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Read This Before Hiring Your Next Product Designer

3 min read • by Vasil Nedelchev

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.The TL;DR is:
1. Design cuts development costs
2. Business sense outweighs pure design skills
3. Hire people who challenge your assumptionsLet'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 codingB2B Software Understanding
– Questions your sales cycle
– Discusses implementation hurdles
– Grasps enterprise adoption patternsConstructive Challenge
– Asks “why”
– Prevents costly mistakes
– Proposes evidence-based alternativesAvoid 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, looselyIf you find a designer who agrees with everything, keep looking. That’s not the challenger you need.

The 5 Critical Design Investments for Early-Stage Founders

5 min read • by Vasil Nedelchev

Most founders think product design is about making things look pretty.That’s why most startups fail before finding product-market fit.I’ve been in the trenches for 17 years now. In my early days working with B2B startups, I saw it everywhere. Roughly 30% of product designs never made it to production. We were all making the same mistake. Diving into feature design before talking to users. Like most founders, we were so passionate about our solutions.Product-market fit felt like a formality — not the crucial journey of discovery it really is.The truth? The best B2B products often look basic but solve problems so well that customers can’t live without them.So, how do you design something indispensable? Start here.

The 5 critical design investments

Here are the ways to invest in design to achieve product-market fit — none of them involve making your product “beautiful.”The TL;DR:– Focus on designing your customer’s journey and core workflows before building complex feature sets.
– Invest in user research, journey mapping, and rapid prototyping to validate solutions.
– When hiring designers, prioritize those who understand B2B problem-solving over pure visual design skills.Let’s break it down to actionable steps:

1. Design Your Customer’s Journey, Not Your Product’s Features

The biggest mistake founders make is jumping straight into feature design.Instead, map out your customer’s entire workflow — from the moment they recognize they have a problem to the point where they’ve successfully solved it with your product.This is why Marty Cagan emphasizes:“A good product solves the customer’s problem as naturally as possible… Customers don’t buy the product, they buy the transformation that solution enables.”
— Inspired: How To Create Products Customers Love by Marty CaganThis principle makes your journey map your true product design north star. It helps you identify:1. Which problems are actually worth solving first
2. Where users face the most friction in their current process
3. What success looks like from their perspective, not yoursStart by mapping out:1. The trigger: What causes customers to seek a solution?
2. The process: Every step they take to solve their problem
3. The handoffs: Where work moves between people or tools
4. The frustrations: Points where they waste time or lose momentum
5. The desired outcome: What “good” looks like for them

2. Invest in Problem Validation, Not Solution Design

Most founders have a solution in mind and try to validate it.Flip this approach: invest in deeply understanding the problem before designing anything.Specifically:1. Conduct problem interviews with 20+ potential customers
2. Document their current solutions and workarounds
3. Measure the time and money they’re wasting on these workarounds
4. Identify patterns in their biggest pain pointsThe challenge is removing our own biases from the equation. As Dan Olsen points out in The Lean Product Playbook:“Start by understanding the problem. Good product discovery is about minimizing your biases and assumptions and understanding the true needs of the customer.”
— The Lean Product Playbook by Dan OlsenTo put this into practice, create a problem validation document that captures:1. The exact steps in their current process
2. Quantifiable metrics around time and resource waste
3. Direct quotes describing their frustrations
4. The cost of the problem (both financial and emotional)
5. Their previous attempts to solve it

3. Design Your “Aha Moment” First

The fastest path to product-market fit is designing a clear “aha moment” — that instant when users first experience the core value of your product.Start by answering:1. What’s the smallest possible action a user can take to experience value?
2. How quickly can you deliver that value?
3. What needs to happen before and after this moment?
4. Then design everything around accelerating users to this moment.This moment is so crucial that Nir Eyal built an entire framework around it:“The ‘aha moment’ is the magical experience when users truly understand the value of your product. It’s a pivotal point in the customer journey, and the sooner you can get them there, the better.”
— Hooked: How to Build Habit-Forming Products by Nir EyalTo engineer this moment effectively, your design should include:1. A clear entry point that requires minimal setup
2. Immediate feedback that shows progress
3. A concrete outcome that matters to the user
4. A natural next step that builds on their success
5. Ways to share their success with teammates

4. Prototype Workflows, Not Wireframes

Stop designing static screens. Start designing dynamic workflows.Use tools like Figma or even paper prototypes to:1. Map out the critical path to value
2. Test different approaches with real users
3. Iterate based on actual usage patternsTeresa Torres captures this mindset shift perfectly:“True prototyping isn’t about creating mockups or screen layouts; it’s about testing the interaction and user flow… Your prototype should answer the question, ‘Can the user achieve the goal?’ before you worry about how it looks.”
— Continuous Discovery Habits by Teresa TorresPutting this into practice, your prototyping process should:1. Start with paper sketches of the workflow
2. Move to low-fidelity interactive prototypes
3. Test with users in their actual work environment
4. Measure completion rates and time-to-value
5. Iterate based on real usage observations
6. Only add visual polish when the workflow worksThe goal isn’t to make it pretty — it’s to validate that users can complete their core tasks successfully.

5. Design for Distribution

The often-overlooked aspect of product design is making it naturally viral within B2B organizations.Consider:1. How does your product spread from one user to their team?
2. What triggers users to invite colleagues?
3. How do you design sharing and collaboration features that feel natural?As Andrew Chen observes in his research on network effects:“Products that spread within organizations do so because they add value to multiple people simultaneously. Shared success is a powerful motivator in collaborative tools.”
— The Cold Start Problem: How to Start and Scale Network Effects by Andrew ChenTo harness this collaborative power, focus on designing:1. Natural collaboration points in the workflow
2. Shared artifacts that provide value to multiple roles
3. Clear visibility into team progress and bottlenecks
4. Easy onboarding for invited team members
5. Value that compounds with each new userHere’s the truth about product design at the early stage: your goal is to build something that solves a problem so well that customers can’t imagine going back to their old way of working.When building your design team or choosing a designer, look for someone who:1. Has experience mapping and validating customer journeys
2. Prioritizes problem understanding over immediate solutions
3. Can rapidly prototype and test assumptions
4. Understands B2B workflow dynamics
5. Focuses on user success metrics over visual polishMelissa Perri frames this holistic approach perfectly:“Great designers don’t just design the product — they design the system that supports the user’s journey and make sure each part of it is aligned with solving their problem.”
— Escaping the Build Trap by Melissa PerriWhether you’re hiring or doing it yourself, this systems thinking approach is what separates good product design from great product design.This is what actually gets you to product-market fit.