An early stage founder's hiring diary

We went from 4 employees to 15 in the past 12 months and we’ll likely double that over the next 12 months. Yes, that means that I haven’t met 75% of the team in person, and by the end of the year, I might not have met almost the entire team.

There are many posts written about hiring & culture and a few written specifically with startups in mind (First Round Review does an incredible job at this). But there’s scant literature from the front lines detailing how early stage startups deal with rapidly scaling an early team in a remote-first world. And, at ANTENNA, we’ll likely be remote empathetic(*) well beyond the Pandemic, so there’s even less literature to borrow from.

(*) Remote empathetic is a term I’ve been using to describe a likely post-COVID model for ANTENNA. We will do things such that you do not need to be in an office to contribute, unencumbered, to every aspect of the company. But we also recognize that not everyone can work from home comfortably, so we’ll try to ensure that going to an office is possible too. I believe Spotify has nailed this approach better than anyone.

So, onto the learnings…

The overarching theme is that recruiting & culture is a lesson in trade-offs. Early stage founders don’t get to be too principled (something I’ve been guilty of at various points in my career). We operate entirely in the gray area in between extremes.

Note: please continue reading under the pretense that these notes reflect what I’ve learned so far. We are early on in our journey, and are far from perfect in any aspect, including recruiting & culture. While there is still much room to improve, chronicling what we learn along the way is important to me, so that’s what I’m doing.

There are lots of cliches about how founders should spend many hours recruiting — take this and multiply it by 100.

If Glengarry Glen Ross were released today, it would probably be about startups, and the famous phrase would probably be “always be recruiting.”

But too often, I see this advice heeded only inasmuch as it relates to “telling the company story.” This is great but insufficient. When I give this advice, I’m talking about every aspect: writing the job description, sourcing thousands of prospects, sending hundreds of outbounds, screening dozens of candidates, interviewing at least the first 50 hires, and so on.

Just to give you a picture of the extremes you might take this to, here’s an image of the first conversation I had with a future employee — who I had been courting for 3 months before we even talked about a job:

And here’s another one, who I was seemingly recruiting while having a conversation about potentially buying software from them:

These employees have both been rock stars since day 1. It may seem like overkill to court individuals one-by-one, especially if you’re not hiring a CTO of VP of Sales. But remember two things:

1. No matter how much money you’ve raised or who your founders are, the average potential candidate doesn’t know or care about you or your startup.

2. If you’re not doing this, well, I am :).

Remote empathetic culture is not a naturally occurring consequence

This is an area of Culture where I’ve been incredibly fortunate to have a few team members step up and proactively ensure we are building one. Note to self: hire people who actively contribute to culture in addition to being incredibly productive at their day job.

What’s worked: wellness stipends, lunch & learns, social “free” lunches, post-product release happy hours, virtual escape rooms, company swag, over-communication during sprints as a way to build empathy between commercial and technology teams, high transparency in Slack & elsewhere.

What I hope we can improve on: Other than the obvious (regular, in-person gatherings), I hope we can continue forming intimate personal relationships with each other even as we scale. Most notably, as we grow too big for me to personally meet with everyone on the team one-on-one multiple times per month, how will I ensure others are having an incredible experience? If you’re at a similar inflection point, I suggest you have a plan before this becomes your reality.

Enlist your early team in creating an incredible culture that is authentic to you

I believe that every great company of the future must take a leadership position on recruiting & culture. This does not mean that it’s the same POV: different companies will define inclusive recruiting, transparency in compensation, and remote empathetic work in meaningfully different ways.

The greatest asset you have to ensure that your company culture does stand for something is to enlist your early team. Not a single one of the “what’s worked” ideas were my own — they were all brought to me by our incredibly engaged early team.

When everyone on your team assumes that building an incredible culture is their job, you start to have an incredibly authentic & cohesive culture, which attracts more people who will culturally fit into the organization and contribute as incredibly productive employees.

Remote ≠ asynchronous

The startups that tend to go hand-in-hand with remote work are Basecamp, Zapier, and Gitlab (handbooks all attached). So, naturally, when I was learning “how to do remote,” these were the names I heard over & over. These companies have built an incredible remote culture – so I am not taking anything away from them – but it’s important to note that you can be remote-first without being largely asynchronous. In short, there should be more, successful remote empathetic playbooks that look nothing like how those companies work.

To date, we’ve decided not to be asynchronous. We have plenty of meetings, weekly 1:1s, and so on. Other than inertia, there’s one major reason: COVID has brought on tremendous social isolation and, sometimes, it’s nice to talk to others about interesting problems!

