Recruit Managers before Junior Execs or other way around?

Have been running a business for a couple of years now but been managing most of the areas of the business myself - web development and marketing - while I have staff who take care of customer service. The problem now is that I really want to start a few more web services but then that would mean having to find someone to take care of my current role + I'd ideally want people as well who can take my new ideas forward while I can just focus on strategising for the future.

So now am confused as to who do I hire and whether I should look at hiring senior pros first like perhaps a Project Manager to take care of web development and have him responsible for scaling up the team, including hiring the right people, and a Marketing Manager who'll take care of everything again along with hiring and building a team. I wish things could be simultaneous and I got everyone I wanted at the same time but I know from experience that getting the right people takes time, so confused on whether to focus on seniors first or to get some juniors, train them on current roles and then hire someone senior to take things forward. But I'd then be spending a lot of my time just managing the juniors again till I got someone suitable. And if I hired senior people, not sure if they'd get down to doing all the daily work themselves till they find suitable staff on board.

How do I scale up, just not able to get my thought process right on this one!

Paul

Perhaps an alternate way of looking at this is to not look at hierarchy but talent, potential and drive. If I were in your position, I would advertise for both roles but pick the candidates that stood out (drive, talent, fit, attitude) irrespective of the role you expected them to play.

In small start ups that I have worked with, the team I built with my hands always out performed the team some other senior manager I hired built with his hands. While you would need to put in extra effort with junior resources you will have the option of molding and directing them as you wish. If you have a clear road map for growth where you (the man) are the guide you also improve retention, loyalty and productivity.

The senior role may not necessarily save you time. You would still need to spend time with the senior guy and you may not agree with his approach, his mindset or his direction. There is a much higher chance of hit or miss with senior positions compared to junior roles. And correcting a bad hire at a senior level is far more expensive in both real as well as opportunity cost compared to a mistake made at the junior level.

In a small company, everyone has to be an individual contributor, so I would rephrase the question to ask whether you want a senior person or a junior person. If you are going to be the CEO, then you could use a personal self-assessment as a way to address this issue. If your strength is marketing, for example, then you could initially take the lead on marketing strategy and hire a junior person to implement your ideas. At the same time, though, you could (should?) look for a senior engineer to take responsibility for the software architecture and implementation. As your company grows, you relinquish more and more of the day-to-day operations, so you will eventually bring in a senior marketing executive. Initially, though, you should find senior people in the areas that complement your own strengths. Having a few senior people on board will also help increase the valuation of your company and raise funds.