diff --git a/.env.prod.example b/.env.prod.example
index c18193c..269950f 100644
--- a/.env.prod.example
+++ b/.env.prod.example
@@ -2,3 +2,7 @@ TZ="Pacific/Auckland"
 PROJECTWORKS_USERNAME=test
 PROJECTWORKS_PASSWORD=test
 SLACK_WEBHOOK_URL=test
+
+CONTENTFUL_SPACE_ID=test
+CONTENTFUL_API_KEY=test
+SLACK_API_TOKEN=test
diff --git a/.env.staging.example b/.env.staging.example
index c18193c..269950f 100644
--- a/.env.staging.example
+++ b/.env.staging.example
@@ -2,3 +2,7 @@ TZ="Pacific/Auckland"
 PROJECTWORKS_USERNAME=test
 PROJECTWORKS_PASSWORD=test
 SLACK_WEBHOOK_URL=test
+
+CONTENTFUL_SPACE_ID=test
+CONTENTFUL_API_KEY=test
+SLACK_API_TOKEN=test
diff --git a/package-lock.json b/package-lock.json
index 6f0f172..eb28dcc 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -9,7 +9,9 @@
       "version": "1.0.0",
       "license": "MIT",
       "dependencies": {
+        "@slack/web-api": "^6.11.0",
         "@slack/webhook": "^7.0.1",
+        "contentful": "^10.6.14",
         "luxon": "^3.4.4",
         "node-fetch": "^2.6.7",
         "node-ical": "^0.17.1"
@@ -1435,6 +1437,14 @@
       "integrity": "sha512-0hYQ8SB4Db5zvZB4axdMHGwEaQjkZzFjQiN9LVYvIFB2nSUHW9tYpxWriPrWDASIxiaXax83REcLxuSdnGPZtw==",
       "dev": true
     },
+    "node_modules/@contentful/rich-text-types": {
+      "version": "16.3.0",
+      "resolved": "https://registry.npmjs.org/@contentful/rich-text-types/-/rich-text-types-16.3.0.tgz",
+      "integrity": "sha512-OfQmAu5bxE0CgQA3WlUleVej+ifFG/iXmB2DmUl4EyWyFue1aiIvfjxQhcDRSH4n1jUNMJ6L1wInZL8uV5m3TQ==",
+      "engines": {
+        "node": ">=6.0.0"
+      }
+    },
     "node_modules/@cspotcode/source-map-support": {
       "version": "0.8.1",
       "resolved": "https://registry.npmjs.org/@cspotcode/source-map-support/-/source-map-support-0.8.1.tgz",
@@ -2309,6 +2319,18 @@
         "@sinonjs/commons": "^3.0.0"
       }
     },
+    "node_modules/@slack/logger": {
+      "version": "3.0.0",
+      "resolved": "https://registry.npmjs.org/@slack/logger/-/logger-3.0.0.tgz",
+      "integrity": "sha512-DTuBFbqu4gGfajREEMrkq5jBhcnskinhr4+AnfJEk48zhVeEv3XnUKGIX98B74kxhYsIMfApGGySTn7V3b5yBA==",
+      "dependencies": {
+        "@types/node": ">=12.0.0"
+      },
+      "engines": {
+        "node": ">= 12.13.0",
+        "npm": ">= 6.12.0"
+      }
+    },
     "node_modules/@slack/types": {
       "version": "2.11.0",
       "resolved": "https://registry.npmjs.org/@slack/types/-/types-2.11.0.tgz",
@@ -2318,6 +2340,49 @@
         "npm": ">= 6.12.0"
       }
     },
+    "node_modules/@slack/web-api": {
+      "version": "6.11.0",
+      "resolved": "https://registry.npmjs.org/@slack/web-api/-/web-api-6.11.0.tgz",
+      "integrity": "sha512-DLShYUc2dE8QrhmrJZ7YuhAuh/VW88Dt3LL7s2KrkEOyxbdfjAtF9bzPOBMlXuWmO6nWLGVevPuhShcYyjwTEw==",
+      "dependencies": {
+        "@slack/logger": "^3.0.0",
+        "@slack/types": "^2.11.0",
+        "@types/is-stream": "^1.1.0",
+        "@types/node": ">=12.0.0",
+        "axios": "^1.6.0",
+        "eventemitter3": "^3.1.0",
+        "form-data": "^2.5.0",
+        "is-electron": "2.2.2",
+        "is-stream": "^1.1.0",
+        "p-queue": "^6.6.1",
+        "p-retry": "^4.0.0"
+      },
+      "engines": {
+        "node": ">= 12.13.0",
+        "npm": ">= 6.12.0"
+      }
