Every IT company you've ever talked to was trying to sell you something. Trailhead doesn't. No hardware. No software. No managed services contract. Just honest advice about what your business actually needs — from someone who has nothing to gain by steering you wrong.
Trailhead Technology Consulting is a vendor-neutral IT consulting practice founded by Justin Bennett and based in Shelburne, Vermont. We serve small businesses (typically 1–150 employees) across all six New England states: Vermont, New Hampshire, Maine, Massachusetts, Connecticut, and Rhode Island.
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.
Most of our clients are running on a mix of tools that just sort of happened over time, with no clear plan and no one to turn to for an honest second opinion. We're that second opinion.
Founder: Justin Bennett
Justin Bennett is a Vermont-based technology professional with hands-on experience across a wide range of business environments — from small local organizations to larger enterprise operations. 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.
Location: 145 Pine Haven Shores Rd. #1000a, Shelburne, VT 05482
IT Consulting Services for New England Small Businesses
We offer three core services, all fixed-fee, scoped upfront, and delivered with no vendor affiliations or referral kickbacks.
Technology Assessment — $250–$500 for most small businesses
A comprehensive audit of your business technology — computers, 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. No surprise invoices. No obligation to continue.
Security exposure — Passwords, software updates, phishing risk, and who has access to what.
Online presence — Website speed, mobile usability, search rankings, and email deliverability.
Vendor value — What you're paying for vs. what you're actually using.
Most assessments — from solo operators to teams of 10 — fall between $250 and $500. Scoped on your free intro call.
Vendor Proposal Review — $175–$500
Before you sign an IT contract, MSP proposal, or software agreement, 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.
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
Stay ahead of problems instead of reacting to them — without the cost of a full-time IT hire. After the 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.
On-demand: $125/hr, 2-hour minimum
Quarterly advisory: typically $300–$600/quarter
Annual advisory: typically $500–$900/year
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:
Retail shops and storefront businesses in Vermont and New England
Restaurants and hospitality operations
Professional practices: attorneys, accountants, healthcare providers, consultants
Reach Out — Send a message and we'll reply personally with a link to schedule a free intro call. No queues, no chatbots.
Free Intro Call — A short, no-pressure conversation to confirm Trailhead is the right fit. Justin takes notes during the call and sends a fixed-fee estimate right after. Once the invoice is paid, you receive a link to book your 1-hour tech consultation.
Tech Consultation — A 1-hour call to walk through your environment and priorities in detail. Justin handles all documentation — you just talk through your situation.
Report Delivered — Your full IT assessment and prioritized roadmap, delivered within the agreed timeline. Clear, actionable, and yours to keep.
Client Testimonials
"I was working with a client who needed help migrating a SQL server. 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."
"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. 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."
"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. 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."
Frequently Asked Questions
What does the process look like?
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. During the call, Justin takes notes. Right after, he sends a fixed-fee estimate. Once the invoice is paid, you automatically receive a link to book a 1-hour tech consultation. Afterward, Justin delivers your full IT assessment and prioritized roadmap.
How much does an IT Assessment cost?
Most assessments — from solo operators to teams of 10 — fall between $250 and $500. Pricing is based on organization size, the number of domains, and any optional add-ons. Fixed-fee, confirmed on your free intro call. No surprise invoices.
Do you manage our systems or provide helpdesk support?
No. Trailhead is a consulting and advisory practice. We do not manage day-to-day IT, act as a managed service provider (MSP), or run a helpdesk. We help you build a clear technology strategy and make smarter decisions. If you need hands-on managed support, we can help you identify the right partner.
Do you sell hardware, software, or cloud services?
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 accurate, unbiased advice.
What's the difference between an MSP and an independent IT consultant?
A managed service provider (MSP) manages your IT infrastructure on an ongoing basis — monitoring systems, running a helpdesk, handling software updates. They earn recurring revenue from your technology spend. An independent IT consultant like Trailhead works differently: we don't manage your systems or earn commissions. We help you understand your technology environment, make smarter decisions, and avoid being steered wrong by vendors who have a financial interest in what you buy.
What should I do if a business email account gets hacked?
Act immediately from a device you trust. Change the password, enable two-factor authentication, then check your email settings for forwarding rules you didn't create. Check your sent folder for messages you didn't send, and notify your bank or payroll provider if those accounts use the same email for login or recovery.
Which states do you serve?
We serve organizations across all of New England: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont. Trailhead is based in Shelburne, Vermont. Most engagements are conducted remotely, with on-site visits available as needed.
A monthly podcast for New England small business owners covering cybersecurity, AI, email security, and practical IT decisions. Hosted by Justin Bennett. Free, no jargon, no sales pitch.
Upcoming episodes:
Episode 1: Your Business Already Has an IT Department — You Just Don't Know It
Episode 2: The Email That Almost Broke the Business — business email fraud and how to stop it
Trailhead Technology Consulting hosts free live webinars for New England small business owners. Topics include email security, phishing defense, and practical technology basics.
Upcoming: Email Security 101 for Small Businesses — June 12, 2026, 12:00 PM ET. Free, open registration.