diff --git a/.github/actions/poetry_setup/action.yml b/.github/actions/poetry_setup/action.yml
new file mode 100644
index 000000000..df04e1e71
--- /dev/null
+++ b/.github/actions/poetry_setup/action.yml
@@ -0,0 +1,88 @@
+# An action for setting up poetry install with caching.
+# Using a custom action since the default action does not
+# take poetry install groups into account.
+# Action code from:
+# https://github.com/actions/setup-python/issues/505#issuecomment-1273013236
+name: poetry-install-with-caching
+description: Poetry install with support for caching of dependency groups.
+
+inputs:
+  python-version:
+    description: Python version, supporting MAJOR.MINOR only
+    required: true
+
+  poetry-version:
+    description: Poetry version
+    required: true
+
+  cache-key:
+    description: Cache key to use for manual handling of caching
+    required: true
+
+runs:
+  using: composite
+  steps:
+    - uses: actions/setup-python@v5
+      name: Setup python ${{ inputs.python-version }}
+      id: setup-python
+      with:
+        python-version: ${{ inputs.python-version }}
+
+    - uses: actions/cache@v3
+      id: cache-bin-poetry
+      name: Cache Poetry binary - Python ${{ inputs.python-version }}
+      env:
+        SEGMENT_DOWNLOAD_TIMEOUT_MIN: "1"
+      with:
+        path: |
+          /opt/pipx/venvs/poetry
+        # This step caches the poetry installation, so make sure it's keyed on the poetry version as well.
+        key: bin-poetry-${{ runner.os }}-${{ runner.arch }}-py-${{ inputs.python-version }}-${{ inputs.poetry-version }}
+
+    - name: Refresh shell hashtable and fixup softlinks
+      if: steps.cache-bin-poetry.outputs.cache-hit == 'true'
+      shell: bash
+      env:
+        POETRY_VERSION: ${{ inputs.poetry-version }}
+        PYTHON_VERSION: ${{ inputs.python-version }}
+      run: |
+        set -eux
+
+        # Refresh the shell hashtable, to ensure correct `which` output.
+        hash -r
+
+        # `actions/cache@v3` doesn't always seem able to correctly unpack softlinks.
+        # Delete and recreate the softlinks pipx expects to have.
+        rm /opt/pipx/venvs/poetry/bin/python
+        cd /opt/pipx/venvs/poetry/bin
+        ln -s "$(which "python$PYTHON_VERSION")" python
+        chmod +x python
+        cd /opt/pipx_bin/
+        ln -s /opt/pipx/venvs/poetry/bin/poetry poetry
+        chmod +x poetry
+
+        # Ensure everything got set up correctly.
+        /opt/pipx/venvs/poetry/bin/python --version
+        /opt/pipx_bin/poetry --version
+
+    - name: Install poetry
+      if: steps.cache-bin-poetry.outputs.cache-hit != 'true'
+      shell: bash
+      env:
+        POETRY_VERSION: ${{ inputs.poetry-version }}
+        PYTHON_VERSION: ${{ inputs.python-version }}
+      # Install poetry using the python version installed by setup-python step.