+    },
+    "node_modules/@slack/web-api/node_modules/form-data": {
+      "version": "2.5.1",
+      "resolved": "https://registry.npmjs.org/form-data/-/form-data-2.5.1.tgz",
+      "integrity": "sha512-m21N3WOmEEURgk6B9GLOE4RuWOFf28Lhh9qGYeNlGq4VDXUlJy2th2slBNU8Gp8EzloYZOibZJ7t5ecIrFSjVA==",
+      "dependencies": {
+        "asynckit": "^0.4.0",
+        "combined-stream": "^1.0.6",
+        "mime-types": "^2.1.12"
+      },
+      "engines": {
+        "node": ">= 0.12"
+      }
+    },
+    "node_modules/@slack/web-api/node_modules/is-stream": {
+      "version": "1.1.0",
+      "resolved": "https://registry.npmjs.org/is-stream/-/is-stream-1.1.0.tgz",
+      "integrity": "sha512-uQPm8kcs47jx38atAcWTVxyltQYoPT68y9aWYdV6yWXSyW8mzSat0TL6CiWdZeCdF3KrAvpVtnHbTv4RN+rqdQ==",
+      "engines": {
+        "node": ">=0.10.0"
+      }
+    },
     "node_modules/@slack/webhook": {
       "version": "7.0.1",
       "resolved": "https://registry.npmjs.org/@slack/webhook/-/webhook-7.0.1.tgz",
@@ -3288,6 +3353,14 @@
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       "dev": true
     },
+    "node_modules/@types/is-stream": {
+      "version": "1.1.0",
+      "resolved": "https://registry.npmjs.org/@types/is-stream/-/is-stream-1.1.0.tgz",
+      "integrity": "sha512-jkZatu4QVbR60mpIzjINmtS1ZF4a/FqdTUTBeQDVOQ2PYyidtwFKr0B5G6ERukKwliq+7mIXvxyppwzG5EgRYg==",
+      "dependencies": {
+        "@types/node": "*"
+      }
+    },
     "node_modules/@types/istanbul-lib-coverage": {
       "version": "2.0.4",
       "dev": true,
@@ -3389,6 +3462,11 @@
         "@types/node": "*"
       }
     },
+    "node_modules/@types/retry": {
+      "version": "0.12.0",
+      "resolved": "https://registry.npmjs.org/@types/retry/-/retry-0.12.0.tgz",
+      "integrity": "sha512-wWKOClTTiizcZhXnPY4wikVAwmdYHp8q6DmC+EJUzAMsycb7HB32Kh9RN4+0gExjmPmZSAQjgURXIGATPegAvA=="
+    },
     "node_modules/@types/semver": {
       "version": "7.5.6",
       "resolved": "https://registry.npmjs.org/@types/semver/-/semver-7.5.6.tgz",
@@ -4800,7 +4878,6 @@
       "version": "1.0.5",
       "resolved": "https://registry.npmjs.org/call-bind/-/call-bind-1.0.5.tgz",
       "integrity": "sha512-C3nQxfFZxFRVoJoGKKI8y3MOEo129NQ+FgQ08iye+Mk4zNZZGdjfs06bVTr+DBSlA66Q2VEcMki/cUCP4SercQ==",
-      "dev": true,
       "dependencies": {
         "function-bind": "^1.1.2",
         "get-intrinsic": "^1.2.1",
@@ -5269,6 +5346,59 @@
         "node": ">= 0.6"
       }
     },
+    "node_modules/contentful": {
+      "version": "10.6.14",
+      "resolved": "https://registry.npmjs.org/contentful/-/contentful-10.6.14.tgz",
+      "integrity": "sha512-FbdT+ApX7W5r2OZ/6GfKRls8BjrVtJBl/0ijz9ZdzZ7jpZavyQTo9JshSWGk7aJAs8vFGGDkrpaWO1gxYdi/tg==",
+      "dependencies": {
+        "@contentful/rich-text-types": "^16.0.2",
+        "axios": "^1.6.0",
+        "contentful-resolve-response": "^1.8.1",
+        "contentful-sdk-core": "^8.1.0",
+        "json-stringify-safe": "^5.0.1",
+        "type-fest": "^4.0.0"
+      },
+      "engines": {
+        "node": ">=12"
+      }
+    },
+    "node_modules/contentful-resolve-response": {
+      "version": "1.8.1",
+      "resolved": "https://registry.npmjs.org/contentful-resolve-response/-/contentful-resolve-response-1.8.1.tgz",
