Using requests

import requests

PING_URL = "https://watchcron.com/ping/your-uuid"

# Signal start
requests.get(f"{PING_URL}/start", timeout=10)

try:
    # Your work here
    run_backup()

    # Signal success
    requests.get(PING_URL, timeout=10)
except Exception as e:
    # Signal failure with error message
    requests.post(f"{PING_URL}/fail", data=str(e), timeout=10)
    raise

Using urllib (no dependencies)

import urllib.request

PING_URL = "https://watchcron.com/ping/your-uuid"

urllib.request.urlopen(PING_URL, timeout=10)

Reusable decorator

import functools, requests

def monitor(ping_url):
    def decorator(func):
        @functools.wraps(func)
        def wrapper(*args, **kwargs):
requests.get(f"{ping_url}/start", timeout=10)
try:
    result = func(*args, **kwargs)
    requests.get(ping_url, timeout=10)
    return result
except Exception:
    requests.get(f"{ping_url}/fail", timeout=10)
    raise
        return wrapper
    return decorator

@monitor("https://watchcron.com/ping/your-uuid")
def nightly_backup():
    # Your logic here
    ...

Python