Job Search Guide

Job searching can be scary and lonely, but it doesn’t have to be that way! Here are some tips I’ve learned along the way.

Targeting

Decide on exactly what kind of role you are looking for. That enables you to target the kind of companies and jobs that you can compete in and spend adequate time preparing for. This is fishing with a spear, not a net.

For example, I would be looking for a Product Marketing Director role at a Conversational AI Scale-up. Have three or four attributes that you can identify. Pick an industry, company (size, series, employee number), role level, etc. The more specific, the better. If you come with that experience, even better.

Networking

It’s not just what you know, it’s who you know. After you have found the right roles, network into the company for informational interviews (see questions below). If they offer a referral, even better. You should also find the hiring manager on LinkedIn and send them a direct message about your interest and qualifications. For example, if I was looking for a Director of Product Marketing role, I would look up the VP of Product Marketing.

Informational Interview questions:

  1. What brought you there in the first place?

  2. Describe the company culture in three words.

  3. Are there any red flags to be aware of?

  4. What is your pulse on the health of the company?

  5. What is unique about working at this company?

  6. What is the biggest challenge the company is facing?

  7. What is the company's competitive advantage?

  8. What do you know about this open role?

  9. Help me understand the team structure.

  10. Tell me about the manager.

Job Search Councils

Job searching doesn’t have to be a lonely pursuit. Find another person in your network that is also looking for a job and have a weekly routine with them to talk about ideas or progress. If you have a group, create a Slack and discuss topics like:

  • Job Postings

  • Connections

  • Resources

  • Events

  • Resume Reviews

  • Interview Tips

  • Good News

I also recommend checkout out the book Never Search Alone by Phyl Terry. You can sign up for free job search councils if you don’t have one already.

Resume

See my dedicated Resume Guide here.

Applications

Don’t apply to a role unless you have reached out to the hiring manager and at least one other person at the company. It will likely be a waste of time as it goes into a black hole otherwise. Screening systems and recruiters are trained to filter applicants out.

A rule of thumb is you should have a 20% Application to Interview rate. If that isn’t happening, go back and reassess you targeting.

Interviews

See my Job Interview Guide here.

Structuring Your Time

If you are in a job, carve out five hours a week divided into two streams:

  1. Finding new opportunities

  2. Preparing for interview

If you are out of the job, treat looking for a job like a full-time job. I recommend the following:

  • Monday: Three hours of Finding and three hours of Preparing

  • Tuesday: Three hours of Finding and three hours of Preparing

  • Wednesday: Three hours of Finding and three hours of Preparing

  • Thursday: Three hours of Finding and three hours of Preparing

  • Friday: Self-care