Watchman Waterproofing

Watchman Waterproofing works out of Pembroke, on the South Shore, and the calls it gets are almost all the same shape: a basement that won't stay dry, a sump pump on its last legs, a crawl space someone's worried about. The company says it has served the greater Boston area for nearly a decade under owner Tim O'Brien, a military veteran and licensed builder — though Better Business Bureau and Angi both put the founding closer to 15 years back, so the exact age is a bit of a moving target. The review volume backs up the reputation: 4.7 stars across 87 Google reviews, 4.9 stars across 193 on Angi, and 72 reviews total spanning six sources since 2019. What keeps showing up, even in 2026, is Tim or the crew walking a property and talking a homeowner out of the bigger job — in March, one customer got referred to a different contractor entirely once it turned out their water problem was a gutter issue, not a foundation one. Victor and his team get named directly for clean, careful installs, including a deck a repeat customer was still getting compliments on months later. Not every recent account is clean. One reviewer this spring described the interior system holding up fine for eight years, but the exterior drainage line cracked and started backing up outside the house, and said the problem still wasn't fixed. It's one report out of nine from the past six months, not a pattern, but it's worth asking specifically how the exterior lines are engineered and what the warranty covers if one cracks. Angi's own summary of the business also flags a handful of older reviews raising similar communication complaints, so pinning down response times for warranty callbacks in writing is a reasonable ask upfront. For a standard wet-basement or sump-pump job, there's enough history here to lean on: an active Massachusetts HIC license, an A+ BBB rating, and years of reviews that keep pointing to honesty over upselling. Anyone dealing with a more complicated exterior-drainage setup should just push a little harder on those specifics before signing.