The best hire I ever made didn't match the job description.
Posted for "Senior Marketing Manager with B2B SaaS experience." Hired someone with zero marketing experience and zero SaaS background.
Two years later, she's running customer success, product marketing, AND business development. Revenue she's directly influenced: $2.8M.
Here's why hiring for people instead of roles isn't just better—it's the only sustainable approach when work itself is constantly changing.
The Death of Static Job Descriptions
Traditional job descriptions assume a world that no longer exists:
What job descriptions assume:
- Roles remain consistent for years
- Skills requirements stay stable
- Work can be defined in advance
- People will do predictable tasks
What actually happens:
- Roles evolve monthly as business needs change
- AI automates existing skills while creating new requirements
- Best work emerges from unexpected combinations of capabilities
- Most valuable contributions weren't in the original job description
Real Example: The Marketing Manager Who Became Everything
Original job posting (March 2022):
- "Senior Marketing Manager"
- "5+ years B2B marketing experience"
- "Expert in demand generation and content marketing"
- "SaaS background required"
Who I hired instead:
- Background: Customer success at fintech company
- Marketing experience: Managed company blog as side project
- SaaS experience: Used SaaS tools, never worked at SaaS company
- Why I hired her: Exceptional customer empathy and clear communication
What she actually did (first 24 months):
Month 1-3: Started in "marketing"
- Created content based on actual customer conversations
- Identified gaps in customer onboarding that no one else noticed
- Naturally gravitated toward customer-facing activities
Month 4-8: Expanded into customer success
- Customers preferred talking to her over dedicated support team
- Developed better understanding of product usage patterns than product team
- Created onboarding process that increased activation 34%
Month 9-12: Moved into product strategy
- Customer insights drove product roadmap decisions
- Built feedback loop between customers and development team
- Became translator between technical team and customer needs
Month 13-24: Leading business development
- Customer relationships generated partnership opportunities
- Understanding of customer problems led to strategic alliances
- Revenue influence: $2.8M through various channels
The insight: Hired for fixed "marketing manager" role, created value across every aspect of business because she understood customers better than anyone.
Traditional hiring would have filtered her out. Person-first hiring revealed someone who could grow with the business.
What Matters When Roles Keep Changing
In a world where job descriptions become obsolete quickly, what creates lasting value?
Adaptability Over Expertise
The expertise trap:
- Hire expert in current needs
- Needs change faster than expertise
- Expert becomes less relevant as role evolves
- Need to hire new expert for new needs
The adaptability advantage:
- Hire person who learns quickly and adapts
- Role changes become growth opportunities
- Person evolves with business needs
- Same person creates value across different functions
Real comparison from our team:
Expert hire (front-end developer):
- 8 years React experience, perfect technical skills
- Could build anything we asked for efficiently
- When we shifted to mobile-first approach, became bottleneck
- Resistant to learning new frameworks, wanted to stick with expertise
- Eventually had to hire mobile developer, creating coordination overhead
Adaptable hire (problem-solver who happened to code):
- 3 years development experience, solid but not expert
- Curious about business context, asked questions about user needs
- When mobile shift happened, learned React Native quickly
- Now handles both web and mobile development
- Contributes to product strategy conversations based on technical constraints
The difference: Expert delivered predictable value within narrow domain. Adaptable person created expanding value across multiple domains.
Learning Velocity Over Current Knowledge
What creates long-term value:
- How quickly does this person understand new concepts?
- Do they ask good questions when encountering unfamiliar problems?
- How do they approach learning something completely outside their background?
- Can they synthesize information from different sources into coherent understanding?
Testing learning velocity in interviews:
Instead of: "How would you set up a React testing framework?" Ask: "Here's a business problem you've never encountered. Walk me through how you'd figure out the right solution."
Instead of: "What's your experience with our tech stack?" Ask: "Tell me about a time you had to learn something completely new under time pressure."
Instead of: "How would you optimize our conversion funnel?" Ask: "If you had to understand why customers weren't buying our product, what would your investigation process look like?"
The pattern: Focus on thinking process, not existing knowledge.
Problem-Solving Approach Over Domain Experience
Domain expertise becomes obsolete. Problem-solving approach is transferable.
