Why

With a shared bid@ inbox already CC'ed on every proposal, you've accidentally built the perfect data source for a CRM that auto-logs email — that's the automation lever you should be pulling. At your volume (call it ~350 bids/month across 7 people = ~50 bids/person/month) the follow-up problem isn't memory, it's that nobody owns "day 7 nudge after bid sent." Five verticals (multifamily, commercial, transportation, gas, electric) means you need multiple pipelines in one tool, not one generic funnel. Between your two candidates, Pipedrive handles multi-pipeline cleanly; Salesflare's email auto-enrichment is stronger but its multi-pipeline UX is weaker.

What you actually need

1. Pipedrive Advanced ($34/user/mo, ~$238/mo for 7 seats) — five separate pipelines (one per vertical), each with stages: Bid Requested → Estimating → Bid Sent → Follow-up 1 → Follow-up 2 → Won/Lost. Connect the shared bid@ inbox so every CC'ed proposal auto-creates or updates a deal.
2. Pipedrive Workflow Automation (included in Advanced) — when a deal moves to "Bid Sent," auto-create two follow-up activities: +7 days and +14 days, assigned to the estimator on the deal. This is the single automation that pays for the tool.
3. A habit — Friday bid-board review — bid coordinator runs the "Bid Sent >14 days, no response" filter every Friday, walks it with the estimators, kills or chases each one.

Do this today

Sign up for Pipedrive's 14-day trial at pipedrive.com on the Advanced plan, then go to Settings → Company → Pipelines and create five pipelines named after your verticals with the six stages above. Then Settings → Mailbox → Email Sync, connect the shared bid@ address with "Smart BCC" / "Email sync" enabled. By tonight every new proposal that hits bid@ creates a deal automatically and you stop typing bid info into a spreadsheet.

What to ignore

Skip Salesflare for your case — its auto-logging is elegant for single-pipeline B2B sales teams but it gets clumsy when you're juggling five verticals with different stage logic. Ignore anyone pitching you Salesforce Sales Cloud (~$165/user/mo) or HubSpot Sales Hub Professional ($100/user/mo) — both are 3-5x the cost for features a 7-person estimating team will never use. Don't bolt on Outreach or Salesloft; you're not running cold cadences, you're chasing warm bids.

What doing nothing costs you

A conservative 10% slippage on 350 bids/month = ~35 bids/month with no follow-up. In utility contracting where a single bid can run $50K–$500K+, even one recovered bid a month from disciplined follow-up pays for Pipedrive for the next decade.

When to revisit this

When you cross 10 estimators or start needing custom bid-margin reporting that Pipedrive's Insights can't build — then look at HubSpot Sales Hub Professional or a vertical tool like BuildingConnected.