Question 1

What does the IT consulting process look like?

Accepted Answer

Reach out through the contact form or email info@trailheadtechvt.com. We reply personally with a link to schedule a free intro call — no prep, no pitch, just enough time to confirm Trailhead is the right fit. During that call, I take notes while we talk. Right after, I send a preliminary itemized estimate. Once approved and the invoice is paid, you receive a link to book your 1-hour tech consultation. I walk through your environment and priorities in detail — there's nothing for you to fill out or prepare. Afterward, I deliver your full IT assessment and prioritized roadmap.

Question 2

How much does a Technology Assessment cost?

Accepted Answer

IT Assessments are fixed-fee projects. Most assessments for organizations up to 10 employees fall between $250 and $500. Pricing is based on organization size (number of employees), the number of domains your business owns, and any optional add-ons. There are no surprise fees and no open-ended retainers.

Question 3

How long does an IT Assessment take?

Accepted Answer

A typical IT Assessment takes two to four weeks from kickoff to delivered roadmap, depending on organization size and how much documentation already exists.

Question 4

Do you offer ongoing re-assessments?

Accepted Answer

Yes. After the initial assessment, you can subscribe to recurring re-assessments on a quarterly or annual basis. Each cycle re-runs the full assessment suite and delivers an updated report. We also offer independent advisory support on an on-demand hourly basis at $125/hr with a 2-hour minimum.

Question 5

What happens after the assessment?

Accepted Answer

You receive a written report and roadmap you can act on immediately — whether that means tackling projects yourself, handing it to a vendor, or continuing to work with Trailhead. There's no obligation to continue. Many clients choose to engage on a recurring basis so the roadmap stays current as their business evolves.

Question 6

Do you provide ongoing IT support or manage our systems?

Accepted Answer

Trailhead is a consulting and advisory practice — we help you build a clear technology strategy, plan the right projects, and make better decisions. We don't manage your day-to-day IT or act as your on-call tech team. If you need hands-on managed support, we can help you identify the right partner for your organization — and stay independent while doing it.

Question 7

Do you sell hardware, software, or cloud services?

Accepted Answer

No. Trailhead does not resell hardware, software licenses, or cloud services. We have no vendor affiliations and no referral kickbacks. Our only incentive is giving you the right advice.

Question 8

What services does Trailhead Technology Consulting offer?

Accepted Answer

We offer three core services. Technology Assessment is a thorough review of your entire technology environment — devices, security, web presence, and software — with a clear report and prioritized roadmap ($250–$500 for most small businesses). Vendor Proposal Review is a flat-fee, independent analysis of an IT contract or vendor proposal before you sign ($175–$500). Ongoing Advisory keeps your roadmap current on a quarterly or annual basis, with on-demand hourly support at $125/hr.

Question 9

We're not a technology company — is Trailhead still relevant for us?

Accepted Answer

Absolutely. Most of our clients are not technology companies — they are professional services firms, nonprofits, construction companies, healthcare practices, and other New England businesses that rely on technology to operate but don't have dedicated IT staff. That is exactly who we built this practice for.

Question 10

We already have an IT person or vendor. Can Trailhead still help?

Accepted Answer

Yes — and this is one of the most common situations we work in. Your IT vendor has a financial interest in what they recommend. Trailhead doesn't. Many clients use us as an independent layer on top of their existing IT support: reviewing vendor proposals before signing, evaluating whether their current MSP is the right fit, or helping leadership understand what they're actually getting from their IT spend.

Question 11

Which states does Trailhead Technology Consulting serve?

Accepted Answer

We serve organizations across all of New England: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont. Trailhead is based in Shelburne, Vermont and most engagements can be conducted remotely, with on-site visits available as needed.

Independent IT Advisor for Small Businesses in New England