The engagement
that did not work.
An honest case study about a Co-Managed engagement that ended at month eleven by mutual agreement - and what Vencer learned about screening for engagement-model fit before either side commits.
FOR: Any operator considering Co-Managed · honest fit-screening lessons
Quick answer
An honest case study: a 55-person Calgary service company Co-Managed engagement that ended at month eleven by mutual agreement. The technical work was sound. The operational fit was not. What Vencer learned about screening for engagement-model fit before either side commits - and the disqualification questions we now ask up front. Sometimes the right answer is "this is not the right shape for us, and here's who is."
A 55-person service company, and a founder who could not let go.
55 people. A directional service company in Calgary, founder-owned and founder-operated. Profitable. Solid customer base. The founder had built the company himself over twelve years and had every right to be proud of what he had built. He was also the bottleneck for almost every operational IT decision in the company - and he was not ready to admit it.
This case study is about an engagement that did not work. We are publishing it because we think prospects deserve to know what bad-fit looks like with us, and because the post-mortem holds more honest insight than most of our success stories. None of the lessons are about the client doing anything wrong. The lessons are about Vencer learning what we should screen for in the first conversation, before either side commits.
The founder - we will call him Rick, though he could have been any of the founder-operators we have worked with through this exact dynamic - called us in early 2024. He had been told by his CFO that the company needed a real IT partner. They had been running on a part-time consultant for eight years. The consultant had been adequate. The CFO believed the company had outgrown adequate and was now at the stage where an actual operating partner mattered. Rick agreed in principle.
The engagement we proposed was Co-Managed - appropriate for a 55-person service company that already had a part-time IT person. The structure was familiar to us: we would handle the depth and the 24/7 monitoring, the existing consultant would keep the day-to-day relationships, the CFO would coordinate. Rick would be involved at the strategic level. He would not be involved in operational decisions. That was the structure we agreed on, in writing, before the engagement started.
The engagement lasted eleven months. It ended by mutual agreement. The CFO and the part-time consultant both wanted us to continue. Rick did not. The reason Rick did not was not the work product, which was solid by every measure both sides agreed to track. The reason was structural - Rick had built his company by being involved in every decision, and the Co-Managed engagement asked him to be involved in fewer of them than he was prepared to be.
A founder who could not let go, and an engagement model that required him to.
The first six months of the engagement looked like every other Co-Managed engagement we run. We assessed the environment, documented the systems, lifted the cyber baseline, deployed the standard monitoring stack, established the offboarding discipline, and built the playbooks for the operational work. The CFO was responsive. The part-time consultant was constructively involved. The cyber posture moved from a 41 to a 62 on the self-score in the first ninety days.
The friction started in month seven. It did not start with any particular incident. It started with a pattern.
- Rick wanted to be in every weekly operations meeting. The meetings were structured for the CFO, the IT consultant, and our account engineer. Rick’s presence changed the meetings - not because he asked bad questions, but because his presence shifted the decisions from operational to strategic, which slowed everything down.
- Rick wanted to review every vendor selection. We had been making vendor recommendations against a documented stack - SentinelOne for endpoint, Proofpoint for email, Veeam for backup, all 2025 Gartner Magic Quadrant Leaders. Rick wanted to do his own evaluation of each before approving. The evaluations took weeks and ended with Rick approving what we had recommended. The pattern repeated five times.
- Rick wanted to know who was doing the work. Not which team. Which named engineer. He would ask in advance, then call them directly to verify their experience, then call us afterward to discuss what he had learned. The engineers were patient. The process consumed senior-team time that the engagement was supposed to free up.
- Rick wanted to see every monthly report twice. Once in draft from our account engineer, once in final from the CFO. He would then meet separately with both, then send notes back to us, then ask for revisions. The reports were the same standardized format we provide to every Co-Managed client. The reviews took longer than producing the reports.
None of this was hostile. Rick was genuinely trying to understand his company’s IT operations more deeply. The problem was that the Co-Managed engagement model assumes a level of delegation from the principal that Rick was not, by nature, able to provide. He had built his company by being involved in every decision. That trait had served him well through twelve years of growth. It made the operating partnership we had agreed on structurally difficult.
The three engagement models covered in Chapter 12 of The Operating System - Fractional, Co-Managed, and Bundled - differ in price, scope, and operational depth. They also differ in the relationship structure they assume between Vencer and the client’s principal. Fractional assumes the principal wants to remain operationally close. Bundled assumes the principal wants to delegate operationally. Co-Managed sits between the two and works when the principal is comfortable with a partner that operates with autonomy on day-to-day matters and reports up on strategic ones.
For founder-operated companies, the right engagement model depends on the founder’s actual operating style - not on the company’s headcount or operational complexity. A founder who genuinely delegates can run a Co-Managed engagement at 25 people. A founder who genuinely cannot delegate will struggle with a Co-Managed engagement at 100 people. The mismatch is not a problem with the founder. It is a structural mismatch with the engagement model, and it should be diagnosed before the engagement starts.
How the engagement actually ran, and where it broke down.
Months one through six ran cleanly. The work product was solid. The cyber posture improved substantially. The CFO was happy. The IT consultant was reinforced rather than replaced. The company was operationally better off than it had been when we started.
Month seven was when we first noticed the pattern. By month eight, the cumulative time Rick was asking us to spend on review meetings and vendor evaluations had grown to roughly 12 hours per week across our team. That was more than 3× what the Co-Managed engagement was sized to absorb. We could have absorbed it for a few weeks. We could not absorb it sustainably.