+      run: pipx install "poetry==$POETRY_VERSION" --python '${{ steps.setup-python.outputs.python-path }}' --verbose
+
+    - name: Restore pip and poetry cached dependencies
+      uses: actions/cache@v3
+      env:
+        SEGMENT_DOWNLOAD_TIMEOUT_MIN: "4"
+      with:
+        path: |
+          ~/.cache/pip
+          ~/.cache/pypoetry/virtualenvs
+          ~/.cache/pypoetry/cache
+          ~/.cache/pypoetry/artifacts
+          ./.venv
+        key: py-deps-${{ runner.os }}-${{ runner.arch }}-py-${{ inputs.python-version }}-poetry-${{ inputs.poetry-version }}-${{ inputs.cache-key }}-${{ hashFiles('./poetry.lock') }}
diff --git a/.github/workflows/py-baseline.yml b/.github/workflows/py-baseline.yml
new file mode 100644
index 000000000..4b1998847
--- /dev/null
+++ b/.github/workflows/py-baseline.yml
@@ -0,0 +1,37 @@
+name: py-baseline
+
+on:
+  workflow_dispatch:
+  push:
+    branches: [main]
+    paths:
+      - "python/langsmith/**"
+
+env:
+  POETRY_VERSION: "1.7.1"
+
+jobs:
+  benchmark:
+    runs-on: ubuntu-latest
+    defaults:
+      run:
+        working-directory: python
+    steps:
+      - uses: actions/checkout@v4
+      - run: SHA=$(git rev-parse HEAD) && echo "SHA=$SHA" >> $GITHUB_ENV
+      - name: Set up Python 3.11 + Poetry ${{ env.POETRY_VERSION }}
+        uses: "./.github/actions/poetry_setup"
+        with:
+          python-version: "3.11"
+          poetry-version: ${{ env.POETRY_VERSION }}
+          cache-key: py-benchi
+      - name: Install dependencies
+        run: poetry install --with dev
+      - name: Run benchmarks
+        run: OUTPUT=out/benchmark-baseline.json make -s benchmark
+      - name: Save outputs
+        uses: actions/cache/save@v4
+        with:
+          key: ${{ runner.os }}-benchmark-baseline-${{ env.SHA }}
+          path: |
+            python/out/benchmark-baseline.json
diff --git a/.github/workflows/py-bench.yml b/.github/workflows/py-bench.yml
new file mode 100644
index 000000000..20ce118d1
--- /dev/null
+++ b/.github/workflows/py-bench.yml
@@ -0,0 +1,71 @@
+name: py-bench
+
+on:
+  pull_request:
+    paths:
+      - "python/langsmith/**"
+
+env:
+  POETRY_VERSION: "1.7.1"
+
+jobs:
+  benchmark:
+    runs-on: ubuntu-latest
+    defaults:
+      run:
+        working-directory: python
+    steps:
+      - uses: actions/checkout@v4
+      - id: files
+        name: Get changed files
+        uses: Ana06/get-changed-files@v2.3.0
+        with:
+          format: json
+      - name: Set up Python 3.11 + Poetry ${{ env.POETRY_VERSION }}
+        uses: "./.github/actions/poetry_setup"
+        with:
+          python-version: "3.11"
+          poetry-version: ${{ env.POETRY_VERSION }}
+          cache-key: py-bench
+      - name: Install dependencies
+        run: poetry install --with dev
+      - name: Download baseline
+        uses: actions/cache/restore@v4
+        with:
+          key: ${{ runner.os }}-benchmark-baseline
+          restore-keys: |
+            ${{ runner.os }}-benchmark-baseline-
+          fail-on-cache-miss: true
+          path: |
+            python/out/benchmark-baseline.json
+      - name: Run benchmarks
+        id: benchmark
+        run: |
+          {
+            echo 'OUTPUT<<EOF'
+            make -s benchmark
+            echo EOF
+          } >> "$GITHUB_OUTPUT"
+      - name: Compare benchmarks
+        id: compare
+        run: |
+          {
+            echo 'OUTPUT<<EOF'
+            mv out/benchmark-baseline.json out/main.json
+            mv out/benchmark.json out/changes.json
+            poetry run pyperf compare_to out/main.json out/changes.json --table --group-by-speed
+            echo EOF
+          } >> "$GITHUB_OUTPUT"
+      - name: Annotation
+        uses: actions/github-script@v7
+        with:
+          script: |
+            const file = JSON.parse(`${{ steps.files.outputs.added_modified_renamed }}`)[0]
+            core.notice(`${{ steps.benchmark.outputs.OUTPUT }}`, {
+              title: 'Benchmark results',
+              file,
+            })
+            core.notice(`${{ steps.compare.outputs.OUTPUT }}`, {
+              title: 'Comparison against main',
+              file,
+            })
diff --git a/.github/workflows/python_test.yml b/.github/workflows/python_test.yml
index 98020f18e..d207b112b 100644
--- a/.github/workflows/python_test.yml
+++ b/.github/workflows/python_test.yml
@@ -29,18 +29,12 @@ jobs:
         working-directory: python
     steps:
       - uses: actions/checkout@v3
-      - uses: actions/setup-python@v5
-        name: Setup python ${{ matrix.python-version }}
-        id: setup-python
+      - name: Set up Python ${{ matrix.python-version }} + Poetry ${{ env.POETRY_VERSION }}
+        uses: "./.github/actions/poetry_setup"
         with:
           python-version: ${{ matrix.python-version }}
-          cache: "pip"
-      - name: Install poetry
-        shell: bash
-        env:
-          PYTHON_VERSION: ${{ matrix.python-version }}
-        # Install poetry using the python version installed by setup-python step.
