As a former agency owner and now the founder of a software company, I’ve experienced the pros and cons of hiring in-house vs. outsourcing. I’ve hired full-time employees, I’ve contracted freelancers (heck, I’ve even been a freelancer), and both have brought benefits and challenges to my businesses.
Let me start by saying that I believe founders should do as much as they can themselves for as long as they can. This familiarizes you with the critical foundational aspects of your business and ensures you understand how things work so you can then lead your team to do them better.
When we started Proposify, my co-founder, Kevin Springer, and I did as much as we could ourselves until we could afford to hire full-time specialists.
For example, I designed every version of our logo and the marketing website myself, and then we contracted other design marketing pieces to freelancers until we finally hired Steve Huntington as our in-house designer.
We handled quality assurance ourselves until we hired Janani Ramani, our head of QA.
I looked after our paid spend (Facebook, Adwords) until outsourcing it to a PPC agency for a year and a half. Then we hired Patrick Edmonds, our growth marketer, and transitioned the management of the paid spend over to him.
Kevin handled most of the sales activity until we hired two sales professionals, Amy Sears and Ryan MacDougall.
In each case it went > founder does their best to get the job done > transitions to freelancer if possible > transitions to new in-house hire.