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The Next Adventure
Yesterday, January 26, 2026, was my last official day as an Amazonian. I was impacted by layoffs in October 2025 after nearly eight years of successful delivery. The moment is bittersweet, as I’ve spent much of my time over this three-month transition period buried in job searches while trying to enjoy the holiday season in spite of the uncertainty. I’ve learned a lot over the last eight years, both what to do and what not to do, and I’ve worked with so many incredible individuals.
Immediately after the layoff occurred, I began looking for next steps. One of the more enjoyable aspects of my Amazon career was being a Document Bar Raiser. Giving back and helping so many people improve their writing was an amazing experience. I prepared a professional service, Hopeful Writing, to engage those who want to be better writers and offer professional help. I’m not sure if I’ll continue it or not if I were to get traction, but I wanted to be prepared in case I was not able to find a new role. Now that I’ve found one, I doubt I will engage much with this, except with interns or students.
That said, I’ve accepted an offer as Senior Engineering Manager at Atlassian, starting in mid-February. I’m super excited to work for Atlassian, and to continue to improve experiences for customers, developers, product owners, document authors, and anyone else involved in building something amazing for their customers. I wanted to find something I could focus on for the next several years, and I’ve been impressed with Atlassian for a while now and can’t wait to get started.
I’ll be posting more about my job search experience and reflections on this period of my life in the coming weeks.
What I Would Look For In A Cover Letter
Recently I wrote about how my approach to cover letters changed during my recent job search. As part of that, I was asked what I would look for in a cover letter.
What I Look For
You’ve put the effort into writing a cover letter. Let’s make sure it delivers on that effort.
- Why You Want The Position
Clearly, everyone seeking a position would like a job for some reason. In this troubled job market, people need to be less selective. That’s understandable. But if you can come up with a compelling narrative for why you are interested, that’s a plus. I have a deep background in business marketplace search engines. If I am applying for a position oriented on search, I open with that relevant experience and my interest in those types of systems.
- Why You Will Succeed In The Position
These first three points are all similar, but have different framing. Take this opportunity to articulate why you will be successful if we hire you. It could be your experience, it could be your excitement about what the position will work on, it could be your drive and ability to learn, but make a case that you are going to succeed.
- What Are Your Relevant Strengths
You have strengths. You have experience. Not all of it will be addressable in depth on your resume. Take this opportunity to include a sentence or two for strengths that are directly relevant and will be helped by expansion. This is not for checklist items such as how much experience you have. For example, when positions mention strong communication or strength in mentorship, I use this opportunity to surface my bar raising roles at Amazon for both document writing as well as engineering manager onboarding.
- How Do You Communicate
Most resumes don’t have the space or the context to provide a chance to showcase communication skills. A cover letter provides a chance for you to show how you communicate, to surface your personality. I would not exclusively use AI for this reason; a seasoned communicator will know when you use it and will know it’s not representative of you.
- You Know Who We Are And What We Do
Hopefully you are interested enough to know who we are and what we do. Take this opportunity to tell the hiring manager what about the company resonates with you, and show that you are willing to take some initiative as you target your job search.
- A High Level Sense Of Who You Are
Inject some of yourself into your cover letter, so that the hiring manager can get a read on who you are. Hopefully my cover letter reads the way I want to come across in interviews, as a calm, confident, competent candidate.
What I Don’t Look For
There are things that I will not look for, or hold against a candidate. I don’t believe in mythical checklists or hidden gates that candidates need to be aware of. I’m a big fan of transparency, and won’t reject a candidate just because they aren’t aware of my preferences, especially if those preferences aren’t publicized.
- Personalization
I have seen suggestions that candidates should deeply research the personnel responsible for the position, including the recruiter and hiring manager. I have seen suggestions that cover letters that aren’t addressed to a specific person should be rejected.
Many positions don’t have this information, and even if they did, that has no bearing on whether or not the candidate is qualified for the position and falls into the category of hidden checklist. I address my cover letter as “Dear Hiring Manager”, and that’s acceptable in my view.
