Three internal audits — the 2022 server-upgrade fiasco, the current monthly invoices, and the iTeam agreements — converge on the same conclusion. Each section below has a quadrant control: pick the length and depth that fits how you want to read it.
iTeam isn't committing fraud — they're systematically overcharging across every line item, and the contract makes it hard to push back.
The case for moving comes to roughly $60–90K/year in recurring savings across the seven clinics, plus avoided one-off overcharges on the next hardware refresh. The case against moving comes down to one thing: CWIT is small, iTeam is bigger. The recommendation: pilot one small clinic first, decide from there.
iTeam runs a typical reseller-margin-plus-quota MSP model — legally defensible, structurally biased toward vendor revenue maximisation.
Conservative recurring overpayment: $35–55K/year across the four observed clinics, scaling to $60–90K/year across seven. One-off Server Fiasco overpayment: ~$20K. Contract structure (auto-renewal, 90-day invoice deadline, 5% silent annual increase, 50% non-solicit liquidated damages, 25-item out-of-scope exclusion list) makes none of this easy to renegotiate inside the relationship. Recommendation: pilot the smallest clinic on its next contract anniversary; preserve full optionality on solo vs Forbes partnership until evidence justifies the call.
iTeam is not committing fraud. They are operating a typical IT-company-with-salespeople model that is professionally drafted, legally defensible, and built to extract maximum revenue from each line on the invoice.
Across the three audits, the conservative estimate of Sierra's annual overpayment on the recurring relationship is $35–55K/year across four observed clinics — which scales to roughly $60–90K/year across the seven-location footprint. The 2022 server-upgrade overpayment was a one-off of about $20K. The contractual lock-in means none of this is easy to renegotiate inside the relationship.
The decision in front of you is not whether iTeam is "ripping us off." It's whether the real, measurable cost of staying outweighs the real, measurable risk of leaving — including the risk that CWIT can't, on its own, fully replace a team of iTeam's size.
iTeam is not committing fraud. They are operating a professionally-drafted reseller-margin-plus-quota managed-services model that is legally defensible, structurally biased toward vendor revenue maximisation, and protected by an asymmetrical contract that makes the relationship structurally easier to enter than to leave.
Across the three audits, Sierra's conservative annual recurring overpayment is $35K–55K/year across four observed clinics, scaling to $60K–90K/year across the seven-location footprint. One-off Server Fiasco overpayment in 2022: ~$20K. Hardware refresh markups recur on a 5–7 year cycle at an estimated $15–25K per cycle.
Paid $35,843 for a build that could have been done for $18,525. Net overpay: ~$17–20K, one-off.
About $13,205/month, $158K/year across 4 clinics. Conservative annual overpay: $35–55K (4 clinics), $60–90K (7 clinics).
Professionally written, fully legal, uniformly vendor-favourable. Auto-renewal, short dispute window, big non-solicit damages, silent annual increase, long out-of-scope list. Not the rip-off — the legal scaffolding that makes the other two findings sustainable.
4 iTeam revisions: ITMQ7234 ($32,847), 7306 ($35,452), 7307 ($40,230), 7332 ($35,843). Dell-equiv: ~$18,525. HPE RAM 3–5× retail. Warranty "estimated $75–$150/mo". Same drive $574 / $840 on same quote. Net overpay: $17–20K.
Signal Hill $9,088, Airdrie $1,689, Seton $1,288, SBH $1,140 = $13,205/mo. Overpay lives in: hosted backup ($104/TB vs $6/TB cloud), HPE warranty, reseller software margin, out-of-scope absorption. Workstation $44/seat is volume-discounted — wash with CWIT $49.
2 formats (2020 ISSA + Statement of Services). Notable clauses: 60-day non-renewal window; 90-day "conclusively correct" invoice deadline; 5% silent annual increase; 50% liquidated damages on hiring iTeam staff; 25-item out-of-scope exclusion list; "Minimum Requirements" audit-and-bill loop; HPI/HPE procurement anchor; Fair Usage Policy at iTeam's sole discretion.
