Why

At 200-500 proposals/month across six estimators, the CC-the-director pattern is a tracking hack that stops scaling around bid #100 — you can see proposals go out, but you can't see which ones haven't been followed up on without scrolling. The job to be done is dead simple: every sent proposal becomes a deal with an owner, a value, and a "next follow-up date." Between Pipedrive and Salesflare, Salesflare is the right pick for your situation specifically because it auto-creates contacts and deals from email and pulls in the thread — that's the "reduce data entry" you asked for. Pipedrive needs more manual logging unless you bolt on automations.

What you actually need

1. Salesflare ($29/user/mo, ~$175/mo for 6 estimators) — connects to each estimator's email, auto-creates accounts and contacts from sent proposals, and surfaces "deals gone quiet for X days." This is the one feature that solves your CC'ing-the-director workaround.
2. Six pipelines mirroring your six bid types — stages: Proposal Sent → Follow-up 1 → Follow-up 2 → Negotiation → Won/Lost. Every proposal sent = a deal created automatically with a 7-day follow-up task.
3. A habit — Monday bid-aging review — you and the estimators walk through every deal in "Proposal Sent" older than 14 days. Chase, requalify, or kill. 20 minutes.

Do this today

Go to salesflare.com, start the free trial, and connect YOUR email first (not all six estimators yet). Import the last 30 days of sent proposals from your bid email, then build pipeline #1 with the five stages above. By tomorrow you'll see every open bid you've been CC'ed on as a deal card with an age in days — which is the view you've been trying to construct in your head for months.

What to ignore

Skip Pipedrive for your specific case — it's a great tool but it assumes someone logs the deal; you explicitly said you want less data entry, and Salesflare's email-sync is the differentiator. Also ignore anyone trying to sell you HubSpot Sales Hub Professional ($100/seat/mo) or Salesforce Sales Cloud — at six estimators sending email proposals, you'd pay 3-4x for features (forecasting AI, territory management, custom objects) you won't touch for two years.

What doing nothing costs you

A conservative 10% slippage on 350 proposals/month = ~35 bids/month with no second touch. In utility contracting, even one recovered mid-five-figure bid per month pays for the entire team's Salesflare seats for a year.

When to revisit this

When you hire a dedicated sales ops person or start needing revenue forecasting by pipeline type — then Pipedrive Advanced or HubSpot Sales Hub Starter is worth a second look.