https://philcalcado.com/2021/12/20/job_hunt.html

Phil Calcado  
About

Five takeaways from looking for a new senior role in tech

Dec 20, 2021

* Management * Leadership * Recruiting *

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:

[spreadshee]

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 resume--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.

Phil Calcado

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