- Early
- Posts
- Dare to Stand Out
Dare to Stand Out
Why Blending in Can Cost You Your Dream Startup Job

JOB SEARCH STRATEGY
Dare to Stand Out.
In the fiercely competitive startup job market, standing out is not just a choice—it's a necessity.
Yet, many talented people fall into the trap of conformity, blending into the crowd rather than showcasing their unique skills and vision.
But why?
Is it the comfort of the known, the fear of rejection, or the lack of guidance on how to differentiate themselves?
Let’s dig in…

The Comfort Zone Dilemma.
🦓 A member of the UpEmployment Accelerator is in the final round of interviews to lead Product Marketing at an early-stage startup that helps job seekers use video referrals to stand out.
The product is sweet and something that can make a huge difference to set a candidate apart from their competition (we’ll likely highlight it here in a future newsletter).
But.. something I didn’t expect happened when she asked for feedback.
As a part of her preparation for her conversation with the CEO, she reached out to the UpEmployment community and shared a link to sign up for the product with a description of what it was and how it could help their search.
She was actively sourcing customer feedback before her interview (this is Jedi-level job seeker value creation and what we teach in the accelerator) so she could share the insights with company leadership.
On the day of her interview, she checked back in with the community to gather their feedback.
How many people do you think signed up?
Zero!
While there were many reasons people cited, they all boil down to one thing.
It was out of their comfort zone.
It was uncomfortable to record a video of themselves.
It was uncomfortable to ask mentors, former coworkers, and bosses to record video testimonials about them.
It was uncomfortable to standing out.
It was uncomfortable to possibly look stupid.
It was uncomfortable to spend time learning something new.
What did they do instead?
They resorted to the methods they were already using.
The methods that were comfortable to them.
The methods that had led them to this stage in their job search.
The methods that were getting them their current level of attention and results.
Look…
Searching for your next job is actively seeking change, and change creates discomfort.
We have a vision for how we want our life to look.
We have a vision for the work we want to do, who we want to do it with, and how we want to feel about it.
But the reason those things are visions and not reality is that you need to make the necessary changes and take the necessary action to get there.
This is where the Comfort Zone Dilemma comes in.
You have two choices.
Choice A = Stay comfortable where you are, doing what you’re doing, getting the results (or lack thereof) you’re getting, and avoiding potential discomfort.
If that’s your choice then own it.
Don’t expect new results and outstanding outcomes.
Or…
Choice B = Lean into the discomfort, knowing that it’s the only way to grow, to see what works, and to create an entirely different outcome than you have ever experienced in the past.
What you’re comfortable with got you to where you are today.
Where you are today may be kicking ass, making >$200k per year, with millions in the bank.
But what got you here and all the things you’re comfortable with today will not get you to where you want to go next.

Photo Credit: Pluggedin.com
The Fear Factor.
🐍 It’s human nature to fear rejection.
We were built to survive, and survival meant fitting in, not standing out, and getting along with everyone else in the tribe.
It meant not drawing too much attention to yourself because while attention can increase your status, it can also bring unwanted risks to your health and safety.
The trouble is, we’re no longer roaming the plains looking for our next meal, staving off predators, and keeping ourselves safe from rival tribes.
We’re looking for great jobs at exciting startups.
But that same aversion to standing out is hard-wired into our brains.
If you’re not standing out, you’re not being seen.
If you’re not being seen, how can you be the chosen one for that dream role?
Who do you think the hiring manager is going to want to hire?
The candidate that looks like everyone else or the candidate that so uniquely showcases themselves and their abilities it’s hard to compare them to anyone else?
It may feel like there’s a threat to your physical safety and well being but that fear is a sign that you’re on the right path to standing out.

Know Your Arena.
⚔️The competition in the tech job market is fierce right now.
Layoffs have poured highly talented people back into the job market, and companies have tightened budgets and are looking for ideal dream candidates.
If you were to assume that everyone applying for your target roles has everything you have.
The same background.
The same skills.
The same experiences.
The same network.
Then what is going to set you apart?
It will be your willingness to do things others aren’t willing to do to stand out.

