A metabolomics/peptidomics and genomics approach, using UPLC-MS<sup>E</sup>, molecular networking, and genome mining, was used to describe the serrawettin W2 lipopeptide family produced by <i>Serratia marcescens</i> NP2. Seven known serrawettin W2 analogues were structurally elucidated along with 17 new analogues, which varied based on the first (fatty acyl length of C<sub>8</sub>, C<sub>10</sub>, C<sub>12</sub>, or C<sub>12:1</sub>), fifth (Phe, Tyr, Trp, or Leu/Ile), and sixth (Leu, Ile, or Val) residues. Tandem MS results suggested that the previously classified serrawettin W3 may be an analogue of serrawettin W2, with a putative structure of cyclo(C<sub>10</sub>H<sub>18</sub>O<sub>2</sub>-Leu-Ser-Thr-Leu/Ile-Val). Chiral phase amino acid analysis enabled the distinction between l/d-Leu and l-Ile residues within nine purified compounds. <sup>1</sup>H and <sup>13</sup>C NMR analyses confirmed the structures of four purified new analogues. Additionally, genome mining was conducted using <i>Serratia</i> genome sequences available on the NCBI database to identify the <i>swrA</i> gene using the antiSMASH software. NRPSpredictor2 predicted the specificity score of the adenylation-domain within <i>swrA</i> with 100% for the first, second, and third modules (Leu-Ser-Thr), 60-70% for the fourth module (Phe/Trp/Tyr/Val), and 70% for the fifth module (Val/Leu/Ile), confirming MS<sup>E</sup> data. Finally, antibacterial activity was observed for compounds <b>6</b> and <b>11</b> against a clinical <i>Enterococcus faecium</i> strain.