-        run: pipx install "poetry==$POETRY_VERSION" --python '${{ steps.setup-python.outputs.python-path }}' --verbose
+          poetry-version: ${{ env.POETRY_VERSION }}
+          cache-key: build-and-test
       - name: Install dependencies
         run: |
           poetry install --with dev,lint
@@ -51,4 +45,4 @@ jobs:
         run: make lint
       - name: Run Unit tests ${{ matrix.python-version }}
         run: make tests
-        shell: bash
\ No newline at end of file
+        shell: bash
diff --git a/python/Makefile b/python/Makefile
index e40f8944b..4ef65ad35 100644
--- a/python/Makefile
+++ b/python/Makefile
@@ -1,4 +1,17 @@
-.PHONY: tests lint format build publish doctest integration_tests integration_tests_fast evals
+.PHONY: tests lint format build publish doctest integration_tests integration_tests_fast evals benchmark benchmark-fast
+
+
+OUTPUT ?= out/benchmark.json
+
+benchmark:
+	mkdir -p out
+	rm -f $(OUTPUT)
+	poetry run python -m bench -o $(OUTPUT) --rigorous
+
+benchmark-fast:
+	mkdir -p out
+	rm -f $(OUTPUT)
+	poetry run python -m bench -o $(OUTPUT) --fast
 
 tests:
 	 PYTHONDEVMODE=1 PYTHONASYNCIODEBUG=1 poetry run python -m pytest --disable-socket --allow-unix-socket -n auto --durations=10 tests/unit_tests
diff --git a/python/bench/__init__.py b/python/bench/__init__.py
new file mode 100644
index 000000000..e69de29bb
diff --git a/python/bench/__main__.py b/python/bench/__main__.py
new file mode 100644
index 000000000..c3e206af9
--- /dev/null
+++ b/python/bench/__main__.py
@@ -0,0 +1,76 @@
+from pyperf._runner import Runner
+
+from bench.create_run_tree import create_run_trees
+from bench.dumps_json import (
+    DeeplyNestedModel,
+    DeeplyNestedModelV1,
+    create_nested_instance,
+)
+from langsmith.client import _dumps_json
+
+
+class MyClass:
+    def __init__(self):
+        self.vals = {}
+
+
+benchmarks = (
+    (
+        "create_5_000_run_trees",
+        create_run_trees,
+        5_000,
+    ),
+    (
+        "create_10_000_run_trees",
+        create_run_trees,
+        10_000,
+    ),
+    (
+        "create_20_000_run_trees",
+        create_run_trees,
+        10_000,
+    ),
+    (
+        "dumps_class_nested_py_branch_and_leaf_200x150",
+        lambda x: _dumps_json({"input": x}),
+        create_nested_instance(
+            200, 150, branch_constructor=MyClass, leaf_constructor=MyClass
+        ),
+    ),
+    (
+        "dumps_class_nested_py_leaf_50x100",
+        lambda x: _dumps_json({"input": x}),
+        create_nested_instance(50, 100, leaf_constructor=MyClass),
+    ),
+    (
+        "dumps_class_nested_py_leaf_200x400",
+        lambda x: _dumps_json({"input": x}),
+        create_nested_instance(200, 400, leaf_constructor=MyClass),
+    ),
+    (
+        "dumps_dataclass_nested_200x150",
+        lambda x: _dumps_json({"input": x}),
+        create_nested_instance(200, 150),
+    ),
+    (
+        "dumps_pydantic_nested_200x400",
+        lambda x: _dumps_json({"input": x}),
+        create_nested_instance(200, 400, branch_constructor=DeeplyNestedModel),
+    ),
+    (
