Guest Stars Clark Gregg as Arthur Sackler, Sr. Carolina Bartczak as Lily Kryger Brian Markinson as Howard Udell Sam Anderson as Raymond Sackler Ana Cruz Kayne as Brianna Ortiz Ron Lea as Bill Havens Jack Mulhern as Tyler Kryger Matt Baram as Dr. Robert Kaiko Jonathan Higgins as Dr. Coyle Daniel Kash as Stanley Dan Fox as Arthur Sackler Jr. Co Starring Olivia Markowski as Toddler Kaylee Vivienne Markowski as Toddler Kaylee David Tompa as Conference Room Lawyer Darrin Baker as Dr. Hartman John Bydevaate as Mechanic #3 Bryan McLelland as Mechanic #1 James Boyd as Mechanic #2 Krista White as Mary Jo White Simon Sinn as Focus Group Doctor #2 Catherine Tait as Jillian Sackler Lesley Faulkner as Elizabeth Sackler Sanjay Talwar as ER Doctor Neil Foster as Handyman Cece King as Shannon's Mom Sean Browning as Mike Chris O'Bray as Focus Group Doctor #3 Wendy Lyon as Facilitator Michèle Kaye as Denise Sackler Maureen Ludford as Focus Group Doctor #5 David Bronfman as Focus Group Doctor #1 Caylie McRae as Coyle's Receptionist Michael Gimera as Shannon's Mom Boyfriend Gary Eisler as Focus Group Doctor #4 Natasha Bromfield as Intake Nurse Maria Ricossa as Else Sackler Lara Daans as Physical Therapist