Read This Before Hiring Your Next Product Designer
I’ve spent 17 years as the first designer at B2B software startups. I’ve watched founders make the same expensive mistakes when hiring product designers. Some of these insights might unsettle you. They might also save you hundreds of thousands of dollars.
Here is the short version
- Design cuts development costs
- Business sense outweighs pure design skills
- Hire people who challenge your assumptions
Let’s break this down:
Design Cuts Development Costs
Most feature requests have simpler solutions. Through research, what begins as “we need an AI recommendation engine” often becomes a basic filter that works better. Each simplified solution means less code to maintain.
Here’s a pattern I keep seeing: A founder hires developers to build their vision. A year and hundreds of thousands of dollars later, they land their first clients. Then reality strikes. Users abandon the product for their spreadsheets. Research reveals the truth: Half the features sit unused. The necessary ones are too complex.
The founders built the wrong thing.
Early design work could have prevented this waste. Changes after development multiply costs. A design adjustment that takes hours before coding takes days after, involving designers, developers, QA, and project managers. Factor in documentation updates, user training, and inevitable bug fixes. The math becomes painful.
You might think: “We need to move fast!” But rushing to development is like sprinting in the wrong direction. You’ll get there faster, but it’s the wrong destination.
Business Sense Outweighs Pure Design Skills
Most designers miss this: B2B software lives or dies by customer onboarding. The interface isn’t the main challenge. It’s getting businesses to adopt the product. Most B2B products fail not because they’re hard to use, but because they’re hard to start using.
“It’s obvious,” founders tell me about their product. It is — to them. They’ve lived it for months. Meanwhile, their customers, buried in quarterly targets, stare at the screen wondering where to begin.
Your interface might shine, but if users can’t start in ten minutes, they won’t stick around. Design choices ripple through your entire business pipeline: discovery, evaluation, purchase, implementation. Marketing promises must match the product experience.
You might think: “Can’t our product team handle the business side?” A designer who doesn’t grasp B2B dynamics will create beautiful interfaces that fail in enterprise environments.
Hire People Who Challenge Your Assumptions
Feature requests often mask deeper problems. When clients ask for features, they’re guessing at solutions. Good designers dig for the real issues.
Consider those apps with so many features that finding the useful ones feels like archaeology. Or dashboards showing thirty metrics when you only track two.
Less functionality, properly focused, delivers more value.
Data should override opinions — even CEO opinions. Strong designers back their challenges with evidence: user research, behavior patterns, market data. When evidence points to a better solution, they speak up.
You might think: “We need someone to execute our vision!” Good challengers don’t block your vision — they enhance it. Every successful product I’ve worked on changed significantly because we questioned assumptions when evidence suggested better paths.
How to Evaluate Designers
Look for these signals:
Values Design Strategy
- Prevents development costs
- Simplifies solutions
- Validates before coding
B2B Software Understanding
- Questions your sales cycle
- Discusses implementation hurdles
- Grasps enterprise adoption patterns
Constructive Challenge
- Asks “why”
- Prevents costly mistakes
- Proposes evidence-based alternatives
Avoid designers who:
- Ignore business metrics
- Agree with everything
- Focus only on visuals
- Can’t link work to outcomes
What Now?
Now that you know what to look for in a product designer for B2B software, you’re probably thinking: “This sounds great, but where do I find one?”
Well, you could spend months interviewing designers and checking for all these qualities… or you could just hire me. (I know, I know — subtle, right?)
But seriously, whether you work with me or not, look for someone who:
- Questions your business model
- Makes you rethink feature requests
- Discusses costs more than trends
- Holds strong opinions, loosely
If you find a designer who agrees with everything, keep looking. That’s not the challenger you need.