+        "dumps_pydantic_nested_50x100",
+        lambda x: _dumps_json({"input": x}),
+        create_nested_instance(50, 100, branch_constructor=DeeplyNestedModel),
+    ),
+    (
+        "dumps_pydanticv1_nested_200x150",
+        lambda x: _dumps_json({"input": x}),
+        create_nested_instance(200, 150, branch_constructor=DeeplyNestedModelV1),
+    ),
+)
+
+
+r = Runner()
+
+for name, fn, input_ in benchmarks:
+    r.bench_func(name, fn, input_)
diff --git a/python/bench/create_run_tree.py b/python/bench/create_run_tree.py
new file mode 100644
index 000000000..29cc84f44
--- /dev/null
+++ b/python/bench/create_run_tree.py
@@ -0,0 +1,9 @@
+from unittest.mock import patch
+
+from langsmith import RunTree
+
+
+def create_run_trees(N: int):
+    with patch("langsmith.client.requests.Session", autospec=True):
+        for i in range(N):
+            RunTree(name=str(i)).post()
diff --git a/python/bench/dumps_json.py b/python/bench/dumps_json.py
new file mode 100644
index 000000000..9937fc062
--- /dev/null
+++ b/python/bench/dumps_json.py
@@ -0,0 +1,84 @@
+import uuid
+from dataclasses import dataclass, field
+from datetime import datetime
+from decimal import Decimal
+from typing import Any, Callable, Dict, Optional
+
+import numpy as np
+from pydantic import BaseModel, Field
+from pydantic.v1 import BaseModel as BaseModelV1
+from pydantic.v1 import Field as FieldV1
+
+
+def _default():
+    return {
+        "some_val": "😈",
+        "uuid_val": uuid.uuid4(),
+        "datetime_val": datetime.now(),
+        "list_val": [238928376271863487] * 5,
+        "decimal_val": Decimal("3.14"),
+        "set_val": {1, 2, 3},
+        "tuple_val": (4, 5, 6),
+        "bytes_val": b"hello world",
+        "arr": np.random.random(10),
+    }
+
+
+@dataclass
+class DeeplyNested:
+    """An object."""
+
+    vals: Dict[str, Any] = field(default_factory=_default)
+
+
+class DeeplyNestedModel(BaseModel):
+    vals: Dict[str, Any] = Field(default_factory=_default)
+
+
+class DeeplyNestedModelV1(BaseModelV1):
+    vals: Dict[str, Any] = FieldV1(default_factory=_default)
+
+
+def create_nested_instance(
+    depth: int = 5,
+    width: int = 5,
+    branch_constructor: Optional[Callable] = DeeplyNested,
+    leaf_constructor: Optional[Callable] = None,
+) -> DeeplyNested:
+    top_level = DeeplyNested()
+    current_level = top_level
+    root_constructor = leaf_constructor or DeeplyNested
+    for i in range(depth):
+        for j in range(width):
+            key = f"key_{i}_{j}"
+            if i < depth - 1:
+                value = branch_constructor()
+                current_level.vals[key] = value
+                if j == 0:
+                    next_level = value
+            else:
+                current_level.vals[key] = root_constructor()
+
+        if i < depth - 1:
+            current_level = next_level
+    return top_level
+
+
+if __name__ == "__main__":
+    import time
+
+    from langsmith.client import _dumps_json
+
+    class MyClass:
+        def __init__(self):
+            self.vals = {}
+
+    def run():
