Remote Connectwise Jobs (NOW HIRING)

Location: Brooklyn/Remote

Department: Partner Growth

Job Type: Full-Time

Position Summary

At My IT Crew (MY IT CREW), we don't just serve clients, we partner with them. As a vCIO, you are the strategic quarterback for assigned accounts. This role blends relational leadership with technical and business acumen to ensure every client relationship is proactive, profitable, and aligned with MY IT CREW's commitment to world-class managed services.
You'll be responsible for client satisfaction, strategic planning, and business expansion across the client lifecycle-from onboarding through ongoing reviews and renewals. You'll lead recurring Technology Review Meetings, build annual IT roadmaps, quote solutions, manage licensing and lifecycle, and serve as the escalation point for account-related concerns. Your impact directly influences MY IT CREW's retention, revenue, and reputation.

Key Responsibilities

Client Strategy & Relationship Management

• Serve as the single point of accountability for assigned clients post-onboarding.

• Lead scheduled Cadence Calls and Technology Business Reviews (TBRs) to ensure alignment with client goals.

• Develop and maintain strategic roadmaps aligned with client objectives and MY IT CREW best practices.

• Anticipate needs through data and relationship cues-resolving concerns before they escalate.

• Assist with third-party vendor relationships to relieve clients of technical burdens.

Opportunity Management & Growth

• Quote and scope solutions for hardware, licensing, services, and projects.

• Identify and execute cross-sell and upsell opportunities-move clients toward standard stack adoption.

• Collaborate with Project Engineers, TAMs, vCIOs, and Sales Engineers to ensure solution fit.

• Coordinate with vendors for competitive pricing and availability.

Lifecycle, Licensing & Asset Management

• Own the lifecycle calendar: warranties, licensing, contract renewals.

• Maintain asset intelligence via ITGlue.

• Present lifecycle and licensing updates as part of proactive roadmap conversations.

• Partner with Inventory & Procurement to ensure timely ordering, delivery, and implementation.

Escalation & Issue Resolution

• Act as the non-technical escalation point for service dissatisfaction or process breakdowns.

• Facilitate internal triage between Service, TAM, and Projects teams to resolve client issues.

• Provide transparency and continuity of communication during escalations.

Process Excellence & Documentation

• Ensure all Technology Review Meetings follow My IT Crew's playbook (agenda, post-review tasks, documentation).

• Keep ConnectWise, IT Glue updated with client notes, roadmap items, and account metrics.

• Maintain up-to-date client budgets including strategic initiatives and anticipated spend.

Cross-Functional Collaboration

• Engage with TAMs, Projects, CS, and Centralized Services to execute client initiatives.

• Deliver feedback loops from client interactions to internal stakeholders.

• Participate in regular internal syncs (weekly AM meetings, EOS L10s, 1-on-1s).

Required Experience & Skills

• 2+ years in vCIO, Account Management, or Client Success within an MSP or IT consulting environment.

• Working knowledge of IT infrastructure, MSP services, and business technology strategy.

• Proficiency with quoting, solution design, and technology budgeting.

• Experience using tools such as ConnectWise, ITGlue.

• Exceptional relationship-building, communication, and follow-up skills.

• Strong documentation, task tracking, and time management.

Performance Metrics (KPIs)

• Client Engagement: % of Cadence Calls and Technology Reviews completed on schedule.

• Client Retention & CSAT: Retention rate of assigned accounts, CSAT from account-related tickets.

• Opportunity Management: Revenue generated from quoting, % closed-won opportunities.

• Lifecycle Execution: % of clients with current lifecycle plans and renewals handled on time.

• Strategic Planning: % of clients with documented roadmaps and annual budgets.

• Ticket Resolution: SLA compliance for account/quoting-related tickets.

Culture Fit & Philosophy

At My IT Crew, we are practical problem-solvers who believe in clarity, accountability, and momentum. We are not vendors, we are partners. Our clients rely on us to lead, not just react. As a vCIO, you will be the voice of that leadership.

We are building something great-and this role is a cornerstone.