The past ten months have felt like a couple of years – so I’ve decided to stop, reflect, and share some of my learnings.

I’ve built up two companies; one from the ground up regarding technology and infrastructure alone, and the other from absolutely nothing. One of those companies has since closed, and the other is still puttering along in my free time.

I made a tough decision to commit my startup journey to moonlighting hours only and find a more stable company to join that’s just as exciting and could help me grow my skills and network. It was time to start a job search.

I’d like to share some of my thoughts and experiences specifically around this job search; what went well, what didn’t go well, warning signs, and when the universe slaps you in the face with something great.

At the time of writing this post, I’m in my mid-late 20’s and I’m extremely lucky and privileged to never have conducted a full-time job search until the summer of 2020.

In mid-July 2020, my company at the time was in rough, uncertain waters. We were waiting to receive signatures committing investors/ business partners to an agreement to help grow our company, and while we received positive verbal commitments, things were not moving forward with signatures on our terms.

I had a tough conversation with the founder.

“What do we do if we never get formal agreements to our terms?"

“Given current events of 2020, working for no salary and sub-founder equity is not a situation I want to place myself in."

“What if these parties turn around with different terms and ask us to build a subset of our product, snuffing out half of our mission and vision – but we still get funding?"

We only had three months of runway, I had built out the entire system and product that we were planning to launch, I was confident that our system could scale – and we weren’t in control of our destiny. Oof.

We decided to run the company to it’s financial limit, and if we did not receive the signatures on mutually agreeable terms before then, we would close up shop and revisit the company should everything line back up perfectly.

I had to start a full-time job search.

First Steps

Never discount your network.

From the start, enabling free channels through AngelList and LinkedIn Jobs were really important. With those I was able to get automatic intros to companies and opportunities that I could filter down based on my preferences. Unfortunately nothing worked out there, but it was great practice.

If you’re currently looking for a new job in tech, and don’t yet have an AngelList profile, use this link to sign up for A-List, AngelList’s top candidate pool. A-List matches you with companies based on your preferences automatically, and you can choose to reply or decline invitations to interview. It’s a great way to get leads without much overhead.

I’m super lucky to have even more channels through my university and from startup accelerators too. What would I do if I didn’t have those networks? I would identify what I want to do, build my brand, and get my message out. It may be tough to start, but after a couple of days of work putting together a resume, website, and spruced up professional social pages – intro call emails will start appearing in your inbox. There are lots of ways to get your LinkedIn or other social profiles trending the way you want. Most importantly, remember that you can’t wait for something to happen, you have to reach out.

Check Yourself

Make sure you’re being honest with yourself about what you can do now, what you can’t do, your learning-rate, and what you can grow into – and if the opportunities you’re applying to align with that.

At the start of my search I applied to every role that was related to software engineering – backend, technical project manager, full-stack dev, SRE, infrastructure, lead, senior, mid-level, entry-level, heck I even applied to principal roles (actually didn’t do too shabby with those!). I also emailed connections in my networks who were focal points that could connect me directly with startups and people in shared networks.

Startups are interesting players in job searching; they want to move fast and grow so they usually turn around with results of an interview quickly.

From my experience, as an applicant, you can fall into one of three buckets with startup interviewing;

  1. You have the right skills and can help immediately – hire!
  2. You don’t have the right skills right now but can learn wicked fast – hire!
  3. You don’t have the skills and haven’t shown that you can learn wicked fast – pass!

Don’t be in the third bucket, and be critical in assessing what bucket you fall into for each job post you think about applying to.

From my experience, startups and small companies are like this up to a point, say less than 50 to 60 employees. Once their engineering org starts growing, evolving into small engineering companies inside larger companies, more complexity is introduced to the engineering hiring process for many reasons. So don’t sweat it if you don’t get an offer and the process sucked; you need to improve for next time, and so does the company that interviewed you.

It’s important to note that your perspective may not be aligned with the perspective on the other side of the job posting. A senior engineer at one company is not a senior engineer at another. I certainly over did it in this respect. I let a bunch of the stress of current events of 2020 get to me, and applied to more roles than I should have. One of my biggest takeaways from this is to trust your gut about a posting and if it undoubtedly maps to your skill-set, experience, and interests, apply! Otherwise, sleep on it.

Trust Your Gut

If you’re unsure, or think you’re a borderline-fit for a position, that’s what recruiters and hiring managers are there for.

Ask to speak to hiring managers first, prefacing that you want to know if you’re a fit. Teetering along an 80% fit can be risky for you and the company you’re interviewing with – as some companies want to find perfect fits that are ready to roll full-steam ahead on day one.

Sometimes companies and recruiters can drag you along for months in a process, take you to a final round with lots of positive feedback and excitement, then give you zero feedback as to why you weren’t extended an offer. Trailing someone as a backup is not the way to treat an interviewee, if they don’t fit the bill, they should know, if they fail an interview, they should know, if someone is a better fit, they should know – do not leave someone in the dark for weeks after an onsite without feedback.