+      "integrity": "sha512-VXGK2c8dBIGcRCknqudKmkDr2PzsUYfjLN6hhx71T09UzoXOdA/c0kfDhsf/BBCBWPWcLaUgaJEFU0lCo45TSg==",
+      "dependencies": {
+        "fast-copy": "^2.1.7"
+      },
+      "engines": {
+        "node": ">=4.7.2"
+      }
+    },
+    "node_modules/contentful-sdk-core": {
+      "version": "8.1.2",
+      "resolved": "https://registry.npmjs.org/contentful-sdk-core/-/contentful-sdk-core-8.1.2.tgz",
+      "integrity": "sha512-XZvX2JMJF4YiICXLrHFv59KBHaQJ6ElqAP8gSNgnCu4x+pPG7Y1bC2JMNOiyAgJuGQGVUOcNZ5PmK+tsNEayYw==",
+      "dependencies": {
+        "fast-copy": "^2.1.7",
+        "lodash.isplainobject": "^4.0.6",
+        "lodash.isstring": "^4.0.1",
+        "p-throttle": "^4.1.1",
+        "qs": "^6.11.2"
+      },
+      "engines": {
+        "node": ">=12"
+      }
+    },
+    "node_modules/contentful/node_modules/type-fest": {
+      "version": "4.8.3",
+      "resolved": "https://registry.npmjs.org/type-fest/-/type-fest-4.8.3.tgz",
+      "integrity": "sha512-//BaTm14Q/gHBn09xlnKNqfI8t6bmdzx2DXYfPBNofN0WUybCEUDcbCWcTa0oF09lzLjZgPphXAsvRiMK0V6Bw==",
+      "engines": {
+        "node": ">=16"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
     "node_modules/convert-source-map": {
       "version": "2.0.0",
       "resolved": "https://registry.npmjs.org/convert-source-map/-/convert-source-map-2.0.0.tgz",
@@ -5861,7 +5991,6 @@
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       "resolved": "https://registry.npmjs.org/define-data-property/-/define-data-property-1.1.1.tgz",
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-      "dev": true,
       "dependencies": {
         "get-intrinsic": "^1.2.1",
         "gopd": "^1.0.1",
@@ -6834,6 +6963,11 @@
         "node": ">=6"
       }
     },
+    "node_modules/eventemitter3": {
+      "version": "3.1.2",
+      "resolved": "https://registry.npmjs.org/eventemitter3/-/eventemitter3-3.1.2.tgz",
+      "integrity": "sha512-tvtQIeLVHjDkJYnzf2dgVMxfuSGJeM/7UCG17TT4EumTfNtF+0nebF/4zWOIkCreAbtNqhGEboB6BWrwqNaw4Q=="
+    },
     "node_modules/events": {
       "version": "1.1.1",
       "resolved": "https://registry.npmjs.org/events/-/events-1.1.1.tgz",
@@ -6939,6 +7073,11 @@
         "node": ">=4"
       }
     },
+    "node_modules/fast-copy": {
+      "version": "2.1.7",
+      "resolved": "https://registry.npmjs.org/fast-copy/-/fast-copy-2.1.7.tgz",
+      "integrity": "sha512-ozrGwyuCTAy7YgFCua8rmqmytECYk/JYAMXcswOcm0qvGoE3tPb7ivBeIHTOK2DiapBhDZgacIhzhQIKU5TCfA=="
+    },
     "node_modules/fast-deep-equal": {
       "version": "3.1.3",
       "resolved": "https://registry.npmjs.org/fast-deep-equal/-/fast-deep-equal-3.1.3.tgz",
@@ -7322,7 +7461,6 @@
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       "resolved": "https://registry.npmjs.org/function-bind/-/function-bind-1.1.2.tgz",
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-      "dev": true,
       "funding": {
         "url": "https://github.com/sponsors/ljharb"
       }
@@ -7376,7 +7514,6 @@
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-      "dev": true,
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         "has-proto": "^1.0.1",
@@ -7522,7 +7659,6 @@
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-      "dev": true,
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@@ -7595,7 +7731,6 @@
