Trust as a Metric: How Strategic Relationships and Face-to-Face Events Accelerate MSP Maturity with Jake Webber-Cadby
If you run an MSP you know the pressure all too well. Scaling revenue while keeping service quality steady. Hiring and retaining the right people. Choosing the right tools without drowning in complexity. Nick and I have spent thirty years building and scaling Australian MSPs and we have seen the patterns that reliably separate businesses that survive from those that thrive. Refer to this episode as a practical example of those patterns in action. In this episode of MSP Mastery: Ctrl Alt Deliver we spoke with Jake Webber from Enforcer. Jake brings vendor level experience from Datto and ConnectWise and a refreshingly practical channel focus. His story is not the headline. It is a peer level case that confirms what Nick and I have been advising MSP owners for decades. Below we unpack the key themes, interpret what Jake reveals about operating an MSP at scale and offer practical actions you can apply now.
MSP Mastery
5/22/20265 min read
Relationships are the bedrock of success
Jeni and Nick perspective
Relationships are the foundation of every successful MSP. Over three decades we learned that the vendor and peer relationships you invest in will influence service delivery, commercial outcomes and staff morale. Good account management from vendors translates directly into better outcomes for your customers. The channel is unique because competitors become collaborators and that changes the way an MSP can operate and grow.
Principle and framework
Treat vendor relationships as strategic assets. Assign clear owners to each relationship, meet regularly, and expect vendors to be partners in customer success not just product sellers. Equally, nurture the peer network. Attend events, share knowledge and build reciprocal referral relationships.
Jake’s supporting evidence
Jake echoed this from his vendor roles and his time at Enforcer. He told us how in person events and regular dialogs have helped his team build trust with MSPs. He recounted seeing competitors at the same table at events and how that openness accelerates practical problem solving.
Why it worked and what it reveals
When vendors show up as partners the MSP has more confidence to trial and adopt solutions. When peers share experience the whole market lifts. That network effect reduces the loneliness of ownership and speeds learning. Jake’s approach to investing in relationships both with distributors and MSPs demonstrates why the channel can be collaborative and commercially effective.
What you should apply
Make vendor relationship management an explicit role. Attend the right industry gatherings with intent and have a short list of outcomes for every meeting. Push yourself to share and to accept help from peers. Relationships are a multiplier for everything else you do.
Onboarding and ramping people is not optional
Jeni and Nick perspective
Hiring is one thing. Getting a hire productive and retained is another. From our time running MSPs we learned that onboarding is a continuous investment. Expecting new starters to be fully operational inside a couple of weeks is wishful thinking in this industry.
Principle and framework
Create a mapped 30, 60, 90 day ramp with clear outcomes and regular checkpoints. Document your processes in a living manual that reflects how your business actually operates. Assume twelve months to reach full productivity for people hired from outside the MSP ecosystem.
Jake’s supporting evidence
Jake described his own baptism of fire joining the channel and how it took many months to be competent with the acronyms, tooling and customer language. He also explained how Enforcer invests in implementation managers to guide MSPs through the critical first 90 days after a purchase.
Why it worked and what it reveals
Onboarding that is structured reduces churn, increases adoption of tools and shortens the time to value. Jake’s experience as both a new hire and a vendor working with MSPs highlights the gap between buying a tool and embedding it into operations. The projects that allocate responsibility and time win.
What you should apply
Map every new hire and every new tool with a ramp plan. Assign a named owner and measurement points. Update your manual as you learn. Expect this to be a repeating cost of doing business not a one time task.
Tool sprawl, evaluation and adoption
Jeni and Nick perspective
Tool sprawl kills margins and creates operational debt. MSPs often amass a stack of products with little attention to who owns them internally or what the measurable outcome should be. We advise defining ideal client profiles and choosing technology that maps directly to that profile.
Principle and framework
Adopt an evaluation gate for new tools. Require business outcomes and an implementation plan before you sign. Reserve resource to drive adoption and measure usage after go live. Consolidate where the benefits of simplicity outweigh the incremental features of many point solutions.
Jake’s supporting evidence
Jake described MSPs buying many tools and then using maybe five percent of their capability. He explained how Enforcer now qualifies customers carefully and focuses on MSPs leaning into the Microsoft pathway so the product delivers clear value to the right buyers.
Why it worked and what it reveals
When a vendor and an MSP share a clear definition of fit adoption rates rise and renewals improve. Conversely, poor fit leads to shelfware and wasted effort. Jake’s emphasis on product fit and dedicated implementation resources shows why aligning product choice to customer profile is a commercial imperative.
What you should apply
Before you buy, document the problem and the outcome you expect. Make implementation resource part of the purchase decision. Be ruthless about retiring tools that no one owns.
Events and face to face still matter
Jeni and Nick perspective
There is simply no substitute for face to face contact when building trust with customers partners and vendors. Events create moments where relationships deepen and decisions accelerate. We have always run events because they do more than sell software. They educate and they build credibility.
Principle and framework
Run events with clear persona targeting and content that delivers immediate value. Mix larger sessions for learning with smaller executive dinners for deep dives. Plan logistics thoroughly and design the event to create follow up opportunities.
Jake’s supporting evidence
Jake told us how Enforcer invested heavily in events and saw strong attendance when they made the timing and agenda considerate to MSP schedules. He also described executive dinners and technical training sessions as high value formats.
Why it worked and what it reveals
Events force the conversations that email and calls cannot. They build brand recall and give your team the chance to listen and respond in real time. Jake’s outcomes show that events are not vanity. They are conversion and retention levers when executed with intent.
What you should apply
Plan fewer events that are better. Choose topics that solve immediate problems and invite the people who can action them. Use events to deepen relationships not just to present slides.
Hero moment case study: turning reluctance into advocacy
Jeni and Nick perspective
A recurring problem for MSPs is internal resistance to new tools. People who have built custom scripts or who take pride in manual processes often see automation as a threat. Our experience is that the quickest way to mitigate resistance is to translate benefits into time and reputation gains for those people.
The story
Jake gave us a clear example. Some MSP technicians build custom scripts and then feel threatened when a vendor offers automation. Enforcer addressed this by showing technicians how the tool would remove repetitive work and free them to work on higher value tasks. They also framed adoption as an opportunity for the technician to become an internal champion whose profile rises inside the business.
Analysis
This worked because it changed the focus from replacement to empowerment. It gave technicians a visible role in the change and clear metrics to demonstrate their impact. It also forced the MSP owner to think about risk if the script owner left. That corporate framing helped get sign off.
Takeaway
When you introduce change make it personal. Show the time saved, the risk mitigated and the internal recognition available. Turn the early sceptic into the loudest advocate.
Conclusion
From our perspective Jake’s journey from vendor roles to building Enforcer confirms several enduring truths. Relationships amplify growth. Rigorous onboarding and implementation are the bridge between purchase and value. Be deliberate about tool selection and ownership. And finally invest in events because face to face still accelerates trust.
If this episode stirred ideas about how you might tighten onboarding, rationalise tooling or run more effective events reach out. Nick and I love talking with MSP owners who are serious about scaling profitably. Connect with Jeni, Nick, and the MSP Mastery team to discuss where you are on the journey and what your next pragmatic step should be.