Example: Non-technical hire who became technical leader
Background: English literature degree, worked in publishing Zero experience: Software development, project management, technical teams Hired because: Exceptional at breaking down complex problems systematically
How she approached technical challenges:
- Asked developers to explain problems in plain English
- Identified patterns between different technical issues
- Created documentation that helped team see bigger picture
- Developed frameworks for prioritizing competing technical needs
Result: Within 18 months, became technical project manager coordinating team of 8 developers. Developers preferred working with her over previous technical managers because she understood the human side of technical work.
The transferable skill: Systematic approach to breaking down complexity, not technical knowledge.
Cultural Chemistry Over Professional Credentials
Professional credentials predict past performance in similar roles. Cultural chemistry predicts future collaboration quality.
What cultural chemistry looks like:
- Do they ask questions that make you think differently?
- Are disagreements productive rather than personal?
- Do they make team meetings more valuable or less valuable?
- Would you choose to work with them if you didn't have to?
The airport lounge test expanded:
Scenario 1: Delayed flight, 6-hour wait
- Do you dread spending time with this person?
- Are conversations energizing or draining?
- Do they handle stress and uncertainty gracefully?
- Can you solve problems together effectively?
Scenario 2: High-pressure project deadline
- Do they stay calm and focused under pressure?
- Can they have difficult conversations without creating drama?
- Do they take ownership when things go wrong?
- Do they make the team more effective or less effective?
Scenario 3: Strategic planning session
- Do they contribute insights that wouldn't have emerged otherwise?
- Can they build on others' ideas constructively?
- Do they ask questions that reveal assumptions?
- Are they comfortable with ambiguity and changing direction?
The insight: Professional skills can be developed. Interpersonal chemistry and work style compatibility are much harder to change.
The Person-First Evaluation Framework
How to evaluate people instead of roles:
Layer 1: Core Thinking Ability
Can they think independently and clearly?
Assessment methods:
- Present unfamiliar problem, observe reasoning process
- Ask them to explain something complex in simple terms
- Give them incomplete information, see how they fill gaps
- Watch how they structure ambiguous challenges
Green flags:
- Asks clarifying questions before jumping to solutions
- Breaks down complex problems into manageable pieces
- Admits uncertainty and explains how they'd resolve it
- Can explain their reasoning process clearly
Red flags:
- Jumps to solutions without understanding problem
- Gets overwhelmed by ambiguity instead of working through it
- Can't explain how they arrived at conclusions
- Avoids questions that reveal gaps in understanding
Layer 2: Learning and Adaptation
How do they approach new challenges and changing requirements?
Assessment methods:
- Ask about time they had to learn something completely unfamiliar
- Present hypothetical scenario where their current skills wouldn't apply
- Discuss how they stay current in rapidly changing field
- Explore how they handle being wrong or making mistakes
Green flags:
- Gets excited about learning new things
- Has systematic approach to acquiring new skills
- Comfortable being beginner again in new domains
- Views mistakes as learning opportunities rather than failures
Red flags:
- Resistant to learning outside their expertise area
- Overwhelmed by prospect of unfamiliar challenges
- Takes mistakes personally or defensively
- Prefers to stay within comfort zone of existing skills
Layer 3: Ownership and Initiative
Do they take responsibility for outcomes or just execute tasks?
Assessment methods:
- Ask about project they drove from idea to completion
- Explore how they handle situations with unclear direction
- Discuss times they identified and solved problems proactively
- Understand how they approach accountability for results
Green flags:
- Takes initiative to solve problems they notice
- Feels personal responsibility for project outcomes
- Comfortable making decisions with incomplete information
- Follows through on commitments consistently
Red flags:
- Waits for detailed instructions before taking action
- Blames external factors when projects don't succeed
- Avoids making decisions or taking clear positions
- Needs constant management and direction to be effective
Layer 4: Communication and Collaboration
Can they work effectively with different types of people?
Assessment methods:
- Role-play difficult conversations or disagreements
- Ask how they handle working with people they don't naturally click with
- Explore how they give and receive feedback
- Understand their approach to building relationships with colleagues
Green flags:
- Can disagree without being disagreeable
- Actively listens and builds on others' ideas
- Comfortable giving and receiving honest feedback
- Adapts communication style based on audience
Red flags:
- Avoids conflict even when it's necessary
- Dominates conversations or doesn't listen well
- Takes feedback personally or becomes defensive
- Only works well with people similar to themselves
Why This Approach Wins Long-Term
Adaptability Creates Compound Value
Role-based hiring creates linear value:
- Person does defined job at expected level
- Value creation predictable but limited
- Need new hires when roles change
- Team capabilities limited by individual specializations
Person-based hiring creates exponential value:
- Person grows capabilities as business needs evolve
- Value creation expands over time
- Same people handle new challenges
- Team capabilities multiply through learning and adaptation
Example: Customer success hire who became revenue driver
Year 1: Handled customer support and onboarding
- Value: Kept customers happy, reduced churn
- Measurable impact: 18% reduction in customer complaints
Year 2: Identified upselling opportunities through customer conversations
If you're finding this useful, I send essays like this 2-3x per week.