- Deep Research
It’s great if you understand what the position requires, have a general awareness of what the company does, and a general awareness of what the company values are should the company articulate them publicly. I don’t expect more than that.
- Appropriate AI Usage
AIs are writing cover letters a lot nowadays, along with other artifacts involved in the hiring process. I can generally glean whether or not writing was done with AI. If I feel like the entire thing is AI generated, that might give me pause; but I encourage candidates to use AI to clean up their writing and narratives.
- Perfect Writing Mechanics
I’ve been a Doc Bar Raiser for Amazon. I know how to evaluate writing mechanics. I can spot typos and other grammatical errors. I’ve also been in meetings where wonderful ideas or highly deserving promotion documents were picked apart due to writing quality. If a document is poorly written, that can be a red flag. But small typos and grammar errors, I’m inclined to ignore.
- Complete Qualification Match
Much like a screening interview, a cover letter is an introduction. The resume is the appropriate place to evaluate qualification matches; a cover letter should summarize why the candidate feels a resume review or a screening interview is in the best interest of both parties.
On the Bay Review: so far ahead of our time.
Most who know me know I’m not always much for nostalgia, but lately I’ve been wondering just what would have happened if I had been able to technically solve a problem back in 2001 given what I know now, and what technologies are available now. As an author, a poet, and an advocate of independent publishing, I do sometimes wonder if the Bay Review, an online journal I started with a friend of mine back in 2000, was simply too far ahead of its time.
In early 2000 I was just starting to get into web development. I had achieved my dream of becoming a programmer with PropertyFirst.com, an online commercial real estate platform that would eventually become LoopNet and be my professional home for close to 17 years. I was also writing a lot and wanted to see what we could do to publish people like myself online. At the time, independent publishing didn’t exist outside of large companies who would charge thousands of dollars to create print books, and there was little to no online publication available to independent authors. The idea of publishing content online was in its infancy.
So a friend of mine and I put up a website called the Bay Review. It was intended to gather submissions from various people via email, and then we’d put them into HTML format and publish them on the site every month. It took off much more than we would have expected, and ultimately we had to shut it down after six months for a variety of reasons that seem easily solvable today, close to 17 years later.
First, the success. Within 5 months we were getting submissions at a rate of close to 20 a day. This was back when Google and Paid Search and SEM and SEO weren’t even a thing. This happened with Yahoo! Search and word of mouth and viral goodness. By April of 2001 we were getting more than 400 submissions a month and it became impossible to keep up. I was converting submissions to HTML by hand because the technology to automatically convert Word documents to HTML did not yet exist in a way that would survive its use. Basically, any attempt to automate Office 2000 died spectacularly on first execution. This was the biggest first failure, and when it was apparent keeping up with our success was going to be a full time job, we had no recourse other than to shut it down so we could stay at our real full time jobs.
And that was because of the 2nd problem; we had no clean way to monetize. A paid subscription might have been worthwhile but seemed unlikely, as this was the early days of starting to get everything for free, and although we had 400+ submissions, our reader traffic was not yet that high, and would not support enough memberships to make it worth our while. We had the same sorts of conversations about monetization strategies you see now in the marketplace, including the possibility of introducing micropayments, or charging readers pennies for pages read as they went through the website. Sadly, though, we had no time to build such a solution under the onslaught we found ourselves.
And the trolls! Or so we would call them now. My friend and I instituted a family friendly standard, meaning no adult content. I had to hand screen or read 400 submissions on top of the conversion, and when we accidentally let a f-bomb through, the message boards lit up with complaints about other works that had been rejected. Instead of an understanding of the difficulty we faced and the effort we put in, we were called out for failure.
It was an impossible situation to maintain, and we closed down.
With all that, I regret many times that we did not have the technology then to do what systems do now, whether its automatic document conversion or automated content screening. We might be sitting here today as one of the pioneers of online publishing.
Long live the Bay Review.
Be welcome and true.
Rob Hope 