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Advice for an Open-Ended Job Search
Are you job searching but open to many titles and organization types? Here's some advice I wrote up for a friend after noticing most job hunting resources were too industry specific.
I’ve compiled a few steps that I think are helpful to creating the front end funnel of a job hunting process. I found that as a young person open to a lot of options, I didn’t find many resources that were geared towards a job search across many titles and organization types.
The goal is that:
You talk to a lot of individuals in a 1:1 format since you are job hunting anyways. This is a compounding investment into both your long term network as well as your understanding of what different position titles, team setups, and types of employment look like on the day to day. This will make future job hunts easier, and will only help you more and more over time.
*If you’re talking to early stage startups, or companies that are just getting off the ground (less than 10 employees) - they can hold higher and more versatile potential for growth, but also hold higher risk potential. Even if the team is super legit, there are always many things that can go wrong as they grow rapidly (or fail to). The more you chat with companies like this the better you get a sense for pattern matching how good their vision is versus how good they are on the details of product roadmap, competitive risk, potential market, sales process - etc
You find ways you can help other people too. You have a lot to bring to the table even if it might be one-off help, favors, or introductions to random specialists you know. The goal is to understand yourself and externally position yourself as someone who brings value to the table too. You may be job hunting, but individuals and employers more broadly should also be selling the company and position to you.
You create more competition for yourself, and for the types of teams/ work you could do. Having 3-6 offers when you get to final stages is ideal. You can negotiate their salaries and other benefits off of each other, and make the best decision about which work culture you might like the most.
My bias is towards not applying to any positions cold / exclusively through an automated system. Contact with any employees at the organization you’re interested in / applying to will massively improve your chances. Thus the focus on 1:1 conversations and outreach!
(85% of open positions are filled through networking; 70% of positions are never even listed online)
Setting a process will ideally help you manage your time without feeling overwhelmed.
Set up a time span and expectations for job hunting. You should devote at least three hours a week and several hours a day to this process, in my opinion. Set up constraints for yourself so you can understand how your search is going.
Think through what you do and don’t know about what you want in a job. You want to form three categories: things I know I want in my job, things I don’t know I want in my job (but can figure out/ will have opinions on), and things you don’t know or don’t have opinions on (and are open to anything on).
For example: my process looked something like this. I know that I want a flexible learning environment that allows me to establish connections with thoughtful people I really admire and I know I want a really good direct manager that I chat with really often, I don’t know but can figure out what position titles this may encompass, across a number of industries, and I don’t know but don’t care to make a decision across a number of large cities that I’d be fine working in.
In short, consider: hard constraints (job location, hours per week, paid time off, salary bracket that’s feasible for you, healthcare), soft things you want the job to help you develop (understanding of what x job in x industry looks like, ability to move to other similar jobs, project management skills, qualifications with certain tools, or maybe just potential for 1:1 mentorship from a manager who you find deeply admirable/the best person to teach you about an industry), and ideas, problems, and work you find fun, engaging, meaningful, etc (maybe you really care about eco sustainability, or opera being perpetuated and integrated in fine arts curriculum, or furthering human rights causes*)
** Having general questions that you think are interesting helps you tell your friends who know you well about specific things you think are interesting. Occasionally super specific projects pop up and you’ll be the first to come to mind, or people will be better at thinking through what organizations they know that do this work!
Reach out to your friends who are thoughtful and work in the professional world. It can be anyone! Compose a small blurb about what you’re looking for - maybe something like, “Hey (friend) - I’m job hunting at the moment and looking consider new organizations / positions especially ones suggested by friends who know me well. I’m looking for positions that allow me x, but most importantly x - If anything comes to mind that I should look into, I’d love to hear about it. Also, if you have any friends who I should chat with as I build up as I explore, I’m happy to send you info if you feel up to making an introduction!”
*there’s a bunch of ways to adjust this ofc but this is the general gist. Context, criteria, open ask for suggestions of organizations and positions, and making sure it’s easy for them to help you.
Create a google doc page to track the tips and suggestions you’re given. The general goal here is to keep track of everything here at a high level, and take notes as you learn more about each opportunity, and make sure you’re following up with them in the necessary ways.
Set up calls, and create next steps to follow up on all the leads you’re given.
If someone gives you a really helpful answer, and you think they’d be open, ask them if they can jump on a quick call and if they have any other advice, or how they got their previous jobs, or to where they are in their career generally.
