Find the gap after the quote
Choose one source of truth for estimate status. Separate sent, viewed, accepted, declined and on-hold proposals. If those states are unreliable, fix the tracking before scheduling messages.
Make every follow-up useful
A helpful reminder references the work and offers a next step. Ask whether the customer needs clarification instead of inventing urgency or discounts. Agree on timing and approval rules with the people who sell and deliver the work.
Measure the whole sequence
Track replies, accepted estimates, opt-outs and complaints alongside the time saved. Deduplicate records and test stop conditions. A higher message count is not the same as a healthier sales process.
Make the next step practical.
Tell us what you do, where the work gets stuck, and what a useful result would look like. Start there.