Job Hunt 2022 Retrospective

I recently took an offer as a Director of Engineering with BlocPower where I will be working on creating the Building Data Collective.

I am writing up my job search because several people have asked me about my experience of landing a job in climate tech. I am also writing it up because its the sort of thing that I just don’t see written about much. I don’t know who is interested in hearing about it, but somebody should be out there being open about their experiences with this stuff and I just happen to be somebody.

My Parameters

I want to state up front where I am coming from as it is not where 99% of job seekers are. This is important to understand for context and hopefully is not so out there as to make the rest completely unrelateable.

  • I was employed while looking around. While I feel like the role I was in was a poor fit, I was not miserable and enjoyed my coworkers and the work itself. While I am well aware that I was underpaid by industry standards, I am financially comfortable so there wasn’t a lot of pressure to “make a move”.
  • I do not tend to optimize for money. I had taken pay cuts for my last two jobs and I wanted to go up for this one, but my bar is still well below what someone with my experience who optimizes for salary would be getting.
  • I am extremely senior and technical. My last 3 roles have been Engineering Director at Surge Consulting, CTO at Operation Spark, and Principal Engineer at findhelp (I was also for a time in an Engineering Manager and Engineering Director here as well).
  • I also do not optimize for people I want to work with. While I believe that this (and money) are perfectly legitimate things to optimize for - and I have in my notes a long list of people I would love to work with - it was not my focus in this case. I was aiming largely for the industry, and a role that would use more of my abilities beyond the technical ones to make the biggest impact.
  • I am extremely confident in my interviewing skills. I have personally interviewed close to 300 senior developers and led teams that interviewed thousands. I have designed interviewing processes at my last 3 companies. I have presented at conferences on interviewing developers. By now there is no impostor syndrome left; I have a very good idea of where I rank alongside others.
  • I believe my resume is very strong. Resumes are a black art and different hiring managers have their own opinions but I’ve been a hiring manager in a wide range of situations and my resume is exactly what I would want to see.
  • Once I make it past initial screening I very rarely get eliminated by interviewing. I far from always get the offer, but its almost always after the very last interview in the process. It has been many years since I walked out of an interview feeling like I’ve anything but nailed it.


  • Total time from starting casually looking to getting hired was eight months.
  • In my notes I applied to 39 companies. Because I was not always fastidious with tracking things (boo on me!), I estimate the actual number is closer to 60. I rarely one-click apply. I always put some significant effort toward each application.
  • Beyond an introductory call, I got into the interviewing process with maybe 15
  • I dropped out of the process purposefully of two.
  • Three companies dropped me midway through the process due to the role disappearing or changing.
  • One company dropped me from consideration for a manager role after the first interview and redirected me to a high level IC role (unfortunately none of those were available at the time).
  • I went through 8 full interviewing processes of 4+ rounds (not counting intro calls) and got 1 offer which happened to match up to my skills and ambitions super well.
  • I never received what I would consider actionable feedback. Much of the feedback I received was along the lines of “it came down to you and one other person and we just felt like they were a better fit”.
  • I mostly applied to companies of 10-200 people. While I did talk to a Big Tech org (Meta), I didn’t enter their interviewing pipeline. I was willing to consider it, but my recruiter contact disappeared and this was not something I was actively pursuing so I let it go.
  • I got some good leads from active and engaged recruiters initially after setting my LinkedIn profile to “casually looking”. This lasted for a month or two. Afterwards, the contacts from recruiters I received were all extremely impersonal and not even close to what my profile clearly stated I was interested in.
  • Even among all-remote companies, location can still be an issue as hiring from a new state implies a whole new tax regime. Two very promising processes had to drop me early due to not having a foothold in Louisiana (I also have friends this has happened to).
  • While getting an internal advocate was the best strategy for landing an interview, it was far from a sure thing. Quite a few times I had passionate advocates (even high-level internal-to-the-company advocates) making connections only to see the ball get dropped for a variety of reasons.