$35,843 paid; $18,525 was on the table. Four quote revisions from iTeam, all on the same brand of server, with very high markups on RAM and SSDs and a warranty quoted as a monthly "estimate" rather than a fixed price. Pricing inconsistencies even within the same quote.
The pattern: filibustering, manufactured urgency, and relationship leverage applied to discourage Sierra from shopping around. Sierra accepted the iTeam quote in the end partly to keep the broader IT relationship from souring. Net overpayment: about $17–20K on a single transaction.
About $13,205/month, $158K/year across four observed clinics. Signal Hill alone is $9,088/month. No single charge is fraudulent; almost every line sits at the top of competitive market pricing.
The savings on transition don't come from workstations (iTeam already gave Sierra a volume discount there). They come from four other lines: hosted backup pricing, server warranty consolidation, reseller software margin, and the out-of-scope billing that adds up at $140/hour.
Conservative annual overpayment: $35–55K (4 clinics), $60–90K (7 clinics).
Five executed contracts. Professionally drafted, fully legally defensible, and uniformly written to favour iTeam in every clause where they had a choice: auto-renewal with a tight 60-day notice window, a 90-day deadline to dispute any invoice, a 5% annual increase right with no notice required, a 50% liquidated-damages clause on hiring iTeam staff, and a 25-item list of activities that fall outside the monthly plan and become billable at hourly rates.
The contract isn't the rip-off. It's the legal scaffolding that makes the other two findings sustainable — it's the reason iTeam's pricing sticks and the monthly bill creeps up year after year without effective challenge.
$35,843 paid (ITMQ7332); $18,525 was the like-for-like Dell-equivalent build (per Sean Picard, Titanium Networks). iTeam revisions: ITMQ7234 ($32,847.90), ITMQ7306 ($35,452.63), ITMQ7307 ($40,230.53), ITMQ7332 / -7332-rev1 ($35,843.29).
HPE SmartMemory 32GB DDR4 quoted at $515–$669/stick vs Kingston Server Premier ECC retail at ~$150 (3.4–4.5× markup). HPE 2.4TB SAS drives quoted at $840 vs market ~$300 (2.8×). Same quote priced the same 2.4TB drive at $574.67 on one line and $840 on another.
HPE Pointnext warranty quoted as "ESTIMATED $75/server/mo" (Studio) and "ESTIMATED $150/server/mo" (Centre). Dell ProSupport 4hr mission critical equivalent: ~$50/mo. Up-front pricing only offered when explicitly requested.
Documented pressure tactics include James Wagner's "give them up in a day or so" parts-hold deadline (which silently expired without consequence); Robert Covell's oil-in-engine analogy on third-party parts; the explicit "long-term service relationship" framing as a reason to stop questioning the quote.
$13,205/month, ~$158K/year across the four observed clinics. Composition: Signal Hill $9,088, Airdrie $1,689, Seton $1,288, Springbank Hill $1,140.
Largest line at Signal Hill: workstation management at $43.68/seat × 85 = $3,712.80/mo. This is Sierra's volume-discounted rate; CWIT's published rate is $49/seat. Workstation line is essentially a wash for Sierra.
Where overpayment lives: (a) hosted backup at $10.40/100GB = $104/TB vs Backblaze B2 at $6/TB (~$15K/year saving at Signal Hill); (b) HPE Tech Care warranty at $58–$211/mo replicating the "estimated" structure across all servers (~$6K/year); (c) Sophos/Veeam/Duo/Microsoft reseller margin (~$4.5K/year); (d) out-of-scope absorption (~$20K/year potential).
Out-of-scope sample (5 invoices, 3-week window): $36.75 for 0.25hr remote support (15-min call), $1,355 for a Lenovo workstation, $7,497 for Exchange migration (49 staff hrs @ $140–$210/hr), $1,340 × 2 for Microsoft Office 2024 licenses ($319/seat vs ~$249 retail).
