monday i gave my main talk at all things open in raleigh: using ai to land your next role. packed room, great questions, and one dm after that just said “mind bending insights.”

if you weren’t there, here’s the whole thing in 5 bullets.

> truly believe personal texting based ai assistant are the new unlock for your job search and your career

> best way to attack this strategy is a 1–2 punch. claude is the brain. your assistant is the hands. the brain holds your story. the hands do the watching, researching and drafting.

> build one project that knows you in claude/chat. call it “job search.” drop in your resume pdf, your linkedin pdf and brain dump your entire career in it then tell it: “honest counselor + recruiter. no flattering.”

> then set up your personal ai assistant i like all of them try all of them but if you just want me to tell you which one use tab

> give it access to as much as you feel comfortable with i.e. email, calendar, linkedin data, x data, etc.

> set up one prompt at a time go slow but everything is possible. first one i’d set up is a watcher to scan linkedin or x for any jobs that are a fit for you

the prompt everyone took a picture of

“i’ve been job searching for [x] weeks. applications sent: [#]. replies: [#]. interviews: [#]. offers: [#]. what does this tell you about where it’s breaking, and what’s the one thing i should change this week?”

no replies = your resume or your list
replies but no interviews = your story
interviews but no offers = practice out loud

brain dump your entire career via voice mode on claude/chat and set up a project and hook your personal ai assistant into that.

thanks again for being here.

Originally published at https://taylordesseyn.beehiiv.com on October 22, 2026.

get these weekly > taylordesseyn.beehiiv.com

if you are a visual learner like me…here is the link to my youtube where i go over this!

https://youtu.be/wRaZH8vA7L4

if you just want the tldr….

• if you do ‘any’ sort of spamming during the job search…it needs to be focused on recruiters. definitely connect with as many a day as linkedin lets you
• make sure you create a ‘note’ every time you message them to make sure your connection goes straight to the top of their inbox
• you’re going to have to kiss a lot of frogs i.e. talk to a bunch of recruiters that wont be able to help you BUT always ask for one piece of advice on your resume, linkedin, or how you are carrying yourself as a job seeker
• how to actually find us: type in ‘tech recruiter’ in the search bar, go to all filters, fill in location in your area
• find a recruiter that has a bare minimum of 2 years experience and at least working at the same company for 2 years….why? bc the bad ones have to bounce around to get any sort of raise bc we are so heavily commissioned
• check their activity section and see if they have been active recently (better chance they respond to you the more active they are)
• i would really try to find recruiters with more than 2k followers (this is just a personable preference)
• if you talk to a recruiter in your area and they don’t have something for you — ask for referrals to other recruiters
• If you see a job posting, message the recruiters you know and ask if they know someone or can refer you

thanks for reading! if you want to connect on other platforms check out my solo.to link below!

-Taylor

solo.to/tdesseyn

if you want to listen to the episode here is the link:

https://open.spotify.com/episode/43ZTC8Hknbl55vTejmma8b?si=JE2vppGKRsOEl8tOB7OXJw

if you just want the tdlr…then here you go….

polywork

• badges — clickable under your name and profile picture. Instead of doing a search on LinkedIn you can search on Polywork based on interests
• polywork (in my mind) isn’t a ‘posting content’ site. it’s a networking focused site (which is why i like it)
• check out the opportunity section of polywork, there are job postings, freelance gigs, and people wanting to get guests on podcasts
• honestly if you wanted to kick start your podcasting career and get on other podcasts i would just use polywork to do that
• polywork is a place where you need to connect with someone in the dm’s then move it to email, i still dont think a ton of folks ‘live’ on polywork even though they just release a mobile app
• one of my favorite parts of polywork is the dm feature. it shows you what that person is interested in collabing on

linkedIn

• check out the interest portion of someones profile…this is a great way to start up a convo in the dm’s with something that the person is actually interested in
• activity section — you can see all the posts that person has done recently…you probably aren’t going to get a response with someone who hasn’t posted anything in 90 days so be aware
• make sure you look at mutual connections, if you have someone in common bring up their names in the dm!

https://www.youtube.com/watch?v=jbeLqobG7DE

The TLDR:

Pro Tip: Talk to us as much as you can!

