Our leadership team

Samer Khouli | Founder & CEO

IDEATION, COMMUNICATION, WOO, POSITIVITY, & ACTIVATOR
GALLUP CERTIFIED STRENGTHS COACH

Before the internet was commonplace, Samer started his business career selling snacks he bought from Price Club to his friends in high school. He then had a small business selling POGS and putting on POG tournaments. For Samer, there is no limit to the amount of knowledge one can achieve and the variety of experiences one can try. When he became frustrated with workers compensation, he went out and got his insurance brokers license, so he could speak directly with carriers, MGA’s, claims reps, etc. With a passion for innovation, desire for efficiency and with over 20 years of experience in HR, staffing and technology, Samer has built TCW into a state-of-the-art home for the biggest contingent workforce geeks. He loves leadership and wants TCW to be an example for other companies in terms of ethics, passion for the task, and love for the people.

Quote
“The best is yet to come.”

Fun Fact
He was president of the chess club in high school… don’t be jealous.

Erica Ostberg | Chief Legal Officer

ACHIEVER, ANALYTICAL, FOCUS, COMPETITION, RELATOR

Erica joined TCW in 2019 as our CCO & General Counsel. Navigating legal and compliance for a company that has over 10,000 contingent workers all over the globe is no easy task. Luckily she brings with her a wealth of knowledge in areas of civil litigation, insurance law, and construction defect litigation. She then transitioned into the field of workers’ compensation, where she worked her way up to the role of office managing partner at a large statewide workers’ compensation defense firm. She has the ability to mesh her legal knowledge, practical litigation experience, and understanding of compliance regulations in a strategic manner to best serve the needs of our clients.

Quote
“To give real service, you must add something that cannot be bought or measured with money, and that is sincerity and integrity.” Douglas Adams

Fun Fact
I have not eaten red meat since I was probably ten. It’s not for activist or health reasons...just purely find the texture gross!

Ryan Anning | Chief Financial Officer

ACHIEVER, DISCIPLINE, FOCUS, LEARNER, & RELATOR

For a lot of “normal” people, balancing a personal checkbook can be a real struggle. Most would find it incomprehensible to manage a business’ budget, revenue, risk, planning, etc., let alone paychecks for tens of thousands of global workers annually. It takes a special breed to manage corporate financials, which is why TCW’s CFO is so stinkin' awesome. With decades of experience yet the youthfulness of a 20-year old, Ryan developed and streamlined our finance and accounting department’s best practices. Ryan competently oversees the finances, accounting, risk and future financial needs of the organization. He provides the team with the data, analytics, and insights to help all the leaders do their jobs effectively and profitably, but always remembering the mission of our organization.

Quote
“Every accomplishment starts with the decision to work hard.” John F. Kennedy

Fun Fact
Ryan’s guilty pleasure is collecting Christmas decorations. His goal is to out decorate Chevy Chase in Christmas Vacation. No, but really.

Leslie Cruz | Chief Operations Officer

 RELATOR, INDIVIDUALIZATION, COMMUNICATION, ARRANGER & RESPONSIBILITY

Leslie has spent most of her adult life living in Austin, Texas, the place where she and her husband raised their two amazing kids. She has spent a majority of her career handling Operations and Project Management. Leslie has built and transformed Client Success along with Service Delivery Teams. “The best part of leading Operations is having the ability to marry the creative and the human elements that make up world class customer service. Efficiency and innovation are the key components that allow organizations to grow.” Ever since she relocated to San Diego, Leslie has been enjoying the beach, going on hikes, and soaking up everything San Diego has to offer. 

Quote

“Incredible change happens in your life when you decide to take control of what you do have power over instead of craving control of what you don’t.” – Steve Maraboli

Fun Fact

Leslie has an irrational fear of birds (especially sea gulls), but that doesn’t stop her from spending time at the beach.

Andy Waggoner | Vice President of Technology Infrastructure

RESTORATIVE, INDIVIDUALIZATION, DEVELOPER, LEARNER, & ANALYTICAL

Originally from Nampa, Idaho and loving his hay day of being a tennis pro, Andy found his transition to San Diego a bit eye-opening. He spent much of his college years learning about crazy California culture and building a strong work ethic while working toward his degree in Organizational Leadership. Fast forward 15 years and you couldn’t tell he was anything but an expert California native, that loves to create places and programs to help people succeed and be effective. Andy is responsible for designing and creating an operable space for our employees to conduct and flourish in business and meeting our business goal. Everything from designing and installing workspaces to managing the expansion of a growing business, Andy is at the helm of TCW’s long-term infrastructure plan. Andy has an awesome, fashion-forward wife, a bunch of great kids, a lot of dogs, 2 guinea pigs and loves to spend time old and new friends alike.

Quote
“Never before in history has innovation offered promise of so much to so many in so short a time." - Bill Gates

Fun Fact
Andy has 5 kids and never, ever, turns down a good burger.

Cooper | Director of Snacks & Wiggles

POSITIVITY, CONTEXT, WOO, HARMONY, & BELIEF

Cooper joined the TCW team in October 2016 during a visit to some of our Texas clients. We adopted her at 8 weeks old! She is filling the paws of Charlie who faithfully served TCW since day one. Cooper loves everyone but plays hard-to-get on occasion. If she sees a closed door, it must be opened (we actually had to change some of our door knobs) because a meeting without Cooper just isn’t a meeting. You’ll find signs of Cooper's love and everyone’s love of Cooper all across the organization - you see this across much of the marketing and even notice a pup's touch in our employee benefits.

Quote
"Ain't no business like show business." - The Fresh Prince

Fun Fact
Cooper considers herself a down-to-earth “southern bell” from Paris, Texas.

Tom Kucharski | Chief Technical Officer

HARMONY, RELATOR, RESPONSIBILITY, ARRANGER & DEVELOPER

CTOs are frequently advised that IT needs to be aligned with the business. However, Tom has always focused his efforts on integrating IT into the business, making IT integral to every aspect of the enterprise. During his 25+ year career, Tom has led IT teams across a variety of business verticals. He drives both operational and software teams to perform efficiently and creatively to get to the core of issues and deliver solutions.    

Quote
"The pessimist complains about the wind. The optimist expects it to change. The leader adjusts the sails.” - John Maxwell

Fun Fact
Tom co-hosts a podcast about his alma mater’s basketball team and has interviewed over 30 former players. Yes, he’s really proud about this.