Hiring - Telling Your Company's Story

Introduction: Hiring Is Storytelling

Hiring is more than selling a gig, it’s about offering a story that people want to live inside. The founding myth. The gnarly obstacles yet to be overcome. The promise of a better world after the dragon is slain. Your place alongside others through that quest.

When you’re building something early, you’re not just selling a job description. You’re offering a narrative people can project themselves into. The numbers, the perks, the glass-door ratings, those are secondary. What matters is the sense that this company is going somewhere, that this moment matters.

This is part two in a series on hiring for CTOs and other early-stage leaders. And while timing and tactics shift with every hiring season (as I covered in A Tale of Two Hiring Seasons), the deeper truth doesn’t: people join stories, not spreadsheets. The tactics evolve, but everyone’s search for purpose doesn’t.

So we’ll look at how to make that story tangible: who you are, what you’re offering, and how to make others care, especially when no one’s heard of you yet.

Regardless of whether you’re passively hoping to attract the right people, or if you are proactively reaching out, the underlying lifecycle is the same: They must become aware of your existence. Your existence must be appealing enough for them to apply and schlep through the process. They must like the prospect of working with you enough to sign on the dotted line. Once they join, you must continuously deliver your side of the promise. All common sense stuff: the execution is the hard part.

Defining Your Identity: Who You Really Are

First and foremost you need to make it clear what you’re all about. Joining you is ultimately an emotional decision, so you need to dial in the vibes just right. The numbers can only do so much if the idea of your company doesn’t move someone.

Why does your company exist? Is there a genuine mission here? Why does it matter? Do you actually care about it, or are you LARPing, checking off the “mission and vision” boxes that every company out there has to have? You want your enthusiasm to be genuine and infectious, so anything that sounds corporate and overly sanitized has to go. Early stage startups are allowed to express themselves and take a strong stance on the world, and if you’re under 100 people and are already trying to sound generic and inoffensive, you’re practically invisible.

It’s ok if you’re not for everybody. You will not be perfectly inclusive. You won’t make everybody happy. Again, that’s a’ight, take a deep breath and internalize it. You’re not Walmart. At this stage, your personality doesn’t have to scale to millions. It has to put a spell on just a few, maybe a dozen, maybe a hundred if you’re lucky. If you’re in the early-to-mid stages as a startup, you should be unpalatable to the majority. The key is to make that polarizing flavor work for you, passively filtering for the kind of people you want on the team.

VC-backed startups make up less than 0.1% of all US businesses. They’re an extreme sport that attracts a mix of young, restless, wacky, ambitious, otherwise possibly unemployable individuals who might not fit at a traditional corpo gig. Startup employees seek a way to prove themselves, grow faster than they could anywhere else. They also take on the risk of worse pay, terrible management, their employer running out of money, atrocious work hours and more. “Small wages, bitter cold, long months of complete darkness” as the apocryphal Shackleton’s ad promised.

Sometimes it’s not just running towards, but also running from. Many applicants want to avoid the predictability, specialization, compliance and conformity of a big co job. There’s a time and place for that, and if you’re successful at your job as a founder, that will be your company’s lot in life as well in a few years. But for now, you should be offputting to most who would be better served in something less speculative than an early stage gig. Great short video here on that subject from Speedrun’s Jordan Carver.

Once you’ve clarified who you are, the next question is: what are you offering?

Make a Promise: What’s in It for Them

What sort of vision are you promising to people considering joining you? Can they picture themselves as part of it? What are they getting out of it, besides cash, which will be lower than just about anywhere else? Put yourself in their shoes and be honest with yourself. Would you join this company if you were hearing about it for the first time? Would the brochure pique your interest?

You can promise infinite riches. Fame and glory. A mission that will make a real difference to people you actually know. Camaraderie, and an opportunity to learn from spectacular coworkers. A brand that will pay dividends for the rest of their career. An invaluable network which will create opportunities and life-long allies for years to come. Adventure. Cultural relevance and coolness factor. Maybe a move to a location they always dreamed of trying out. The list goes on, get creative. Most of these are intangible. That doesn’t make them any less important to figure out.

