Watchman Waterproofing

Watchman Waterproofing is a Pembroke basement-waterproofing company run by Tim O'Brien, a military veteran and licensed builder. More than one reviewer describes him showing up to quote a job and instead recommending something far cheaper — a larger dehumidifier instead of a full system in one case, capping an old well conduit instead of a new sump pit in another — after other companies had quoted thousands more for the same problem. Its Massachusetts home improvement contractor registration is active, and Google shows 87 ratings at 4.7 stars with Angi higher still at 4.9 from 193. Reviewers name Tim personally along with staff like Victor, Paul, Amanda and Kevin for basement inspections, French drains, sump pump installs and battery backups. One family says the system has kept their high-water-table home dry for seven years running, and several others describe a thorough walk-through of the basement before any work was proposed. There's a real concern to weigh against that. Spread across 2020 through 2026, several reviews describe slow or absent follow-through on warranty and post-installation problems: a 2024 Angi review says a $15,000 installation didn't fix the water issue and a different company later did it for $10,000, a 2021 review describes a five-day wait for emergency pump service after the company stopped offering 24-hour service, and multiple reviews from 2024 to 2026 mention unreturned calls about ongoing water problems or missed warranty visits. A 2020 review also names a former co-owner, David Kingsley, described in that account as no longer actively involved in the business. For a straightforward basement or crawlspace assessment, Watchman is worth calling, and its no-upsell reputation stands out among waterproofing companies — but given how many complaints involve follow-up and warranty service, get any guarantee spelled out in writing and ask directly what happens if you need them back.