+        res = create_nested_instance(200, 150, leaf_constructor=MyClass)
+        start_time = time.time()
+        res = _dumps_json({"input": res})
+        end_time = time.time()
+        print(f"Size: {len(res) / 1024:.2f} KB")
+        print(f"Time taken: {end_time - start_time:.2f} seconds")
+
+    run()
diff --git a/python/poetry.lock b/python/poetry.lock
index e95cacc4d..861e0f392 100644
--- a/python/poetry.lock
+++ b/python/poetry.lock
@@ -799,13 +799,13 @@ files = [
 
 [[package]]
 name = "openai"
-version = "1.47.1"
+version = "1.50.0"
 description = "The official Python library for the openai API"
 optional = false
 python-versions = ">=3.7.1"
 files = [
-    {file = "openai-1.47.1-py3-none-any.whl", hash = "sha256:34277583bf268bb2494bc03f48ac123788c5e2a914db1d5a23d5edc29d35c825"},
-    {file = "openai-1.47.1.tar.gz", hash = "sha256:62c8f5f478f82ffafc93b33040f8bb16a45948306198bd0cba2da2ecd9cf7323"},
+    {file = "openai-1.50.0-py3-none-any.whl", hash = "sha256:8545b3e37aa28a39e5177adbb6142f3e2b2b9e2889ae002c0ba785d917e466e2"},
+    {file = "openai-1.50.0.tar.gz", hash = "sha256:fc774e36ad96839b9fc14f1097093527b8abd1348ed824e25818309820afa344"},
 ]
 
 [package.dependencies]
@@ -983,6 +983,22 @@ files = [
 [package.extras]
 test = ["enum34", "ipaddress", "mock", "pywin32", "wmi"]
 
+[[package]]
+name = "py-spy"
+version = "0.3.14"
+description = "Sampling profiler for Python programs"
+optional = false
+python-versions = "*"
+files = [
+    {file = "py_spy-0.3.14-py2.py3-none-macosx_10_7_x86_64.whl", hash = "sha256:5b342cc5feb8d160d57a7ff308de153f6be68dcf506ad02b4d67065f2bae7f45"},
+    {file = "py_spy-0.3.14-py2.py3-none-macosx_10_9_x86_64.macosx_11_0_arm64.macosx_10_9_universal2.whl", hash = "sha256:fe7efe6c91f723442259d428bf1f9ddb9c1679828866b353d539345ca40d9dd2"},
+    {file = "py_spy-0.3.14-py2.py3-none-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:590905447241d789d9de36cff9f52067b6f18d8b5e9fb399242041568d414461"},
+    {file = "py_spy-0.3.14-py2.py3-none-manylinux_2_17_armv7l.manylinux2014_armv7l.whl", hash = "sha256:fd6211fe7f587b3532ba9d300784326d9a6f2b890af7bf6fff21a029ebbc812b"},
+    {file = "py_spy-0.3.14-py2.py3-none-manylinux_2_5_i686.manylinux1_i686.whl", hash = "sha256:3e8e48032e71c94c3dd51694c39e762e4bbfec250df5bf514adcdd64e79371e0"},
+    {file = "py_spy-0.3.14-py2.py3-none-manylinux_2_5_x86_64.manylinux1_x86_64.whl", hash = "sha256:f59b0b52e56ba9566305236375e6fc68888261d0d36b5addbe3cf85affbefc0e"},
+    {file = "py_spy-0.3.14-py2.py3-none-win_amd64.whl", hash = "sha256:8f5b311d09f3a8e33dbd0d44fc6e37b715e8e0c7efefafcda8bfd63b31ab5a31"},
+]
+
 [[package]]
 name = "pydantic"
 version = "2.9.2"
@@ -1107,6 +1123,23 @@ files = [
 [package.dependencies]
 typing-extensions = ">=4.6.0,<4.7.0 || >4.7.0"
 
+[[package]]
+name = "pyperf"
+version = "2.7.0"
+description = "Python module to run and analyze benchmarks"
+optional = false
+python-versions = ">=3.7"
+files = [
+    {file = "pyperf-2.7.0-py3-none-any.whl", hash = "sha256:dce63053b916b73d8736a77404309328f938851b5c2c5e8493cde910ce37e362"},
