A few months ago, I left SeatGeek without much of a plan of what to do next. My green card was finally issued in 2021, which means that I didn’t have to scramble to find a new job in forty days. For the first time in the fifteen years I have lived abroad, I could finally take my time without fear of getting on the bad side of immigration authorities. As someone who has been on a work visa for the last fifteen years of my life, this was wild.
At first, I tried the whole funemployment thing, basically when you are not actively looking for a job. I posted a tweet about leaving but did nothing much around job seeking aside from answering a few messages here and there.
I have recently signed with a new place. Before I talk about the new challenges ahead, I want to share five things I learned during this process. While bits and pieces are applicable for any tech role, this article explicitly focuses on senior leadership roles, which were what I was looking for. I define these roles as executive roles for small companies (I would say fewer than 50 engineers) or Vice President of Engineering and above for mid-sized (say 50-500 engineers), or Director and above for larger organizations (500+).
1. It will likely take longer than you expect
More senior roles are usually not evergreen. In recruiting, we use the term evergreen role when talking about positions that are always open, featured on a company’s career page indefinitely. Every company has budget restrictions on how many people they can add to payroll, but the reality of a hot job market means that most of them can always add another back-end/front-end/mobile engineer to their team.
And even if they are not evergreen per se, you will also find a lot of first-level engineering manager roles open at any given time. This happens because companies will need a new manager for every few Individual Contributors (ICs) they hire. Given that companies are constantly hiring ICs, they also need to add new managers regularly.
However, this relationship doesn’t hold as you go higher in the seniority ladder. Senior roles usually open up when someone needs replacement, if a reorg creates some leadership vacuum, when the company has reached a new growth stage, or when it starts a new strategic initiative and needs a leader.
As you might imagine, companies only go through these events every so often in their lifetime. It might be that you are fortunate, and by the exact time you are looking for something, a great role comes up, but it is unlikely.
Worse, people might be looking for a leader way ahead of time, which can be very frustrating. For example, I talked to a mid-sized company CEO about a role under them. In our first call, they explained that their product is being disrupted by competition and needs to change drastically or become obsolete. They thought of me as the perfect fit to lead this new initiative, and I was very excited about it. After a few exploratory chats over Zoom, I wanted to talk about the interview process. Then I realized that there was no actual role—at least not yet. The executive laid out their plan to first fire this one person, then get this other person to fill in for them, then get this other person to change teams… and many more steps that would have created the perfect role for me. When I asked how long they thought it would take, their estimate was one month. Putting aside the Game of Thrones vibe, it’s been three months since, and they haven’t even fired the first person from the list.
In hindsight, a better strategy for me would be to have started having these conversations at least three months before I left my previous job. I already had a feeling my journey there was not going to be that much longer, and when this feeling first kicked in I should have started looking around, even if casually.
2. Independent headhunters and recruiters are a valuable resource
To add another variable to your job search equation, not only do companies only open senior roles when there is a specific need, but they also are usually shy to make them public, especially on job boards. In my experience, small or medium companies only put these openings up if they have been looking for a while or some compliance framework requires that.
Companies do that for various reasons. Sometimes, the imminent departure of a leader might not be public information yet—sometimes even to the person leaving! The company might not want the outside world to know of a new strategic initiative or pivot, even for net-new roles. One of the folks I talked to is moving their business from B2B to B2C, and they don’t want to telegraph the move by having a “Vice President of Engineering, Retail” role open.
So how do you know about open roles in the market? The first step is to reach out to people in your network and let them know that you are looking. This will usually yield a few interesting leads, but the most efficient way is to use headhunters.
When I started in this industry, headhunter meant something specific: a recruiter for senior and/or hard-to-find positions. These days we use the term to refer to any independent recruiter that gets paid handsomely when they fill a position. Even when I am not looking for a new job, I try to at least skim over every recruiter email I get. As you undoubtedly have experienced first-hand, the vast majority of unsolicited messages from recruiters is irrelevant, and badly automated spam. Still, now and then, a recruiter seems to have invested five seconds trying to research you and really thinks the position would be a good fit. These you want to build a relationship with, even if you are not looking for a job yet. I always reply, thanking them for the message and saying that I am unavailable, but I will let them know if anything changes. I also apply a Gmail label to these conversations to quickly find these good eggs when the time comes.
You probably already have some of those reach out to you before. Go on your email and search for “your impressive background,” “opportunity,” and “well-funded startup.” I am sure you have a few of those in your inbox from over the years. Your Linkedin inbox might also be filled with these messages that you have likely completely ignored in the past.
Good headhunters can be an invaluable resource in your job hunt. Not only do they have access to the still-confidential openings we talked about, but also they work in networks. Recruiters share the jobs they are working on with their network and split the commission if someone helps them fill the position. This means that you will get a lot of the same roles from different recruiters, but also that even if that one headhunter you are talking to doesn’t have openings for you, they will likely know of other openings coming through their network.
