Your First 100 Days with ConnectWise: A Proven Roadmap for MSP Success

Feeling overwhelmed by ConnectWise? Follow this day-by-day roadmap to get confident, not confounded, with your MSP platform.

ConnectWise is supposed to be the command center for your managed services business. But for most newly minted users, the first login feels a bit like being dropped into air traffic control—with two blinking monitors, six phone calls holding, and no one's left you a manual.

How do you move from panic to power user in the first 100 days? This friendly guide is your clear, step-by-step ConnectWise roadmap. We’ll walk through exactly what to do (and why) so you actually build a foundation that works for your business—with less “wait, why isn’t it ticketing?” and more high-fives from your team.

Each section includes quick context, what you must do, and a dash of humor. Because, friend, you’ll need it.

Laying the Groundwork 

Days 1-10

Why This Matters 

If you don’t set up ConnectWise right from day one, you’re climbing a mountain with the snowshoes on the wrong feet. Get your house in order first.

The Steps:

• Clarify your business goals and pain points. You can’t configure what you can’t articulate.
• Inventory your current IT operations. Know what data, tickets, and workflows need to migrate.
• Assign your ConnectWise champion. This is not the time for a committee. One accountable leader keeps early work on track.
• Book a Bering McKinley onboarding meeting. If you’re reading this, you’re likely in partnership already. Use expert support.
• Set your first ConnectWise login and access permissions. Decide who gets admin rights, and resist the temptation to “give everyone everything.” Your future self (and compliance auditor) will thank you.

Pro Tip: ConnectWise doesn’t explode if you click the wrong thing, but a tight permissions structure keeps your data and sanity in check.

Core Configuration 

Days 11-30

Why This Matters 

ConnectWise is customizable, but a buffet of choices can mean analysis paralysis. Think like a chef, not a short-order cook.

The Steps:

• Map out your service catalog. What are you actually offering? Tickets and SLAs are only as useful as the business logic behind them.
• Set up ticketing workflows and statuses. Don’t settle for the default meal; define statuses that make sense for your business. 
• Configure business hours, holidays, and escalation rules. Yes, those settings really matter. If every issue is urgent, nothing is urgent.
• Audit notification settings. Minimize notification overload, or you’ll have the world’s fanciest spam filter.
• Integrate with your PSA, accounting, and RMM tools. Siloed systems defeat the purpose of ConnectWise. 

Humor Break: If ConnectWise sends you enough emails to crash your phone, congrats! You’ve configured notifications like 98% of new admins.

Ticketing, Service Desk, and RMM 

Days 31-60

Why This Matters 

This is where ConnectWise earns its keep. If your ticketing is a mess, so will be your customer satisfaction and cash flow.

The Steps:

• Customize ticket templates and set mandatory fields. Stop chasing missing data. Make ticket intake foolproof.
• Automate recurring tasks and service ticket assignments. If you’re using a clipboard for any recurring task, ConnectWise can handle it automatically.
• Enable Remote Monitoring & Management (RMM). Connect your devices and endpoints to start benefiting from proactive ticket creation and issue resolution.
• Design a customer-facing portal. Give clients a smooth way to log and track service requests.
• Regularly review open, stale, and closed tickets. Dashboards aren’t just for decoration. Use them to spot trouble (or overdue pizza orders on Friday).

Finance, Billing, and Reporting 

Days 61-80

Why This Matters 

Leaving your invoicing or reporting to gut feelings or spreadsheets? That’s like flying a 747 with a compass and a prayer.

The Steps:

• Connect (and test) your accounting software. QuickBooks, Xero, whatever you use. Do a test invoice run to catch silly mistakes early.
• Configure contracts, time tracking, billing rules, and automated invoicing. Accurate inputs equal accurate outputs.
• Establish approval workflows for billing exceptions and credits. No more “who approved this $30,000 donut run?”
• Build standard and custom reports in ConnectWise. Financial performance, contract profitability, SLA attainment, you name it.
• Use dashboards for core KPIs. Visual aids keep teams focused and reduce management check-ins (“Did we bill Acme for Q3 yet?”)

Customer Relationship Management and Project Management 

Days 81-90

Why This Matters 

A tight CRM module saves you from “mystery client syndrome.” Project management keeps big deliverables predictable, not panic-inducing.

The Steps:

• Standardize client data and contact records. Garbage in, garbage out. Use required fields, not sticky notes.
• Integrate CRM with marketing and support modules. One client database to rule them all.
• Set up project templates and milestones. Every PM has war stories about bad onboarding or fuzzy deadlines. Set up templates and timelines to keep everyone honest.
• Assign project resources and check capacity dashboards. Avoid “the project manager said yes, but the engineers are already double-booked.”
• Track project progress with real-time reporting. Weekly check-ins reduce fire drill meetings.

Automation, Security, and Best Practices 

Days 91-100

Why This Matters 

This is where ConnectWise morphs from “just another tool” into the backbone of your MSP. Automation frees up your humans for what only they can do; security protects those hard-won clients.

The Steps:

• Audit and refine workflow automations. Less “oops, forgot to close that ticket” and more “the system just did it for me.”
• Deploy patch administration and endpoint security features. Ransomware waits for no one.
• Configure compliance and access logs. Play defense before auditors come sniffing.
• Run quarterly audits and solicit client feedback. Tune your processes as your MSP grows (and new ConnectWise features roll out).
• Book a performance review with your Bering McKinley consultant. They’ll offer seasoned feedback and “aha”s you won’t find in the user manual.

Chart Your Success with ConnectWise and Bering McKinley

Those first 100 days with ConnectWise can feel like an endurance triathlon. You’ll have moments of confusion (“What on earth is a workflow rule set?”), quick wins, and maybe a few “did the system just do that for me or against me?” questions.

But step by step, you’ll trade confusion for clarity and hesitation for confidence, turning ConnectWise from a scary dashboard monolith into the nerve center of a thriving MSP.

Don’t stop at “good enough.” ConnectWise is always evolving, and your clients’ expectations are rising with it. Stay curious, stay in touch with the latest features, and draw on the expertise of partners who know how this road is paved.

Wherever you are in your MSP maturity, Bering McKinley is here to help you rethink, refine, and master ConnectWise. Book a call, join a peer group, or get a workflow assessment. After all, success in managed services isn’t about being perfect from the start. It’s about constant progress—with the right guide at every milestone.

Start your ConnectWise transformation with Bering McKinley today.