommend the right next step — a Technology Assessment, fractional CTO, advisory, or a scoped project.