Which plan fits your stage
Lite (US$14) fits a solo seller or a team that only needs a shared pipeline and contact list. It stops fitting the moment you want to automate a follow-up or sync bulk email; that is Growth's job, and you will hit the wall fast.
Growth (US$39) fits the working small team: email sync, automation, and forecasting in one plan. It stops fitting when you need lead routing across reps, e-signatures in-app, or custom scoring: the signals that you have outgrown it.
Premium (US$59) fits a larger or more structured sales org that genuinely uses routing, contracts, and tighter permissions. Ultimate (US$79) fits only when account-security controls and enrichment are real requirements, rare under a dozen seats.
The trigger to move up
Do not upgrade on a feeling that you are "probably ready." Upgrade when a named task is blocked: a follow-up you cannot automate (Lite → Growth), leads you cannot route to the right rep (Growth → Premium), a security control you are required to have (Premium → Ultimate). The blocked task is the escalation signal; the plan tier is just its price.
If Pipedrive's per-seat rate is simply too rich for a very small or budget-bound team, the better alternative is a cheaper-entry CRM rather than a stripped Pipedrive plan you will fight. Nutshell, for instance, starts its entry plan at $13 (per user, per month) with no seat minimums or maximums, worth a look before you commit. The full field is ranked in the best budget CRM guide.
Once you have your plan, total the real cost in the cost worksheet and pick a term with the break-even guide.