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Heat 1 Tbsp. oil in a large skillet over high. Cook beef, breaking up with a wooden spoon, until browned but not completely cooked through, 5–7 minutes. Transfer to a medium bowl with a slotted spoon.
Reduce heat to medium and add remaining 1 Tbsp. oil to skillet. Cook onion, tomatoes, chile, garlic, cumin, pepper, and 1 Tbsp. Diamond Crystal or 1¾ tsp. Morton kosher salt, stirring, until tender but not browned, about 5 minutes. Return beef along with any juices to pan and add potato and stock. Bring to a simmer and cook, stirring and scraping up browned bits, until potato is tender and beef is cooked through, 20–25 minutes. Season with more salt if needed.
Mix in cilantro just before serving.
Do Ahead: Picadillo (without cilantro) can be made 3 months ahead. Transfer to an airtight container and freeze.