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     "node_modules/has-property-descriptors": {
       "version": "1.0.0",
-      "dev": true,
       "license": "MIT",
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@@ -7608,7 +7743,6 @@
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-      "dev": true,
       "engines": {
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@@ -7618,7 +7752,6 @@
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     "node_modules/has-symbols": {
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-      "dev": true,
       "license": "MIT",
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@@ -7645,7 +7778,6 @@
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-      "dev": true,
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         "function-bind": "^1.1.2"
       },
@@ -8015,6 +8147,11 @@
         "url": "https://github.com/sponsors/sindresorhus"
       }
     },
+    "node_modules/is-electron": {
+      "version": "2.2.2",
+      "resolved": "https://registry.npmjs.org/is-electron/-/is-electron-2.2.2.tgz",
+      "integrity": "sha512-FO/Rhvz5tuw4MCWkpMzHFKWD2LsfHzIb7i6MdPYZ/KW7AlxawyLkqdy+jPZP1WubqEADE3O4FUENlJHDfQASRg=="
+    },
     "node_modules/is-extglob": {
       "version": "2.1.1",
       "dev": true,
@@ -9126,6 +9263,11 @@
       "dev": true,
       "license": "MIT"
     },
+    "node_modules/json-stringify-safe": {
+      "version": "5.0.1",
+      "resolved": "https://registry.npmjs.org/json-stringify-safe/-/json-stringify-safe-5.0.1.tgz",
+      "integrity": "sha512-ZClg6AaYvamvYEE82d3Iyd3vSSIjQ+odgjaTzRuO3s7toCdFKczob2i0zCh7JE8kWn17yvAWhUVxvqGwUalsRA=="
+    },
     "node_modules/json5": {
       "version": "1.0.2",
       "resolved": "https://registry.npmjs.org/json5/-/json5-1.0.2.tgz",
@@ -9340,8 +9482,12 @@
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       "resolved": "https://registry.npmjs.org/lodash.isplainobject/-/lodash.isplainobject-4.0.6.tgz",
-      "integrity": "sha512-oSXzaWypCMHkPC3NvBEaPHf0KsA5mvPrOPgQWDsbg8n7orZ290M0BmC/jgRZ4vcJ6DTAhjrsSYgdsW/F+MFOBA==",
-      "dev": true
+      "integrity": "sha512-oSXzaWypCMHkPC3NvBEaPHf0KsA5mvPrOPgQWDsbg8n7orZ290M0BmC/jgRZ4vcJ6DTAhjrsSYgdsW/F+MFOBA=="
+    },
+    "node_modules/lodash.isstring": {
+      "version": "4.0.1",
+      "resolved": "https://registry.npmjs.org/lodash.isstring/-/lodash.isstring-4.0.1.tgz",
+      "integrity": "sha512-0wJxfxH1wgO3GrbuP+dTTk7op+6L41QCXbGINEmD+ny/G/eCqGzxyCsh7159S+mgDDcoarnBw6PC1PS5+wUGgw=="
     },
     "node_modules/lodash.memoize": {
       "version": "4.1.2",
@@ -9856,7 +10002,6 @@
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       "resolved": "https://registry.npmjs.org/object-inspect/-/object-inspect-1.13.1.tgz",
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-      "dev": true,
       "funding": {
         "url": "https://github.com/sponsors/ljharb"
       }
@@ -10051,7 +10196,6 @@
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-      "dev": true,
       "engines": {
         "node": ">=4"
       }
@@ -10097,11 +10241,53 @@
         "url": "https://github.com/sponsors/sindresorhus"
       }
     },
+    "node_modules/p-queue": {
+      "version": "6.6.2",
+      "resolved": "https://registry.npmjs.org/p-queue/-/p-queue-6.6.2.tgz",
