Executive Team | Affordable American Insurance

Chris Fernandez

CEO & President

“I’m dedicated to all of our agents, to make sure they have the best tools available so that they can make fast better decisions and become better business owners. ”

My passion lies in building great teams and expanding companies while fostering a culture of support and growth. I started my career as an entry level IT technician and worked my way up to lead a company that helps small business owners and entrepreneurs thrive.

I believe that small businesses are the backbone of America, and there's nothing more rewarding than helping someone take their first step toward independence. Being part of that journey whether it's helping them launch their agency or scale it is what fuels me every day. At AAI, we’re not just in the business of insurance; we’re in the business of empowering people. Insurance is ultimately about protection and peace of mind, and I’m proud to lead a company that helps people and businesses protect what matters most.

Over the years, I’ve led AAI through key transitions and milestones from expanding our footprint across 27+ states to acquiring agencies and reaching new heights in revenue and premium growth.

What drives me is creating an environment where people love to work and can do their best work. I’m motivated by my family, the desire to leave a positive legacy, and building a company rooted in long term success, flexibility, and meaningful relationships.

Outside of work, I love to spend time with my wife and 3 kids. I’m also passionate about giving back to my community and setting an example for my kids on the importance of perseverance, service, and vision.

Conor R. Crawford

Executive Vice President | General Counsel

"In a democratic society like that of the United States, where fortunes are small and ill-secured, everyone works and work leads to everything." --Alexis de Tocqueville

Conor joined AAI in April 2021, after working extensively with AAI in private practice since 2018. Conor oversees legal, HR, and compliance at the company. He also plays a key role in agency and carrier relations. Conor has helped agencies with a variety of matters, including business strategy, book acquisitions, human resources, and perpetuation planning.

Conor previously worked at an Am Law 100 firm in its Business & Transactions division, where he specialized in mergers and acquisitions, emerging companies and venture capital, and securities and capital markets. Conor also served as Judicial Law Clerk to the Honorable James E. Gritzner in the United States District Court for the Southern District of Iowa.

Conor is a graduate of Yale University (B.A., History) and the University of Virginia School of Law (J.D.). Conor also graduated from Godolphin Flying Start, the world's preeminent management training program for thoroughbred industry leaders, where he completed equine business studies in Ireland, England, Australia, and Dubai.

In his free time, Conor helps his father with a family business, Donegal Racing, which campaigned 2022 Belmont Stakes Champion Mo Donegal. Conor loves reading, skiing, hiking, golfing, and spending time with his wife and son.

Josh Woods, CIC

Director of Agency Operations

"Passionate about improving systems, strategy, and culture in great organizations"

After working in the nonprofit sector for several years post-graduation from Western Oregon University (BA History; MA, Teaching), Josh started in insurance in 2015 as an account executive for a church and non-profit-focused agency. The following year, he moved into an operations management role and in 2019, he was named Chief Operating Officer of a regional agency network in the Pacific Northwest.

Since joining AAI in 2023, Josh has been working to improve network operations and consulting with network agency owners to tailor business strategies to the unique goals of their agencies.

Josh lives in Washington State with his wife and two school-aged sons, along with an Australian shepherd and a husky. When not reading up on the latest insurance news, Josh enjoys travel, music, and volunteering with Wide Awake International, a disability-focused non-profit working in Ukraine.

Marie Destito

Director of Agency and Carrier Relations

“Our greatest asset is the relationships we build. Each morning, I ask myself how I can deepen a connection I have or create a new one."

With 25 years of experience in a family-owned strategic branding and communications agency servicing Fortune 500 clients in the leisure industry, Marie held various roles, including account supervisor, account director, group account director, and branding group director. After the agency was acquired by an international advertising firm, she spent 10 years at home raising her three boys, further refining her skills of adaptability, patience, and negotiation.

When she re-entered the workforce with AAI in 2014, insurance was a new venture, but she was excited to bring her extensive business experience to another family-owned environment. It didn’t take long for her to fall in love with the industry. Marie is deeply committed to the industry, to AAI, and to continuing to build strong relationships with agents and carriers, leveraging her business experience and people skills to foster collaboration and mutual success. She is passionate about working in team settings to achieve the best possible outcomes for all involved.

In her free time, Marie loves spending time with family, friends, and her dogs, entertaining, nurturing her yard and gardens, traveling, and exploring the great outdoors of Colorado. She is also a big sports and music fan and enjoys attending games and concerts.

Cristina Pope

Financial Controller

"Finance works best when it informs strategy, not just reports results"

Cristina Pope is a senior finance executive with more than 20 years of experience leading accounting, finance, and operational functions for companies across manufacturing, distribution, wholesale, professional services, and financial services industries.

Cristina has held progressive leadership roles including CFO, Controller, and Finance Manager, partnering closely with executive teams, private equity stakeholders, and international corporate offices to deliver accurate financial reporting, strengthen internal controls, and support strategic growth initiatives. Her expertise spans financial statement preparation and analysis, cost and inventory management, cash flow forecasting, tax compliance, ERP implementations, and process optimization.

Known for her hands-on leadership style and analytical approach, Cristina has successfully built and led high-performing teams, implemented scalable policies and procedures, managed complex multi-entity environments, and driven operational efficiencies across organizations with diverse business models.

Cristina holds a Bachelor of Science in Accounting and is highly proficient in a wide range of financial and ERP systems, including NetSuite, SAP, JD Edwards, Sage, Hyperion, and QuickBooks. She is recognized as a collaborative, results-driven professional with a strong commitment to operational excellence and continuous improvement.

Cristina lives in North Carolina with her husband and son, along with two sweet puppies. Cristina enjoys traveling, reading, sports (especially college football) and spending time with her husband and son.

MEET OUR EXECUTIVE TEAM