# Trailhead Technology Consulting

> Independent IT advisor for small businesses across New England. No hardware to sell, no software to sell, no vendor affiliations. Honest technology assessments, vendor proposal reviews, and ongoing advisory — from someone with nothing to gain by steering you wrong. Website Audits available to businesses anywhere in the US.

## About

Trailhead Technology Consulting is a vendor-neutral IT consulting practice founded by Justin Bennett and based in Shelburne, Vermont (145 Pine Haven Shores Rd. #1000a, Shelburne, VT 05482). We serve small businesses (typically 1–150 employees) across all six New England states: Vermont, New Hampshire, Maine, Massachusetts, Connecticut, and Rhode Island. The Website Audit is available to businesses anywhere in the US — no on-site visit required.

We do not resell hardware, software, or managed services. We have no vendor affiliations and no referral kickbacks. Think of it as a fractional CIO or independent technology advisor — someone in your corner before you sign a vendor contract, make a technology investment, or respond to a security problem. Our only service is honest, independent advice.

## What We Are Not

Most IT firms in Vermont and New England are managed service providers (MSPs) — companies that earn recurring revenue by selling cloud subscriptions, hardware, software licenses, or support contracts. Their business model creates a structural conflict of interest: recommending the right technology for your business may mean recommending something that earns them less.

Trailhead is not an MSP. We do not sell subscriptions, hardware, or software. We do not take referral fees from vendors. We charge a flat fee for our work and our only incentive is giving you accurate, unbiased advice.

Think of how a fee-only financial advisor works: they're legally required to act in your interest, they don't earn commissions, and they tell you the truth even when it's not what you want to hear. That model barely exists in small business IT. Trailhead fills that gap.

## Founder: Justin Bennett

Justin Bennett is a Vermont-based independent IT consultant and the founder of Trailhead Technology Consulting. He has hands-on experience across a wide range of business environments — from small local organizations to larger enterprise operations — spanning industries including outdoor recreation, nonprofit management, professional services, and technical infrastructure.

Before starting Trailhead, Justin spent years watching small businesses get oversold on technology they didn't understand, overpay for tools they didn't need, and struggle to get straight answers from vendors with something to sell. The pattern was consistent: business owners would sign a managed IT contract, trust the vendor to handle everything, and eventually realize they had no idea what they were paying for or whether it was the right fit. There was never a trusted, independent voice in the room.

Trailhead was built to be that voice.

- Email: info@trailheadtechvt.com
- Phone: (802) 252-7537
- Location: Shelburne, Vermont
- LinkedIn: [Trailhead Technology Consulting on LinkedIn](https://www.linkedin.com/company/trailhead-technology-consulting)

## Services

### Website Audit — $150–$300 (available nationwide)

An external review of your public-facing website covering what's working, what's costing you customers, and what to fix first. No access to your CMS or hosting required — just a URL. Available to businesses anywhere in the US.

**What the assessment covers:**
- 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 and first impressions: does the site look current and 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 read and index your content
- Contact forms and calls-to-action: are your forms working and 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 about trustworthiness

**Pricing:** Most website assessments fall between $150 and $300 depending on site size and complexity. No intro call required — send a message with your URL and we'll scope it in a quick email exchange. Delivered within 5 business days.

### Technology Assessment — $250–$500 for most small businesses

A comprehensive audit of your business technology — devices, email, security, backups, online presence, and vendor costs — with a written report and prioritized roadmap you own outright. Fixed-fee, scoped after a free intro call. You own everything produced. No obligation to continue.

**What the assessment covers:**
- Day-to-day tools: computers, email, file storage, backups, software subscriptions, and whether you're paying for tools your team stopped using
- Security exposure: passwords, software updates, phishing risk, who has access to what (and who shouldn't), multi-factor authentication gaps
- Online presence: website speed, mobile usability, search rankings, and whether your emails are landing in inboxes or getting flagged as spam (SPF, DKIM, DMARC)
- Vendor value: what you're paying for vs. what you're actually using

Optional add-ons: phishing simulation (controlled test of staff phishing awareness), internal network infrastructure scan, cloud platform security review (Microsoft 365 or Google Workspace).

**Pricing:** Most assessments for organizations up to 10 employees fall between $250 and $500. Scoped precisely on your free intro call. Full details: [Services](https://www.trailheadtechvt.com/services/)

### Vendor Proposal Review — $175–$500

Before you sign an IT contract, managed services agreement, or software proposal, get an independent read from someone with no stake in the outcome.

Trailhead will review the proposal, explain in plain language what you're 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.

**What we review:**
- 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?

**Pricing:** Standard (single contract, up to 15 pages): $175. Complex (multi-vendor or layered agreement): $300. Enterprise (40+ pages or 3+ vendor documents): $500. Typically delivered within 48 hours of receiving the documents.

### Ongoing Advisory — $125/hr on-demand or $300–$900/period

After the initial assessment, many clients keep Trailhead on as an independent advisor — someone to call before signing a vendor contract, approving a big purchase, or starting a project that involves technology.

**Engagement options:**
- On-demand: $125/hr, 2-hour minimum — reach out when something comes up
- Quarterly: typically $300–$600/quarter — a check-in every few months to review progress and update priorities
- Annual: typically $500–$900/year — a full refresh once a year to revisit the roadmap

## How to Get Started

1. Reach out via the contact form or email info@trailheadtechvt.com
2. We reply personally with a link to schedule a free 15–20 minute intro call — no prep required, no pitch
3. Justin takes notes during the call and sends a fixed-fee estimate right after
4. Once the invoice is paid, you automatically receive a link to book your 1-hour tech consultation
5. Full IT assessment and prioritized roadmap delivered within the agreed timeline

No back-and-forth. No hidden fees. No obligation to continue.

