Last December, I started a new role at a small, family-owned e-comm company. Two months later, my manager (the founder / CEO) and I realized that the role wasn’t a fit and we parted ways. For the first time since college, 18 years ago, I didn’t know what my job was. This is the story of my search for my new role.

Acknowledging privilege

Up front, I want to recognize my privilege. I had financial security and insurance throughout the process. I have supportive family and friends. I’m a college-educated white male US citizen with experience in Tech as a software dev and manager.

At the start of my search in late February, tech hiring going gangbusters.

It’s valid if readers find my search shockingly easy. I feel blessed. I’m just sharing what I did, why, and how it worked out in the hopes that it helps job seekers set expectations.

Search criteria

I wrote these criteria early, and it was very helpful for me to focus my efforts and clarify what really mattered to me. A superficial, ego-stroking part of me certainly wants a prestigious title. But as I go back to my search criteria, it’s really not important. I’d much rather be in an organization where I feel supported and can learn a lot regardless of title. I’m pleased that the role I accepted nails each of the criteria and preferences below.

I shared these eagerly with hiring managers if they asked (usually verbally and more concisely).

I view my job search as an optimization problem to maximize learning and get exposed to new perspectives and types of expertise. I’m particularly interested in Product/Program management, Strategic Finance, Operations, and non-Ruby tech stacks.

I set a fairly high bar for:

1. Products and business opportunity that will have clear positive impact on society.
2. A self-aware, supportive org culture. IMHO, every company says they’re supportive. Self-awareness is correlated and easier to assess as an interviewer. E.g. do interviewers speak frankly to the challenges and trade-offs of the culture and leadership decisions?
3. A company that appreciates in-house software engineering as a strategic asset (i.e. most “tech companies”)
4. Compensation policies are within ~20% of market rate as determined by Glassdoor, recent offers, and conversations w/ peers. An important aspect of comp is to incentivize working through challenging situations rather than leaving for greener pastures. While comp is far from the most important factor, it establishes a baseline of appreciation.

Beyond those requirements, I’m flexible:

• individual contributor vs management: open to both
• local vs remote: open to both
• company size: I have a soft preference for larger Eng teams (100+). I’ve spent most of my career on teams of 5-50 engineers. I think a larger team would better serve my #1 goal of being exposed to new perspectives. But I know I enjoy and can thrive on small teams as well.

One thing I’m just realizing in writing this post is that I don’t have a specific next-level career achievement I’m shooting for. My goal is basically ‘learn and enjoy the journey’ rather than say, ‘retire early’ or ‘acquire enough experience to start my own company’.

Flow chart

This Sankey diagram shows the outcomes of the 21 companies I considered. See the raw data here.

Here’s how to interpret the chart. Starting on the left, there were three sources of companies:

1. Referral (9 companies) - I had a personal connection to someone at the company. These ranged from casual acquaintances to close former colleagues.
2. Organic (5 companies) - I applied via the company job board.
3. Recruiter (7 companies) - An in-house recruiter contacted me, and I responded with interest.

I’m not counting recruiters that I ignored. I chose not to work with external recruiting agencies b/c I think our incentives would be misaligned.

And on the right, there are four outcomes:

1. No response (6): After some interaction, I didn’t hear back from the company (aka ghosted).
2. Rejected (6) : the company decided to not move forward with me for any current roles
3. Declined (8): I decided to not move forward with the company for any current roles
4. Accepted (1): my new job!

In the middle was a mostly conventional hiring funnel.

1. Recruiter screen (5/10 pass rate): brief conversation w/ an in-house recruiter about the role(s), my experience, and what I’m looking for. In 5 cases, we skipped this and went straight to…
2. Hiring Manager screen (3/10 pass rate): usually a general discussion about our approaches with a handful of specific anecdotes. This is key to build rapport w/ my potential manager.
3. Main panel (3/3 pass rate): a slate of 3-4 deep-dive interviews.
4. Extra panel (2/3 pass rate): in one case, the extra panel was an anticipated chat with the CEO and virtual lunch with several team members I’d manage. In the other 2 cases, it was unconventional! I’d done well in the main panel, that the team wanted to consider me for different, more senior roles.

The extra panels were quite valuable because 1️⃣ it’s a strong positive signal that the company likes you if they’re willing to have cross-functional discussions about whether you’re a fit for an unconventional role, and 2️⃣ it gave me more opportunities to meet the team and see how they make decisions. Of the 3 companies where I’d done extra panels, I had video chats with 10-13 employees per company.

Timelines

I didn’t have a good intuition for how long I could reasonably wait to hear back about a role I applied for.

In my case, the median time from when I replied to a recruiter or applied to a job to having my first screening was 3 days.

Only 2 screenings took more than 6 days, and those were special cases with active email threads coordinating around travel and PTO.

My conclusion is that if you haven’t heard back within 6 days, you probably won’t.

The later stages were similar: within a week, usually less, modulo any scheduling accommodations.

Learnings and surprises

The extra panels showed me that as roles get more senior, adapting the interview process is key. The interview loops evolve from cookie-cutters to snowflakes. On the hiring side, I’ve put in a lot of effort to make predictable, standardized interview loops for early career through middle-management roles. I expect most SVP or C-level roles would have uniquely personalized interview loops. Currently, I’m somewhere in the middle.

I accepted a role to which I applied organically rather than via a referral. That was surprising b/c referrals are usually easier to navigate since the referrer can advocate for me and/or share helpful context about the company’s needs and quirks. Most of my recent jobs have come via my personal network.

The in-house recruiters play a critical role in broadcasting company culture. Are they organized? Engaging? Well-informed? If not, it’s a 🚩 red flag — one unfortunate recruiter couldn’t speak to the interview process past the HM screen, and later sent me the wrong on-site panel, apparently confusing me with another candidate. Was the whole company like that disorganized? OTOH, great recruiters would share thorough interview guides, and have detailed explanations for why they were hiring particular roles, skills, and traits. I come away from this process with a deeper appreciation for the strategic value of recruiting teams to keep strong candidates in the pipeline.

Shadow interviewers are a good sign. Shadowers are employees in training for how to conduct interviews. They mostly observe and answer candidate questions at the end. I liked seeing shadowers because 1️⃣ it’s evidence that the company values rigorous hiring practices and employee development, and 2️⃣ I got an additional perspective to my questions about the team/company/role.

So that was my job search! I hope that this helps clarify and set expectations for what can be a confusing, time consuming, and emotional process.