Hiring for your deficiencies is one of those “it depends” questions.
Who you hire first depends on your team’s current deficiencies, and your deficiencies are defined by what you are trying to accomplish. If you’re a typical startup creating a software product (apps, website, etc.), there are typically a few standard roles and capabilities you’re going to need to fill: product, sales and engineering. These are not the only capabilities and roles you’ll need to fill to make a company work, but they’re capabilities that are 100% necessary.
Who you need to hire depends on what you can do. You already have one or more founders. What can those founders do? While you’re searching for product market fit, do you need sales? Maybe that’s covered by one or more founders, for now. Maybe it’s not, and you are at a point where you need to build and scale a sales team. Can one of your founders code or lead external engineers? Perhaps not, and you need to hire someone to do one or the other.
In general, the main things you should make sure your team can do are the three capabilities I listed, plus one:
Let’s dive into these four capabilities, and who will be responsible for each one:
Vision is what’s left over, and is almost always the main responsibility of the CEO. Vision is the mental understanding of what your business will be, as well as what it is now. It’s the understanding both of what you think the market will grow to and how you can take your business, as it is today and build it into what it will be tomorrow. Vision has ramifications in all three other areas. It’s what ties them all together and becomes your means of communicating a future view of the world with your employees and your customers.
Product is the job of the person who takes vision and translates it into the different products and services your company provides. They maintain the mental image of what those products and services are now and how they can be modified in the future to help guide the company toward a realization of the vision. A good product person will have the ability to inform engineering on how they should build product, and they should do so in a way that asks for metrics to be collected on the functionality created. Product teams should use these metrics to provide feedback to vision, which will guide which product direction should be continued in the future.
Engineering is the technical implementation of products. To build them well, you need to hire quality people who have the capability to implement the products and services you want to create. This means someone on the team has to have the ability to either create quality engineering outputs or to judge them and guide others to create them. This is either a CTO, VP of engineering, lead engineer or manager in the case that they are not technical but can lead.
Sales is a different animal than the above, but it’s arguably more important. A sales organization is both a sole means for achieving revenue for a company, as well as a feedback mechanism for product and engineering. A good sales lead will have the ability to set up an organization so that it is driven by incentives and judged by concrete metrics. Sales organizations are almost always internally competitive.
So, you’ll need to figure out what capabilities you need and how each person involved is differentiated. You’ll also need to figure out how to distribute equity amongst them. Are they essential to running the business? Perhaps they’re essential enough that you consider them a founder.
If not, think of what percentage of ownership feels motivating but is larger than what a future standard employee will get. An engineer on your already built-out team will likely get one-tenth of one percent of the employee equity pool. A good rule of thumb for equity is to give between that and what you give to yourself — somewhere in that range is what your first hires should get.