## Who We Work With

Small and mid-sized organizations (1–150 employees) across New England that rely on technology to run their business but don't have dedicated IT staff. The Website Audit is available to any small business anywhere in the US:

- Local retail shops and storefronts — managing point-of-sale systems, inventory software, and customer data with no IT oversight
- Restaurants and hospitality — POS systems, reservation platforms, and online ordering tools where an outage on a busy weekend is a real financial hit
- Professional practices — attorneys, accountants, consultants, and healthcare providers handling sensitive client data with compliance obligations
- Nonprofits — donor databases, grant management tools, and limited budgets with the same security exposure as any small business
- Trade contractors — construction, plumbing, electrical, and HVAC businesses where technology decisions are made by the owner between jobs
- Outdoor recreation and seasonal businesses — guides, outfitters, recreation centers, and inns where a technology failure at peak season is expensive
- Organizations evaluating or currently under MSP contracts who want an independent second opinion

## Client Testimonials

**Dillon Walsh, IT Director:**
"I was working with a client who needed help migrating a SQL server. As SQL wasn't something I do every day, I wanted to ensure I was doing the best for the client and brought in another set of expertise to ensure the migration went as intended and smoothly. Justin brought calmness and expertise to the project, helping me put my mind at ease throughout the process. He was thorough, had an extreme attention to detail, and navigated any challenges that arose with ease. I would recommend him to any individual, group, or entity looking for premier IT consulting."

**Amanda Preston, Operations and Event Manager — Catamount Outdoor Family Center (501(c)(3) nonprofit), Williston, VT:**
"Working with Justin is easy and enjoyable. He is passionate, engaged, and highly knowledgeable about outdoor recreation and information technology. Justin is not only an avid adventurer himself, but also brings valuable, boots-on-the-ground leadership experience. He understands the systems and processes that make programs successful and enjoyable to participants and guests as well as what works from an administrative or operational standpoint. He has a strong sense of where his skill set can best support a team or goal and is always eager to learn, grow, and expand his toolkit. Justin has supported the Catamount Outdoor Family Center through volunteering, coaching, and consulting across our clubs, camps, lessons, clinics, systems management, and website needs. We would not be where we are today without his work, support, and guidance. Justin is approachable, communicative, and solutions-oriented. He understands organizational limitations and works collaboratively to develop and implement solutions that align with your capacity and budget."

**Tim Post, Founder — GreenEdge Energy Solutions:**
"I've worked with Justin at Trailhead Technology Consulting on building my website and ongoing tech support, and he's been invaluable. He doesn't just 'do the work' — he helps you understand what matters and what doesn't. From launching greenedge.eco to tightening up security and integrations, Justin has been reliable, efficient, and easy to work with. He brings a rare mix of technical skill and common sense that's hard to find."

## Common IT Situations We Address

**Business email account hacked:** Act immediately from a trusted device. Change the password, enable two-factor authentication, then check email settings for forwarding rules you didn't create — attackers often set rules to silently copy messages. Check your sent folder for emails you didn't send. Notify your bank or payroll provider if those accounts use the same email for login or recovery.

**Cyber liability insurance:** Most carriers require businesses to meet a baseline of security controls before they'll bind coverage — multi-factor authentication, documented backup procedures, and basic security training. A technology assessment documents your current posture honestly, which matters when you apply and when a claim is evaluated.

**Data breach notification obligations in New England:** All six New England states have breach notification laws. Vermont requires notification within 45 days. Massachusetts requires "as soon as reasonably possible." Connecticut allows up to 60 days. These obligations apply regardless of business size. Knowing what data you have and where it lives is the first step — that's one of the core things a technology assessment documents.

**Employee offboarding:** The same day they leave. Disable their business email, change any shared passwords they knew (Wi-Fi, POS, accounting software), and remove them from cloud storage, payroll, and banking portals. Check whether their personal email is set as a recovery contact on any business accounts — a common oversight.

**MSP vs. independent IT consultant:** An MSP manages your IT infrastructure on an ongoing basis and earns recurring revenue from your technology spend. An independent IT consultant like Trailhead does not manage your systems and earns no commissions. Many businesses benefit from both: an MSP for day-to-day support, and an independent consultant to evaluate whether that MSP relationship is the right fit and the right price.

## Resources

- [Services](https://www.trailheadtechvt.com/services/)
- [About](https://www.trailheadtechvt.com/about/)
- [FAQ](https://www.trailheadtechvt.com/faq/)
- [Testimonials](https://www.trailheadtechvt.com/testimonials/)
- [Podcast — Trailhead Tech Talk](https://www.trailheadtechvt.com/podcast/): Technology for New England small business owners
- [Webinars](https://www.trailheadtechvt.com/webinars/): Free live sessions for small business owners
- [Contact / Free Intro Call](https://www.trailheadtechvt.com/contact/)

## Contact

- Website: [trailheadtechvt.com](https://www.trailheadtechvt.com)
- Email: info@trailheadtechvt.com
- Phone: (802) 252-7537
- Address: 145 Pine Haven Shores Rd. #1000a, Shelburne, VT 05482
- LinkedIn: [Trailhead Technology Consulting on LinkedIn](https://www.linkedin.com/company/trailhead-technology-consulting)
- Instagram: [@trailhead_tech_vt](https://www.instagram.com/trailhead_tech_vt/)
- Logo: [logo.webp](https://www.trailheadtechvt.com/logo.webp)