diff --git a/.circleci/config.yml b/.circleci/config.yml
index 0203ad67f..259841090 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -234,7 +234,15 @@ jobs:
            install-and-test-ext --target check-citus-upgrade-mixed --citus-pre-tar /install-pg11-citusv8.3.0.tar
           no_output_timeout: 2m
 
-
+  check-merge-to-enterprise:
+    docker:
+      - image: buildpack-deps:stretch
+    working_directory: /home/circleci/project
+    steps:
+      - checkout
+      - run:
+          command: |
+            ./src/test/scripts/check_enterprise_merge.sh
 
 
 
@@ -242,6 +250,7 @@ workflows:
   version: 2
   build_and_test:
     jobs:
+      - check-merge-to-enterprise
       - build
       - check-style
       - check-sql-snapshots
diff --git a/src/test/scripts/README.md b/src/test/scripts/README.md
new file mode 100644
index 000000000..23fdabd74
--- /dev/null
+++ b/src/test/scripts/README.md
@@ -0,0 +1,33 @@
+
+# check-merge-to-enterprise Job
+
+When you open a PR on community, if it creates a conflict with enterprise-master, the check-merge-to-enterprise will fail. Say your branch name is `X`, we will refer to `X` on community as `community/X` and on enterprise as `enterprise/X`. If the job already passes, you are done, nothing further required! Otherwise follow the below steps:
+
+- You first need to get approval from your reviewer for `community/X`. Only follow the next steps after you are about to merge the branch to community master. Otherwise, the `check-merge-to-enterprise` check might falsely pass. (For example when you added new commits to `community/X` but forgot to update `enterprise/X`).
+- You need to synchronize the same branch, `X` locally on enterprise (ideally don't push yet). For example if `community` is added as a remote in your enterprise repo, you can do the following:
+
+```bash
+git fetch --all # this will fetch community/X
+git checkout community/X
+git checkout -b X # now you have X in your enterprise repo, which we refer to as enterprise/X
+```
+
+- You need to merge `enterprise-master` to `enterprise/X`. Solve any conflicts( and make sure to remove any parts that should not be in enterprise even though it doesn't have a conflict), on enterprise repository:
+
+```bash
+git checkout enterprise-master
+git pull # make sure enterprise-master in your local is up-to-date
+git checkout X
+git merge origin/enterprise-master # assuming origin is the remote of citus-enterprise
+```
+
+- You should push this to enterprise and open a PR so that the job on community will see this branch. Also this will trigger CI to verify changes are correct.
+- You should get approval for the merge conflict changes on `enterprise/X`, preferably from the same reviewer as they are familiar with the change.
+- You should rerun the `check-merge-to-enterprise` check on `community/X`. You can use re-run from failed option in circle CI.
+- You can now merge `community/X` to `community/master`.
+- You can merge `enterprise/X` to `enterprise-master`.
+- Manually merge `community master` to `enterprise-master`. [https://github.com/citusdata/citus-enterprise/blob/enterprise-master/CONTRIBUTING.md#merging-community-changes-onto-enterprise](https://github.com/citusdata/citus-enterprise/blob/enterprise-master/CONTRIBUTING.md#merging-community-changes-onto-enterprise)
+- You can use `git checkout --ours <conflicting file names>` for all conflicting files. This will use local/our version to resolve the conflicts.
+- Now you can push to `enterprise-master`. Now you can rerun the check on `community/master` and it should pass the check.
+
+The subsequent PRs on community will be able to pass the `check-merge-to-enterprise` check as long as they don't have a conflict with `enterprise-master`.
diff --git a/src/test/scripts/check_enterprise_merge.sh b/src/test/scripts/check_enterprise_merge.sh
new file mode 100755
index 000000000..2e1055682
--- /dev/null
+++ b/src/test/scripts/check_enterprise_merge.sh
@@ -0,0 +1,55 @@
+#!/bin/bash
+
+# fail if trying to reference a variable that is not set.
+set -u
+# exit immediately if a command fails
+set -e
+
+# try_merge sees if we can merge "from" branch to "to" branch
+# it will exit with nonzero code if the merge fails because of conflicts.
+try_merge() {
+    to=$1
+    from=$2
+    git checkout "${to}"
+    # this will exit since -e option is set and it will return non-zero code on conflicts.
+    git merge --no-ff --no-commit "${from}"
+
+}
+
+cd /tmp
+if [ ! -d citus-enterprise ]; then
+    git clone https://${GIT_USERNAME}:${GIT_TOKEN}@github.com/citusdata/citus-enterprise
+fi
+
+cd citus-enterprise
+git config user.email "citus-bot@microsoft.com"
+git config user.name "citus bot"
+
+# reset repository into usable state if script ran before
+git fetch origin
+git reset --hard
+git checkout enterprise-master
+git reset --hard origin/enterprise-master
+
+branch_name="${CIRCLE_BRANCH}"
+
+# check if the branch on community exists on enterprise
+# the output will not be empty if it does
+if [ `git branch -r --list origin/$branch_name` ]
+then
+    try_merge enterprise-master origin/$branch_name
+else
+    # add community as a remote if not already added
+    set +e
+    if ! git ls-remote community > /dev/null; then
+        set -e
+        git remote add --no-tags community git@github.com:citusdata/citus.git
+    fi
+    set -e
+
+    # prevent pushes to community and update branch we care about
+    git remote set-url --push community no-pushing
+    git fetch community $branch_name
+
+    try_merge enterprise-master community/$branch_name
+fi