Helper Connectwise Jobs in Springfield, MA (NOW HIRING)

Senior Case Agent 

Summary 

Paragus IT is the largest outsourced IT vendor in the Pioneer Valley, and we are just getting started.  We aspire of serving 1000 customers across the entire country, and we won’t stop until we get there. Ranked as one of Forbes Small Giants, we have an intense focus on culture, people, process, and continuous improvement. We are determined to be the best at everything we do, and we aren’t afraid to do the hard work required to get there. 

We’re on a mission to deliver peace of mind through human-first IT experiences. We’re not just fixing problems - we’re building trust. As a Senior Case Agent, you’ll be the go-to expert for our most complex technical challenges, leading with empathy, precision, and expertise. You’ll support clients across networking, Microsoft 365, and application environments - all while mentoring your peers, strengthening documentation, and modeling what exceptional IT service looks like. This position is part of our Service Desk team and reports directly to the Service Team Manager. The ideal candidate is an independent problem-solver who knows when to raise the flag and loves turning chaos into calm. 

You will succeed in this role if you: 

• Can troubleshoot complex issues involving networking, Microsoft 365 and Application support. 

• Communicate clearly and compassionately, translating technical fixes into client peace of mind. 

• Can swat away a nerf dart while troubleshooting an issue 

• Take ownership of tough cases and raise the flag quickly when you need backup. 

• Mentor other technicians through documentation, training, and collaboration. 

• Thrive in a fast-paced environment and can adapt priorities in a client crisis. 

• Live by our Service Excellence principles - combining technical precision with exceptional human connection. 

Qualifications: 

• 5+ years of experience in IT support, systems administration, or network engineering 

• Strong technical expertise across Microsoft 365, including mailflow, Exchange Online, and security compromise response 

• Advanced knowledge of networking concepts such as firewalls, VPNs, and routing/switching 

• Proficient in application support, endpoint/server troubleshooting, and security fundamentals 

• Proven experience conducting Root Cause Analyses (RCA) and documenting clear, lasting resolutions 

• Familiarity with help desk ticketing systems such as ConnectWise, Autotask, or similar MSP tools 

• Excellent communication skills—able to translate technical findings into clear, empathetic explanations for clients and colleagues 

• Calm under pressure with the ability to stay composed and effective during client crises 

• Naturally curious and resourceful, asking great questions and digging deep to find solutions 

• Highly self-motivated and accountable; takes ownership of complex issues while knowing when to escalate for support 

• Strong mentoring mindset; enjoys coaching and guiding others to improve their technical capability 

• Proactive contributor to process improvement, documentation, and automation efforts 

• Ability to balance speed with quality, ensuring solutions are efficient and built to last 

• Scripting or automation experience is a plus 

Responsibilities 

• Troubleshoots and resolves technical issues either remotely or at a client site within defined SLAs 

• Participates on projects as assigned 

• Provides technical assistance for escalated issues 

• Appropriately manages expectations of clients and peers 

• Provides on-call 24/7 support after business hours at least 3 weeks per year 

• Lead and perform Root Cause Analyses (RCA) for recurring or complex client issues. 

• Apply Service Excellence Principles in daily workflow to deliver human-first solutions. 

• Maintain high standards for case documentation and communication. 

• Proactively identify opportunities to improve documentation, internal processes, or client configurations. 

Ideal Candidate 

You’re curious, calm under pressure, and thrive when helping others. You bring a mix of deep technical skill and genuine empathy - knowing that clients don’t just want fixes, they want confidence. You can lead yourself, but you’re quick to collaborate and raise the flag when a case needs backup. You’re passionate about building lasting client relationships through trust and transparency, mentoring others, and sharing your ideas about how we can make Paragus an even better company.  Lastly, we hope you love beer – whether that be Root Beer or a local IPA – because we certainly enjoy ending a successful day with a pour from one of our private taps in our staff pub. Beer not your thing? That’s fine, we’re also really into great coffee and tacos.   

Compensation and Benefits:  

     As a Partner at Paragus, you'll enjoy:   

• Culture, culture, culture! Think: fun events, good beer, and great snacks, but most importantly, amazing people that you’ll look forward to seeing every day. 

• Employee ownership; that’s right, you’re not just an employee, you’re an owner! 

• Self-driven Career Advancement opportunities 

• 401K Plan + Matching up to 4% 

• Medical, Dental and Vision Insurance (Paragus pays up to 90% of your Premium) 

• Extra-curricular optional committees, training classes, Paragus University Courses and mentorship  

• A monthly stipend for your cell phone 

• Need a car for a day or so, just borrow ours! 

Hybrid Work Policy: Whether you’re saving on gas, time, or just enjoying the freedom of flexibility, remote work can directly contribute to your health and happiness. As a full-time employee you will be eligible to work remotely two days a week once you have successfully completed your onboarding.  

Paid Time Off: We at Paragus strive to not only promote but more importantly, prioritize a healthy work-life balance. As a full-time employee you will be eligible for our Flexible Vacation policy, which provides our employees with an un-capped bank of paid time off to use for vacation. Outside of the Flexible Vacation policy we also provide 5 days of sick time and personal leave, as well as 6 paid holidays.  

Employee-owned company: Why be an employee when you can be an owner? As a Partner of Paragus IT, what you say matters! We highly value our partners insights, and many times put recommendations to play. Additionally, you’ll see the direct impact of accomplishments through our ESOP program! 
 

Status: Full Time, Salaried, Exempt 

Hours: Monday-Friday 8 am to 4:30 pm 

Compensation: $74K-$130K 

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