+    {file = "pyperf-2.7.0.tar.gz", hash = "sha256:4201c6601032f374e9c900c6d2544a2f5891abedc1a96eec0e7b2338a6247589"},
+]
+
+[package.dependencies]
+psutil = ">=5.9.0"
+
+[package.extras]
+dev = ["importlib-metadata", "tox"]
+
 [[package]]
 name = "pytest"
 version = "7.4.4"
@@ -1746,103 +1779,103 @@ files = [
 
 [[package]]
 name = "yarl"
-version = "1.12.1"
+version = "1.13.0"
 description = "Yet another URL library"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "yarl-1.12.1-cp310-cp310-macosx_10_9_universal2.whl", hash = "sha256:64c5b0f2b937fe40d0967516eee5504b23cb247b8b7ffeba7213a467d9646fdc"},
-    {file = "yarl-1.12.1-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:2e430ac432f969ef21770645743611c1618362309e3ad7cab45acd1ad1a540ff"},
-    {file = "yarl-1.12.1-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:3e26e64f42bce5ddf9002092b2c37b13071c2e6413d5c05f9fa9de58ed2f7749"},
-    {file = "yarl-1.12.1-cp310-cp310-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:0103c52f8dfe5d573c856322149ddcd6d28f51b4d4a3ee5c4b3c1b0a05c3d034"},
-    {file = "yarl-1.12.1-cp310-cp310-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl", hash = "sha256:b63465b53baeaf2122a337d4ab57d6bbdd09fcadceb17a974cfa8a0300ad9c67"},
-    {file = "yarl-1.12.1-cp310-cp310-manylinux_2_17_s390x.manylinux2014_s390x.whl", hash = "sha256:17d4dc4ff47893a06737b8788ed2ba2f5ac4e8bb40281c8603920f7d011d5bdd"},
-    {file = "yarl-1.12.1-cp310-cp310-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:a8b54949267bd5704324397efe9fbb6aa306466dee067550964e994d309db5f1"},
-    {file = "yarl-1.12.1-cp310-cp310-manylinux_2_5_i686.manylinux1_i686.manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:10b690cd78cbaca2f96a7462f303fdd2b596d3978b49892e4b05a7567c591572"},
-    {file = "yarl-1.12.1-cp310-cp310-musllinux_1_2_aarch64.whl", hash = "sha256:c85ab016e96a975afbdb9d49ca90f3bca9920ef27c64300843fe91c3d59d8d20"},
-    {file = "yarl-1.12.1-cp310-cp310-musllinux_1_2_i686.whl", hash = "sha256:c1caa5763d1770216596e0a71b5567f27aac28c95992110212c108ec74589a48"},
-    {file = "yarl-1.12.1-cp310-cp310-musllinux_1_2_ppc64le.whl", hash = "sha256:595bbcdbfc4a9c6989d7489dca8510cba053ff46b16c84ffd95ac8e90711d419"},
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 ]
 
 [package.dependencies]
@@ -1855,4 +1888,4 @@ vcr = []
 [metadata]
 lock-version = "2.0"
 python-versions = ">=3.8.1,<4.0"
-content-hash = "546941bdd68403dda7ee3a67954b3741133c4f80a1a9a810ff450959278021d0"
+content-hash = "efc464f40b1618531c35a40a249abccadcbd52c081f8f36ea06a6abd796ecfd9"
diff --git a/python/pyproject.toml b/python/pyproject.toml
index 53767d95c..0a47ed049 100644
--- a/python/pyproject.toml
+++ b/python/pyproject.toml
@@ -57,6 +57,8 @@ fastapi = "^0.110.1"
 uvicorn = "^0.29.0"
 pytest-rerunfailures = "^14.0"
 pytest-socket = "^0.7.0"
+pyperf = "^2.7.0"
+py-spy = "^0.3.14"
 
 [tool.poetry.group.lint.dependencies]
 openai = "^1.10"
@@ -103,6 +105,7 @@ convention = "google"
 "langsmith/schemas.py" = ["E501"]
 "tests/evaluation/__init__.py" = ["E501"]
 "tests/*" = ["D", "UP"]
+"bench/*" = ["D", "UP", "T"]
 "docs/*" = ["T", "D"]
 
 [tool.ruff.format]