Decision: Should we replace the single $99/month plan with tiered pricing this quarter, and at how many tiers? Options: - Stay on the single plan. No change. - Three tiers (entry, standard, enterprise). The conventional B2B SaaS structure. - Two tiers plus a custom enterprise track. Lower build cost, captures the high end through sales conversations rather than self-serve. - Keep $99 as the standard tier and add only an enterprise tier now; add a cheaper entry tier later. Sequenced to fit the bandwidth constraint. Criteria that actually matter: 1. Revenue captured from accounts you're currently losing or underpricing. This is the whole reason to act. 2. Engineering cost this quarter. You said bandwidth is tight; a full three-tier self-serve build with metering and gating is not a small job. 3. Sales motion fit. Big accounts wanting security features are usually closed by a person, not a pricing page. 4. Churn risk on existing $99 customers if they get reshuffled into a worse tier. Tradeoffs: - Three tiers now: captures both ends, but the metering, feature-gating, and migration work is the most expensive option and collides directly with your bandwidth constraint. - Two tiers plus custom enterprise: gets most of the upside (the lost big accounts close through sales) at a fraction of the build. You give up self-serve capture of the high end, which at your size you aren't doing well anyway. - Enterprise tier only, entry tier later: smallest immediate build, unblocks the deals you're losing now. You give up the small-account revenue for a quarter. Recommendation: Add an enterprise tier now (sales-assisted, with the security features gated to it), keep $99 as the standard tier, and defer the cheaper entry tier to next quarter. Confidence: medium. What would change this: - If the lost small accounts are larger in count and aggregate revenue than the lost big accounts, flip to building the entry tier first. - If the security features are already built and just need gating, the cost argument weakens and full three-tier becomes viable now. - If sales is losing big accounts purely on seat count and not features, you may not need a new tier at all, just seat-based add-ons on the existing plan. What I'd need to know: - Dollar value and count of the big accounts lost in the last two quarters versus the underpriced small accounts. - Which security features are being asked for and whether any are already built. - Whether the $99 plan is per-seat or flat for the whole account.