Use us to perfect your interview style, resume, and LinkedIn

Recruiters are a living breathing pulse on the market in REAL TIME! Ask us all the things and if it seems a recruiter doesn’t know what’s going on…move on!

2 main types of recruiters:

• Agency — This is me! These recruiters work with different clients and different companies, we literally work with a TON of companies at one time
• Corporate — These are inhouse recruiters so one recruiter works with one company. The internal in-house recruiter has better knowledge of the company and can potentially be more intentional with you. (Usually agency recruiters are the ones that give the industry at bad rep because we only get paid if we place you)

Follow-up — communication is a two-way street — you HAVE to follow up with us…always. And shoot us an email or text NOT a phone call. We are always in meetings.

How do you find recruiters?

• Go to LinkedIn and type in technical recruiter, filter by your city and start DMing recruiters
• If you haven’t messed around with the search filters in LinkedIn, I would HIGHLY advise doing so

How do you know what recruiters to message? Use the two and two rule to do the initial filtering….

• How long have they been at that company? Should be at least two years. Why? It takes two years to get their feet wet and gain traction.
• How long have they been recruiting? Should be at least two years. For the most part things start clicking a little more around the two year mark in the industry.

Soft Skill Tips to Level Up Your Game

• Find a way to know the people you work with — living in a virtual world its IMPERATIVE to get to know your colleagues
• Be comfortable talking as a real person over a video call — be your whole self at work and if your work doesn’t accept that…move on
• Be open about who you are and your interests — the only way you can build relationships is sharing your passions with others
• Have a conversation as if you were already an employee as you are interviewing
• You are a person not a machine so stop acting like it in the interview process
• Create a visual deliverable when talking through your accomplishments — which will help your interviewing changes
• Prewrite notes, a cover letter if you will, ahead of your interview
• Keep the conversation going — THIS IS HUGE. never said ‘I don’t know’ and stop talking
• Bring a notebook so you can write questions down to avoid interruptions

Here are the cliff notes from our talk! If you want to listen to the entire episode here you go:

https://open.spotify.com/episode/0mpwaJI3tTZET6ohsGkNZi?si=269e1e9a0a0f4971

Building Good Engineering Culture

Starts with Company Values

• Teams first approach
• People want to grow so provide that opportunity
• Compassionate candor is vital
• Be honest with your employees
• Diversity is more than a word
• Have fun is not emphasized enough
• Little things matter, especially leading remotely

Define Success, what does it look like

• Team engagement
• Participation in discussions
• Planning and estimation
• Be Intentional
• Document
• Time management
• Create process
• Progress tracking
• Issue management
• Personal growth

Reviews are a MUST

• Reviews need to be scheduled regularly, like weekly
• Align to values
• Do you understand your responsibilities
• Are you still fulfilled in your role
• Is this a job that you can succeed at
• Where do you want to go in your career
• How do we get you there

Content Creation is needed

• Company leaders should be pushing out content
• You’ve done your job/career for a LONG time…..share your knowledge
• People that are aligned with your values will align with your content
• It will assist in building out your team

If you want to watch the actual episode on where I break all this down on my live stream — https://youtu.be/KRSvEOjrVYE

Banner cover photo, take advantage of this

• This is a way to endear yourself to your followers
• Bring something about you to your banner photo

Your profile picture is the very first impression people get of you

• Look happy…if you are moody and a hiring manager comes upon your profile they won’t want to hire a moody person

The bio description is very important

• Talk about who you are, what you do and what you tweet about

Location

• Enter this… a lot of times recruiters still want to know where you are located even if its a remote job