There’s a nasty side to fully asynchronous work we also hope to avoid. This can be best summed up by a really smart remark in Slack by someone on our team:

Said less eloquently, we do not want to start talking to each other like we speak with customer service reps in our worst moments!

D&I at the early stages is HARD

Another disclaimer: I do not write this as an excuse to ignore it in any way, shape, or form. Please don’t interpret it as such :).

Like most tech startups, we struggled early. For example, our early team was only ~20% female. Remember how I mentioned that our team is incredibly proactive about building a strong culture? I meant it. One of our employees very succinctly explained why this was a problem that needed solving immediately: “if you want women to feel comfortable here, you need to surround them with other women to relate to at every position in the company.” That struck a chord. As of this writing, I’m happy to report that we have improved that % to ~45% — far from “mission accomplished” but certainly a minor victory worth smiling about.

The reality is that it’s 2021 and we should care about building a diverse & inclusive workplace — and, frankly, I think it’s going to be very tough to build a successful, scaled technology company if you’re not thinking about this from the early days.

Here are a few other things I’ve learned:

• Spell out your mandate, over & over, and it will become true. I did not feel comfortable establishing any firm goals and/or talent quotas so early on because I had no clue what hiring might look like. But I did communicate that this was not acceptable and we should take steps to improve it. Our team was incredibly receptive to this. Another lesson: find a way to communicate to your entire team before you have “the final answer.” One thing that will make you a great early stage leader (and beyond?) is communicating your thought process even before you have the answer to complicated subjects.

• D&I focused Job Boards are mandatory but insufficient. Diversify Tech, Women Who Code, Tech Ladies were amongst the best I found for the specific topic at hand.

• Be open to a wider variety of backgrounds. There are tons of incredible Data Scientists who have experience in academia (rather than startups) and might offer from a wider pool of backgrounds. If it is actually a pipeline problem, change the definition of the pipeline.

The bottom line: My best advice on this topic is to try your best to separate signal from noise; understand & appreciate the trade-offs (e.g. you may require a longer recruiting cycle but you may also set your company up for long-term success if you think about D&I earlier) and, at the same time, be very receptive to any critical feedback on your progress.

Recruiting ≠ Culture ≠ HR

In the early days, I would err heavily on the Recruiting element of these three oft-confused pillars of Operations. Why? Because Culture is the sum of the way you, as the founder, carry yourself and the early team you hire (insert link to the many quotes and/or tweets extolling this truism). It’s certainly come true for us (see several references above to how our team leads the way in setting our Culture).

Want to build a great culture? Hire incredible people who take it upon themselves to have serious conversations with the CEO about how they can build a more inclusive workplace or think more actively about creating learning and bonding opportunities on a more regular cadence.

There are a lot of things you can learn-by-reading. I don’t think Culture is one of those things. The problem with emulating a Harvard Business School case study, or whatever your favorite tech founder says, is that Culture is deeply personal to the human beings that comprise the early team. Unless you have some sort of PayPal mafia type situation, it is highly likely that the group of people on your early team are materially different than the people at whatever company you are trying to emulate. Beware of trying to emulate outputs with materially different inputs.

If you retain one thing from this (needlessly lengthy) post: hiring is not done when you send an offer letter, it’s done when you have a successfully onboarded & productive employee

I am partial to the 30/60/90 new hire plan and ensure that every single hire sees their 30/60/90, at latest, on their first day.

There’s at least two core elements of a good 30/60/90:

1. Quick, achievable win in the first 30 days: Extremely important to establish your exceptional new hire as capable both in the eyes of their new colleagues and in their own eyes (never underestimate self-confidence as a precursor to success).

2. “Fully onboarded” by day 90: The definition is up to you but I like including a task that is significant enough and meaningful enough to the business that justifies this.

3. A mix of learning and doing: Some people learn by doing, and others learn by, well, learning. At a startup, you always have a bias towards action — learning on the job. But you must carve out at least some time

Leverage your team to train new hires. Early employees are your co-owners. They are extremely motivated to ensure the success of every new employee. Plus, it’s incredible ad hoc management training for young leaders who will scale with your organization and eventually lead large teams within it.

Lastly: Leverage the power of networks — your own

I kick myself for not doing this earlier. I would like to roll out internal referral bonuses, explicitly create a step in our hiring process that involves asking each incoming candidate the three best employees from their last company, and then create a process to bring those people to ANTENNA.

If you are recruiting excellent people, investing in their success via 30/60/90s and other plans, and asking them to leverage their networks; this should create an incredible feedback loop that can scale for as long as your company needs.