When to hire your first design leader.
Hiring a designer is easy if you're a designer. Here's a guide for everyone else.
Hiring a designer is easy—if you’re a designer. Design training allows us to separate timelessness from trend, strategy from bullshit. To further complicate things, the value of design changes as an organization matures.
Conception
Making it work
Often at this stage, the primary goal is to convince a non-user stakeholder (investors or other peers) that your idea works. Most young startups I’ve worked with say the same thing: “We need to be real.” Being real takes a trained eye, so if you’re reaching out to solo designers for contract work during this phase, look for a senior contributor, ideally one who would like to transition into leadership as you grow. These folks can have titles like:
Senior Designer
Principal Designer
Design Lead
Leaning in
If your pitch is heavily dependent on design and brand strength as a differentiator, consider making this person a full-time hire. You want a great relationship with them and between them and your team so they can nail the brand and expand it into your product. Bonus if this person has some front-end skills.
Formation
If you've made it this far by faking the design function—outsourcing, leaning on a cofounder, getting by—and now realize you need someone full-time, you need a leader, ideally one who's built a team before. A sudden need for design signals that your firm is growing, and you want to start getting design right fast.
Look for folks with the following experience:
They’ve grown a design practice from one to many
They have experience in big tech; they know what the finished design org looks like and will work backwards as they hire
A range of design experience from branding to user research to software
As the design team grows their hires will become more differentiated, and they should look for mid-level or senior folks who can grow as part of the team’s succession planning.
Establishment
If your design team is in place, look for someone with experience in organizational development, someone who has led reorganizations at scale. This person should be as comfortable with decks as they are with designs, and understand how to work with senior and mid-level leaders from other disciplines, even beyond Product and Engineering.
At this stage of your growth, your design leader’s primary concern is keeping the user experience cohesive from end to end. With dozens, possibly hundreds of people delivering experiential touch points (marketing funnel, internal communications, in-person, socials, products) the trick is to make it feel like a single thing. Customers don’t care if they’re hearing from Marketing, Sales, or Customer Success — they just want to access your services or products easily, and that means consistent messaging and UIs.
Look for the following qualities:
Know how to make a single brand feel coherent across many touchpoints
Worked with external creative agencies on one-off campaigns, and integrated them strategically into the growth of the firm
Make decisions faster than most senior people, but explain them slowly
Coach those around them — designers and non-designers — to align professional and organizational goals