If you, as the candidate, realize that this is happening to you, move on. Sure signs that you’re being dragged along include unclear feedback on interviews, inconsistency to tell you what role you’re interviewing for, and consistent reassurance/ offer negotiations but you never get an offer.

You might run into some conversations with points like the following. All of the statements below gave me gut reactions to avoid the companies I was talking to, and I’m really happy I trusted that feeling. These are real statements, some paraphrased, that individuals shared with me while interviewing.

Are you looking for a paid position or a Startup position? Sorry i should have posted: Join an early team or are you looking for employment

Whenever you want to do something that isn’t in a ticket or on the road-map I make, let’s talk about it and I’ll decide.

Your full-time offer is contingent on co-locating with us. Well we could actually do a contract, could you work 40+ hours per week for as long as you possibly can?

Well some people thought you weren’t invested enough and that the salary range is just not right for someone like you.

Pretty rough right? Actually makes me feel gross after typing that. No worries, there won’t be any more of those in this post.

For technical interviews, I had calls where the interviewers were completely amazing and the problems were near impossible to solve in the time allotted – and I passed!

Other times, the questions were easier, the interviewer grilled me about cloud provider superiority and about the fact that I had never worked for a FAANG company before, and gave no feedback about why they didn’t like a perfectly acceptable, and performant solution to their problem – and I failed! And sometimes, I just flat out missed the question full stop – we all have those days.

My take away from those technical interviews is that great people build with you and not against you during your interview.

For interviewers, please read this post which is about theory versus practice on algorithmic interviews – please don’t critically grade someone on an interview that is unrelated to their day to day work – if you do ask such a question, make it an exercise to see how well you work together, and less about correctness or completeness.

If your company isn’t Google, you don’t have to interview like Google! Be unique, be personable, be challenging and constructive.

Fortunately, I worked with quite a few companies and people that really impressed me, one of which I accepted an offer from! They were honest about what they were looking for, polite and intelligent, kept me well updated throughout the process, and we got expectations about the role and me out of the way immediately to take care of any misconceptions.

Even in cases where things didn’t work out, I’m happy to have made meaningful connections with amazing people and companies who now understand the extent of my experience and skills. Some of them are even keeping in touch for future opportunities where I’m a better fit! Talk about awesome 🙌

Buried Treasure

I think the most important asset we have is time.

I reached a point in my job search where I was taking on serious water. My ratio from starting conversations to receiving offers was not good.

I would start conversations with companies that reached out to me, line up phone screens with hiring managers, move to the technical screen, and do that for a few companies per day. This was a poor strategy because I wasn’t fully invested in exploring every opportunity email that arrived in my inbox – I was expecting to spend about 25 hours interviewing each week where I was only excited about 25% of that time. It was draining, and I was to blame.

Sure, some say it’s great practice and I agree – but know when you’re reaching diminishing returns to starting new conversations. It took me a few weeks to realize I was spinning my wheels and decided to focus on strong network links and postings where I was undoubtedly a great fit.

In one case, I reached out to a company founder whom I had messaged six years ago about internships to signing an offer to work with them in under two weeks. I mapped up to the opening well, I liked the team, company and mission, and it all made sense. 🚀

The thought of digging through my emails to find something like this became apparent when I cut out the noise and urge to feel wanted. It feels good to get those intro emails and follow ups in your inbox, it’s exciting, it’s a dopamine hit. But you have to know when to stop once you’ve found your groove, you’re all you need to care about here, not how many companies are interested in talking with you. Trust your gut and look for buried treasure.

Work and interview with strong connections when times are tough, those connections will want the best for you. Work for places that see you as a person, not a resource.

Ride Your Wave

When considering where to work, I keep three things in mind.

Compensation, skill building, and networking.

If you’re joining a company and equity is on the table – be sure to ask everything about it. Equity can have nasty rules attached to it, especially when it comes to preferred shares and common shares, knowing how that impacts your compensation is important. Checkout this post by a16z that helped me form a stronger understanding about what to consider when it comes to options, equity, types of shares, and what kinds of questions to ask.

You’re also worth so much more than you know. So it’s worth negotiating for the compensation you deserve. Please spare me, and most importantly yourself, the notion that it’s good and nice to take the first offer you get; companies don’t think the same way as employees and companies want to hire people that know they’re awesome and will stand up for themselves.

I love this post about salary negotiation tactics for software engineers. It’s a long read but extremely valuable and well worth it. Obviously, you can’t negotiate much regarding salary with pre-seed startups given lack of cash, but as soon as you’re negotiating with companies that have raised multiple rounds of funding – you certainly can negotiate across multiple parts of your compensation.

All of this has to map back to you. If you’re going to join a company, and you’re certain you can improve it 10x over Y years – are you going to be improving 10x over Y years too – across compensation, skills, and network? Anything less isn’t an opportunity you should consider, especially if the company doesn’t want to negotiate.

Go where you can grow, perform, and be compensated well for the work you do; then all you have to do is trust the process, and good things will follow.