Hiring a Personal Assistant or House Manager in Chicago (and beyond)
Pennyworth proudly serves families across the entire United States, from the sun-soaked shores of California to the iconic New York island. We cater to many major regions, with a special focus on two dynamic hubs—Silicon Valley to Wall Street—ensuring we connect exceptional individuals with our valued clients, regardless of where they are located. With a dedicated presence in the heart of the Chicagoland area, spanning from vibrant Chicago to charming Lake Forest, Glencoe, Hillsdale, Deerfield, Winnetka, and Wilmette, we bring our expertise to your doorstep. Whether your family seeks assistance within the household, at the bustling office, or in the virtual realm, we've got you covered. And for those with multiple residences throughout the country or the world, our services extend seamlessly to ensure you have the right support, wherever you are.
Pennyworth has a mission to match the perfect candidates with the unique needs and preferences of your family, no matter where you call home. From coast to coast, we're here to make your household run smoothly and efficiently, ensuring that you have the support you need, exactly when and where you need it.
Hiring a House Manager or Personal Assistant in the Chicagoland area is a significant decision, and it's crucial to consider various factors to ensure a successful and harmonious working relationship.
Here are ten essential things to keep in mind:
Local Employment Laws: Familiarize yourself with Illinois labor laws, including minimum wage, overtime regulations, and employment taxes. Ensure you comply with state and federal employment requirements when hiring and compensating your house manager or personal assistant. We can help send you in the right direction for questions you need answers to from local experts.
Taxes and Benefits: Understand the tax implications of hiring a household employee. You may be responsible for withholding and paying payroll taxes, as well as providing benefits like workers' compensation and unemployment insurance. Your accountant with specific knowledge on state and federal taxes will be your source of truth.
Experience and References: Seeking candidates with relevant experience in house management or personal assisting is key. We always ask for references and thoroughly check their backgrounds to ensure reliability and trustworthiness. When thinking locally - we like to ensure our candidates know the stomping grounds you’ll need their knowledge and relationships the most.
Responsibilities and Expectations: It will be important to clearly define the roles and responsibilities of your house manager or personal assistant for your Illinois based hire. Tasks like household organization, scheduling, errands and family coordination are part of the normal role. If you have multiple residences, such as spending winters in Florida or California, or summers in Europe - understanding how your employee will fit into that schedule will be instrumental in finding the right person from the start.
Cultural Fit: Ensure that the candidate aligns with your family's values, lifestyle, and cultural preferences. Effective communication and compatibility are vital for a successful working relationship.
Weather Considerations: Illinois experiences a range of weather conditions, from snowy winters to humid summers. Discuss how your house manager or personal assistant will handle weather-related responsibilities such as snow removal, lawn care, and seasonal maintenance. Although these responsibilities apply most anywhere and differ by climate - it will be critical to understand any physical labor requirements of the role from the beginning.
Transportation and Commute: Take into account the Chicago and its suburbs traffic and public transportation options. Consider if your candidate has reliable transportation and whether their commute aligns with your location. If you are supplementing their commuting costs, parking, or providing them with a work-vehcile, that should be discussed during the hiring process to ensure the offer letter clearly outlines what the position offers (or does not).
Tech Savvy: In today's digital age, it's essential that your house manager or personal assistant is comfortable with technology. They may need to manage digital calendars, online grocery shopping, and home security systems. If they will be working with complicated systems to maintain various assets and projects, it is helpful to assess those understanding during the interview process.
It is important to keep in mind that hiring domestic staff is a two-way street. It is not just about finding the right candidate, but also about being an informed and supportive employer when it comes to attracting and retaining talent. Ensure that you are prepared to provide clear guidelines, offer competitive compensation and benefits, and foster a positive work environment in order to ensure a successful partnership for the long run.
Pennyworth takes pride in its diverse and deep network from coast-to-coast. We help recruit and place for domestic and corporate employees in many major cities including San Francisco and the broader Bay Area / Silicon Valley (Palo Alto, Menlo Park, Atherton, Mountain View, Burlingame, San Mateo, Marin County, Walnut Creek, Tiburon), Southern California (Los Angeles, Orange County/Newport Beach, San Diego, Santa Barbara), Texas (Dallas, Austin), Colorado (Aspen, Denver), Montana (Yellowstone Club), Wyoming (Jackson Hole), Florida (Naples, Palm Beach, Miami, Boca Raton, Tampa, Pinecrest, Weston), Illinois (Chicago, Glencoe, Lake Forest, Highland Park, Highwood, Lake Bluff, Winnetka, Wilmette, South Barrington, Hillsdale, Deerfield), Minnesota (Minneapolis), Massachusetts (Boston, Dover, Weston, Wellesley, Brookline), New York (Manhattan / New York City, Long Island, Southampton), and more.