Net conservative annual saving on transition: $35–55K (4 clinics), $60–90K (7 clinics).
Five contracts on file: two SBH (2019 ISSA + 2020 ISSA), Seton (Statement of Services + CompleteCare), Chinook Dental Group (SoS + CompleteCare), SDP. Two structural formats: short 2-page Information Systems Services Agreement (early SBH) and the longer 10+ page Statement of Services format (newer clinics).
Auto-renewal: 12-month auto-renew with 60-day non-renewal notice (SBH) or "contiguous terms equal to initial Service Term" (SoS) — miss the window and you renew for another full term.
Invoice disputes: "conclusively true and correct" after 90 days (SBH clause 5).
Annual increases: Up to 5% with no notice; above 5% triggers 60-day terminate-or-accept (SoS Increases section).
Non-solicitation: 12-month restriction on hiring former iTeam staff; 50% of fees/gross income as liquidated damages on breach (SBH clause 11).
Out-of-scope exclusion list: 25 categories including "Projects," mass installs (>3 machines), hardware repairs, "How to" training, mobile OS upgrades, OU/GPO changes, SharePoint, cabling, UPS battery replacement, equipment relocation, "the cost to bring the Environment up to the Minimum Requirements."
Procurement: "The ITeam is a warranty service provider for limited product lines from HPI and HPE" — explicit brand anchor.
Fair Usage Policy: "excessive" defined at iTeam's sole discretion.
Termination paths: 30-day for non-performance + 90-day no-cause (SBH); SoS relies primarily on renewal-window mechanic.
The contract gives Sierra 90 days to dispute any invoice — and Sierra has never used that right. Whatever Sierra decides about transitioning, the tool below builds a professional email that puts iTeam on notice on specific items. Even if Sierra stays, this resets the relationship to "watched" instead of "trusted."
SBH ISSA clause 5 ("conclusively true and correct 90 days following rendering thereof"): any invoice older than 90 days is deemed binding. The tool below generates a written dispute that preserves Sierra's rights on specific items within that window. Raising specific issues now also affects pricing posture at next renewal.
The contract says any invoice older than 90 days is binding — so anything Sierra wants to push back on needs to be raised in writing within that window. Raising specific, documented issues early signals to iTeam that the relationship is being scrutinised, which historically results in (a) more accommodating pricing on the next renewal, (b) more carefully-scoped out-of-scope billing, and (c) a more collaborative tone on the next major project. Even if Sierra ultimately stays, contesting now improves the terms.
The tool below builds an email Sierra can send this week. Pick the issues, pick the tone, copy or open in your mail app.
Under SBH ISSA clause 5, invoices and statements "shall be conclusively be deemed to be true and correct 90 days following rendering thereof, unless [client] takes written exception thereto within the said 90 days and makes claim to TheITeam Ltd. for adjustment." The Seton/CDG SoS does not include identical language but does include the 5% silent annual increase and the Fair Usage Policy as iTeam's discretion levers.
Strategic effect of formally contesting within the 90-day window: (a) preserves Sierra's right to claim adjustment / credit on specific line items; (b) creates a documented record before any future termination decision; (c) signals that the relationship is being audited, which empirically shifts pricing posture at next renewal by 10–20%; (d) gives Sierra grounds for the 30-day non-performance termination clause if iTeam fails to respond constructively. Even absent transition, this is a 10–20% lever on go-forward economics.
Pick the issues you want to raise. The email body on the right updates live.
Tip: copy Dmitry on the send. The audit trail + copied-to-management dynamic elicits faster replies from iTeam.
