diff --git a/.gitignore b/.gitignore
index 438f867..ad9a234 100644
--- a/.gitignore
+++ b/.gitignore
@@ -1,2 +1,3 @@
 dist
 bin
+.idea
diff --git a/README.md b/README.md
index b6d66a1..cbf29a1 100644
--- a/README.md
+++ b/README.md
@@ -49,3 +49,46 @@ Once initialized, the CLI is ready to use:
 ```shell
 workos [cmd] [args]
 ```
+
+### Environment Variables
+WorkOS CLI support environment variables for initialization and environment management.
+
+| Environment Variable                  | Description                                                                                                                                        | Supported Values     |
+|---------------------------------------|----------------------------------------------------------------------------------------------------------------------------------------------------|----------------------|
+| WORKOS_ACTIVE_ENVIRONMENT             | Sets the selected environment in your .workos.json file. Use `headless` to override environment configs with other environment variable overrides. |                      |
+| WORKOS_ENVIRONMENTS_HEADLESS_NAME     | Sets the name of the environment                                                                                                                   |                      |
+| WORKOS_ENVIRONMENTS_HEADLESS_ENDPOINT | Sets the base endpoint for the environment                                                                                                         |                      |
+| WORKOS_ENVIRONMENTS_HEADLESS_API_KEY  | Sets the API key for the environment                                                                                                               |                      |
+| WORKOS_ENVIRONMENTS_HEADLESS_TYPE     | Sets the env type for the environment                                                                                                              | Production / Sandbox |
+
+#### Examples
+
+##### Set the active environment
+
+```shell
+export WORKOS_ACTIVE_ENVIRONMENT=local
+```
+
+`.workos.json`
+```json
+{
+  "environments": {
+    "local": {
+      "endpoint": "http://localhost:8001",
+      "apiKey": "<YOUR_KEY>",
+      "type": "Sandbox",
+      "name": "local"
+    }
+  }
+}
+```
+
+##### Headless Mode
+
+```shell
+export WORKOS_ACTIVE_ENVIRONMENT=headless
+export WORKOS_ENVIRONMENTS_HEADLESS_NAME=local
+export WORKOS_ENVIRONMENTS_HEADLESS_ENDPOINT=http://localhost:8001
+export WORKOS_ENVIRONMENTS_HEADLESS_API_KEY=<YOUR_KEY>
+export WORKOS_ENVIRONMENTS_HEADLESS_TYPE=Sandbox
+```
diff --git a/internal/config/config.go b/internal/config/config.go
index 9d42df3..090a287 100644
--- a/internal/config/config.go
+++ b/internal/config/config.go
@@ -3,17 +3,19 @@ package config
 import (
 	"encoding/json"
 	"errors"
-	"io/fs"
-	"os"
-
 	"github.com/spf13/cobra"
 	"github.com/spf13/viper"
+	"io/fs"
+	"os"
+	"strings"
 )
 
 const (
-	FilePrefix    = ".workos"
-	FileExtension = "json"
-	FileName      = FilePrefix + "." + FileExtension
+	EnvVarPrefix       = "WORKOS"
+	EnvVarHeadlessMode = "headless"
+	FilePrefix         = ".workos"
+	FileExtension      = "json"
+	FileName           = FilePrefix + "." + FileExtension
 )
 
 type Config struct {
@@ -44,22 +46,50 @@ func (c Config) Write() error {
 	return nil
 }
 
-func LoadConfig() *Config {
-	// Look for .workos.json in HOME dir and create an empty version if it doesn't exist
-	homeDir, err := os.UserHomeDir()
-	cobra.CheckErr(err)
-	_, err = os.Stat(homeDir + "/" + FileName)
+// Creates an empty config file if it doesn't exist
+func createEmptyConfigFile(dir string) {
+	_, err := os.Stat(dir + "/" + FileName)
 	if errors.Is(err, fs.ErrNotExist) {
 		emptyJson := []byte("{}")
-		err = os.WriteFile(homeDir+"/"+FileName, emptyJson, 0644)
+		err = os.WriteFile(dir+"/"+FileName, emptyJson, 0644)
 		cobra.CheckErr(err)
 	}
+}
+
+// Loads config values from environment variables if active environment is set to headless mode
+// Supports overriding nested json keys with environment variables
+// e.g. environments.headless.endpoint -> WORKOS_ENVIRONMENTS_HEADLESS_ENDPOINT
+func loadEnvVarOverrides() {
+	viper.SetEnvPrefix(EnvVarPrefix)
+	// replace '.' in env var names with '_' to support overriding nested json keys
+	viper.SetEnvKeyReplacer(strings.NewReplacer(".", "_"))
+	// read in environment variables that match
+	viper.AutomaticEnv()
+
+	_ = viper.BindEnv("active_environment")
+	activeEnvironment := viper.Get("active_environment")
+
+	// Binds environment variables to nested json keys which allows unmarshalling into struct
+	if activeEnvironment == EnvVarHeadlessMode {
+		_ = viper.BindEnv("environments.headless.endpoint")
+		_ = viper.BindEnv("environments.headless.type")
+		_ = viper.BindEnv("environments.headless.name")
+		_ = viper.BindEnv("environments.headless.api_key")
+	}
+}
+
+func LoadConfig() *Config {
+	homeDir, err := os.UserHomeDir()
+	cobra.CheckErr(err)
+	createEmptyConfigFile(homeDir)
 
 	// Load config from ~/.workos.json
 	viper.AddConfigPath(homeDir)
 	viper.SetConfigType(FileExtension)
 	viper.SetConfigName(FilePrefix)
-	viper.AutomaticEnv() // read in environment variables that match
+
+	loadEnvVarOverrides()
+
 	err = viper.ReadInConfig()
 	cobra.CheckErr(err)