+      "integrity": "sha512-RwFpb72c/BhQLEXIZ5K2e+AhgNVmIejGlTgiB9MzZ0e93GRvqZ7uSi0dvRF7/XIXDeNkra2fNHBxTyPDGySpjQ==",
+      "dependencies": {
+        "eventemitter3": "^4.0.4",
+        "p-timeout": "^3.2.0"
+      },
+      "engines": {
+        "node": ">=8"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
+    "node_modules/p-queue/node_modules/eventemitter3": {
+      "version": "4.0.7",
+      "resolved": "https://registry.npmjs.org/eventemitter3/-/eventemitter3-4.0.7.tgz",
+      "integrity": "sha512-8guHBZCwKnFhYdHr2ysuRWErTwhoN2X8XELRlrRwpmfeY2jjuUN4taQMsULKUVo1K4DvZl+0pgfyoysHxvmvEw=="
+    },
+    "node_modules/p-retry": {
+      "version": "4.6.2",
+      "resolved": "https://registry.npmjs.org/p-retry/-/p-retry-4.6.2.tgz",
+      "integrity": "sha512-312Id396EbJdvRONlngUx0NydfrIQ5lsYu0znKVUzVvArzEIt08V1qhtyESbGVd1FGX7UKtiFp5uwKZdM8wIuQ==",
+      "dependencies": {
+        "@types/retry": "0.12.0",
+        "retry": "^0.13.1"
+      },
+      "engines": {
+        "node": ">=8"
+      }
+    },
+    "node_modules/p-throttle": {
+      "version": "4.1.1",
+      "resolved": "https://registry.npmjs.org/p-throttle/-/p-throttle-4.1.1.tgz",
+      "integrity": "sha512-TuU8Ato+pRTPJoDzYD4s7ocJYcNSEZRvlxoq3hcPI2kZDZ49IQ1Wkj7/gDJc3X7XiEAAvRGtDzdXJI0tC3IL1g==",
+      "engines": {
+        "node": ">=10"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
     "node_modules/p-timeout": {
       "version": "3.2.0",
       "resolved": "https://registry.npmjs.org/p-timeout/-/p-timeout-3.2.0.tgz",
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-      "dev": true,
       "dependencies": {
         "p-finally": "^1.0.0"
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@@ -10437,10 +10623,9 @@
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-      "resolved": "https://registry.npmjs.org/qs/-/qs-6.11.0.tgz",
-      "integrity": "sha512-MvjoMCJwEarSbUYk5O+nmoSzSutSsTwF85zcHPQ9OrlFoZOYIjaqBAJIqIXjptyD5vThxGq52Xu/MaJzRkIk4Q==",
-      "dev": true,
+      "version": "6.11.2",
+      "resolved": "https://registry.npmjs.org/qs/-/qs-6.11.2.tgz",
+      "integrity": "sha512-tDNIz22aBzCDxLtVH++VnTfzxlfeK5CbqohpSqpJgj1Wg/cQbStNAz3NuqCs5vV+pjBsK4x4pN9HlVh7rcYRiA==",
       "dependencies": {
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+      "version": "0.13.1",
+      "resolved": "https://registry.npmjs.org/retry/-/retry-0.13.1.tgz",
+      "integrity": "sha512-XQBQ3I8W1Cge0Seh+6gjj03LbmRFWuoszgK9ooCpwYIrhhoO80pfq4cUkU5DkknwfOfFteRwlZ56PYOGYyFWdg=="
+    },
     "reusify": {
       "version": "1.0.4",
       "dev": true
@@ -20921,7 +21259,6 @@
       "version": "1.1.1",
       "resolved": "https://registry.npmjs.org/set-function-length/-/set-function-length-1.1.1.tgz",
       "integrity": "sha512-VoaqjbBJKiWtg4yRcKBQ7g7wnGnLV3M8oLvVWwOk2PdYY6PEFegR1vezXR0tw6fZGF9csVakIRjrJiy2veSBFQ==",
-      "dev": true,
       "requires": {
         "define-data-property": "^1.1.1",
         "get-intrinsic": "^1.2.1",
@@ -20959,7 +21296,6 @@
     },
     "side-channel": {
       "version": "1.0.4",
-      "dev": true,
       "requires": {
         "call-bind": "^1.0.0",
         "get-intrinsic": "^1.0.2",
diff --git a/package.json b/package.json
index 8642447..6b37d74 100644
--- a/package.json