In month nine, we had a direct conversation with Rick and the CFO. We named the pattern as we had observed it. We proposed three options:
- Restructure the engagement to Bundled. At Bundled, we are the IT department, the decisions are ours to make against documented service levels, and the review structure shifts to monthly strategic conversations rather than weekly operational ones. This is the engagement model that fits a founder who wants depth without the delegation requirement. The cost would be higher.
- Restructure the engagement to Fractional. At Fractional, we provide a defined monthly scope and the client’s team owns more of the day-to-day. Rick’s involvement would be appropriate rather than excessive. This is the engagement model that fits a founder who wants to remain operationally close. The capability we could provide would be less.
- Continue Co-Managed but with explicit scope-of-review constraints. Rick’s involvement would need to be bounded by agreed protocols. This was the option we recommended against because it would have asked Rick to operate against his natural style. We did not think it would work for him, and we would not have wanted to ask him to try.
Rick chose to continue Co-Managed. He acknowledged the pattern and committed to changing it. We agreed to give the new approach ninety days. During the ninety days, the pattern resurfaced. Not because Rick was acting in bad faith - he was genuinely trying - but because the pattern was deeper than the agreement.
The conversation that ended the engagement.
In month eleven, the CFO called us. She had spoken with Rick over the weekend. They had reached the conclusion that the engagement was not the right structure for the company. She wanted to know whether we would be open to ending it cleanly, with no blame, with the documentation preserved, and with a referral relationship to whichever firm came next. We said yes.
The exit took six weeks. We documented everything we had built. We transferred the operational runbooks. We introduced the CFO to two other firms we thought might fit Rick’s style better. We did not bill for the transition time. The relationship ended in a way that allowed both sides to refer the other in the future without awkwardness. Two years later, the company is still operating, the CFO is still in her role, and the IT consultant is still there. Rick is happier with the engagement model he chose after us. We are happier knowing the structure suited the founder, not just the company.
What we learned. What we now screen for.
The honest assessment of this engagement is that the technical work was good, the operational improvements were real, and the relationship structure was wrong. That third factor mattered more than the other two combined. Vencer’s value proposition relies on a working partnership; a working partnership requires alignment on operating style, not just on technical scope.
What we changed in our screening process as a result of this engagement:
- We added a structured conversation about decision-making style early in the qualification process. Specifically, we ask founder-operators to walk us through how they made a recent vendor decision, how they handled a recent operational issue, and how involved they expect to be in week-to-week IT operations. The conversation is not a pass-fail screen. It is an alignment check. If the founder’s style suggests Bundled rather than Co-Managed, we propose Bundled. If the style suggests Fractional, we propose Fractional. We do not propose Co-Managed if the conversation tells us the founder is more comfortable being deeper than the model assumes.
- We added explicit language about engagement-model fit to our proposals. Every Co-Managed proposal now includes a paragraph describing the assumed delegation structure. The client’s leadership has to acknowledge that paragraph in writing. This sounds like paperwork. It is actually the early diagnostic for the issue that ended the Rick engagement.
- We give ourselves and the client a structured 90-day check-in at the engagement start. At day 90, both sides answer the same three questions: is the work product meeting the agreed standard, is the relationship structure working, and would we choose to continue if we were deciding today? If any answer from either side is no, we have a structured conversation about adjustment rather than letting the issue grow.
- We are honest in early conversations that we are not the right partner for every founder. If a prospect’s description of how they want to work with us sounds like Bundled but they want to pay for Fractional, we name the gap. Many of those conversations have ended without a contract. Several have ended with the prospect choosing a different scope than they originally proposed, and the engagement working better as a result.
The moment it mattered.
The moment that taught us the most was not the conversation that ended the engagement. It was a phone call we had with Rick about eight months after the exit. He had called to ask for a reference for an unrelated firm. The call was civil and friendly. Toward the end, he said, unprompted: “You should have told me in the first conversation that I was probably the wrong client for the engagement you were proposing.”
He was right. We had not had the language for that conversation at the time. We have it now. The screening process we use today exists because Rick was generous enough to name what we should have seen ourselves. Every engagement we have started since that one has been better diagnosed at the front end, and we have lost fewer engagements that should never have started.
The engagement-model framework covered in Chapter 12 of The Operating System is structured around scale, operational reality, and posture. The implicit fourth dimension - how the founder or principal actually operates - is at least as important as the other three. Founder-operators who genuinely delegate fit Bundled. Founder-operators who genuinely cannot delegate fit Fractional. Co-Managed sits between the two and requires honest self-assessment about which side of the line you actually sit on.
Vencer is not the right partner for every Canadian oil and gas company. We are a strong partner for companies whose leadership wants to work with a real operating partner over a multi-year horizon, on terms that respect both parties’ expertise. If that does not describe your operating style, an honest conversation in the first meeting will save both of us time. We would rather know in the first call than in month eleven.
Does this story sound familiar?
The pattern in this case study has played out across dozens of Canadian oil and gas companies in the 10 to 100 person range. If you recognize parts of it in your own operation - or you suspect you might - the next step is a structured conversation with a Vencer engineer.
The IT-and-the-Cycle Assessment is a 3 to 5 day structured review of your specific operational situation. We pressure-test where your IT stands today, where it needs to be for what you intend to become, and what one bad day looks like at current state. You leave with a written report, a 90-day plan, and named owners. No hype. No vendor pitch. Just the truth about where you are and what to do next.
For a faster diagnostic, three free tools at vencergroup.com cover the same territory in less time: the Hidden IT Cost Calculator (12 minutes, quantifies your IT cost burden across three price-cycle scenarios), the Cyber Risk Self-Score (5 minutes, scores your cyber baseline against 12 critical controls), and the IT Myth-Buster sheet (the seven objections you’ll hear from inside your own company and how to think about them).
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