I am reinforced in my belief that for very experienced people (and perhaps most others), the big impediment to getting hired at most companies is not resume, skill, or even ability to demonstrate skill, so much as the fact that the vast majority of companies simply do not have their hiring sh*t together. Positions are far less solid, needs are far less thought through, and hiring processes are simply not welled tuned. I fully believe that somewhere around half of all online job applications go into a queue that no one monitors in a system rarely logged into. I suspect this is often due to turnover or confusion on the part of hiring managers. I realize that sounds like a rationalization but I have been on the other side of the table as well. I have personally taken over a hiring process that had only a trickle of candidates, only to discover a whole tab in Lever bursting with submissions that no one had known to check.

I believe that this is doubly so the case in climate tech. While I think it an incorrect stereotype that most climate tech companies are bootstrapped 5-people shops without a serious product, I do think that as an industry overall they are far less mature on the process side. As one of many indicators, consider that in a good interview process the final round should be largely a double check, not a significant filter. Every moment that you spend talking to a candidate who you do not end up hiring is a waste of both your and the candidate’s time. If a company is having 4, 5, 6 rounds of interview then with each successive round they should be less likely to eliminate someone, a final-round elimination might be necessary but should be considered a failure of process worthy of retrospective and adjustment. This seems to be rarely the way people in climate tech are thinking about things.

Similarly, I consider interviews where a large cross-section of a department/company has to meet you to be a signal of insecurity. When unsure of the effectiveness of the hiring process it is not uncommon for managers to seek consensus from the team. While understandable, and usually an attempt to de-bias, the distribution of responsibility has the opposite effect by granting everyone veto power - a situation where bias is all but guaranteed!

I think far too many people in hiring are unsure of themselves and feel a predisposition to zero-risk. However, hiring ultimately is a risk, there is only so much mitigation possible.

Strategy and Job search evolution

After applying and as I start hearing back from applications, I naturally spend more time engaging with those companies and less applying to new opportunities. Hence my job searches tend to cluster into natural rounds.

Round 1

My initial job search started in early March 2022 as a result of a few particularly despiriting months at work combined with some difficult departures, and no acknowledgment from leadership that they agreed with nor even saw the same problems I was calling out repeatedly. As this was largely about frustration, my efforts were minimal and unserious - consisting largely of asking around in a few Slacks, casually browsing TechJobsForGood listings, and toggling the “show recruiters I’m available” switch on LinkedIn. I also wrote down and made clear my criteria which, at the time, was jobs that could check multiple of the following check boxes.

  • In the climate tech industry (using a loose definition)
  • Building productivity tooling - especially developer productivity tooling
  • Companies doing something non-trivial with AI/ML so I could work adjacent to it and get my toes wet
  • Companies committed to functional programming - especially any LISP

For roles I was looking specifically for staff+/principal developer or engineering manager/director positions where I could help set technical and product direction.

This resulted in a round of interviewing that lasted until approximately mid-June. Deep into the process, one company rethought their needs. Another I dropped out of due to misalignment of expectations. Two had my initial contact leave the company and the process get abandoned. Four other companies (2 climate tech, 2 productivity tech) moved me all the way through multiple rounds only to get no offer.

Reading between the lines a bit where they did not tell me explicitly (sometimes they did), the reasons were roughly

  • A misalignment when talking to the (final interview) COO between his and my expectations of how much I would work on product direction versus just heads-down coding
  • Another hire was a better fit (possibly due to me having no professional experience with Clojure)
  • A discomfort with my contracting background due to specific bad previous experiences within a smaller startup. To their credit, they took the time to actually call me up and talk to me about their hesitations and apologized for not previously having this as a filtering criteria.
  • A last-minute change in direction for the role, orienting it toward more junior managers and a better fitting candidate for the new direction

This was of course very despiriting as I spent significant time getting to know all these companies and envisioning myself working there. As I geared up for another round I decided a shift in strategy might be appropriate.