Single most important area of a Twitter profile is the Pinned Tweet

• Pinning a Tweet means it’s the first one someone will see when they visit your profile
• Make sure you absolutely capitlize on this pinned tweet (check out my video I have on mine) no you don’t need a video but this is PRIME real estate

Use lists in Twitter

• Lists help you to connect with the RIGHT people
• Helps you start connecting with folks in a community that are applicable to you

Posting

• Just start
• Be short but be frequent
• Be consistent
• Like and comment and Interact
• Be engaged everyday
• Hashtags — periodic use is sufficient

What makes a Senior Engineer

What is your skillset and what are you as an Engineer

• Push yourselves
• Outline your skills
• How do you lead
• Your problem-solving skills might be at a higher level than your competition
• Keep a journal of what you have accomplished and translate it into more tangible language. “I helped our team by off boarding this process that was costing us x amount of hours to someone else that has increased our efficiency. This leads to a value-add conversation.
• Take your most important journaling notes and add them to your cover letter
• What do you do to contribute and how do you stand out from your peers

Be Open and Honest about your Competencies

• Your might not know ALL the languages but you have the ability to pick up quickly
• Understand what you want to be and understand how to level up

How do you define Mid, Jr and Sr Level Engineers

• Jr is expected to deliver your piece and to be a good teammate impact yourself in your area
• Mid-Level should be impacting your team and delivering your work but you are also ensuring that your team is delivering and setting standards
• Sr Level Engineer should be impacting your group. Setting direction and impacting all teams even though it might not be in your job description

How do you manage title change when transitioning to another job

• Ask yourself, why are you where you are in your job
• Most times your title is tied to your years of experience
• The climate now is about how you have contributed across the company and the teams you interact with

Hire for tomorrow, not for today

• Invest in your best people and don’t let them walk out the door
• Companies should have a robust retention plan

I posted about this last week and had so many responses that I wanted to share them with you! If you have friends that want to get into tech then send them this list!

• Tech Recruiter
• Business Analyst
• Data Analyst
• Project Manager
• Product Owner
• Scrum Master
• Manual Test Engineer
• IAM Engineer
• Develop Relations & Tech Community Management roles
• Solution Architect
• Customer Success Manager
• Implementation Consultant
• HR
• DEI Program Manager
• People Operations

Here are some other comments that were made by individuals on my post:

• “My career started with a technical support role and it laid such a great foundation for all of the roles that followed. Support shouldn’t be overlooked for those looking to get into the field!
• “I went from working in hospital labs/blood banks for two years, then transitioned into healthcare IT (but not as a developer). Been there for the last 20 years!”
• “CISSP opens a ton of doors for security roles, devops is a big thing, and there’s the whole network / infrastructure / hardware/ support side of things as well.”

I had the chance to interview Jonny Scharer who is a Career Coach from a non-technical background on my podcast Guidance Counselor 2.0. I want to share some tips on how to stand out in the job search. Yes, I do realize a lot of this is what everyone preaches, but hopefully something resonates with you!

Link to the interview: https://www.youtube.com/watch?v=92o8Hy30mPM&t=9s

We are now in an environment, because of work from home, where anyone can get a job from anywhere. You now have global competition. You have to do more work to stand out but you will have more opportunities coming your way if you stand out

• Break job opportunities down into tiers, so you can evaluate what makes sense to really go after vs just easy apply….

1. I really love this company, I vibe with them

2. This company is ok, could help me get to my end goal of (whatever it is)

3. This company is an easy apply

• Don’t just target recruiters, connect with people who work where you want to work AND LET THEM KNOW THAT
• Find commonality with people you are reaching out to, get personal (the more personal the better because you really stand out when you do)
• Be an advocate for somebody else — by connecting others with your network you start to be known as more than just a job seeker
• If you are interested in applying for in person work, you are already beating out 99% of the competition
• PUT YOURSELF OUT THERE…engage with others on social media, ask questions when you post a piece of content for engagement, just put yourself out there!
• Treat conversations like a bank…. invest before you withdraw (the more you give the greater the ask you can have)