Jumping from a Stable Ship

Tips for job hunting when there’s nothing really wrong

I’m early in my career, in an industry that’s growing and in a role that is not going anywhere particularly soon — I appreciate that I’ve been fortunate to have fallen into tech sales, and absurdly lucky to actually enjoy it enough to keep making a career of it.

There was nothing wrong with my job really. A couple of challenges around growing pains and limited opportunities for career progression but that’s about it. I just wasn’t happy and it felt like it was time. I was still grateful to be working with a generally amazing company with an awesome product and genuinely supportive and talented colleagues, I was doing well and could count on my pay check. Receiving an email on a Sunday morning about a compensation plan change and suddenly I found a myself with a wine in hand, and for the first time in my grown-up-career life, looking for a new job. The search initially started as more of a cathartic exercise than a genuine job hunt that afternoon.

When I got a call back (or a lot) on Monday I quickly accepted that it was time to leap into the great unknown and found myself completely overwhelmed. Underprepared for the process and experience of finding my next role, I wrote down what I would do differently, God forbid, I’m ever in this position again in the near future.

1. This sucks, avoid having to do it again

I hate being bored or disengaged at work. I love working as sick as that may sound and when it’s frustrating it tends to spill into other areas of my life. Once the initial anger and desperation of wanting an out wore off, I realised the day to day of my current role wasn’t actually unbearable. Plus it paid the bills.

With some wise counsel from a mentor, I took a breath and realised I had the gift of time. Time to stop and think, time to go through longer interview processes, time to find my next step rather than any job.

I learnt I hate job hunting. I didn’t want a quick fix. If I wasn’t prepared to invest time personalising a cover letter for a role, it wasn’t the role for me.

Monday — I’m going to resign before the end of the month

Friday — if I’m more excited to leave a job than to start the new one there’s an issue. Let’s make it three months.

2. What do you want?

That mentor was a goldmine. She’s an absolute goddess and uniquely talented in asking questions to help with a self realisation.

You’re in a good spot I’m not going to let you add a tier 2 name, or a six month stint, to your resume from here. So..

SaaS or hardware? Vendor or reseller? SMB or Enterprise? What sort or patch? Commercial, education or public sector? Channel or direct? Established business or start up? Is money my priority? Travel? Experience? Brand name?

I was looking for a tech sales role, but yes I should have thought this through before hitting apply. Yes I felt stupid when asked, I had no answers. When I thought about it, I did have preferences. A lot of them surprisingly.

In retrospect, the amount of stress I could have saved by not managing every possible job interview on top of my 9–5 pains me. The time I wasted (both mine and a few recruiters) applying for jobs that didn’t fit my brief could have been much better spent.

3. Recruiters will be a blessing and a curse (if you let them)

My advice, don’t get involved with a recruiter until you can elevator pitch what you’re looking for and are prepared to say no to opportunities not of interest. If you are working with more than one recruiter, which you probably are, attending job interviews can quickly become a full time role unless you are selective.

A good recruiter will be a phenomenal support. Tips, coaching and warm introductions — they’re there to help. Be clear with what you’re looking for and they will be an incredible help.

One certain recruiter was painfully insistent, almost aggressively so. Despite explaining what I was looking for and my concerns about a product and customer base were that write not for me, over several emails and phone calls he continued to insist that I meet with the team.

There are fantastic recruiters and bad recruiters. Be prepared, be comfortable saying no, and you won’t waste time with the the latter.

4. Aim high, but be ready for a reality check.

An old colleague of mine used to say if you’re rejected from some of the roles applying for, great. It’s the fastest way to effectively gauge where your experience is at on the open market.

I’m not suggesting expressing interest in a marketing director role because you’ve previously sold marketing software. Spoiler alert — the role I would end up in after this experience I wouldn’t have applied for if it wasn’t for some liquid courage.

Apply for roles you’re not quite ready for and you might surprise yourself. Recruiters will cull after reviewing your CV, you’ve got to be in it to win it. Just remember you need to shit-kick before you land your dream job.

5. Do your homework

Polish your resume and cover letters. Get feedback.

Give your references a heads up, not only to expect a call but fill them in on which roles. Get feedback.

Research the company — the culture, the product, how they’re going in market. Speak to people about whether they think it will be a good fit for you.

If you’re serious about the hunt, put in the effort to make sure you’re a good fit for the role as much as the role will be a good fit. Then get another opinion. Feedback is a gift and your network is an invaluable resource in ensuring you do yourself justice.

At the end of it, I’m now on gardening leave. Which is lucky, because I’m frantically preparing for a bigger leap of faith professionally and personally than I ever thought I would be. I’m excited. It’s worth it. It’s worth doing properly.

Short term pain, long term gain and all that.

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