Robert
Bettencourt

Founded and run CowboyMSP as a registered freelance web development business, designing and shipping custom, hand-coded websites and production-grade web applications for clients and for my own portfolio. Worked after hours alongside my full-time IT management role, taking each project end to end — from discovery and design through development, deployment, and ongoing support — with no page builders, no templates, and no recurring platform lock-in.

• Built professional multi-page business sites for service-industry clients — including Lindy Adams (a live client portfolio with gallery and contact form), Steele Cabling, Concrete Creations, and home-services demos — each engineered to rank in search and convert visitors into customers
• Designed and shipped custom countdown and event sites for trips, launches, and milestones, with live timers and bespoke theming delivered on a fixed 5–7 day turnaround
• Developed the Financial Calculator Hub, a suite of 24 free financial calculators backed by live mortgage rates, stock history, and currency data through a secure Cloudflare Workers layer
• Developed WorkTools Hub, a no-signup platform of salary, paycheck, hiring, and career tools for employees and employers, with AI-assisted tools routed through a privacy-preserving proxy
• Built QBTime, a multi-tenant SaaS platform that extends QuickBooks Time with scheduling and automated attendance reporting, featuring mandatory MFA, encrypted token storage, and a tamper-evident audit log
• Built Credential Vault for Confluence, an Atlassian Forge app providing client-side AES-GCM 256 encryption, PBKDF2 key derivation, live TOTP generation, and breach checking — published by CowboyMSP for the Atlassian Marketplace
• Created an interactive demo theme explorer so prospective clients can preview color palettes, typography, animations, and layouts before a build begins
• Hand-coded every project in HTML5, CSS, JavaScript, and React, deploying from Git to Cloudflare Pages and Workers with each site on its own subdomain — clients own their code outright
• Handled the full business side independently: scoping, quoting, client communication, project delivery, hosting, DNS, and SEO setup

Lead IT operations and service delivery for a Managed Service Provider and telecommunications company, overseeing a team of IT professionals across multiple client accounts. Serve as the primary escalation point for complex technical issues while driving operational maturity, process standardization, and long-term infrastructure strategy for clients throughout the region.

• Direct day-to-day operations of the IT support team, including workload management, performance reviews, mentorship, and professional development planning
• Own and enforce SLA compliance across all managed accounts, implementing monitoring dashboards and escalation workflows to maintain uptime and response commitments
• Authored and maintain the company-wide cybersecurity policy, including acceptable use, incident response procedures, and vendor access controls
• Lead end-to-end infrastructure projects for clients — scoping hardware refreshes, cloud migrations, and application deployments from initial design through vendor coordination, scheduling, budget management, and post-completion documentation
• Manage Microsoft 365 tenant administration, Azure AD / Entra ID, Intune MDM, and endpoint security across managed client environments
• Oversee deployment and configuration of SonicWall and WatchGuard firewall appliances, VPN solutions, VLAN segmentation, and network switch infrastructure
• Design and implement backup and disaster recovery strategies, conducting regular restore testing to validate RTO/RPO targets
• Evaluate, negotiate, and manage relationships with technology vendors, carriers, and third-party service providers on behalf of clients
• Standardize internal documentation, runbooks, and onboarding procedures using IT documentation platforms to improve team consistency and reduce institutional knowledge risk
• Collaborate with sales and account management teams to scope new client engagements, contribute to proposals, and ensure technical solutions align with client budgets and business objectives

Served a statewide distribution warehouse for 15 years across a dual role spanning enterprise software development and full-scope systems administration. Functioned as the primary technical resource for all application development initiatives and infrastructure operations, building systems and maintaining environments that the business depended on around the clock.

• Designed, developed, and maintained enterprise business applications in C# and Visual Basic (.NET), integrating Crystal Reports, IBM iSeries data, Exchange, and third-party REST APIs to support warehouse and distribution operations
• Architected and launched a customer-facing iOS application in Swift, delivering real-time order management, inventory visibility, and rebate tracking directly to field sales representatives
• Administered all company servers on a 24/7 on-call basis — including Active Directory, Exchange, SQL Server, IIS, Remote Access, File Services, and line-of-business application servers
• Managed user lifecycle across Active Directory and Microsoft 365, including provisioning, group policies, permissions, and offboarding procedures
• Maintained SQL Server databases including schema design, stored procedures, query optimization, backup schedules, and disaster recovery planning
• Introduced Git and Bitbucket source control to the development team, establishing branching strategies, code review workflows, and version management best practices
• Planned and executed hardware refresh cycles, server upgrades, and datacenter maintenance with minimal disruption to warehouse operations
• Configured and maintained firewall appliances, VPN access, network switches, and DHCP/DNS infrastructure across multiple physical locations
• Authored the company's cybersecurity policy, establishing acceptable use guidelines, data handling procedures, and security awareness standards
• Served as sole internal IT escalation point, providing Tier 3 support across all platforms and resolving issues independently without vendor dependency
• Coordinated with external vendors, software providers, and hardware suppliers to evaluate solutions, manage licensing, and support business growth initiatives