Yes.
You need to fix your service delivery stack before any CRM will help you.
What's really going on
You're a consulting startup, so your "pipeline" is really three separate flows: prospects you're courting, hours you're billing, and quotes you're sending. One tool won't cover all three well. And at startup stage in Chicago, your bottleneck is almost certainly not tracking — it's landing the next client. Buying a CRM now means paying monthly for a pipeline with five names in it.
What to do instead
- Google Sheets or Notion (free) — one sheet, three tabs: prospects, active clients, quotes sent. This IS your CRM until you have 30+ live leads.
- Toggl Track or Harvest (free tier, check current pricing) — start the timer when you open a client's file, stop it when you close it. Time tracking is a habit, not a feature.
- A quote template in Google Docs — one page, your rates, scope, terms. Duplicate per client.
Today, in 30 minutes: open a new Google Sheet, name it "Pipeline", and list every conversation you've had in the last 30 days with a person who could hire you. Add columns for last contact, next step, and quote status.
What you're being oversold
Someone will pitch you Pipedrive or HubSpot because "consultants need a CRM." At your stage, with a handful of prospects, a $15/user/mo pipeline is a $180/year way to feel professional while doing the same work a sheet does. Worse, the field-service tools like Jobber quote-to-invoice flows don't fit consulting engagements. Doing nothing costs you almost nothing right now — the real cost is buying software you'll abandon in three months.
When to revisit this
When you're juggling more than 30 active prospects or you've lost a deal because you forgot to follow up.
The part worth getting right
Here's the fork: are you selling fixed-scope projects, or hourly retainers? If it's fixed-scope, quoting is your leverage — a good template and a scope-creep clause matter more than any CRM, and you'll want quote-tracking eventually (Pipedrive fits later). If it's hourly retainers, time tracking IS your billing system, and picking the wrong one means re-entering months of hours into QuickBooks by hand. Pick wrong and you rebuild your stack in six months. Which model are your first three clients actually on?