Even the aesthetics of your career page matter, and complement the storytelling about who you are. The visuals, the consistent voice, a unified vision for how it all ties together.

One of the first things we did at Double Dusk was to invest into a beautifully hand-crafted landing page using tasteful, organic art and a parallax effect to make it obvious that this was a place for craftsmen and auteurs, that we took the art of making games seriously and wanted to find others who felt the same. We weren’t about quick asset flips and AI slop, we wanted our customers to feel the love that went into the product, feel like the people crafting it viscerally cared about the medium.

Was that the best business decision? Meh, probably not, but we took a stand and were genuine about who we were. We couldn’t be any other way if we wanted to, this wasn’t an artificially focus-groupped conclusion. In the end the people joining us were exactly who we were hoping for, they found a tribe that embodied their same values. Their first encounter with us started with a unique visual impression, especially important for a firm priding itself in its standout art direction.

Solving a seemingly insurmountable problem really helps. Would you rather work on making humanity space-faring, shooting 5000 ton rockets into the stratosphere, or on slightly tweaking an HR software portal with a few ChatGPT calls on top? Life’s short, for many, the choice is obvious, especially earlier in people’s careers when taking bold bets is worth more than safety and predictability of cash flow.

You can lean into a particular philosophy, think TDD and Extreme Programming for Pivotal Labs. Or on a particular technology that offers a unique approach. Or a unique way of working together. Think Gitlab and their early push for remote work in the 2010s. Or Subscript who only work asynchronously, no meetings ever. Weird, right? Yes, but it also attracts a particular type that’s going to absolutely love it there, and turn off many who would be driven nuts by that type of work style.

At Freckle I united the team around the vision of using purely functional programming through Haskell (see my article Haskell at Front Row), the most sophisticated tool on the market for building complex backends that never break, can be iterated on fearlessly, and where bugs are a rarity, rather than everyday reality. Controversial opinion? Absolutely. But it was also a beacon attracting engineers who dreamed of working professionally in that kind of environment, being able to learn from some of the best active practitioners in the industry. The pool of applicants was small, but half or more of those who applied were worth an interview. It was an effective passive filter that did much of the selection work for us.

Don’t forget to paint a picture of the work style you follow. This is understandably top of mind for most people applying. Maybe the culture is mellow and friendly, with a four-day workweek and a focus on balance. Or maybe it’s a 996-style grind for the foreseeable future. Some teams thrive on competition, others on collaboration. Some are experimental and action-driven, while others lean heavily on theory and deliberate design. A company might attract doers who ship fast and learn by trying, or thinkers who obsess over frameworks and precision.

The environment itself could resemble a 20-something hacker dorm in San Francisco: developers taking drags from their vapes with one hand, flipping through TikToks with the other, all while waiting for Claude Code to finish. Or it could be a more mature team with families, soccer practice, and suburban homes. Those crazy-hour startups trade experience for hustle, the more seasoned teams trade hustle for proven talent that doesn’t live in a sleeping pod. Whether that tradeoff fits your current stage is another conversation, but it’s a choice worth making consciously. Now that you know what story you’re telling, it’s time to show it.

Show, Don’t Tell: Choosing The Medium

Getting tactical for a moment, how you go about painting this picture can take all sorts of forms. This is nothing but content marketing repackaged for hiring, there’s nothing mystical about it, just a lot of elbow grease and trying to dial in the language and the channels until you get them right, and until they eventually become shitty.

If you’re handy with videography, there’s nothing quite like shooting OpenAI and Anthropic-style videos to show more about how the sausage is made, showcase some of the work and some of the more interesting people at your company. It’s a lot of effort, but this creates a sense of familiarity with you, and some people will resonate with how you tell your stories. It doesn’t have to be highly produced either, there’s something endearing about the authenticity of an early stage team, the scrappiness of it all. Use it as your strength, rather than trying to copy what $500B companies are doing.