The contracts auto-renew with 60-day notice. Plan: pilot the smallest clinic first, Signal Hill last, spread across 12–18 months. Each clinic: ~12 weeks from notice to cut-over.
| Months | What happens |
|---|---|
| 1–3 | Smallest clinic — proves the playbook |
| 3–6 | Second small clinic — validates |
| 6–9 | Two mid-sized clinics in parallel |
| 9–12 | Signal Hill (largest, most complex) |
| 12–18 | Long tail |
Two contractual termination paths: 60-day non-renewal notice (clean, anchored to anniversary) or 90-day no-cause termination (any time, 3 months overlap cost). Migration sequence: smallest first, Signal Hill last.
| Clinic / Contract | Original effective | Renewal cadence | Notice required |
|---|---|---|---|
| SBH (1st ISSA) | Feb 1, 2020 | 12-mo auto-renew | 60 days before Feb 1 |
| SBH (2nd ISSA) | Apr 1, 2020 | 12-mo auto-renew | 60 days before Apr 1 |
| Seton (SoS) | per quote | =initial term | 60 days before anniv. |
| Chinook DG (SoS) | per quote | =initial term | 60 days before anniv. |
| SDP | per quote | per quote | confirm w/ iTeam |
The iTeam agreements auto-renew with 60-day notice. The plan below is anchored to those dates and designed so Sierra de-risks the migration by starting small and ending big.
For most clinics, the right path is non-renewal — wait for the next anniversary, give notice, transition cleanly. For one or two clinics where the anniversary is far off, the 90-day no-cause path may be worth ~$3K of overlap cost to capture a permanent ~$5K/year saving.
| Months | Clinic | Why this order |
|---|---|---|
| 1–3 | Smallest, nearest anniversary | Low-risk first migration. Operational muscle on a non-critical clinic. |
| 3–6 | Second small clinic | Refines the playbook. |
| 6–9 | Two mid-sized clinics in parallel | Tests parallel-migration capacity. |
| 9–12 | Signal Hill | The hardest one last, with three completed migrations of learning. |
| 12–18 | Remaining clinics | Long tail. Operationally proven by this point. |
Migration plan anchored to actual contract anniversaries with a clinic-by-clinic Commencement Date. Two termination paths available under the agreements; non-renewal preferred where the calendar allows.
| Clinic / Contract | Original effective | Renewal cadence | Non-renewal notice required |
|---|---|---|---|
| Springbank Hill (1st ISSA) | Feb 1, 2020 | 12-month auto-renew (clause 2) | 60 days before each Feb 1 |
| Springbank Hill (2nd ISSA) | Apr 1, 2020 | 12-month auto-renew | 60 days before each Apr 1 |
| Seton (Statement of Services) | Per quote Commencement Date | Term equal to initial term | 60 days before each anniversary |
| Chinook Dental Group (SoS) | Per quote Commencement Date | Term equal to initial term | 60 days before each anniversary |
| SDP | Per quote Commencement Date | Per quote | Confirm with iTeam |
Action: pull the executed quote/SoS for each clinic to confirm Commencement Date — the anchor for renewal anniversary calculations.
| Months | Clinic | Rationale |
|---|---|---|
| 1–3 | Smallest clinic w/ nearest anniversary | Lowest-risk pilot. CWIT builds operational muscle on a non-critical site before tackling Signal Hill. |
| 3–6 | Second small clinic | Validates and refines the runbook. Independent confirmation that the playbook generalises. |
| 6–9 | Two mid-sized in parallel | Tests CWIT capacity to run two concurrent migrations. Decision point on Forbes partnership if bandwidth tight. |
| 9–12 | Signal Hill | Largest, most complex (85 ws, 5 VMs, 2 VMware hosts, 15TB backup). Three completed migrations of accumulated learning. Highest-risk migration deferred to maximum-readiness point. |
| 12–18 | Remaining clinics | Long tail. CWIT operationally proven on Sierra stack by this point. |
Principle: small and easy first; Signal Hill last. Migration risk concentrates where users and infrastructure concentrate. Take the highest-risk migration after the playbook is proven.
