Why Sexy Resumes Can Be Dangerous for Startups: when startups + enterprise mindsets don’t mix

When you’re a startup founder, every hire is crucial, and every role is pivotal. You have a pretty good idea of the type of role you need, until a glittering resume lands in your inbox—complete with big-name enterprise experience—and you feel like you’ve struck gold.

“This person worked at [insert sexy enterprise company here]. How flattering! This’ll be perfect experience to apply to my startup!”

This is a scenario we’ve seen play out pretty unsuccessfully many times over. So let’s jump into some Do’s and Don’ts and “Let’s Considers” if you’re weighing your options between candidates with sexy enterprise experience and candidates that don’t.  

Resumes Don’t Build Startups—People Do

A big-name company on a resume might suggest a certain level of expertise, but it doesn’t always translate to success in a scrappy, fast-paced environment. That doesn’t mean enterprise veterans can’t thrive in startups—they absolutely can. But it’s crucial to dig deeper during the hiring process to ensure they’re ready to roll up their sleeves and get to work.

Startups Need Builders, Not Delegators

Enterprise veterans are often experts at managing large teams, overseeing established processes, and executing within clearly defined roles. But at a startup, there’s little room for delegation—every leader is a hands-on contributor.

Your marketing lead might be outlining campaign strategy one minute and crafting the tagline, designing the mockups, or scheduling posts the very next. If a candidate hesitates to jump into the trenches or struggles without a team to delegate to, they may not be the right fit.

Resource-Heavy Backgrounds Can Be a Misstep

In an enterprise, access to resources can feel limitless: agencies on retainer, substantial ad budgets, dedicated researchers, and high-end tools to optimize every project. At a startup, the reality is often quite different. Your “team” might be just you and an intern, and your “budget” might be what’s left after office snacks.

Startups need someone who can make the most out of tight constraints—someone who can stretch a dollar and still deliver impact. If a candidate is accustomed to relying on big budgets and extensive support, they might struggle to adjust. And more importantly, they might struggle to deliver the results you need. 

Startups Demand Speed and Agility

Large companies operate at a deliberate pace, with extensive meetings, cross-department alignments, and well-defined timelines. Startups, on the other hand, require quick decisions, rapid iterations, and the ability to pivot without hesitation.

The best hires are comfortable navigating ambiguity, solving problems creatively, and moving forward without waiting for perfect processes. If a candidate thrives in bureaucratic predictability or struggles to adapt quickly, they may face challenges in a startup environment.

What to Look for in Startup Talent

When evaluating candidates, look beyond the resume and focus on qualities that indicate startup readiness:

• Proven Execution
  Can they show you tangible results from their work—a deck they created, a campaign they led, a website they built? Look for evidence of hands-on experience.
• Adaptability and Resilience
  Have they worked in environments where ambiguity, resource constraints, or rapid change were the norm? If not, ask how they’ve handled similar challenges in the past.
• Curiosity and Humility
  Startups are learning environments. Candidates who approach challenges with curiosity and a willingness to roll up their sleeves are more likely to thrive. And when you're operating in an environment full of educated guesses, humility goes a long way when things go awry. Because they will. They always do.
• Alignment with Your Mission
  A deep connection to your mission can fuel the dedication startups require. Look for candidates who show genuine passion for what you’re building. This is pretty easy to do: ask them why they're interested in joining your team. What drives them?

Asking the Right Interview Questions

To determine whether a candidate is ready to thrive in a startup environment, consider asking:

1. Can you share an example of a time you had to execute a project with limited resources?
2. How do you handle ambiguity or shifting priorities?
3. What’s the most hands-on project you’ve led or contributed to?
4. What excites you most about joining a startup?
5. How would you approach building something from scratch without a predefined process?

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Do’s and Don’ts:

Do’s

• Focus on Skills Over Titles: Prioritize candidates who can demonstrate their ability to execute, adapt, and thrive in ambiguity.
• Ask for Examples: Request tangible proof of past projects—presentations, campaigns, designs, or anything that showcases their hands-on work.
• Assess Startup Spirit: Look for experience in scrappy environments or clear evidence of resourcefulness and creativity.
• Test for Adaptability: Ask situational questions that gauge how they handle changing priorities or work outside of rigid structures.
• Align on Mission and Vision: Ensure candidates are genuinely passionate about your startup’s purpose, as that alignment often drives commitment and resilience.

Don’ts

• Don’t Be Dazzled by Logos: A resume full of big-name enterprises can look impressive but doesn’t always translate to the startup environment.
• Don’t Ignore Red Flags: If a candidate shows hesitation around hands-on work, small budgets, or fast-paced change, take it seriously.
• Don’t Skip the Grit Test: Avoid hiring someone based solely on strategic thinking; startups need doers who can execute.
• Don’t Assume Experience Equals Fit: A decade in enterprise roles doesn’t guarantee a candidate can handle the unique challenges of a startup.
• Don’t Underestimate Culture Fit: Even a skilled candidate can create friction if they’re not aligned with your startup’s pace, values, or goals.

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Focus on finding candidates who align with your company’s needs today, not just its aspirational future. Look for individuals who can help you build from the ground up, instead of operating within a system that’s already established.

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