In 1607 he was among the sailors sent to the New World to establish Jamestown, in particular being one of the two dozen colonists led by Captain Christopher Newport that explored the upper James River in a pinnace as far as the falls near present-day Richmond, Virginia in late May of that year.
On 6 May he came within sight of a mountain on the south coast of Spitsbergen, which he named Muscovy Company’s Mount (modern Hornsundtind).
"[3] His report of the number of whales found around Spitsbergen led the Muscovy Company to send two ships there the following year, 1611.
The Mary Margaret spent the month of June hunting whales and walruses, while Poole explored to the southwest, searching for Henry Hudson's elusive Hold with Hope.
In late July, while riding at anchor on the north side of the island, Poole came into contact with three sailors sent by Edge and Bennet.
Coming to Foul Sound he found the Mary Margaret's other men, who had been carried there by an interloper from Hull, the Hopewell, under Thomas Marmaduke.
Here, on 7 August, while transferring the cargo of the stricken Mary Margaret, the Elizabeth, not having enough in her hold to ballast herself, was capsized, nearly taking Poole with her.
Poole was in the hold when the accident occurred, and twice while trying to climb through the hatches barrels of beer and "diverse other things" knocked him down.
In early June Poole met with another interloper, the Hopewell of Hull, again under Thomas Marmaduke, which may have been fitted out this year to hunt for whales.
The ships returned to London later that year with 180 tons of oil from the capture of seventeen bowhead whales and two walruses.
Poolepynten (Poole Point), on the southeastern coast of Prins Karls Forland (Prince Charles Foreland), was named in his honor.