Dysfunctional CRM is a money pit
How much is yours costing you?
I advise enterprise and scaling B2B revenue teams on the CRM architecture, system drift, and structural issues that create that dysfunction. My focus is primarily on Sales Force Automation, the pipeline, opportunity, lead management, contact governance, and marketing attribution layer where most structural CRM problems live. With 30+ years at the intersection of business process and IT systems across ERP and CRM environments, I resolve problems at the root cause, restoring functionality, operability, data quality, and process flows so you finally realize the full ROI your CRM system was built to deliver.
Jon Cottrell: Enterprise CRM Systems Advisor
Common CRM system ISSUES
Most CRM issues are misdiagnosed. What looks like a reporting problem, adoption issue, or data quality challenge is usually a deeper system problem, the accumulated drift between how your CRM was designed and how your business actually operates today. I help enterprise and scaling B2B organizations identify and resolve these structural issues at the root cause.
Common System Problems I Diagnose and Fix:
Pipeline Reporting That No Longer Reflects Reality:
Pipeline reviews turn into debates. Forecasts require constant manual adjustment. Stage definitions no longer match how deals actually progress. Divisional Operations teams build shadow reports because they don’t trust the CRM numbers.
Marketing Attribution Sales Leadership Doesn’t Believe:
Marketing presents numbers that Sales dismisses. Attribution debates are endless because there is no trusted, system-generated source of truth. Investment decisions are made on contested data.
Lead Routing That No Longer Matches How the Business Sells:
Leads reach the wrong teams. High-value opportunities sit unworked. Duplicates multiply. Exception handling has become the norm.
Contact Data That Is Ignored:
Sales reps no longer trust the contact records. Duplication is rampant, data is stale, and governance at the source is missing. Cleanup projects keep repeating because the root causes are never addressed.
Systems That Have Drifted:
The system works. Just not the way it should. Users have built workarounds around functionality that was never delivered, never fixed, or never updated to reflect how the business now operates. Manual steps exist where automation should.
If several of these feel familiar, you likely have a system problem.
If your CRM isn’t delivering ROI, the issue is almost always deeper than the tools. I help you and your team find and fix the real problem.
The good news: These issues are diagnosable and fixable when approached from the right perspective.
Book a Free Discovery Call to discuss your specific situation.
These are not just tool issues. They are system design issues.
Stop fixing the tool. Fix the system.
MY APPROACH
Most consulting produces recommendations. This engagement produces resolution. I work directly alongside your Revenue Operations team, guiding them through structured diagnostic sessions, to transfer knowledge and experience and to uncover and resolve the real structural issues in your CRM system.
Your team does the work and owns every outcome. My role is to bring the external view, deep systems-layer perspective and diagnostic discipline that makes the work faster, more accurate, and more durable.
Key Elements of How We Work
Small, focused working group — Capped at 8 people from RevOps, Data Stewardship, and IT. The people who own and can change the system.
Structured, purposeful sessions — Pre-defined topics, live investigation or review format, always focused on high-value diagnostic work.
Clear division of responsibility — I direct diagnosis and guide solutions. Your team runs queries, documents findings, implements changes, and owns all outputs.
Remote by default — Efficient Zoom-based sessions with optional short on-site visits for more intensive periods of work.
Knowledge transfer built in — The goal is a stronger more capable internal team that no longer needs me.
This collaborative model is deliberately designed to avoid dependency and deliver lasting capability.
Expected Outcomes & ROI
A well-scoped engagement delivers two things. Both matter to leadership. Both compound over time.
1. Resolution — or a clear, verified path to it.
The scoped issue is diagnosed to its structural root cause. Your team will have a precise understanding of what is wrong, why it is happening, and what needs to change to resolve it. Where production changes require development cycles or patching windows, the engagement transitions to retained advisory, maintaining continuity through to verified resolution in production. The issue is closed properly, not handed off incomplete.
Along the way your team will also gain a clearer picture of how related parts of the system function, often surfacing context that accelerates resolution of other issues, or simply building the systemic understanding that makes future diagnostic work faster.
2. A more capable internal team.
The working group that participates in the diagnostic process leaves the engagement with something that stays with the organization permanently, deeper understanding of their own system, tested methodology they can apply independently to future issues, and the confidence that comes from having resolved something that previously felt intractable.
Equally important: the manual workarounds your team was running to compensate for the dysfunction, the ones that consumed time, created risk, and distracted from higher value work, are eliminated or significantly reduced. Your RevOps team gets that capacity back. They get to do the work they were hired to do.
For leadership, these two outcomes are compounding. A resolved issue reduces cost and risk. A more capable team reduces future dependency on external help for the same class of problem. Both improve the return on the engagement over time.
Book a Discovery Call to explore what outcomes are realistic for your specific environment.
THE EXPERIENCE THAT MATTERS
Deep Systems Expertise at the Intersection of Business and IT. Thirty years working with production ERP and CRM systems at global scale.
Most CRM advisors start with the tool. I start with how the system actually behaves in production, the accumulated configuration decisions, integrations, workflows, governance practices, and operational history that determine real outcomes.
