I'm encountering the same thing on a fresh installation of Ubuntu 20.04.

Here is what happens right after a reboot:
jeff@bridges:~$ ll /run/ | grep dhcp
jeff@bridges:~$ sudo systemctl status isc-dhcp-server
[sudo] password for jeff:
● isc-dhcp-server.service - ISC DHCP IPv4 server
     Loaded: loaded (/lib/systemd/system/isc-dhcp-server.service; enabled; 
vendor preset: enabled)
     Active: active (running) since Tue 2020-04-28 23:59:43 MST; 11s ago
       Docs: man:dhcpd(8)
   Main PID: 1374 (dhcpd)
      Tasks: 4 (limit: 19047)
     Memory: 6.9M
     CGroup: /system.slice/isc-dhcp-server.service
             └─1374 dhcpd -user dhcpd -group dhcpd -f -4 -pf 
/run/dhcp-server/dhcpd.pid -cf /etc/dhcp/dhcpd.conf

Apr 28 23:59:44 bridges dhcpd[1374]:
Apr 28 23:59:44 bridges dhcpd[1374]: Listening on 
LPF/enp2s0/2c:60:0c:c6:a4:be/192.168.1.0/24
Apr 28 23:59:44 bridges sh[1374]: Listening on 
LPF/enp2s0/2c:60:0c:c6:a4:be/192.168.1.0/24
Apr 28 23:59:44 bridges sh[1374]: Sending on   
LPF/enp2s0/2c:60:0c:c6:a4:be/192.168.1.0/24
Apr 28 23:59:44 bridges sh[1374]: Sending on   Socket/fallback/fallback-net
Apr 28 23:59:44 bridges sh[1374]: Can't create PID file 
/run/dhcp-server/dhcpd.pid: No such file or directory.
Apr 28 23:59:44 bridges dhcpd[1374]: Sending on   
LPF/enp2s0/2c:60:0c:c6:a4:be/192.168.1.0/24
Apr 28 23:59:44 bridges dhcpd[1374]: Sending on   Socket/fallback/fallback-net
Apr 28 23:59:44 bridges dhcpd[1374]: Can't create PID file 
/run/dhcp-server/dhcpd.pid: No such file or directory.
Apr 28 23:59:44 bridges dhcpd[1374]: Server starting service.
jeff@bridges:~$ sudo systemctl restart isc-dhcp-server
jeff@bridges:~$ ll /run/ | grep dhcp
drwxr-xr-x  2 root                root                  60 Apr 29 00:00 
dhcp-server/
jeff@bridges:~$ ll /run/dhcp-server/
total 4
drwxr-xr-x  2 root root   60 Apr 29 00:00 ./
drwxr-xr-x 39 root root 1140 Apr 29 00:00 ../
-rw-r--r--  1 root root    5 Apr 29 00:00 dhcpd.pid


I can hardcode the PID file names like Nicorac above mentions, but I'd rather 
things just work out of the box without needing to apply random workarounds 
like that.

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https://bugs.launchpad.net/bugs/1448657

Title:
  isc-dhcp-server: Can't create PID file /run/dhcp-server/dhcpd.pid:
  Permission denied

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