+++ b/package.json
@@ -25,7 +25,9 @@
   "author": "Ackama Developers <developers@ackama.com>",
   "license": "MIT",
   "dependencies": {
+    "@slack/web-api": "^6.11.0",
     "@slack/webhook": "^7.0.1",
+    "contentful": "^10.6.14",
     "luxon": "^3.4.4",
     "node-fetch": "^2.6.7",
     "node-ical": "^0.17.1"
diff --git a/src/handlers.ts b/src/handlers.ts
index 42a47ea..daabd2b 100644
--- a/src/handlers.ts
+++ b/src/handlers.ts
@@ -3,6 +3,7 @@ import * as daylightSavingsChangeReminder from './daylightSavingsChangeReminder'
 import * as leaveReminder from './leaveReminder';
 import { Notifier } from './notifier';
 import * as publicHolidayReminder from './publicHolidayReminder';
+import * as significantStaffDatesReminder from './significantStaffDatesReminder';
 
 export const weeklyReport: ScheduledHandler = async () => {
   const notifier = new Notifier();
@@ -17,6 +18,7 @@ export const dailyReport: ScheduledHandler = async () => {
   await leaveReminder.generateDailyReport(notifier);
   await publicHolidayReminder.generateDailyReport(notifier);
   daylightSavingsChangeReminder.generateDailyReport(notifier);
+  await significantStaffDatesReminder.generateDailyReport(notifier);
 
   await notifier.sendBufferedMessages();
 };
diff --git a/src/significantStaffDatesReminder.ts b/src/significantStaffDatesReminder.ts
new file mode 100644
index 0000000..b10d2ae
--- /dev/null
+++ b/src/significantStaffDatesReminder.ts
@@ -0,0 +1,183 @@
+import { WebClient } from '@slack/web-api';
+import * as contentful from 'contentful';
+import { DateTime } from 'luxon';
+import { Notifier } from './notifier';
+
+declare global {
+  namespace NodeJS {
+    interface ProcessEnv {
+      CONTENTFUL_SPACE_ID: string;
+      CONTENTFUL_API_KEY: string;
+      SLACK_API_TOKEN: string;
+    }
+  }
+}
+
+interface ContentfulStaffMember {
+  name: string;
+  slackHandle: string;
+  bornOn: string;
+  startedOn: string;
+  birthdayNotificationEnabled: boolean;
+  workAnniversaryNotificationEnabled: boolean;
+}
+
+interface Member {
+  id?: string;
+  real_name?: string;
+  profile: {
+    display_name?: string;
+  };
+}
+
+const CONTENTFUL_SPACE_ID = process.env.CONTENTFUL_SPACE_ID;
+const CONTENTFUL_API_KEY = process.env.CONTENTFUL_API_KEY;
+const SLACK_API_TOKEN = process.env.SLACK_API_TOKEN;
+
+// Slack has no API to lookup a single user by name so we have to get all
+// users via `cacheSlackUsers` below. This is an expensive operation both in
+// latency and also Slack rate-limits it so we cache the results here.
+let allSlackUsers: Member[] = [];
+
+const cacheSlackUsers = async (): Promise<void> => {
+  if (allSlackUsers.length > 0) {
+    return;
+  }
+
+  const client = new WebClient(SLACK_API_TOKEN, {
+    retryConfig: { retries: 0 }
+  });
+
+  try {
+    // Docs: https://api.slack.com/methods/users.list
+    const response = await client.users.list();
+
+    allSlackUsers = response.members as Member[];
+  } catch (error: unknown) {
+    console.log('Failed to get list of users from Slack. Error:', error);
+  }
+};
+
+const getNameFromSlack = (slackHandle: string): string => {
+  // user.profile.display_name is what you seen in slack as the user's slack
+  // name e.g. `user.profile.display_name === 'Riker'` means you see `@Riker` in
+  // Slack.