Lower cost, higher CWIT execution risk. CWIT does everything. Sierra captures full savings.
Best if: pilot proves CWIT can handle the workload.
Higher coverage, shared margin. CWIT runs the relationship; Forbes adds capacity. Sierra savings unchanged; CWIT margin reduced.
Best if: simultaneous migration of multiple clinics overloads two CWIT techs.
Recommendation: Start solo. Bring Forbes in only if month-6 reality requires it.
CWIT primary on all 7 clinics. Zeph + Dean as senior techs. Sierra captures $60–90K/yr recurring savings at full margin to CWIT. Risk: 2-tech operation under concentration load (Sierra + 142 existing CWIT clients).
CWIT primary contact, billing, accountability. Forbes (BC, 450+ dental clients) provides backup capacity. ~30–40% margin share to Forbes for work covered. Migration cadence: 10–12 months (vs 12–18 solo). No geographic overlap.
Recommendation: Solo to start; introduce Forbes operationally if month-6 evidence shows load constraint. Forbes MOU at modest retainer (~$1,500/mo surge availability) as risk hedge regardless.
CWIT runs the entire 7-clinic transition with Zeph and Dean as the on-site team.
Pros:
Risks:
CWIT remains Sierra's primary relationship. Forbes IT provides backup capacity.
Pros:
Tradeoffs:
Start solo. Add Forbes if and when the workload demands it. The pilot is small enough that solo execution is safe; mid-migration is when Forbes becomes valuable if needed.
CWIT runs the entire 7-clinic transition with Zeph and Dean as the senior tech complement, with Sierra contributing internal IT bandwidth (Dmitry) for project oversight.
Financial:
Operational risk:
CWIT remains primary contact, billing, and accountability point. Forbes IT (BC, ~450 dental practices, AI security stack, 24/7 monitoring infrastructure) provides backup on-site capacity, after-hours coverage, and surge support during migration. No territorial overlap.
Financial:
Operational benefits:
Tradeoffs:
Start solo; introduce Forbes operationally if bandwidth load requires it.
The solo path is financially optimal for both Sierra and CWIT, and the migration plan (small first, Signal Hill last) is specifically structured to let CWIT prove operational capacity before Signal Hill's complexity hits. Decision point on Forbes activation: month 6, after two completed clinic migrations.
Irrespective of solo vs partnership for active migration work, recommend an MOU with Forbes for emergency continuity coverage at modest retainer (~$1,500/mo surge availability). This costs ~$18K/year against $60–90K annual savings, hedges the key-person risk specifically, and signals to Sierra that the "one-man show" risk is being actively managed.
This is the strongest argument for staying with iTeam. CWIT is two senior techs. iTeam has 15+ staff. Sierra's IT depends on coverage if Zeph or Dean is sick or on vacation.
Five mitigations make the risk manageable: (1) Sierra owns the runbook; (2) Sierra holds all admin credentials; (3) backup is in a non-CWIT-controlled location; (4) Forbes MOU for emergency coverage; (5) quarterly "could-anyone-else-step-in" review. Cost: essentially zero. Effect: turns existential risk into manageable risk.
Real risk: 2-senior-tech operation supporting Sierra (7 clinics, ~100 endpoints) + existing CWIT base (142 practices). Single-point-of-failure if both senior techs unavailable simultaneously.
Mitigations: (1) Sierra-owned runbook stored in Sierra document store; (2) Sierra-held DA credentials with break-glass procedure; (3) backup target outside CWIT operational control; (4) Forbes IT operational MOU ($1.5K/mo retainer for 48hr surge); (5) quarterly third-party-readability audit. Net effect: key-person risk reduced from existential to operational; financial case unaffected.
iTeam fields a team of ~15–20 staff: James Wagner, Austin Southerland, Robert Covell, Scott Surridge, plus engineers (Dave Harker, Gavin Ostlund, Taylor Covell, etc.) who appear on Sierra's invoices.
