When should an early-stage organization hire its first design leader?
Hiring a designer is easy — if you’re a designer. Design training allows us to separate from timelessness from trend, strategy from bullshit, and good attitudes from bad ones. To further complicate things, the value of design changes as an organization matures.
Don’t worry, if you’re hiring a designer and you’re not one, this post is for you.
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 your team so they can nail the brand and expand it into your product. Bonus if this person has some front-end skills, ideally AI prompting and code generation.
Formation
If you’re a more mature organization who has faked the design end of things until now, and realize you’re in need of a designer soon, you need someone with leadership experience — ideally team-building. 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 constant messaging and UIs.
Look for the following qualities:
Understand how to build a brand experience across a series of experiences
Worked with external creative agencies on one-off campaigns, and integrated them strategically into the growth of the firm
Listen more than they talk
Coach those around them — designers and non-designers — to align professional and organizational goals
Consider a design recruiter
It’s not common, but the bet way to maximize your hiring spend is to outsource it to a design leader. Technical recruiting firms almost never have designers on staff, as they’re built mostly for engineering searches. Enlist a design leader in your network to help write the job description and possibly source candidates, review portfolios (more important than resumes), and conduct interviews.
Involving them at any stage of the hiring process will provide a stopgap. Hiring is expensive; a bad design hire will double your cost, and lead to a loss of productivity.
