At what stage do startups hire a secretary?

When would you know, as a startupper, that your company needs to hire an in-house secretary to offload some of the non-mission critical work? How do you manage delegating tasks vs. making sure that sensitive aspects (e.g. PR, very sensitive in our case) are handled well by a secretary or bounced back to you?

The moment you need it?

Seriously, this is asking like when to go to the toilet.

When you realize you spend half your day doing coordination / paperwork and can gain more from that you realize it makes financial sense.

How do you manage delegating tasks vs. making sure that sensitive aspects (e.g. PR, very
sensitive in our case) are handled well by a secretary or bounced back to you?

Hire someone competent, train them. Control it.

I'm not sure what 'secretary' means for you - sounds like you simply mean another pair of hands, and someone who's happy to turn their hands to anything.

So this question seems to me to reduce to, "When do we need someone else on the team? "

Easy. When you don't have time for the mission-critical work. Which you will notice because it will get really, really stressful.

What should you be delegating? Delegate mission-critical stuff and sensitive stuff. The stuff that's dull but necessary? Maybe, but in my view that stuff you should spread around, or outsource to cheap, reliable, distant help. If you create a job called 'dull but necessary stuff' then, guess what? You'll hire a weak team member, who will then either get very bored, find lots of things and start labelling them 'necessary,' or kick-start you right into office politics.

So hire someone bright, energetic and motivated. Share the work. Don't worry about the job title or the career progression. If the person fits the team, and expands your capability (broadening the skill base and blending personalities is often a weakness for startups), then how could you lose?

When you say secretary like an office administrator? Someone to handle HR, payroll, and stuff? For us, I think it was at the end of our first year. When doing all that stuff started taking too much time and we couldn't focus on the work or look for clients.

Do an ROI => How much time do you spend doing something someone else could do? How much worth is your time, multiple the two:

if opportunity cost > salary (+ overhead) => hire.