All is Fair in Love and Startups

By Glo Robinson

‘Tis the season of Valentine’s Day and love is on everyone’s mind!

From Tinder to Bumble, Hinge to OkCupid, there are no shortage of options for would-be Romeos and Juliets. In this humble writer’s opinion, there exist a number of parallels between dating and hiring (sans the intimacy, dear God!). Much like dating, recruiting—with its interviews, case studies, and references—is a whole song and dance. Except in the best case scenario you end up with a job, not nuptials.

To explore these similarities, we turned to Glo Robinson. Both a regular Stonks contributor and Product Management/Growth consultant, Glo is a Jill of all trades. After running her own startup, she quickly realized product teams could run more efficiently by improving their documentation process. She designed a framework to centralize product documentation and repurpose it to improve go-to-market content. Glo has helped startups build their products from zero to one and has developed growth strategies to increase both activation and retention rates.

Prior to Glo’s consulting practice, she was the founder and CEO of a startup called Go Off!, a social experience platform to help content creators and mission-driven brands reduce their content creation time and increase follower engagement and retention.

Over to Glo!

With the evolution of remote work and constant pressure to return to the office, the concept of getting paid hundreds of dollars an hour to sit in front of a computer and "do stuff" sounds sexy.

And believe me, it can be. After all, the stock market seems to be as volatile as Rachel and Ross's relationship in Friends... That said, I have noticed two emerging trends among recent grads on the job hunt these days:

1. Recognition that rising the corporate ladder is not the only way to make millions

2. Optimization for meaning and impact more than mere paycheck

Why Big Tech lost its lust(er)

While the term "recession" looms over the zeitgeist like a gray cloud, we're not completely ready to recognize the upcoming downpour. Nevertheless, the golden age of "big tech" has taken a gloomy turn.

During the past decade, we idolized the gilded lifestyle of wearing sweatpants to the living room (everyday), eating catered lunches from Michelin-grade chefs, and Silicon Valley's venture capital firms subsidizing a technology-dependent way of life (from ordering food on our phones with a touch of a button to using a texting-like platform to communicate with our coworkers because email became too formal).

If there's one major take-away from the pandemic: people care about how they spend their time, and remote work is here to stay.

Work is not just for cash in the bank

The average person spends at least 1/3 of their life working. We might as well feel motivated to show up and do our job, but a majority of tech workers have begun to wonder: is it worth it to stay at a large company and not feel like they're making an impact?

It's no surprise thousands of tech workers from big institutions like Meta and Google have left to work at high-growth venture backed startups.

But why?

Millennials in their early thirties are leaving corporate America to become "solopreneurs" and Gen-Zs fresh out of college are living at home taking their sweet time to discover what they actually want to be when they “grow up” (because getting a college degree doesn't help people answer this question anymore).

A reality check on "startup life"

In light of these pressing realities, one consistent sector actively hiring is early-stage startups. Though a turbulent time to actually fundraise, startups are always working against the clock and badly need manpower in order to grow as quickly as their investors would like.

So if you're looking for a cause to pour your heart into and get your "street MBA," I recommend applying to early stage startups (i.e. pre-seed to series B).

As a former founder and consultant that’s worked with numerous startups, below are six insights and realities to consider about the early stage startup hiring process:

The Hiring Process

1. The Initial Super-Swipe: Let's say you find a startup, you love their product and mission and they have a position you are qualified for. Think of this like super-swiping on someone's Tinder profile or "sending a rose on Hinge," you're really hoping they will respond to your cold email or application.

2. What's the “Instagram-stalking” equivalent for startups? The startup gets back to you within a few days and you're having your first conversation. You're so excited because you're one step closer to joining the venture of your dreams, but don't put your rose-colored glasses on just yet. Like venture capitalists, you're entitled to conduct your own round of due-diligence:

• Conduct due diligence on:
  • The founders: Like dating, we're always curious to know of someone's history, who were their partners before us, right? In this case, if the founders have founded a startup prior or served as early employees at startup, it's a safer bet they're more prepared to operate a small, rapidly-growing company. It doesn't mean they are necessarily better, but let's just say, it's not their first time (if you know what I mean).
  • The company: How much funding have they received? Who are their investors? How many employees do they have? How long have they been working there? How long has the company existed?
• Critical questions to ask: If public companies are like celebrities, their lives are on public display. In this case, looking up their financial performance or employee retention is necessary. This is critical because then when you meet with them, you'll be able to ask questions such as:
  • What are your core value propositions?
  • What makes your product unique?
  • What's your roadmap for next year?
  • Where are you lacking resources in terms of hiring? (this will indicate how much support you'll be given)
  • What milestones are you trying to hit in the next quarter?
  • Who are your competitors?
  • What's your runway?
• References for diligence: Linkedin, Crunchbase, Pitchbook, Product Hunt, and Twitter

