| Duprey, Michelle | Deputy Corporation Counsel | Corporation Counsel | (203) 946-7962 |
| LaMarr, Catherine | Deputy Corporation Counsel | Corporation Counsel | (203) 946-7974 |
| Williams, Roderick | Deputy Corporation Counsel | Corporation Counsel | (203) 946-7966 |
| Hladun, Stephen | Deputy Director | Parks Department | (203) 946-8576 |
| Patton, Jeffrey | Deputy Director | Public Safety Communications | (203) 946-6234 |
| _, Vacant | Deputy Director | Youth and Recreation Department | (203) 946-6071 |
| Chavez-Brumell, Luis | Deputy Director | Public Library | (203) 946-2279 |
| Futrell, Kim | Deputy Director | Arts, Culture and Tourism | (203) 946-7172 |
| NOTGHI, BIJAN | DEPUTY DIRECTOR - OPERATION | Transportation, Traffic & Parking | (203) 946-8069 |
| HOFFMAN, ERIC | DEPUTY DIRECTOR - PARKING | Transportation, Traffic & Parking | (203) 946-8077 |
| Schroeter, Catherine | Deputy Director Administrative Services | Housing & Development Administration | (203) 946-8274 |
| Graves, Cathy R. | Deputy Director Economic Development | Economic Development Administration | (203) 946-7050 |
| Hendricson, Courtney | Deputy Director Economic Development | Economic Development Administration | (203) 946-8295 |
| Buenaventura, Glenda | Deputy Director Environmental Health - Lead | Health Department | (203) 946-7373 |
| Stroud, Mark | Deputy Director Housing Code Inspector | Livable City Initiative | (203) 946-8266 |
| D'Amore, Frank | Deputy Director Neighborhood & Property Services | Livable City Initiative | (203) 946-2258 |
| Dasent, Tariq | Deputy Director of Admin & Planning | Public Works Department | (203) 946-6738 |
| Logan, Brooke | Deputy Director of Health | Health Department | (203) 946-8351 |
| Shashinka, Felicia | Deputy Director of Operations | Youth and Recreation Department | (203) 946-8088 |
| Kaiser, Rick | Deputy Director of Programs | Community Services Administration | (203) 946-8605 |
| Hougrand, Nate | Deputy Director of Zoning | City Plan | (203) 946-6375 |
| Huggins, Ronald | Deputy Director Youth Services | Youth and Recreation Department | (203) 946-7665 |
| Eyzaguirre, Carlos | Deputy Economic Development Administrator | Economic Development Administration | (203) 946-5761 |
| _, Vacant | Deputy Economic Development Director | Economic Development Administration | (203) 946-5891 |
| _, Vacant | Deputy Fire Marshall | Fire Services | (203) 946-6227 |
| Kirby, Tamara | Deputy Tax Collector | Finance – Tax Office | (203) 946-7075 |
| Gardner , Mamie | Deputy Town Clerk | City Clerk | (203) 946-8342 |
| Aurora, Joe | Detective | Fire Services | (203) 946-6230 |
| Webster, Max | Director | Parks Department | |
| Kemp, Tirzah | Director Community Resilience | Community Services Administration | (203) 946-7846 |
| Veale, Tomi | Director Elderly Services | Community Services Administration, Elderly Services | (203) 946-7854 |
| LaBuff, Patrick | Director Emergency Management | Chief Administrator's Office | (203) 946-8224 |
| Sawicki, Chet | Director Information Technology | Information Technology | |
| Speiller, Lenny | Director of Communications | Mayor's Office | (203) 946-4933 |
| Jefferson, Adriane | Director of Cultural Affairs | Arts, Culture and Tourism | (203) 946-8378 |