Once someone directs you to a place of employment, research what they do. Linkedin stalk their employees and see what their position titles are and what experience they had previously. Google the job titles and “daily responsibilities” to get an idea of what you’d do. Look up the organizations on glassdoor to see if employees have left negative reviews and to get an idea of the salary bracket. See if you have any mutual connections, or one away connections with people at those employers. (remember that a lot of people unexpectedly have sway in hiring at their organization, casual conversations are great but don’t forget that they could advocate for hiring for you if you seem like a great fit, so general rules of professional convos are good).
Some good questions to ask
“What did you not expect at all about the position you hold now?” “What’s the team structure like at your company, and who shapes it the most?” “Where does your money come from? (If not a simple to understand business, or a nonprofit)” “Why did you take this job?” “How long will you be at this company and what would you do after?:”
Set up calls with people at the organization in question. Send them calendar invites and follow up when you’re done with polite emails. The calls can just be to learn about the role they hold, how they got to where they are if their job sounds interesting, or to ask if they know if any of the teams are hiring internally. even if they have no job listings there’s a 50% or higher chance they have at least one position open.
Keep doing your own research to expand your ‘top of funnel’ (early leads) as well. Search positions and for organizations generally doing work similar to what you like. Look at competitors to organizations you find interesting, and apply there too (knowledge from other organizations doing similar work will also give you a leg up when chatting with the team)!
The goal is to then create a list of organizations you’re interviewing at, and run “processes” with them at the same time. You should talk to multiple people in the org, have an idea of what person or people would be your manager and meet them, and know what your month over month performance indicators of success would be. As I mentioned at the beginning, this also increases your success at finding a great job - the more you chat with managers and hear how people answer questions, the better you’ll know which team has the most to offer you.
How to easily multiply your chances at succeeding at an interview without being any smarter:
Strategically email adjacent people and gather information in advance
Research the organization and what they need, their teams internally, and try and present this to establish trust and your ability to pro-actively show them that you can take initiative (a little goes a long way, but I've heard of people entirely pitching projects to companies to solve problems that they guessed the company had based off of their research)
Some questions that are great to ask
“What has been most challenging about your current role at the company?” “what’s most critical to this company in the next year?” “What’s something most people are surprised to learn about company?” “Do you get a lot of professional mentorship here?” “How easy is it to move positions internally from different teams”
For early stage startup positions generally: here’s a list of other great questions to ask either explicitly or to sense out from people around the organization.
Imo, the biggest is “If this business didn’t succeed, why would that be?” Variations of - if the business died in a year, five years, etc. Startups have a lot of risk, and to be a part of an early team you need to understand the executive teams view of theses risks, and know that they’ll be reasonably honest with you about them.
Check your email every morning for an hour or so if you don’t already. Scheduling and following up quickly is an important indicator for a lot of employers.
💡 Here’s the Gmail extension: https://boomeranggmail.com/
Resume Formatting: I’m a big advocate for customizing your resume per each job you apply to. Because my bias is towards not applying to any positions cold / exclusively through an automated system, you should be able to customize the descriptions of each work experience you had, to match what your potential employer is looking for.
Some people also recommend keeping a document at any job where you take note of the deliverables you’ve met, projects you’ve produced, issues you’ve solved - etc. The idea is that you’ll be your best advocate - both for promotions, and for easy input into future resumes - especially if information around the work you’ve done might be harder to retrieve / remember in the future!
Salary Negotiation. If you read one thing, it should be this article. It’s geared towards software developers but generally applies to everyone. This will deepen and reshape your perspective on negotiating offers no matter what. It’s not only great practice to start on now rather than in a decade, but a good way to weed out any employer that reacts negatively. Good employers want someone on their team who has done their research, knows their value, and will bring the energy of hustling for their salary internal to the company by hustling in your future position!
Interviewing for Venture Capital. If you’re interviewing for venture capital (since this is the type of job I do, I figure there’s a slightly higher likelihood this is the case) - here’s some good advice about the process.
I think the point within about building “context” is also relevant for anyone who’s cross-industry job searching. For venture or otherwise, as I mention above, being conversant in industry basics and a few favorite topics will really go along way, especially if you’re trying to signal your ability to learn about a new category, rather than prove your experience.
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