Trick Dog Technology
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Position Title: vCIO – Technical Solutions Consultant 

Department: Development 

Reports To: Director of IT

 

In this full-time leadership position, you will partner with Account Managers and work directly with SMB customers (typically between 20-200 users) to assess their IT and security needs and develop proactive solutions. As virtual CIO, you’ll consult with clients, collaborate internally with team to craft technology action plans and detailed Statements of Work (SOWs).  

 KEY RESPONSIBILITIES

  • Client Consultation & Needs Assessment: Collaborate with account managers to engage clients, understand their business objectives, and evaluate their current IT environment and security posture. Meet and consult with clients regularly.  Conduct on-site or virtual assessments to identify pain points and opportunities in areas such as cloud services, data protection, and network security.
  • Technology Roadmap Development: Design IT action plans and strategic roadmaps that address each client’s needs. Ensure plans align with the clients’ budgets, compliance requirements, and growth goals.
  • Proposal & SOW creation: Translate recommended initiatives into clear, detailed Statements of Work and proposals. Define project scope, deliverables, timelines, and resource requirements for each solution (for example, deploying a new SonicWall firewall configuration or rolling out M365 information protection features).
  • Subject Matter Expert on key client technologies: For example, Microsoft 365 platform & security (Azure AD/Entra ID, identity management, DLP setup, Conditional Access configuration), network security (SonicWall firewall policies, VPN setup, IDS/IPS), and wireless infrastructure (Aruba or similar enterprise Wi-Fi solutions). 
  • Collaboration: Work closely with internal engineers and support teams to hand off SOWs and ensure successful project execution. Monitor project progress, assist in resolving highlevel technical issues, and verify that delivered solutions meet the outlined objectives. Maintain clear communication with clients throughout implementation to manage expectations and achieve high customer satisfaction.
  • Relationship Management: Build long-term relationships and act as a virtual CIO for clients. Become a trusted technical advisor, explain technical concepts to clients in simple terms. o Lead regular technology review meetings (e.g. quarterly business reviews) to report on IT health, discuss emerging needs, and adjust action plans. 

                

JOB REQUIREMENTS

  • The ideal candidate has a strong technical background in cloud and network security, excellent communication and empathy in client interactions, and the ability to translate business requirements into actionable technical roadmaps.
  • 5+ years of experience in IT consulting, solutions architecture, or technical account management – preferably within an MSP or servicing SMB clients.
  • Proven track record of translating business requirements into technical solutions and managing multiple client engagements.
  • Familiarity with the business challenges of small to midsized organizations and the ability to tailor solutions accordingly.
  • Broad expertise in Microsoft 365 (administration of Exchange/Teams/SharePoint, Azure AD identity and access management) and its security capabilities (configuring DLP policies, Conditional Access, compliance settings).
  • Strong understanding of networking and security infrastructure, including hands-on experience with firewalls (SonicWall or similar) and enterprise wireless networks (Aruba or comparable APs).
  • Experience with enterprise Wi-Fi deployment and troubleshooting
  • Solid grasp of information security practices – e.g.,  endpoint protection, email security, backup and disaster recovery, internet/web filtering.
  • Consultative & Organizational Skills
  • A consultative mindset with the ability to collaborate effectively across sales and technical teams.
  • Skilled at leading strategic discussions with client stakeholders and guiding decision-makers through options and recommendations. 
  • Strong organizational skills to juggle multiple client projects, priorities, and timelines without loss of detail or quality.
  • A customer-centric approach to align IT solutions with business goals  
  • Broad understanding of SMB IT environments 
  • Strategic planning and solution design abilities  
  • Experience creating technical roadmaps aligned to business goals 
  • Excellent technical writing and documentation skills  
  • Excellent communication skills, both written and verbal, with an ability to convey technical concepts in clear, non-technical terms.
  • Active listening and empathy to truly understand client concerns and user experience. 
  • Adaptability to adjust solutions and communication style as client needs or technologies evolve.
  • Ability to foster trust, build relationships, manage expectations, and maintain longterm client partnerships.

 

 CERTIFICATIONS 

Preferred but not required:  

Microsoft 365 Fundamentals (MS-900), Sonicwall CSSA, CiscoCCNA (or comparable), CompTIA Network+/Security+ CompTIA Cloud+, MS-102, SC-900  

 

BENEFITS

  • Competitive Salary 
  • Health care including vision and dental 
  • Paid Vacation
  • Paid training and professional certifications 
  • 401K with 5% matching 
  • Career advancement opportunities 
  • Great team of talented peers 
  • Opportunity for leadership in a fast-moving, constantly learning environment  

 

WORKPLACE

•        Location: Three days onsite at Manhattan (Chelsea) office.  Two days remote.  Soon to be 4 days onsite. 

•        Hours: Full-time 9:00 AM-6:00 PM

•        Travel: Minimal, virtually all in NYC  

 

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