Strategy shift

In addition to having spent many years mentoring tech job seekers, I have been a bootcamp CTO where I worked with grads seeking their first job directly. I have built up a long repository of advice for how one should conduct and strategize about a job search. As in my mind I hadn’t been “seriously looking”, I had so far been implementing very little of it.

In a conversation catching my father up on the previous round, he called me out that whatever I was doing wasn’t working. “It’s fine, I don’t think of this as a failure at all” I told him through clenched teeth. That evening I acknowledged quietly to myself that he’s probably right. If I was going to be serious about what I was doing, I should practice what I preach.

So, suggestion #1 (well, not technically #1 on everyone’s list, more the big one I wanted to try out) was to build up a series of internal advocates at companies by focusing on an industry. I would do this by joining an industry-focused community and participating within it. In my case this meant taking a first step of narrowing down my own criteria even further. Fortunately I already had a pretty good idea of what I wanted to do. Earlier that year, and wanting to be more intentional about my charitable giving, I had taken the Effective Altruism introductory course. And, while I find myself disagreeing with much of the ways in which this community construes their arguments (a whole different topic, but Doing Good Better is full of spurious correlation, lazy analysis, and some strangely colonialist thinking), I also agree wholeheartedly with many of their general points. In this particular case, the argument goes that to do the most good, you should either optimize your career for money and donate most of it, or find an important industry in a role that you can do significantly better than others. Well, I really believe that climate change is a society-level threat, I really do think that climate tech will have to be a large part of our way out of the mess, and - not sure if anyone’s noticed here - but I do have a bit of an ego. So toss everything else out the window, I should be focusing explicitly and ruthlessly on climate tech and specifically on roles where I can use my specific blend of contracting, mentoring, business-strategy, community-building, and technical experience to make the biggest impact possible.

The general idea of this join-a-community strategy is that, by becoming an active participant, you build up your visibility. Others in the community - the most active of whom are typically movers and shakers themselves - tend to take notice. You request informational interviews, chat, build up relationships and have them become advocates for you within their extended network. That - as I tell people often - is networking; it’s not just eating crappy pizza in the back of a dev meetup.

Again, in my case I already had a community in mind. In my late-night-kitchen-cleaning sessions I had listened to, and enjoyed, a couple episodes of the MyClimateJourney podcast. In these podcasts they heavily promote their exclusive (and paid) slack community. Well, $10 per month for a slack is a lot sure, but its nothing if the end result is being able to execute better on a strategic roadmap. Just a few leads from there could easily pay off. I signed up and started introducing myself.

I’ll also note that I purposefully did not pick an area of specialization within climate tech. The entire field is somewhat new but highly technical with tremendous amounts of low-hanging fruit many unproven approaches. I figured that - given the little time for research I have available - so long as I avoided the obvious scammers, one guess at what area might be highly impactful would be as good as another. We’re talking about making an impact here, I can get excited about the details later.

Rounds 2 and (spoiler alert) 3

So I joined, having made a point of being active (difficult as I am in, like…15 other slacks and an IRC, and work) and started connecting. I would monitor the Slack’s job listings for postings that seemed interesting (many in the summer, starting to thin out significantly into the fall), answer questions when I could, and just try to engage in general chat for the sake of community presence. (Pro tip for technical communities - make a technical statement that is mildly controversial and watch the engagement roll in.)

I connected with people almost immediately with a couple reaching out directly to me, and myself making the effort to reach out to others for an introductory conversation whenever I saw something that seemed interesting. In the meantime I monitored ClimateBase and - as I was now more focused on getting an insider edge - connecting to people on Slack (MCJ or Rands Leadership Slack) and LinkedIn.

So did all this work?

Well somewhat. I certainly got a great round of initial interest and quickly entered several interview processes.