Podcasts are great too, they allow you to go in depth into as many topics as you want, trading length for high production values. Having the founders or a few talented team members showcase their passion for the work and what’s coming next can be infectious.

Blogging is a tried and true method as well, again with its own pros and cons, starting a conversation on sites like Hacker News where team members can chime in and create a sense of community with the broader technology ecosystem.

Conferences are solid as well. Send a few engineers to do a talk about something interesting you’re working on, a non-obvious insight you have obtained, or a fresh take on something people might be already doing. Generate content for your company in the process, re-use it for years to come. A variant of this is running a meetup on a particular topic, positioning your team as the experts in a particular space. Whoever shows up to these will be likely a great candidate for future hiring pushes, just make sure you make time for people on your team to socialize with the attendees.

Social media can work as well here, not my forte, but some people are really artful at it and will generate outcomes, although I’m unclear how well they compare to the other methods here.

Hackathons and other events you organize are also a well-trodden option, they allow people to meet your team, perhaps see your offices, build a more personal connection with your brand and the work that you do, perhaps even win a prize or get to ask your team questions about what it’s like to work there. I’ve always been surprised by how hard some companies make it to ask their employees what it’s like to work at that company and act as ambassadors for your company. I suppose it’s a waste of time in most cases, but carving time for promising potential applicants who are trying to learn what it’s like to work with you seems valuable.

This all sounds sensible, but what’s the catch?

The Tradeoff: Storytelling Is a Long Game

Unfortunately, this all takes time and effort, and is typically not the expertise of a technical CTO who’d rather be in the terminal all day. None of it is urgent, and none of it produces instant results. That’s a cursed mix. In startup land that’s code word for “we’ll never actually do this, way too much other hair-on-fire work we already aren’t getting to”.

Unless there’s someone at your company who owns this, it will always be a nice-to-have. Every team regresses to doing nothing about building the brand until it’s time to post a new job description. Suddenly you realize you don’t have solid warm connections who might be ready to jump ship and what you’re getting in the inbox is far from the bar you were hoping to meet. “Can someone crank out a blog post and push it to Hacker News in the next couple of days” is not what you want to hear as you begin hiring again.

All I can say is try to run tiny experiments here and see what resonates with you and with the outside world.

Does anybody on the team have the chops and the interest in occasionally contributing in one of these formats? Be constantly on the lookout for something interesting you’re doing that you can talk about, whether that’s using Haskell to generate AWS Cloudformation templates or if your artists are painting with watercolors and scanning in those textures to be applied onto your game’s terrain. Someone, somewhere is going to find that inspiring, and will remember you.

Keep the Fire Lit: The Process Is King

Of course, if you temporarily happen to be the hottest company on the block and the wind is in your sails, you may not need any of the above. If you’re Lovable, Wiz, Deel, Cursor, or early days of OpenAI and Anthropic, ambitious people will naturally flock to you seeking challenge, glory, and a mind-shattering equity package at a company raising 2-3 rounds a year.

But your good fortune will not last forever, and once the temperature comes down, you will wish you had your storytelling flywheel dialed in. After all, if you base your whole identity on “this place is where you come to make money”, what are you offering once growth tapers off and people take off for the next rising S-curve?

Wrapping Up

Hiring done well isn’t just attraction. It’s filtration. The clearer your story, the more the company becomes a magnet for the right kind of oddballs. The people who read your manifesto and think “finally, someone gets it.” And the more it makes others go “Absolutely not, you guys are f*****g nuts!”

Even outbound recruiting depends on this. Every candidate you message is silently asking: “Who are these people, really? Is this quest for me? What role will I play?” If your presence online answers that with clarity, conviction and personality, half your job is done before the first call. And for people deciding to opt out, you’ve just saved them and your team a ton of time.

Tell a compelling and authentic story, and the right ones will find you.