·No spam
- Value: Generated expansion revenue
- Measurable impact: $340K additional revenue from existing customers
Year 3: Built customer advisory program that informed product roadmap
- Value: Product development driven by actual customer needs
- Measurable impact: 67% increase in feature adoption rates
Year 4: Leading customer-driven partnership development
- Value: Strategic alliances based on customer demand
- Measurable impact: $1.2M revenue from partnership channels
Total value: Hired for $65K/year customer support role, created $1.5M+ annual value through evolution and growth.
Resilience Through Uncertainty
Role-specific teams are fragile:
- Key person leaving creates significant gap
- Industry changes make specialized roles obsolete
- Economic pressures require role elimination
- Competitive pressures demand new capabilities
People-based teams are antifragile:
- Team members can cover for each other across functions
- Changing industry needs become growth opportunities
- Economic pressures drive efficiency through versatility
- Competitive pressures spark innovation through diverse thinking
Real example: COVID pivot story
Pre-COVID team structure:
- 2 in-person sales reps
- 1 event marketing manager
- 1 customer success manager
- 1 product manager
COVID impact on roles:
- In-person sales impossible
- Event marketing eliminated
- Customer success moved remote
- Product priorities completely changed
Team response (because hired for adaptability):
- Sales reps learned digital marketing and lead generation
- Event marketing manager became customer experience specialist
- Customer success manager built remote onboarding program
- Product manager shifted to customer retention features
Outcome: Instead of layoffs and hiring, same team generated 23% more revenue in 2020 than 2019 through role adaptation.
Innovation Through Diverse Thinking
Specialized roles create predictable solutions:
- Marketing person thinks about marketing solutions
- Technical person thinks about technical solutions
- Sales person thinks about sales solutions
- Each perspective valuable but limited
Adaptable people create novel solutions:
- Technical understanding + customer empathy = better product decisions
- Marketing intuition + operational experience = more effective campaigns
- Sales experience + strategic thinking = partnership opportunities
- Cross-functional perspective generates ideas specialists miss
Innovation example: Customer problem that required multiple perspectives
Problem: Customers loved our product but struggled with implementation Traditional approach: Hire implementation specialist or consultant
Our approach: Asked our most adaptable team member to own the problem Background: Marketing background, strong customer empathy, technical curiosity
Solution developed:
- Interviewed customers about implementation challenges (marketing skills)
- Worked with engineering to build guided setup flow (technical learning)
- Created implementation methodology that customers could self-serve (systematic thinking)
- Built measurement system to track implementation success (analytical approach)
Result: 89% reduction in implementation time, 156% increase in feature adoption, became competitive differentiator.
The insight: Diverse perspective in one person generated solution that no single specialist would have developed.
Common Objections and Responses
"But we need specific expertise"
When expertise is actually required:
- Regulated industries with licensing requirements
- Deep technical challenges requiring specialized knowledge
- Client-facing roles where credentials matter for credibility
- Safety-critical functions where mistakes have serious consequences
The hybrid approach:
- Hire for expertise + adaptability, not expertise alone
- Look for experts who can also think beyond their domain
- Combine specialists with generalists rather than hiring all specialists
- Ensure experts can communicate and collaborate effectively
Example: Hired experienced lawyer for compliance (expertise required) who also had startup experience (adaptability). She handles legal requirements but also contributes to business strategy and operational decisions.
"This seems inefficient for immediate needs"
Short-term vs. long-term thinking:
- Role-based hiring optimizes for next 6 months
- Person-based hiring optimizes for next 3-5 years
- Learning curve is real but usually short
- Adaptable people often exceed specialists quickly
Mitigating short-term inefficiency:
- Provide more context and training initially
- Pair adaptable hires with existing team members
- Set expectations that first 90 days are learning investment
- Measure value creation over 12+ month timeline
"How do you evaluate without clear role requirements"
Shifting evaluation criteria:
- From "Can they do this specific job?" to "Can they learn what we need?"