I spent more than three decades at Oracle contributing to its first global support renewals platform, leading the Support Renewals and Installed Base workstreams across six major acquisitions (PeopleSoft, Siebel, Sun Microsystems, RightNow, Taleo, and Eloqua), driving the concept and requirements for the Mid-Funnel Marketing Attribution system that became the accepted source of truth for marketing’s contribution to closed-won revenue, and managing the global CRM contact dataset with up to 25 million records, for over 10 years while reducing duplication to under 0.5%.
That depth of production experience created a diagnostic discipline that cannot be replicated through vendor certifications, consulting frameworks, or tool-specific training. I see structural patterns others miss because I have lived the consequences of architectural decisions at enterprise scale, when systems drifted, when they failed, and when they were successfully restored.
I now bring that same systems-layer perspective to enterprise and scaling B2B organizations. Whether you are building new revenue systems to prevent future issues or repairing accumulated drift in mature environments, my role is to help your team diagnose root causes, reason from first principles about what “right” looks like, and implement durable solutions.
The goal is never to create dependency. It is to transfer enough diagnostic judgment that your internal team can govern and evolve its CRM systems more effectively long after our engagement ends.
WHAT I DO
I offer structured and scoped engagements designed to diagnose and resolve system-level CRM problems while transferring capability to your team.
All engagements start with a free Discovery Call
Core Services
Problem Solver Call
For a specific, contained CRM system question. One-hour intake call + up to 48 hours thinking time + one-hour response call.
CRM System Diagnostic
Standalone forensic engagement to reveal exactly what your CRM is doing in production and where it has drifted.
SUBSCRIPTIONS
Ongoing Advisory Subscriptions
Monthly retainers that flex with your need:
Add On Services
Hour Blocks Add-on for Subscription Clients.
Active subscribers can purchase blocks of 10 additional hours. Perfect for intensive sprints, on-site work, or peak periods.
| Tier | Hours / Month | Best For |
|---|---|---|
| Full | 16 | Active diagnostic & design phases |
| Standard | 8 | Steady working phase |
| Light | 4 | Light work in between intensive sessions |
| Retained Advisory | 2 | Continuity between active phases |
FREQUENTLY ASKED QUESTIONS
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A tool problem is a limitation in the platform being used to fulfill a specific need. This could be a bug, missing features, existing features that force a process change to match the tool architecture. Tool problems are solved by configuration changes, upgrades, platform switches, or sometimes by accepting the constraint and designing around it.
A system problem is structural. Your CRM environment is not always a single tool or platform. It can be a stack of tools. From different vendors, each with its own configuration, connected by integration logic, and governed by policies and processes that define how the whole thing should behave. A system problem is what happens when that accumulated structure drifts away from how your business actually operates today. The tools are working exactly as configured. The system has drifted. Two organizations running identical CRM systems can have completely different system problems, because they have different histories of decisions, changes, and drift. Changing the tools does not fix a system problem.
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The diagnostic always starts with the symptom as the client presents it, supported by data that demonstrates the problem in the system. Not a description of what feels wrong, but evidence of what the system is actually producing.
From there the diagnostic works backwards. The data points to where in the system the problem is visible. Following the data through the system reveals where the behavior originates, whether in the tools configuration, the process logic, the governance layer, or at the connection point between systems. Each step is verified in the base table data, in real time, so conclusions are grounded in what the system is actually doing rather than what it is supposed to do.
This is structured, methodical work. It requires direct access to the system, the right people in the room, and the discipline to follow the evidence rather than assume the cause. Most CRM problems have been misdiagnosed before we start. The presenting symptom is rarely where the root cause lives.
The result is a root cause that is evidenced, understood by the team, and traceable back through the system to its origin. Not a hypothesis. Not a best guess. A finding the team can act on with confidence.
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No. The work is diagnostic and advisory.
The diagnostic process identifies the structural root cause of the problem and guides the internal team through understanding what needs to change and why. The changes themselves are designed, documented, and executed by your own team, through your own development and change control processes.
This is deliberate. Your team owns the system. They need to understand what changed, why it changed, and how to govern it going forward. An external consultant making changes directly to your production environment creates dependency and leaves your team no better equipped than before.
All findings, documentation, and outputs produced during the engagement belong to your team. Not to me.
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The diagnostic work is platform agnostic. System drift, the accumulated gap between how a CRM environment was designed and how the business actually operates today, occurs regardless of which platforms an organization runs. The diagnostic methodology follows the data and the system behavior, not the platform.
My deepest production experience is in Oracle CRM environments, across ERP and CRM integration at enterprise scale. The diagnostic principles and systems-layer thinking that experience produced apply equally across Salesforce, HubSpot, Microsoft Dynamics, and any other enterprise CRM platform or stack.
Any platform-specific knowledge required during the engagement comes from your team. They know their tools. The diagnostic brings the architecture and systems-layer perspective that sits above the tools and connects them. That combination is what makes the work effective.
The conversation starts with the problem, not the technology.
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Book a free 30-minute Discovery Call. It is a conversation to establish whether this is the right kind of problem for this practice, and whether this is the right engagement model for your situation.
There is no commitment and no obligation. Come with a description of the problem you are experiencing and any data that illustrates it. That is enough to have a productive first conversation.
Most clients have a clear picture of whether and how to proceed after one call.