When it’s time for a new job, I send a note to folks in that Gmail label saying that I am open to new opportunities. Usually, they will try to book an introductory call. Recruiters love phone calls and don’t like doing things over email or text. This means that it is very easy to get overwhelmed by the number of recruiters trying to call you, and we will explore time management a little further down the text.
Introductory calls are usually 30 minutes over the phone or video. Do not let them book you for longer; it is more than enough time. They usually will spend a few minutes telling you about who they are and the recruiting agency they work for, if any. Besides the fluff about how they are different from others and only take on the best openings (they all say that…), pay attention to the type of clients they work with. Are those the right size, industry, etc., you want to explore?
They then ask you for your story. I recommend that you think about this before talking to any recruiter. Create a text document with a description of your professional history, previous jobs, and more significant accomplishments—at this stage, what is much more important than how. Do not forget to add something about why you left each job, especially if you were there for fewer than four years. Then edit repeatedly until it only includes information relevant to the role you want and has a straightforward, linear narrative.
There are a few reasons why I do this. First, I like to force myself to tell my history concisely. It helps ensure that I don’t forget important details or find a rabbit hole that will eat up minutes on an introduction to no benefit.
Then there is the fact that you are playing a game of telephone between recruiters and people from the hiring company. Do not be surprised or frustrated if every new person you talk to about a role asks you to introduce yourself from scratch, even if the recruiter had arguably briefed them. A “canonical” written version that you use repeatedly can help keep your story consistent across various interviews and interviewers.
After the first introduction call, the recruiter will likely send to your email some positions they think would be a good fit for you. Usually, this is a mixed bag. Not only does the recruiter not yet know you that well, but they also will likely add both roles that you are not qualified for to show off and some that are a terrible fit, but they have been trying to fill for ages and might as well spam everyone.
And this is something to keep in mind working with recruiters: they work for the hiring company, not for you.
One recruiter I was working with guided me through the process with a small startup. Over four weeks, I had talked to most people at that company and was waiting for one last call with some engineering leader who, or so I was told, had been on vacation during that time. The invitation for the call never comes, and all I have from the company is radio silence for a week. I reached out to the recruiter, and they told me that everything was ok. They were just going over a big launch that week and a little busy. Following Monday, I get this message:
Hey Phil, just a quick heads up that we had a candidate accelerated through a process with The Company and has accepted an offer. The match for them was very strong and they decided to act quickly, so there was nothing they needed to compare against in their minds. I do appreciate your time on this one and hope we can work together again soon. Did you get a chance to check out That other company? www.that-other-company.com
After some Linkedin stalking, the person hired had already worked with some of the executive team before. I completely understand the move but was very pissed with a wasted week.
This kind of thing happens, and you need to understand that this is a transactional relationship. Still, it is in the recruiter’s best interest to have great relationships with senior candidates, so they will avoid doing anything that will piss you off.
3. Use your project management skills to keep your sanity
Finding a job in a hot market is one of the most challenging projects you will ever manage. You don’t have control over most aspects of the process, and even the influence you have needs to be managed carefully to avoid coming across as a demanding asshole. But the most complicated part is how the scarcity of you looking for one single job amongst many different options creates a textbook Game Theory problem.
These days, I try to be very structured around this effort, which—you guessed it—means I have a spreadsheet for it.
Below is a screenshot of the spreadsheet I’ve used most recently:
I don’t want to make the file available because it matters how one uses it, not the template.
I add every opening sent by a headhunter to the spreadsheet, even those I don’t find interesting.
The most critical data to keep tabs on are:
- How excited am I about this role? How much Priority do I want to give it?
- How much do I feel the hiring company (not the headhunter) is excited about me?
- When was the last update on this process, from either them or I
- Who is supposed to take the next step? Is the ball on my court or theirs?
Time allowing, surely I will act on any items blocked on me, but things aren’t that simple.
You need to make sure you have the headspace to prepare and research your tier 1 opportunities. You also need to pay attention to the various other things going on in your life, especially if you still have a full-time job. And, most important, you need to avoid burning out because this is a very stressful process.
Every time I interact with the headhunter or hiring organization, I update the spreadsheet. I use conditional formatting to make the “last update” cell green/yellow/red based on how long the last contact was.
I also use sorting and conditional formatting on the spreadsheet to help me quickly identify the status of the roles that both parties are excited about, which tend to be my high Priority.
The first thing I do every morning is to check the high-priority roles and make sure that I don’t drop the ball in getting back to them and do a check-in if they are taking too long to get back to me.
After whatever actions for the high-priority ones, I go over the other ones in priority order and reassess them. Should they go higher or lower in Priority? Did any new information come that changed how I feel about them?
