Who We Work With
Trailhead works with small businesses across all six New England states — Vermont, New Hampshire, Maine, Massachusetts, Connecticut, and Rhode Island — that rely on technology to operate but don’t have a dedicated IT person on staff. If your business has a handful of devices, a mix of software subscriptions, and customer or employee data you’re responsible for protecting, you’re exactly who we built this practice for. The Website Audit is also available to businesses anywhere in the US — no on-site visit needed, just a URL.
Managing point-of-sale systems, inventory software, and customer data — often with seasonal staff and no IT oversight.
POS systems, reservation platforms, and online ordering tools — where an outage on a busy weekend is a real financial hit.
Attorneys, accountants, consultants, and healthcare providers handling sensitive client data with compliance obligations they may not fully understand.
Donor databases, grant management tools, and limited budgets — with the same security exposure as any small business, and less margin for error.
Construction, plumbing, electrical, and HVAC businesses where technology decisions are made by the owner between jobs, without a second opinion.
Operations that spike in summer or foliage season — and where a technology failure at peak time isn’t just inconvenient, it’s expensive.
Technology Assessment
A clear, honest picture of where things stand — and a prioritized roadmap for fixing what matters — from someone with nothing to sell you.
Includes everything in the Website Audit, plus your full IT environment — devices, security, backups, email, vendor costs, and more. Not ready for that level yet? Start with a Website Audit →
- Day-to-day tools — Computers, email, file storage, backups, and software subscriptions.
- Security exposure — Passwords, software updates, phishing risk, and who has access to what — and who shouldn’t.
- Online presence — Website speed, mobile usability, search rankings, and whether your emails are landing in inboxes or getting flagged as spam.
- Vendor value — What you’re paying for vs. what you’re actually using.
What you get: A written report and prioritized roadmap that you own outright — ready to act on yourself, hand to any vendor you choose, or use to evaluate a new IT partner. Fixed-fee, scoped after a free intro call. No surprise invoices. No obligation to continue.
Most assessments — from solo operators to teams of 10 — fall between $250 and $500. Scoped precisely on your free intro call. Read the FAQ →
Website Audit
An outside look at what your website is doing for your business — and where it’s losing you customers.
Most small business websites were built years ago and haven’t been looked at critically since. We review your public-facing site from the outside — no access to your CMS or hosting needed — and tell you honestly what’s working, what isn’t, and what to fix first.
- Mobile usability — How the site performs for visitors on a phone, where the majority of searches now happen.
- Page speed — Load times, oversized images, and anything dragging performance down — with specific findings, not generic advice.
- Visual design & first impressions — Does the site look current? Does it represent your business the way you’d want a first-time customer to see it?
- Accessibility — WCAG 2.1 basics: keyboard navigation, color contrast, image alt text, and common barriers that affect visitors with disabilities.
- SEO health — Title tags, meta descriptions, heading structure, and whether search engines can actually read and index your content.
- Contact forms & calls-to-action — Are your forms working? Are they easy to find? Is it obvious what you want a visitor to do next?
- Security basics — HTTPS, security headers, and what your site is signaling to browsers and visitors about trustworthiness.
What you get: A written report covering every area above, findings ranked by impact, and a plain-language explanation of each issue — no jargon. Delivered within 5 business days. No access to your systems required; just your URL. Available to businesses anywhere in the US.
Most website assessments fall between $150 and $300 depending on site size and complexity. No intro call required to get started — send a message with your URL and we’ll scope it in a quick email exchange.
Vendor Proposal Review
Before you sign, get an independent read from someone with no stake in the outcome.
You’ve received a proposal from an IT company, managed services provider, or software vendor. It sounds reasonable. But it was written by someone who gets paid when you say yes.
Trailhead will review the proposal, explain in plain language what you’re actually agreeing to, flag anything unusual or overpriced, and give you an honest assessment of whether it’s a good fit for your business — or not.
- MSP and managed IT contracts — Is the scope right? Are the terms fair? Are you locked in longer than you need to be?
- Software and SaaS agreements — What are you actually paying for? What happens to your data if you leave?
- Hardware and infrastructure quotes — Is this the right equipment at a fair price, or an upsell?
- Cloud migrations and project proposals — Is the timeline realistic? Are there gaps in what’s included?
What you get: A written summary of findings and a recommendation — in plain language, with no agenda. Flat-fee, typically delivered within 48 hours of receiving the proposal documents.
Most reviews fall between $175 and $300. Standard (single contract, ≤15 pages) is $175. Complex (multi-vendor or layered agreement) is $300. Enterprise packages (40+ pages or 3+ vendor documents) are $500. Scoped in a quick call or email exchange before we start.
Ongoing Advisory
Stay ahead of problems instead of reacting to them — without the cost of a full-time IT hire.
After the assessment, many clients keep us on as an independent advisor — someone to call before signing a vendor contract, approving a big purchase, or starting a project that involves technology. We’re not your IT department; we’re your independent second opinion. Just honest advice when you need it.
Flexible Engagement Options
A check-in every few months to review progress, address new challenges, and update priorities.
Typically $300–$600/quarter — scoped after the initial assessment.
A full refresh once a year to revisit the roadmap and set the agenda for the year ahead.
Typically $500–$900/year — scoped after the initial assessment.
Reach out when something comes up.
$125/hr — 2-hour minimum.
How it usually starts: Most advisory relationships begin with a Technology Assessment — so every conversation forward has real context behind it.
Training Sessions
Custom sessions designed around the real threats and decisions your team faces — not a generic slide deck.
We offer live training sessions facilitated over Google Meet, built around the specific tools, risks, and challenges relevant to your organization. Whether you need a one-time team session or a more structured onboarding experience, sessions are scoped and priced as flat-fee projects.
- Security Awareness Training — A 60-minute session for your whole team covering phishing, passwords, and safe practices. Flat fee based on attendee count.
- Post-Assessment Roadmap Review — A deeper walkthrough of your IT Assessment findings with key stakeholders or your board.
- Vendor Decision Workshop — Structured evaluation of 2–3 competing tools or vendors before you commit.
- IT Onboarding for New Staff — A practical orientation for new hires covering your tech stack, security expectations, and best practices.
What you get: A focused, practical session with no filler. All sessions are live, facilitated, and tailored to your organization. Scope and pricing confirmed after a 15-minute discovery call.
Not sure if you need us? That’s fine.
That’s exactly what the intro call is for. No pitch, no pressure, no prep required. If we’re not the right fit, we’ll tell you that too.