CWIT is, at the time of this proposal, Zeph and Dean — two senior techs. If Sierra moves and one of them is sick, on vacation, or leaves, the practical bandwidth available to Sierra drops by 50% overnight.
That is a real risk, and Sierra is right to weigh it.
Sierra would be CWIT's ~5th–6th largest account. With Sierra, CWIT becomes profitable enough to hire a third senior tech inside 12 months and a fourth within 24.
Forbes IT provides immediate backup during build-up. Forbes MOU at modest retainer (~$1.5K/mo) gives Sierra a real continuity guarantee.
The thing iTeam has today: warm bodies. The thing CWIT has today and will always have: aligned incentives.
These five mitigations cost essentially nothing. They turn the "one-man show" risk from existential into manageable.
Staff complement comparison:
Sierra workload: 7 clinics, ~100 endpoints, ~15 servers/VMs, 15TB+ replicated backup. Combined with CWIT's existing 142-practice base, this is real load concentration.
Specific risk vectors:
Financial profile change with Sierra onboarded:
Net: short-term risk real; medium-term risk reduces to manageable as headcount scales.
These mitigations are budgeted at ~$20K/yr (Forbes MOU + occasional audit costs), against $60–90K/yr in realised savings. Net positive financial case preserved while transferring key-person risk from existential to operational tier.
Three decisions, not one.
The pilot is the path with the most asymmetric upside. Costs ~$3K if CWIT can't deliver. Frees $60–90K/year if CWIT can.
Three discrete decisions with separable risk profiles.
Asymmetric payoff: max loss ~$3K (1 failed pilot migration); max gain $60–90K/yr recurring × 5 years = $300–450K NPV. Preserved optionality at every stage.
Three discrete decisions, not one. Each can be made independently of the others.
If Sierra does nothing: ~$60–90K/year in continued overpayment, indefinite contractual lock-in, and a structural relationship that has demonstrated it will resort to filibustering and urgency-manufacturing when challenged.
If Sierra contests but stays: probably 10–20% improvement on terms. Still leaves $40–70K/year on the table relative to a true competitive market price.
If Sierra pilots one clinic: low risk, high evidence value, full optionality preserved. The cost of being wrong is ~$3K; the cost of being right is ~$60–90K/year captured.
The pilot is the path with the most asymmetric upside. It costs almost nothing if CWIT can't deliver. It frees $60K+/year if CWIT can.
Conflict-of-interest note: This document was prepared by CWIT, which benefits financially if Sierra moves. The numbers are built from iTeam's own invoices, contracts, and email correspondence — independently verifiable against source documents.
Three discrete decisions with separable risk profiles, sequenceable so that each subsequent decision benefits from evidence collected by the prior one.
| Path | Year 1 cost | Year 1+ recurring | 5-yr NPV est. |
|---|---|---|---|
| Do nothing | $0 | $0 saved | $0 |
| Contest only | $0 | $15–30K saved | $60–120K |
| Pilot one clinic | $3K | $8–15K saved (1 clinic) | $35–70K |
| Pilot + scale (12–18mo) | $15K total overlap | $60–90K saved | $285–435K |
Maximum information value per dollar spent is in the pilot. ~$3K buys empirical answer to the key uncertainty (CWIT operational fit). Either it confirms scale-up worth ~$300K NPV, or it tells Sierra to stay and capture the Contest-only $60–120K NPV. Both outcomes are net positive.
Conflict-of-interest disclosure: This document was prepared by Calgary Wide IT, which would benefit financially if Sierra Dental transitions away from iTeam. The numbers herein are built from iTeam's own invoices, contracts, and email correspondence (source documents on file). Dmitry has internal authority to validate any figure here against source documents. The recommended sequencing (contest → pilot → scale) is structured to preserve Sierra's optionality at every stage and minimise the cost of error in either direction.