Building a Connected Revenue Engine for a Cybersecurity Company
- ConnectWise Manage (PSA)
- HubSpot (fragmented usage)
- ZoomInfo
- PhoneBurner - Power Dailer
- 3CX phone system
- Manual spreadsheets for reporting
- Mapped ConnectWise fields into HubSpot for both sales and ops — one source of truth across the PSA and CRM.
- Built lead routing, lead scoring, and chat flows so the right rep gets the right lead without manual triage.
- Replaced disconnected outreach tools with HubSpot sequences and PhoneBurner integration.
- Stood up cold, warm, and hot nurturing workflows so no lead goes dark.
- Delivered sales dashboards and goal-tracking reports leadership can actually use.
- PSA integration isn't optional for cybersecurity companies — it's the foundation. Without ConnectWise field mapping, sales and ops are always working from different data.
- A four-stage implementation keeps scope manageable and delivers value at each phase rather than waiting for a big-bang launch.
- Automation only works when the underlying data is clean and the routing logic is intentional. Garbage in, garbage out.
- Training and documentation aren't afterthoughts — they're what makes the system stick after the build is done.
A little background
MAD Security is a managed security services company. Their team sells and delivers cybersecurity services to organizations that can't afford to get it wrong — and that means their own internal operations need to be just as tight as the security posture they're selling.
Before working with Image in a Box, MAD Security had the tools. ConnectWise Manage was running service delivery. ZoomInfo was feeding the prospecting engine. PhoneBurner was handling outbound calls. HubSpot was in the mix. But none of it was talking to each other in any meaningful way.
Sales reps were working from one set of data. Operations was working from another. Reporting lived in spreadsheets. And the marketing side of HubSpot was barely scratching the surface of what it could do.
The team was capable. The tools were capable. The problem was the connective tissue between them.
Where did it go wrong?
The disconnect between ConnectWise and HubSpot was the biggest friction point. ConnectWise is where the service delivery work lives for most cybersecurity companies and MSPs — it's the operational backbone. But it doesn't do what HubSpot does: marketing automation, lead scoring, pipeline visibility, nurture workflows, or attribution reporting.
When those two systems aren't mapped to each other, you end up with sales reps manually reconciling data, ops teams working from stale contact records, and leadership with no clean view of what's actually in the pipeline.
On top of that, ZoomInfo wasn't structured for the way MAD Security's team actually worked. PhoneBurner was running independently from HubSpot sequences, so outreach activity wasn't being captured in the CRM. And without lead routing or scoring in place, every inbound lead required manual triage.
The result: a team spending real time on coordination work that should have been automated.
hours
wasted daily and manual entry
How MAD Security turned it around
Image in a Box ran a four-stage Clarity Implementation across Sales & SalesOps, Marketing & MarketingOps, Service & Ops, and Reporting & Documentation. Each stage built on the last.
Stage 1: Sales and SalesOps
The first priority was getting the sales motion onto a solid operational foundation.
That started with a full sales process discovery — mapping out how deals actually moved, where reps spent their time, and what data was missing or unreliable. From there, the team built out HubSpot sequences to replace the manual outreach cadences reps were running on their own.
The ConnectWise field mapping for sales was the critical piece. Getting the right fields from ConnectWise into HubSpot — and keeping them in sync — meant sales reps finally had a single place to work from instead of toggling between systems. ZoomInfo was restructured and segmented so list quality matched the way MAD Security's team actually prospected. PhoneBurner was integrated with HubSpot so call activity started showing up in the CRM where it belonged.
A monthly newsletter built from existing blog content was also set up during this stage — a low-effort, high-consistency touchpoint for the existing contact base.
Stage 2: Marketing and MarketingOps
With the sales foundation in place, the focus shifted to the marketing engine.
Lead routing was built out for both chat and forms — so inbound leads went to the right rep based on defined criteria, not whoever happened to check the queue first. Lead scoring was configured to give the sales team a signal on which contacts were worth prioritizing.
A sales rep dashboard was built so individual reps could see their own activity and pipeline without needing a manager to pull a report. Chat flows were designed for the sales context — not generic support flows, but conversations built to qualify and route prospects.
The nurturing infrastructure got a full build-out: cold, warm, and hot workflows so contacts at every stage of the funnel were getting relevant follow-up. An in-person event workflow was built as a cloneable template, so the team could spin up event-based outreach without rebuilding it from scratch each time.
Stage 3: Service and Ops
The third stage extended the ConnectWise integration from sales into operations.
Field mapping was built out for contacts and companies on the ops side — so the data flowing between ConnectWise and HubSpot reflected the full customer relationship, not just the pre-sale activity. A HubSpot to 3CX integration was configured so phone activity connected back to contact records.
On the customer experience side, an NPS nurture flow was built to follow up with clients after key service milestones. A support chat flow was added for the service context. A feedback survey was set up to capture structured input from clients.
Stage 4: Reporting and Documentation
The final stage was about making the system usable and sustainable.
Up to three dashboards were built for sales and goal tracking — giving leadership a clean view of pipeline, activity, and performance without needing to pull data manually. New hire documentation was created so onboarding new team members into the HubSpot environment didn't require tribal knowledge. Three one-hour onsite HubSpot training sessions were delivered to make sure the team could actually use what was built.
The results
MAD Security came out of the Clarity Implementation with a revenue engine that actually connects. Sales reps work from HubSpot with confidence that the data reflects what's in ConnectWise. Inbound leads route automatically. Outreach activity — calls, sequences, emails — shows up in the CRM. Nurture workflows run without manual intervention. Leadership has dashboards they can trust.The ConnectWise integration is what makes this work for a cybersecurity company. Most CRM implementations treat the PSA as a separate system. This one treats them as two parts of the same operational picture.
"Having a partner who understands both our sales motion and our PSA was a game-changer. We finally have visibility into what's working."
Glen G. | VP of Sales | MAD Security
Finalized Platform
- HubSpot Marketing Hub
- HubSpot Sales Hub
- HubSpot Content Hub
- HubSpot Data Hub
- ConnectWise Manage (integrated)
- ZoomInfo (restructured)
- 3CX (integrated)
- Connect and Sell
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