Kassandra Kaine-Calhoun

Starfleet Academy Training:
4 Years - age 17 to 21
Major: Command
Minior: Administration/Operations
Assignments:
Starbase 01 - Yeoman to Captain Tomston
USS MacGuyver - Yeoman to Captain Mica - Ensign
Recruited into Section 31
Assignments - Starbase Baldur - Trainee
Transferred to 414th Fleet - Admiral Ryder's personal assistant.
Yeoman to Captain Angelica Ryder - Starbase Byron
Operations Officer - Ensign
Intelligence Operations - Lt. JG
Presidential Secretary to President Isabella Price - later President Jonathan Price
--
Kassandra is a young officer, recruited straight out of the Academy to be on the Yeoman track. Considered to have immense potential and is very bright and intelligent. Graduated top of her class and was the class Valedictorian. Had a natural aptitude for leadership and for organization. Was watched closely by Section 31 due to her ability to present a neutral face to classified matters. Follows orders to the letter and knows when to 'buck them'. A driven and focused young woman, Kassie was chosen by Admiral Ryder when he needed to take on a new personal assistant. 
Has a fatherly/daughterly relationship with the Admiral, although she was secretly attracted to him and didn't get too upset when his wife left him, not that she expected him to act on any part of it, although they are rather playful together. He'll make comments about her legs, how cute she is, but only when they're alone and admits that 'may be married, but I'm not blind or dead.' Feels protective toward her and gives her potential boyfriends a full background check. Which annoys her to a point, but she kind of likes knowing what she's getting into as well.
Kassandra has dreams of following in his daughter's footsteps and maybe getting an assignment on a flagship and potentially a command of her own someday. But realizes that she's never seen the kind of combat Angel has seen and knows that to be a true commander, she needs to see it. Hopes that her posting as Admiral Ryder's assistant is short term, but if it lasts longer, she wouldn't be too upset.
-- Update -- 
After serving for nearly four years on Starbase Byron as both an Operations Officer and later as an Intelligence Operations officer Kassie has served with distinction in numerous operations and missions, many of her later Intel missions with her husband, Jason Calhoun-Ryder. Finally marrying him after dating for nearly 2 and a half years, she now serves as President Price's personal assistant. Giving up her commissioned rank to serve as part of the Presidential support staff.
Personality wise Kassie has matured and yet has also become freer. She speaks her mind more and is more open to other people. Kassie is something of a nudist at home or other places where it is acceptable and has a very complex sexual relationship with her husband Jason. One would even call her 'kinky', sometimes even wearing collars and other chokers as part of her daily fashion at the office and engaging in intimate acts with her husband Jason in relatively public places. Which has become something of an 'in joke' among Presidential Compound staffers, they call it 'pulling a Kassie and Jason'. Wearing collars or chokers of certain types on certain days was her way of signaling Jason what she was in the mood for that day. Typically dressed in revealing outfits, has no real 'shame' when it comes to what people see and if they get aroused. Very much like her actress mother in that regard, which is where she got her more liberated sexual attitude from. 
Kassie is still a very loyal, very dedicated family friend of the extended Ryder family and considers her role as Isabella and Jon Price's secretary a very special role. Even though she was gifted a small starship from her father in law for a wedding present, and still maintains her Intelligence and special operations clearances, just in case they need to bug out in a hurry. Kassie has been attempting to have a child with her husband, Jason.