3. Will I see you again? The first meeting goes well and both of you want to proceed forward. For most early stage startups, there's a greater risk to bringing on a full-time hire. They only have so much cash to try out different hires in order to meet their metrics.Back to the dating analogy-as much as startups are always on the prowl, they're not necessarily in a rush to officially commit. They want to try you out and make sure you're invested and it's a match on both sides. More often than not, they might want to "casually date you" and have you work on a project and pay you as a contractor. This is a good thing and allows you to evaluate them just as much as they are evaluating you.Some initial data points to evaluate when you work as a contractor:

• Are the deliverables clear? (make sure this is in writing, at the end of your project when they are evaluating you, this is an objective source)
• How are they measuring your performance, what are your metrics of success? (make sure this is clear and in writing).
• Is the hourly compensation fair? (remember: as a contractor you don't receive benefits so you can charge a higher hourly rate, don't let them low-ball you!)
• Is there a clear timeline and frequency to check-in with you? (I recommend weekly check-ins to hold both parties accountable. Additionally, write a clause about blockers. When you're working on a project, you'll be collaborating with someone on their team and most likely they'll be slow. Don't let them impact your performance).
• Make sure it's clear who you are directly reporting to. (i.e: The CEO might hire you, but you might be working with the CTO. Who you directly report to in your contract role will most likely be the person you will work for).
• How do they integrate you into the team over time? Do you get a sense of the culture and who else you might work with?
• When they give you feedback, do you feel they value your work?

4. Are we exclusive yet? So it's been a month and you complete the consulting project. You're trying to evaluate their actions and decipher the yellow versus the red flags. Working at a small startup is not a typical job, if you want to do it well. More than anything, it’s a lifestyle change (especially for the pre-seed to seed stage), where you’re on a journey with this cast of characters to arrive at that mythical place known as product-market-fit (PMF). Before you commit to this journey, some key insights to consider:

Questions to ask yourself:

• Will I grow with this company?
• Am I ready for this lifestyle change?
• What am I most passionate about? the sector, the product?
• Do I respect the insight and feedback that would be given by the person I would be directly reporting to? Do I actually feel like I can learn from them?

Data points to evaluate the company:

• ask for their most recent investor updates (i.e. last two months)
• ask about employee retention rates. This is critical (while startups are notorious for turnover, if patterns start to emerge-like women leaving-don’t brush over it).
• How does my company measure the success of my performance?
• Where are they on the map of achieving product-market-fit?

5. Let’s go steady

Now you get the official offer letter and you couldn’t be more excited. It’s a special day. You’ve been chosen. The ambiguous mist in the air of will-they won’t-they has been decimated. While couples make cheesy posts on Instagram they are official with the unsaid expectation they hope to be together forever, I recommend waiting at least 3 months before you make an official job update post on Linkedin. Remember how many phases and crushes you probably had during your angsty teen years? Just think of this being the corporate equivalent. Especially for startups, three months is a lifetime. A lot can happen.

During your early days at your new swanky startup job, it’s crucial to always communicate and prove how you’re providing value (especially if you’re not an engineering hire). Below I’ve outlined top three discussion points to address with the leadership team to ensure you have your bases covered to set you up for success:

1. Outline a 30-60-90 day plan: While the first three months are a “probationary” period, it’s critical to know how the company is measuring your success. Now, the common pitfall startups run into is pivoting-make sure your work is geared for pivots. I can’t express the numerous times I’ve done work for clients only to learn they’ve iterated to a new direction. While it’s common and they’re trying to stay ahead of the market, make sure your work will be valued and the leadership team can understand what value you bring. (If the founders are made up of engineers, non engineering hires have to work harder to prove their value, it’s just a fact).
2. Become fluent with their metrics and roadmap: Within the first week, try to be fluent on the company’s goals and metrics and how your deliverables impact specific OKRs. It keeps you accountable and your company too.
3. Initiate the onboarding process: Most of the time, early stage startups won’t have a traditional onboarding process. It might be as simple as you asking all the questions. While things are moving at a lightning speed, don’t let their disorganization impact your work:
   1. Establish your first deliverables-scope some briefs to make sure the projects you’re working on are correlated with the metrics your company is trying to achieve and estimate when you’ll be able to evaluate the results. It could be months, but setting a goal to evaluate your work is critical to show value and setting expectations.
   2. Understand their communication methods-how often do they have meetings? Do they have daily standups? What’s a typical feedback cycle like-who gives the final say? In early stage startups, there’s almost little to no structure so it’s important to assess your resources and how to communicate when you need help.
   3. Become fluent with their “tool-stack”-every company operates differently using various tools. The faster you can get up to speed with the tools they use, the quicker you’ll be able to do your work.

6. The End

While we all hope to become billionaires based on an early employee equity package, that fantasy doesn’t always come to fruition. However, it’s good to prepare for the end of an era.

There are three main takeaways to consider if you'd like to work for an early stage startup:

1. Conduct due diligence on the startup for which you want to work. Investors invest their money, while employees invest their time.
2. Track your progress and articulate your value.
3. Tie everything you deliver to an actionable company metric.

Startups are a lot like the “bad-ass skater boys.”

If they succeed, you were lucky to meet one that was ready to settle down.

If they shut down, you know they were never meant to be in a long-term relationship in the first place.

Best of luck finding the one that leads you to happily ever after! <3