+  const user = allSlackUsers.find(u => u.profile.display_name === slackHandle);
+
+  return `${user?.real_name} <@${user?.id}>`;
+};
+
+const hasUpcomingWorkAnniversary = (person: ContentfulStaffMember) => {
+  return (
+    person.workAnniversaryNotificationEnabled &&
+    yearlyAnniversaryIsCloseEnoughToToday(person.startedOn)
+  );
+};
+
+const numYearsAgo = (dateStr: string): number => {
+  const now = DateTime.now().year;
+  const then = DateTime.fromISO(dateStr).year;
+
+  return now - then;
+};
+
+const prettyDate = (dateStr: string): string => {
+  return DateTime.fromISO(dateStr).toFormat('d LLLL');
+};
+
+const buildWorkAnniversaryMessage = (person: ContentfulStaffMember): string => {
+  const tenure = numYearsAgo(person.startedOn);
+  const name = getNameFromSlack(person.slackHandle);
+  const date = prettyDate(person.startedOn);
+  const message = `:tada: Congratulations ${name} - as of ${date}, you will have worked at Ackama for ${tenure} years! :tada:`;
+
+  return message;
+};
+
+const buildBirthdayMessage = (person: ContentfulStaffMember): string => {
+  const age = numYearsAgo(person.bornOn);
+  const name = getNameFromSlack(person.slackHandle);
+  const date = prettyDate(person.bornOn);
+  const message = `:birthday: Happy birthday to ${name} who is turning ${age} on ${date}! :birthday:`;
+
+  return message;
+};
+
+// Is the yearly anniversary of the given date happening today or one of the
+// next two days (if today is Friday).
+const yearlyAnniversaryIsCloseEnoughToToday = (dateStr: string): boolean => {
+  // Use NZ timezone. Melbourne is only 2hrs behind so this should give the
+  // correct date there too.
+  const todayInNZ = DateTime.local().setZone('Pacific/Auckland');
+
+  const daysOfInterest = [todayInNZ.toFormat('MM-dd')]; // always check today
+
+  // if today is Friday then we check the upcoming weekend days too
+  if (todayInNZ.weekdayShort === 'Fri') {
+    daysOfInterest.concat(todayInNZ.plus({ days: 1 }).toFormat('MM-dd')); // Saturday
+    daysOfInterest.concat(todayInNZ.plus({ days: 2 }).toFormat('MM-dd')); // Sunday
+  }
+
+  const query = dateStr.replace(/^\d{4}-/u, '');
+
+  // check if today is a day of interest
+  if (!daysOfInterest.includes(query)) {
+    return false;
+  }
+
+  return true;
+};
+
+const hasUpcomingBirthday = (person: ContentfulStaffMember) => {
+  return (
+    person.birthdayNotificationEnabled &&
+    yearlyAnniversaryIsCloseEnoughToToday(person.bornOn)
+  );
+};
+
+const fetchStaffMembersFromContentful = async (): Promise<
+  ContentfulStaffMember[]
+> => {
+  const client = contentful.createClient({
+    space: CONTENTFUL_SPACE_ID,
+    accessToken: CONTENTFUL_API_KEY
+  });
+  const staffMemberEntries = await client.getEntries({
+    content_type: 'staffMember'
+  });
+
+  return staffMemberEntries.items.map(
+    entry => entry.fields as unknown as ContentfulStaffMember
+  );
+};
+
+const sendBirthdayNotifications = (
+  staffMembers: ContentfulStaffMember[],
+  notifier: Notifier
+): void => {
+  staffMembers.filter(hasUpcomingBirthday).forEach(staffMember => {
+    const msg = buildBirthdayMessage(staffMember);
+
+    notifier.bufferMessage(msg, 'section');
+  });
+};
+
+const sendWorkAnniversaryNotifications = (
+  staffMembers: ContentfulStaffMember[],
+  notifier: Notifier
+): void => {
+  staffMembers.filter(hasUpcomingWorkAnniversary).forEach(staffMember => {
+    const msg = buildWorkAnniversaryMessage(staffMember);
+
+    notifier.bufferMessage(msg, 'section');
+  });
+};
+
+export async function generateDailyReport(notifier: Notifier): Promise<void> {
+  await cacheSlackUsers();
+
+  const staffMembers = await fetchStaffMembersFromContentful();
+
+  sendBirthdayNotifications(staffMembers, notifier);
+  sendWorkAnniversaryNotifications(staffMembers, notifier);
+}