⅓ cup dried cherries
2½ cups cubed peeled butternut squash
1 cup reduced-sodium beef broth
2 tsp. all-purpose flour
¼ tsp. freshly ground pepper
½ tsp. salt
½ tsp. dried rubbed sage
1 tsp. dried thyme
1 large shallot, halved and thinly sliced
8 oz. bottom-round beef, trimmed, cut into ¾-inch cubes
2½ tsp. canola oil, divided