Starting Five Technology in Baltimore: On-Site and Remote IT Support for Small to Midsize Businesses
Starting Five Technology is a Baltimore-based IT services firm that handles both managed IT support and one-off project work for small to midsize businesses across the region, with a stated focus on keeping systems running and security threats out rather than pursuing enterprise-scale contracts.
What Starting Five Technology actually does
The firm operates as a hybrid managed services provider. It takes on retainer clients who receive ongoing monitoring, maintenance, and priority support, and it also accepts project-based engagements like network buildouts, server migrations, or security audits. The company serves roughly 40 to 60 active clients, a scale that allows faster response times than larger regional competitors but requires it to maintain clear boundaries on scope. Technicians handle both in-office visits and remote troubleshooting; the firm operates out of a single Baltimore location and does not maintain satellite offices.
Services and pricing
Starting Five's managed IT retainers begin around $800 per month for a small office (five to ten users) and scale with user count and infrastructure complexity; most clients with 15 to 30 users fall in the $1,500 to $3,000 monthly range. That covers 24/5 remote monitoring, patch management, email and data backups, and next-business-day onsite response for hardware failure. After-hours emergency support costs extra and is not bundled into the base retainer.
Project work is quoted individually. A typical network assessment runs $1,500 to $3,000 depending on complexity. Server migrations and new-office buildouts usually land between $5,000 and $15,000. Hourly rates for break-fix work are $150 per hour, with a one-hour minimum.
Verification note: retainer pricing adjusts annually; confirm current rates directly before budgeting.
How it compares to other Baltimore IT services
Most Baltimore IT firms fall into two camps: large regional integrators (Carahsoft, SHI) that focus on government contracts and enterprise clients, and solo freelancers or very small shops that lack formal backup coverage. Starting Five occupies a middle ground. It is larger than a one-person operation and offers accountability (a company entity, documented SLAs, a second technician for coverage), but smaller than firms that bill $200+ per hour or require $10,000 minimums.
Compared to Dyn Systems, another Baltimore-based managed services provider with a slightly larger client base, Starting Five charges less for small-office retainers (roughly 20 percent lower) but does not offer the same depth of advanced security services like penetration testing. For a business with five to fifteen employees and a standard technology stack, Starting Five delivers faster decision-making and lower overhead. For a firm needing compliance-intensive security work or multiple concurrent projects, Dyn Systems may be the better fit.
Solo techs and local repair shops (abundant in Canton and Fells Point) cost less per hour but offer no 24/5 monitoring, no guaranteed response time, and no disaster recovery planning. They suit one-off repairs; they do not suit businesses that cannot afford unexpected downtime.
Who it suits and who it does not
Starting Five works well for professional services firms, nonprofits, small manufacturers, and medical offices with ten to thirty employees, a few servers or a cloud-dependent setup, and a need for reliable, predictable support without enterprise-level complexity. The firm also takes on single-project work for larger clients, such as a network redesign for a regional chain opening a new Baltimore warehouse.
It is not the right fit for solo operators with minimal IT needs (you'll pay for a retainer you don't use), for organizations running custom legacy software that requires vendor-specific expertise, or for firms that demand 24/7/365 support with guaranteed one-hour response times. Startups bootstrapping on free cloud services typically don't need managed services yet.
What the first visit involves
Initial contact usually happens via phone or email. The firm schedules a no-charge 30-minute discovery call to understand current systems, pain points, and budget constraints. If there is interest, a technician visits the office (or conducts a remote session) for a deeper assessment, producing a written proposal within five business days. That assessment costs $300 if no retainer is signed; the fee is credited against the first month's service if the client becomes a managed customer.
Once onboarded, a technician handles device imaging, backup configuration, and any immediate fixes, a process that typically takes one or two half-day visits for a small office.
Hours, location, and logistics
Starting Five operates from an office in Canton and keeps standard business hours, Monday through Friday, 8:30 a.m. to 5:30 p.m. Remote support and incident resolution extend to 6:00 p.m. on weekdays; after-hours emergencies are handled case-by-case at a higher rate. Parking is available on-street or in a shared lot; most work happens either at client sites or remotely, so the office visit is brief.
For scheduling or to request a discovery call, contact the firm directly to confirm current availability.
Starting Five fills a legitimate gap in Baltimore's IT services landscape: it is competent enough to handle the systems a growing small business depends on, but scaled to treat each client as more than a line item in a support queue.
