Great question — answering as the UphillTech team:
Two automatic follow-ups: day 2 ('any questions on the quote?') and day 7 ('price valid till Friday, want me to hold the slot?'). Converts 20% of dead quotes.
Automation removes the awkward — it's the system following up, not you nagging.
We set this up as part of every site: https://www.uphilltech.ca.