VP of IT

Simpatico Systems is a group of engineers and innovators who align our goals with our customers’ organizational objectives—delivering IT, cybersecurity, automation, and AI-driven intelligence solutions. We design systems that are simple, effective, affordable, and results-driven. We take the time to understand business needs and create solutions that improve efficiency, reduce friction, and enable meaningful outcomes. 

Most of all: We have a ton of fun solving business and technology problems! 

As a company, Simpatico Systems was incorporated in 2013 from the merger of Ironfish Technologies and Business Audio Environments (BAE). With a rich history of delivering exceptional service for nearly 50 years, our teams are committed to helping customers (and each other) do their best work. As we continue expanding into new markets and scaling our MIP (Managed Intelligence Provider) model, we are looking for a strong, forward-thinking leader to help shape the future of our technical operations and innovation strategy. 

Our Opportunity 

The Vice President of IT plays a critical executive leadership role in driving the performance, scalability, and evolution of Simpatico’s service delivery organization. This leader is responsible for overseeing the Helpdesk, Escalation, Project Delivery, and SOC teams—ensuring operational excellence, technical accountability, and exceptional client outcomes. 

This role requires a balance of hands-on technical competency and strategic vision. You will lead during high-stress scenarios such as system outages or security incidents while also shaping long-term infrastructure strategies for both Simpatico and our customers. 

In addition, this role will own and lead all AI and automation initiatives across the organization, helping transform how we deliver services, improve efficiency, and create differentiated value in the marketplace. 

As a member of the Executive Leadership Team, this individual must embody our culture, drive alignment across departments, and serve as a key leader in our continued growth and transformation. 

What you’ll do: 

In this role, you will lead a diverse team of technical leaders and engineers while building scalable systems, improving operational discipline, and driving innovation across the organization. Your responsibilities include: 

• Lead and manage all core IT service delivery functions, including Helpdesk, Escalation, Project Delivery, and SOC 

• Establish clear accountability, performance standards, and KPIs across all technical teams 

• Serve as the senior escalation point for major incidents, outages, and high-risk technical situations 

• Ensure rapid, effective response and resolution during high-pressure scenarios 

• Design and execute infrastructure strategies for both internal systems and customer environments  

• Create, maintain and hold accountability for complete department budgets including: resource usage, staffing, and cost control accounting. 

• Partner with sales and customer success teams to align service delivery with customer expectations 

• Drive continuous improvement in service delivery processes, tooling, and documentation 

• Lead the development and execution of Simpatico’s AI and automation strategy across all departments 

• Identify and implement automation opportunities that reduce operational friction and improve scalability 

• Collaborate cross-functionally with operations, sales, finance, and executive leadership 

• Build and mentor high-performing leaders within each technical function 

• Continuously evaluate emerging technologies and incorporate them into service delivery where appropriate 

• Work with Simpatico’s CISO to ensure adherence to security, compliance, and best-practice frameworks (NIST, SOC2, etc.) 

• Contribute to strategic planning and decision-making as a member of the executive leadership team 

What you have: Required 

• 10+ years of experience in IT, service delivery, or technical operations leadership 

• Proven experience managing multiple technical teams (helpdesk, engineering, security, or project delivery) 

• Strong technical foundation across infrastructure, networking, cloud, and cybersecurity 

• Demonstrated ability to lead during high-stress situations such as outages or security incidents 

• Strategic mindset with the ability to design scalable systems and long-term infrastructure plans 

• Experience driving operational efficiency and process improvement in a fast-paced environment 

• Strong understanding of AI, automation, and digital transformation concepts 

• Excellent leadership, communication, and decision-making skills 

• Ability to balance technical depth with executive-level thinking 

• Passion for building teams, developing talent, and creating a strong culture 

Nice to Have 

• Experience in an MSP, MSSP, or technical services organization 

• Familiarity with ConnectWise, ITGlue, RMMs, or similar MSP tool stacks 

• Experience implementing AI or automation platforms (Copilot, RPA, workflow platforms, etc.) 

• Knowledge of ITIL, NIST, CIS, or other service/security frameworks 

• Experience participating in executive leadership or board-level discussions 

• Background in scaling operations within a high-growth organization 

What you’ll get 

• Comprehensive Compensation and Benefits package 

• Work/Life Balance: Company-sponsored training, certifications, and leadership development 

• A seat at the executive table, helping shape the future of Simpatico Systems 

• Not just a job, but a career—with the opportunity to lead the evolution of IT, AI, and automation in a rapidly growing organization 

Culture Fit Matters 

At Simpatico Systems, culture is not an afterthought; it’s a requirement. We are looking for a leader who: 

• Leads with integrity, accountability, and humility 

• Thrives in a collaborative, fast-moving environment 

• Brings energy, curiosity, and a passion for innovation 

• Can inspire teams while holding a high bar for performance 

• Believes in aligning technology with real business outcomes