Anindependenttechnicalreadbeforeyousign.

How I structure a vendor evaluation

A structured software vendor evaluation has four layers. First, requirements: what does the system actually need to do, ranked by priority — not a wish list, a weighted set of must-haves and nice-to-haves. Second, vendor qualification: a scored criteria matrix covering functional fit, technical integration requirements, security and compliance posture (SOC 2, ISO 27001, data residency), vendor financial health, support model, and roadmap alignment. Third, TCO modeling: 3-year total cost per vendor, built from implementation fees, per-seat or usage-based pricing, projected overages, integration work, and eventual migration cost. Fourth, contract review: a 15-20 item red-flag checklist applied to every shortlisted vendor's contract before any negotiation begins.

I join vendor demos when useful — the dynamic changes when a technical person is in the room asking questions the sales team hasn't heard before. I've seen vendors quietly revise their SLA terms after a 20-minute demo debrief.

Contract terms I push back on every time

Vendor contracts run through a consistent set of traps. Here are the ones I flag on nearly every engagement.

Data rights: default contracts frequently grant vendors broad rights to use your data for "service improvement" and model training. The fix is limiting those rights to pure service delivery only. SLAs: a 99% uptime guarantee equals roughly 7 hours of downtime per month. For production systems, I target 99.9% or higher, with defined financial penalties, not just credits. Auto-renewal: contracts with 90-day notice windows are common. I push for 30-day notice, and I flag the renewal date on the first day of the engagement. Exit clauses: "you get 60 days of data export on termination" is the standard; I negotiate 90 days plus documented migration assistance. Liability caps: most vendors cap liability at one month of fees. For mission-critical systems, I target 12 months' fees as the cap. Termination for convenience: some vendors forbid it outright. It belongs in every contract.

TCO modeling: where the headline price falls apart

The sticker price is usually the least important number in a vendor comparison. The costs that determine true TCO are mostly invisible until you're 18 months in.

Implementation: vendor onboarding fees ($2k–$20k per week depending on the platform), internal team time allocated to the project, and any second-vendor integration work. Ongoing: per-seat fees that escalate faster than your headcount, overage charges on API calls, transactions, or active users that only appear after you hit scale, and add-on modules that turn out to be essential but weren't in the demo. Migration: exit costs when you eventually leave, which every vendor makes as painful as possible by design.

I build a 3-year TCO model per finalist. In most engagements the cheapest headline-price vendor is not the cheapest at 36 months. I've seen cases where the vendor with 2x the monthly cost works out 40–50% cheaper when onboarding, integration engineering, and likely exit costs are priced in honestly.

When to run an RFP versus direct vendor outreach

An RFP (request for proposal) is the right tool in a narrow set of situations: the buyer has well-defined, documented requirements; multiple qualified vendors exist; and the evaluation needs to be defensible to a board or procurement committee. For most early-stage and growth-stage companies I work with, a structured RFP is overkill. It takes 8–12 weeks, vendors submit polished proposals that tell you less than a 2-hour technical demo, and the process delays a decision that could have been made faster and better.

Most of my vendor work runs as direct-outreach evaluation: define requirements, build a shortlist of 3–5 vendors, run structured demos with a scoring sheet, model TCO, and review contracts. That process takes 2–3 weeks, not 10. If your situation genuinely requires an RFP — regulatory requirement, public procurement, or board-mandated process — I can structure and manage that as a longer engagement.

Real-world context: 40+ vendor integrations at bolttech

At bolttech — a $1B+ unicorn operating across 15+ markets with 40+ payment providers integrated — vendor selection was continuous work, not a one-time event. Every new market required local payment provider relationships. Every regulator required specific partner certifications. Every product line involved build/buy tradeoffs under deadline pressure.

The evaluation framework I use today comes directly from that experience. Structured scoring beats sales-team persuasion every time. TCO matters more than headline price. Contract discipline — especially exit clauses and data rights — prevents expensive problems years later. The principles are the same at a 10-person startup as at a $1B+ unicorn; the volume differs, the discipline doesn't.

Scope, pricing, and when to skip this engagement

Single-decision vendor reviews (one category, 3–5 shortlisted vendors) fit a 2–3 week fixed-scope engagement under the Fractional CTO service at $5,499/mo. Larger vendor programs — category-wide strategy, multi-vendor RFPs, enterprise procurement support — fit an ongoing retainer.

Deliverable: requirements document, scored evaluation matrix, 3-year TCO model per vendor, contract red-flag review, negotiation strategy memo. 14-day money-back if the deliverable doesn't change how you approach the decision. Work Made for Hire on all written output.

Not every vendor decision needs this. Under $5k/year SaaS tools where you have strong internal familiarity, or vendors with 5+ peer references from companies at exactly your stage — those don't warrant consulting overhead. I'll tell you that in the first call. The engagement economics only make sense above roughly $20k/year per vendor, for mission-critical categories, or where the contract terms have multi-year exit implications.