- From skills assessment to capability assessment
- From experience verification to potential evaluation
- From cultural fit to cultural addition
Practical evaluation methods:
- Case study discussions instead of technical tests
- Problem-solving scenarios instead of resume reviews
- Trial projects instead of traditional interviews
- Reference checks focused on adaptability and growth
Implementation: The Person-First Hiring Process
Stage 1: Attraction (Finding Adaptable People)
Job postings that attract the right candidates:
Instead of: "Senior Marketing Manager with 5+ years B2B SaaS experience" Write: "Customer-obsessed problem solver who wants to grow with a fast-changing business"
Instead of: "Full-stack developer with React/Node.js expertise" Write: "Technical thinker who loves building solutions that customers actually use"
Key elements:
- Emphasize growth and learning opportunities
- Focus on problems to be solved rather than tasks to be completed
- Highlight adaptability and change as features, not bugs
- Attract people who want ownership and impact
Stage 2: Screening (Identifying Learning Potential)
Phone/video screening focused on:
- How they approach unfamiliar challenges
- Examples of learning something new quickly
- Times they took ownership beyond their defined role
- Questions they ask about the company and role
Red flag responses:
- Can't think of examples outside their expertise area
- Seem overwhelmed by ambiguous or changing requirements
- Ask only about specific tasks and responsibilities
- Show no curiosity about business context or challenges
Stage 3: Deep Evaluation (The Airport Test in Practice)
Extended interview/trial period:
- Work on real problem together for 2-4 hours
- Give them incomplete information and see how they handle it
- Include multiple team members in evaluation process
- Focus on collaboration quality and thinking process
Key questions to answer:
- Would I want to work with this person every day?
- Do they make our team discussions more valuable?
- Can they handle disagreement and uncertainty gracefully?
- Do I trust their judgment and decision-making process?
Stage 4: Integration (Setting Up for Success)
First 90 days designed for learning and adaptation:
- Clear context about business, customers, and challenges
- Pairing with team members across different functions
- Regular check-ins about role evolution and growth opportunities
- Permission to question existing processes and suggest improvements
Success metrics focused on:
- Quality of questions and insights they bring
- Speed of learning and contribution to solutions
- Team feedback about collaboration and communication
- Initiative in identifying and solving problems
The Long-Term Competitive Advantage
Building Antifragile Teams
Traditional teams:
- Optimized for current needs and challenges
- Fragile to changes in market, technology, or competitive landscape
- Require hiring/firing as business needs evolve
- Limited by collective expertise of individual specialists
Adaptable teams:
- Thrive on change and uncertainty
- Generate new capabilities as challenges emerge
- Grow stronger through variety of experiences
- Create value through synthesis and creative problem-solving
Creating Learning Organizations
When everyone is adaptable:
- Knowledge sharing becomes natural rather than forced
- Cross-training happens organically
- Innovation emerges from diverse perspectives
- Team becomes more valuable than sum of individual parts
Cultural benefits:
- People excited about growth rather than threatened by change
- Mistakes viewed as learning opportunities rather than failures
- Success measured by value creation rather than task completion
- Retention improves because work stays interesting and challenging
The Future of Work
AI will accelerate the trend toward person-first hiring:
What AI makes obsolete:
- Routine task execution
- Predictable problem-solving
- Standard analysis and reporting
- Specialized knowledge that can be automated
What AI makes more valuable:
- Judgment about what problems to solve
- Creativity in approaching novel challenges
- Relationship building and trust development
- Strategic thinking and decision-making under uncertainty
The implication: Hire people who can direct AI and make decisions about its outputs, not people who compete with AI on execution tasks.
The companies that win will be built by teams of people who:
- Adapt quickly to changing tools and requirements
- Think strategically about business problems
- Collaborate effectively under uncertainty
- Create value through relationships and judgment
These are human qualities that can be developed but not easily taught. They're revealed through person-first evaluation rather than role-based screening.
Conclusion: The Relationship Revolution
The shift from role-first to person-first hiring isn't just about better recruiting. It's about building companies that can thrive in an unpredictable world.
Role-based hiring assumes you know what work needs to be done. Person-based hiring assumes the work will change and the people need to change with it.
The best hire I ever made didn't match the job description because the job description was based on what we thought we needed, not what we actually needed as we grew.
What we actually needed:
- Someone who could grow with the business
- Someone who understood customers better than we did
- Someone who could adapt as our needs evolved
- Someone we genuinely wanted to work with every day