Operator's view11 min
The 'Fix the Data First' Trap at $50M Operators.
Vendors say your data is not AI-ready and need 12 months of warehouse work first. The actual failure data says otherwise. Here is what to do instead.
By TreyTag
Custom Software.
32 articles tagged custom software.
Teardown11 min
Harvey vs Spellbook vs CoCounsel: $40M Law Firm Teardown.
At $40M, Harvey is mostly out of reach, Spellbook is the practical default for transactional work, and CoCounsel makes sense if you live in Westlaw.
By TreyOperator's view10 min
Why PE Pays 14x EBITDA for HVAC Data Center Contractors.
The HVAC private equity multiple has split. Generic commercial shops clear 7-10x. Contractors with documented data center backlog clear 12-14x.
By TreyTeardown11 min
Odessa vs NetSol Ascent vs Aspire for $50M Lessors.
Three platforms dominate the mid-market equipment finance LOS conversation. Here is what a $50M independent lessor actually gets from each.
By TreyOperator's view11 min
Why Your AI Strategy Doc Is Not the Bottleneck.
Mid-market boards keep asking for AI strategy decks. The data on pilot failure rates says the strategy doc is not what is actually blocking production.
By TreyOperator's view10 min
Where Commercial Insurance AI Capital Landed in 2026.
Q1 2026 insurtech funding hit $943M with 75% flowing to AI-native platforms. Here is where the money went and what a $50M broker should do about it.
By TreyTeardown12 min
Sage Estimating vs STACK vs PlanSwift: $50M GC Teardown.
Mid-market GCs evaluating estimating software end up at three platforms. Each is built for a different shop. Here is the honest decision matrix.
By TreyTeardown12 min
Plex vs Epicor Kinetic vs Global Shop: $50M Manufacturer.
At $50M, most manufacturers outgrow QuickBooks but pick the wrong ERP. Here is what Plex, Epicor Kinetic, and Global Shop actually deliver.
By TreyOperator's view9 min
When Your AI Problem Is Actually a Process Problem.
We've turned down four AI projects this quarter. None of them needed AI. What looks like an AI problem is usually a workflow, integration, or knowledge problem.
By TreyTeardown11 min
Epicor Prophet 21 at $50M: What Breaks and What's Next.
Your $50M distributor runs on Prophet 21 and you know exactly where it breaks. Here is what to do about it before the 2029 sunset deadline.
By TreyOperator's view10 min
Why PE Is Paying 14x EBITDA for Mid-Market CPA Firms.
Mid-market CPA firms are selling to PE at 11x to 15x EBITDA. The multiple is not about the book of business. It is about a binding operational constraint AI is breaking.
By TreyField notes11 min
Concentration Risk: The Spreadsheet Every Factor Maintains.
Mid-market factors run concentration risk on a spreadsheet because the LMS does not report it the way credit committee needs to see it. Here is the fix.
By TreyPlaybook11 min
How $50M Fire Protection Contractors Track 5,000 Inspections.
Mid-market fire protection shops run 5,000+ NFPA inspections across 200 sites. Here is the operating model that prevents the misses.
By TreyTeardown11 min
Tamarac vs Orion vs Black Diamond: The $40M RIA Teardown.
PortfolioCenter is gone. Morningstar Office is sunsetting. Here is how Tamarac, Orion, and Black Diamond actually compare for $40M-$2B RIAs.
By TreyOperator's view12 min
Where $50M Operators Are Actually Spending AI Budgets.
Gartner says 2026 is the AI inflection year. The mid-market reality is smaller, sharper, and decided by the software you already pay for.
By TreyTeardown12 min
nCino vs Salesforce FSC vs Q2 for $100M Specialty Lenders.
None of the three big lending platforms were built for non-bank specialty finance. Here is what nCino, Salesforce FSC, and Q2 actually solve, and where each breaks.
By TreyOperator's view12 min
The Hidden Cost of Running Five Systems at $50M.
Five operational systems is the mid-market default. The combined cost rarely shows up on any line item. Here is what it actually runs at a $50M operator.
By TreyOperator's view11 min
Why Healthcare RCM Is the Next Mid-Market AI Roll-Up.
In 18 months PE took R1 RCM private at $8.9B and built a $5B payment integrity platform. The next wave hits mid-market healthcare admin firms.
By TreyTeardown12 min
NetSuite vs Sage Intacct: The $40M Distributor Teardown.
Stop comparing them as ERPs. NetSuite is an operational ERP, Sage Intacct is a financial system. A $40M distributor making the wrong comparison overspends by six figures.
By TreyTeardown12 min
Wealthbox vs Redtail vs Salesforce FSC for $40M RIAs.
Wealthbox, Redtail, and Salesforce FSC each pitch the same $40M RIA. Here is the cost math, custodian reality, and where AI changes the decision.
By TreyOperator's view11 min
The Case for Hiring an Internal AI Ops Lead at $50M.
Mid-market AI engineers run $230K to $310K all-in. Boutique services run $75K to $200K a year. Here is how to think about the hire and when it pays back.
By TreyPlaybook11 min
Work-in-Process Visibility for $40M Manufacturers.
Most mid-market manufacturers run their shop floor on paper travelers and a foreman's walk-around. Here's the middle answer between clipboards and a full MES.
By TreyOperator's view11 min
PE Is Rolling Up Field Service Software. Three Options..
Private equity poured $3.5B into field service software in 18 months. Here is what $50M HVAC, plumbing, and electrical operators should do.
By TreyTeardown11 min
QuickBooks Enterprise at $50M: What Breaks and What's Next.
At $50M revenue, three QuickBooks Enterprise limits hit first: record count, multi-entity consolidation, and custom workflows. Here is what to do.
By TreyField notes11 min
Why AI Pilots Stall at the Same Point Every Time.
Across mid-market rollouts, AI pilots stall at the same moment. It is not data, models, or budget. It is the handoff nobody plans for.
By TreyTeardown11 min
Practice Management Software for $40M Law Firms.
Clio, MyCase, PracticePanther, Aderant: an honest assessment of what each delivers for mid-market law firms, where the math breaks, and what to do about it.
By TreyField notes12 min
Why Insurance Applications Get Keyed Three Times Over.
Mid-market carriers re-key the same application into lead, workbench, policy admin, and archive. The fix is connecting two systems you already own.
By TreyOperator's view11 min
Why Specialty Finance Is the AI Vertical Nobody Is Targeting.
Harvey hit $11B with $190M ARR. Meanwhile $1.34T in equipment finance, 15,870 RIAs, and a wide-open vendor map sit ignored. Specialty finance is the bet.
By TreyTeardown9 min
Procore vs. the Field: What $40M Contractors Need.
Procore is built for ENR-ranked firms doing $200M+ in volume. Here is what mid-market GCs actually need and what they should pay for it.
By TreyTeardown10 min
No ERP Does Everything. Here Is What Works Instead..
Your ERP handles accounting and job costing fine. Quoting, knowledge capture, field coordination, and claims routing need something else.
By TreyOperator's view11 min
What AI Actually Costs for a 20-Person Shop.
AI vendors quote $150K. Your shop does $8M in revenue. Here is what AI realistically costs, what it doesn't, and where the money actually goes.
By TreyOperator's view9 min
Build vs. Buy AI: What No One Tells Mid-Market Leaders.
Most build-vs-buy AI advice targets Fortune 500 or startups. Here is the framework for the $30M to $100M company stuck in between.
By Trey№ 005Get in touch
Tell us the workflow.
It's a conversation, not a sales call. You tell us what's broken, we'll tell you if we can fix it.
hello@granular.to