Standing Out.
🦸So what is going to make you stand out from the crowd in this highly competitive landscape?
Here are a few things to lean into.
Personal Branding: If you took your LinkedIn headline and it could describe another person, then it’s not good enough. You want to highlight who you are, what you do, the results you drive, and your uniqueness. The point is to stand out, not to fit in. So make it colorful, make it professional, make it something you’re proud to send to other people as a showcase of the badass you are and the badass results you drive. Make sure you have a professional headshot (you’d be surprised how much this impacts people’s decisions to consider you as a candidate) and an updated banner image.
Storytelling: When someone asks you to “tell me about yourself,” don’t revert to the comfortable robot version of yourself. Instead, inject that passion, personality, energy, and drive that got you to this conversation in the first place. Tell them a story about the badass you are today but that it wasn’t always that way and how everything in your past has led you to be perfectly positioned for the conversation you’re having today. Do it well, and you’ll have people talking about you (in a good way) long after your meeting.
Video: Everyone will send a resume. Almost no one will send a video. My video outreach to get in contact with potential mentors has had a 100% success rate so far. It works for two reasons. One is because no one else does it. And two is because it allows them to see your passion, initiative, and willingness to do things others aren’t doing to secure an opportunity. Those are the types of people hiring managers want on their team. BONUS: You can record a video of yourself but you can also get videos from former managers, coworkers, vendors, clients, and mentors singing your praises, the results you drove for them, and how much they enjoyed working with you. Anyone can send written recommendations. Only a few brave ones will have the courage to ask for and send video recommendations.
Free Work: This newsletter started with a perfect example of free work. The candidate was in the interview process for a role and took it upon herself to do customer research, collect data, and share that with the team. The vast majority of candidates WILL NOT DO THIS. They feel they should be paid for it and that it’s an unfair expectation. Do things that aren’t asked of you. Solve problems for your target companies. Provide resources you think will help them. Be the person who, at every turn, is there with something of value. The majority of people show up to their interview, and that’s it. Don’t be like most people. Give all that you can give.
Your goal is not to create a new category of candidate.
One who does things they have never seen from others they have interviewed.
That’s how you become memorable.
That’s how you land competitive jobs at the best companies.
OPEN ROLES
Who’s Hiring?

What They Do: Next Insurance has built a platform that changes how small businesses experience insurance. They provide custom liability insurance options for a variety of sectors like fitness, cleaning, and education at competitive prices, making it easier and more affordable for these businesses to get the specific coverage they need.
Total Raised To Date: $1.16B
Company Valuation: $4.00B 🦄
Last Raise Date: November 1st, 2023
Recent Raise: $265.00M
Series: F
Number of Employees: 700
Open Roles? Yes
Pitchbook Success Probability: 98% Success
What They Do: Chainguard creates security software that helps businesses protect their software supply chains. By using zero-trust principles (not automatically trusting anything inside or outside the company), their software ensures that every stage of creating and delivering software is safe. This helps businesses reduce the risk of security threats in their software supply chain.
Total Raised To Date: $116.00M
Company Valuation: $411.00M
Last Raise Date: November 1st, 2023
Recent Raise: $61.00M
Series: B
Number of Employees: 70
Open Roles? Yes
Pitchbook Success Probability: 96% Success
What They Do: Huel makes nutritious powder mixes that are easy to use, good for your health, and won't break the bank. Their powders come in various flavors and pack a bunch of important nutrients like vitamins, minerals, protein, and fiber, all from sustainable sources.
Total Raised To Date: $182.93M
Company Valuation: $472.70M
Last Raise Date: November 1st, 2023
Recent Raise: $100.39M
Series: B
Number of Employees: 368
Open Roles? Yes
Pitchbook Success Probability: 97% Success
So there you have it, why it’s essential to get over your fear, lean into the discomfort, and stand out from the herd.
It has never been easier to contact and connect with people working at the companies where you want to work.
But the more you stand out in their eyes, the more they’re going to give you the opportunities you desire.
Let’s become career champions together 🏆
Kyle
Reply