As a self-imposed SLA, I try never to take longer than 24 hours to reply to tier 1 opportunities, not longer than three days for tier 2, and a week for the rest. This spreadsheet’s value comes from being an easy, visual, process to manage my SLAs.
Speaking of time management, something that has helped me immensely is to use Calendly. Calendly and similar tools allow you to send a link that will enable people to book meetings in your calendar, drastically reducing the back-and-forth of finding a good time for everyone. You will see that many headhunters use it, but you should have your own account and make sure that it is in sync with your personal and professional calendars.
4. Be strategic around your interviews and chats
I am very intentional with how I design recruiting processes for folks I hire, and I try to follow these same general principles to the process when I am on the other side of the table.
My guiding philosophy in both scenarios is that it is impossible to know if a candidate is a good fit for a job. So, with this in mind, instead of trying to validate if it would be a good match, I start from the assumption that it would be and then try to falsify the hypothesis as early as possible.
When looking for a job, I first list what I am looking for and what I don’t want in my next position. Usually, this has the kind of role and titles, the organization’s size, profitable vs. pre-revenue vs. growth-oriented, how many rounds of funding or close to an exit they might be, etc. The current job market for tech is so hot that even if you cannot choose where you will work, you can definitely choose where you will not.
I usually do not share this list with headhunters or hiring companies. I don’t want them to take the list literally and end up missing out on an opportunity that could be actually pretty good, even if not perfect. Also, if they really want me to apply (maybe because the headhunter really needs to show their clients that they are sourcing good candidates!), they will find ways to present whatever role they are working on as a perfect match.
Following this process, when you decide to move ahead with a position someone sent over, you assume this would be a good fit. Your task now is to use every interaction to falsify this assumption, searching for evidence that the role does not fulfill what you have listed as your requirements. Take some time beforehand to think of questions that can help you in this discovery. Keep in mind that it is rarely a good idea to ask directly about subjective topics. People are in sell mode when talking to you. While it is OK to ask how many engineers a company has, or if they intend on getting new funding soon, questions like “what do you think of your engineering culture?” aren’t going to surface helpful information.
I strongly recommend that you keep your questions laser-focused on the list of requirements you wrote, but I do tend to have a few more general questions I ask every person I talk to. My favorite is “What is your current bottleneck? What is the one thing that prevents you from moving as fast as you think you should move”? Then, depending on the answer, I have a follow-up: “If this constraint would magically disappear tomorrow, what do you think would become the next one?” This line of questioning is from the Theory of Constraints and gives you a good idea of how folks work and think. For example, it is common for the answer to be “We don’t have enough engineers”. This is almost always an indicator that the leadership team isn’t as experienced as they might present themselves. Nobody ever wants to hire engineers; there is something they want, and they believe that hiring engineers is the only way to get there—and that is seldom the case.
Something else to falsify as early as possible is where the position lies in the organization. Titles can be very misleading, a company might have a director managing three people while other of similar size have a manager of thirty, but make sure that your new title won’t sound like a demotion or stagnation in your resumé—this might bite you on the back the next time you are looking for a job. In my experience, the best way to find good evidence if the position they have is close to what you want is to find out whom you would report to and who would report to you. Understandably, this might be a little fuzzy in small companies, but make sure that their seniority doesn’t feel misaligned with your expectations. Also, please make sure you spend a considerable amount of time with your boss-to-be during the process.
5. Do not waste your time, but part as friends
This should be a guiding principle when applying for any job, but it is even more important for senior leadership roles. They require massive time investment from busy people such as you and the hiring organization leaders, so being honest and upfront can save everyone enormous time, money, and energy.
Following the process from the previous section, once I realize that a position does not meet the requirements I had listed, I tend to email the headhunter and the hiring organization the next day. I still give it until the following day so that I have some extra time to think about it and avoid a potential knee-jerk reaction to a single lousy interview or something like that, but if I make my mind, I will email them within 24 hours, tops.
There is always the question of how much feedback you want to give the various people you might have talked to during this process. You absolutely should volunteer the primary reason driving your decision (e.g. “I am currently interested in more senior roles/smaller organizations/moving out of the finance industry”), but keep details and secondary reasons to yourself. And, unless the process was an absolute clusterfuck and you want the hiring company to know, I would only send feedback on the process to the recruiter, not people from the hiring company. Remember: you want to keep a good relationship with the headhunter, and getting between them and their client introduces massive risk for no benefit to you.
And also, keep in mind that just because the company doesn’t have a role for you now doesn’t mean that it won’t ever have it in the future. The organization will grow and expand its needs and possibilities. There will be reorgs and departures that will create all sorts of opportunities. So be kind with your words and make yourself available for a regular catch-up and networking.
In fact, in the recent past, I have developed advisor relationships with organizations that were not a good fit. These relationships deserve their own article, but it is something to consider bringing up as you part ways.