  • One petered out after a very enthusiastic recruiter interview. When following up, the recruiter had left the company and their replacement was unwilling to push me along without the department pulling me in. My contact within the company in the meantime kept telling me the position was open and he had no idea what counted as a “pull”…Ah, big-org problems.
  • Another moved me along for about half the process with final rounds scheduled when I got word they filled the role
  • A third passed me through their full process with great feedback and multiple rounds of direct engagement from their CTO only to ultimately get a rejection and no feedback whatsoever. Very disappointing for how open they had been earlier in the process.
  • A fourth also passed me through their full process and multiple panel interviews with the hiring manager himself as my advocate. He did me the favor of calling me with the rejection. Apparently I had high marks throughout but the members themselves of the team I’d be managing felt like we “didn’t gel”. Yeah, not a lot I can do with that one.

And this put me into the third round. Now by this time things had gotten markedly better at work and - while my Effective Altruism-acquired logic still applied - I was no longer approaching things with the same vigor. Still, even without heavy enthusiasm, by now the process itself was humming along.

  • One company I had started conversations with months ago that were slow-walked ended up taking me through the entire process only again to end in a “we found someone else” situation. (Lest I sound bitter, I think this is absolutely legitimate for a startup. For example many need a high-level person who can handle their ops. I, in the meantime, lead with “I really dislike doing ops”. Picking someone else over me here totally makes sense, I simply wish they could realize that sooner.)
  • A second company, I ultimately talked to the CTO who basically explained the bulk of their needs were just some UI performance optimization - not a great fit for what I’m looking for.
  • A third I was in process and heading into final rounds when I hit pause as…
  • I got an offer. This was a company I had started conversations with at the very end of Round 2. It seemed scrappy and disorganized and like it will be a real pain in the ass at least for a while. But also potential for building up some fascinating connections, having some fun, making a real outsized impact, and a task that - on paper at least - I can’t think of anyone else who is more qualified for than me.

And hence where I am now.

Retrospective and Takeaways

To start with, it doesn’t matter how hot the market is. If you have something specific in mind and no pre-existing connections, its going to take longer than you think.

I am also more convinced than ever that if you are targeting high-level non-IC positions at smaller companies your best bet is one of two options:

  • Start as an IC - maybe even at the risk of taking a career-step backwards - establish yourself as a power-player, and work to transition
  • Build up a network of internal advocates, ideally multiple.

Without the above it is simply too common that you get lost among the shuffle. A company might know they need a Head of Engineering, but they likely have very little idea of how to filter resumes for one. Unless you’re rolling in with a resume that happens to hit their preconceived notions of the role directly on the head it’s going to be hard to even open a conversation.

I also think that I spent more time chasing companies than I needed to. A few places that seemed extremely exciting to me in the digital-twin modeling space, I could never get a hold of anyone either via applying, follow-ups, cold reach-out on LinkedIn, or even occasional referrals. If a place is giving you complete radio silence, there might just not be anyone on the other end to pick up the phone.

I do wish I had identified and focused on what I wanted earlier. I also think I could have taken time to investigate other climate tech communities, participated even more, and reached out to others even more than I did. At another time (read: pre-kids) I might have even done significant research into the area on my own time, doing literature reviews and building up strong opinions on what seemed the most exciting. That said, the process of interviewing was very educational in itself. “What questions do you have for us” usually translated into me learning something about the state of the industry.

Having switched jobs 3 times in 6 years (2 layoffs and this), I hope I’ve found a great long-term home and to be done with it for a while, but if I find myself in the position in the future I might try to apply to enough places so that I can run some hypothesis testing. Does a custom cover letter actually reliably get me the best results? What is the best response rate I can get just by cold-applying with a really strong resume? Do connections made via an individual that vouches for me (even if we met relatively recently) work better than ones I made myself by a cold approach? All interesting stuff that I have opinions on and would love to gather some data on.

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