Virtual Chief Information Officer (vCIO)

Virtual Chief Information Officer (vCIO)

At simpleroute, a Vermont-born Managed Service Provider, our Virtual Chief Information Officers (vCIOs) are the strategic backbone of our client relationships, guiding businesses toward technology solutions that drive growth and stability. Rooted in our commitment to understanding clients unique needs, our vCIOs blend technical expertise with business acumen to deliver tailored recommendations. As a vCIO, you ll lead our upper-tier clients - those with significant revenue or complex compliance requirements - through strategic planning, leveraging tools like MyITProcess to align technology with their goals. Join our collaborative team in South Burlington to make a lasting impact, building trusted partnerships and shaping simpleroute s growth in the Green Mountain State and beyond.

Responsibilities

This role has an approximate workload breakdown as follows:

Strategic Client Engagement: 50%
Technology Alignment and Planning: 25%
Team Collaboration and Growth Initiatives: 15%
Professional Services Support: 10%

A list of job responsibilities includes:

• Strategic Client Engagement: Build and maintain trusted relationships with upper-tier clients (e.g., $7k+ MRR or compliance-driven), acting as their primary strategic advisor to align technology with business objectives.
• Technology Roadmapping: Develop and implement comprehensive technology plans using MyITProcess, ensuring alignment with client goals and industry best practices.
• Compliance and Risk Management: Guide clients through compliance requirements (e.g., HIPAA, PCI), recommending solutions to mitigate risks and ensure regulatory adherence.
• High-Level Technical Oversight: Provide technical guidance on complex projects (e.g., VLAN configurations, router setups, virtualization), coordinating with Professional Services for execution while stepping in for critical tasks as needed.
• Client Onboarding and Transitions: Lead onboarding for high-value clients, coordinating with internal teams and client stakeholders to ensure seamless transitions to simpleroute s management.
• Business Growth Contributions: Identify opportunities to expand simpleroute s services, leveraging insights from client engagements to inform business development strategies.
• Team Collaboration: Partner with Operations, Professional Services, and other vCIOs to deliver cohesive client support, sharing insights to refine processes and enhance service delivery.
• Reporting and Documentation: Maintain detailed records of client plans, alignment activities, and compliance status, generating reports to highlight progress and opportunities.
• Time Capture: Accurately log 100% of work hours in our Professional Services Automation (PSA) software to support operational efficiency.
• Continuous Learning: Stay current on industry trends, technologies, and TruMethods best practices to provide informed recommendations.
• Process Improvement: Identify opportunities to streamline client engagement processes, contributing to the evolution of simpleroute s vCIO framework.
• Other Tasks: Perform additional duties as assigned by management to support simpleroute s mission.

Requirements

Candidates should demonstrate expertise in strategic IT planning and client relationship management, supported by a combination of formal education, certifications, and work experience. A minimum of five years in IT leadership roles, including vCIO or professional services experience, is required.

Among other criteria, the following requirements will be evaluated:

• Proven ability to develop and execute technology roadmaps that align with business goals, ideally using frameworks like TruMethods or MyITProcess.
• Strong understanding of compliance requirements (e.g., HIPAA, PCI) and risk management strategies.
• Advanced technical knowledge in networking (e.g., VLANs, routing, firewalls), virtualization (e.g., Hyper-V, VMware), and cloud platforms (e.g., Microsoft 365, Azure).
• Experience with Professional Services Automation (PSA), Remote Monitoring and Management (RMM), and ticketing systems.
• Exceptional verbal and written communication skills, with the ability to translate complex technical concepts for non-technical stakeholders.
• Strong interpersonal skills to build client trust and address concerns with empathy and professionalism.
• Excellent analytical and problem-solving skills to navigate complex client challenges.
• Reliable transportation for occasional on-site client visits within Vermont.
• Personal background check required prior to employment.

About simpleroute

Founded in 2009 in South Burlington, simpleroute is a Vermont-grown Managed Service Provider dedicated to delivering exceptional IT services. Our team thrives on understanding our clients, anticipating their needs, and providing solutions that empower their success. We foster a challenging yet fun environment, offering ample opportunities for growth through education and hands-on projects. Join us to make a difference for our clients and contribute to our tight-knit, community-driven culture.

simpleroute offers a competitive benefits package, including:

• 10 paid holidays
• Up to 4-weeks PTO with seniority
• 1-week of sick leave
• 401k program with up to 4% match
• Health, dental and vision programs
• AD&D, life insurance and disability
• Education opportunities and approved certification reimbursement
• Gym membership
• Flexible and fun work environment

For inquiries, contact us at or