Job bait and switch or opportunity to hone my AI skills?

I made it to the final round for a full-time tech job. Then they asked how to use AI to scale myself. By Amy Cuevas Schroeder

Don’t get angry at AI, get even. Prepare to scale yourself with AI.

My story will become more common as companies try to incorporate AI into workflows. Are you prepared?

By

Amy Cuevas Schroeder

“We let the last person go because they needed to be told what to do.”

That was one of the first things the friendly English recruiter living in Columbus, Ohio, told me during our initial call. A few days earlier, the company’s Head of Marketing invited me to apply for a content marketing role, and I was psyched about the opportunity. I appreciated the recruiter’s transparency for sure, but wondered if I should view the last person’s layoff as a red flag or an opportunity to show how I don’t need to be told what to do.

“We usually ask applicants to do a content exercise as the initial step,” he said, “but we wanted to make sure we spoke with you first.” I took that as a good sign. Recruiter then said the company was preparing to raise a Series C round of funding and the team was investing long hours to get there. “No problem. Series C is an exciting time,” I said. Having worked for tech startups like Etsy and Writer AI, I thrive on the hustle and excitement of building businesses to the next level. My startup vibes percolated.

Why was I looking for a new full-time job?

After wrapping a content strategy contract for a major tech company’s first AI product, I was attracted to the remote startup’s full-time job description. I’m not in the mood to pick a fight, so I’ll spare the actual JD and the company’s real name. Let’s call them Bait and Switch.

At the onset, the more I learned about the fast-growing startup, the more intrigued I became. I mean, check out the perks advertised in the job description:

🫂 Comprehensive health, vision, and dental insurance for you and your dependents

🏦 401k match. 100% matching for up to 3% and a 50% match for the next 2%

💸 Equity options

🏠 100% remote work environment

🏖️ Flexible paid time off, with a recommended minimum of 3 weeks

🎨 $10,000 home office makeover with personal access to an interior designer

🛜 $150 per month toward cell phone and wifi

💻 The best tools to do your work, including a Mac laptop and top-of-the-line hardware.

🏥 24/7 access to a Health Advocate & free annual membership to One Medical

👶 12 weeks of paid family leave

Step 1: Pass the test

I eagerly dedicated a couple of focused hours on Bait and Switch’s content strategy test and submitted my work the same day. I’ve been crafting content strategies since before “content strategy” was a thing, and my process is pretty ironclad. Once I articulated my recommendations for thought leadership, SEO, and distribution, I used Jasper to help produce a snappier version of a previously published wordy product launch story.

The recruiter said I did well on the test, so the next day I spoke with the hiring manager — a product marketing wonder woman with five children. Hiring Manager Zoomed from a hotel because her daughter was preparing for an out-of-town dance competition that weekend. That was a plus in my book — I love that she was able to work and help her family live life to the fullest.

After the Zoom with Hiring Manager, Recruiter called to prep me for the next step: a Zoom with the Head of Product, a well-respected leader in tech. Apparently other candidates failed to drive the conversation with Head of Product, so the recruiter was kind enough to tip me off via text to prepare. I read up on Head of Product on Linkedin and was impressed by his background as a leader, investor, and entrepreneur. Turns out we shared more than a dozen contacts in common.

I went into the Head of Product interview armed with questions and started by saying that I’d spoken with Hiring Manager about the vision for the company’s marketing. When I asked if he could tell me more about the product vision and incorporation of AI, he didn’t exactly answer my question, but the conversation flowed easily. Revisiting the topic of the company’s marketing, he said the company’s content “sucks” but he was prolific about the future of AI and excited to create commentary about it.

We hit it off. This guy is f#cking smart, hands-on, articulate, and forward-thinking. In my opinion, we were a perfect pairing — he a thought leader and me a thought shaper. As a contentpreneur and former journalist, I ask questions and validate points in such a way that shapes executives’ thoughts into tangible content like this article I produced for TechCrunch.

The 30-minute time slot with Head of Product progressed into more than an hour. By the end of the call, we’d recorded the bud of a story, which I converted into what I call an “outline-plus” (goals, headline options, first draft of a proposed story structure, and follow-up questions). Things went so well apparently that Hiring Manager asked me to meet again with her and Head of Product asap.

Early the next day, I came prepared with an agenda and structured questions, and by the end of the session we generated enough material to turn around a solid start of an article and a follow-up white paper. During our call, we agreed that I’d submit the next iteration by early next week. An hour later, Hiring Manager emailed to ask if I could turn it in by the end of the day. My adrenalin kicked in and within a couple of hours, I produced a 1,300-word draft with a dozen headline options, recommendations for an additional white paper, a bit of competitive research, and a proposed distribution strategy.

That was a Friday afternoon. Then I waited. Saturday, Sunday, and Presidents Day. On Tuesday Hiring Manager called to say that they thought I did well but that they were unsure of how I would use AI to scale future content. She asked if I’d consider working as a contractor for a short period of time; after the contractorship, the relationship might convert into a full-time role — but no guarantee. I said I’d consider contracting and, per her request, emailed 30 minutes later with my proposed hourly rate and suggested start date of the following Monday.

Then Head of Product texted me: “Do you have two secs to chat?” This is when the conversation became really interesting.

The new AI model that changed the job description into a question mark

Head of Product called and said he enjoyed reading my draft and content plan and was able to generate additional content based on what I’d started. He then explained that over the weekend a new AI model was released that caused him to doubt whether they needed a full-time human to produce their content. “We’d like to work with you to see how you’d scale yourself with AI — but your rate is too high. I was thinking about [this lower rate] for, say, four to six weeks and maybe we could back-track equity if things work out. … We’re talking with engineers about this approach, too.”

I said I understood where he’s coming from and understood that Bait And Switch needs to be careful about who they bring aboard pre-Series C. I said I, too, thought over the weekend about how to scale myself with AI. I concurred that companies must be thoughtful in how they approach content at scale because they might end up producing more generic content than their audience can actually consume. “But,” I said, “becoming a contractor with no guarantee for a full-time role is a big risk for me. I’m interviewing for other full-time roles right now.” Head of Product said I should forward him any competitive offers.

After 15 minutes of back-and-forth banter and expressing my interest in being “an experiment,” I said I’d think about it. “Text me back,” he said. Then I thought about it:

Is it strange that we’re negotiating what started as a full-time job and is now an uncertain contract whose terms are not in writing?

If I successfully scale myself into a Content Super Machine and document my processes using various AI tools, will they let me go after the four weeks and adopt my process without me?

I decided to email him, Hiring Manager, and Recruiter so that we had something in writing. I offered to do the contract for less than my original proposal but a little more than Head of Product’s counter offer, and that we’d negotiate after the four-week contract if we decided to continue to work together.

They replied to say my terms were not a good fit, and I decided the whole thing was a weird situation. :) I was annoyed that I’d spent so much time showing them my content strategy process and providing them with content they could like publish. But I’m glad it didn’t work out. While I embrace using AI to scale myself, I don’t think Bait And Switch handled the situation professionally. I’m sure their product will continue to kick ass, but I envision a rocky evolution for the company’s team dynamics.

Unsurprisingly, the job description is no longer listed and I wished them well. The bright side of Bait And Switch? They inspired me to master my own “super stack” as a content strategist. And, like many weird experiences, I learned a few things that will apply for fellow tech workers and eventually other sectors.

2 things I learned about the “future” of work with AI

1. Employers are in the early stages of understanding how to scale their employees with AI

Even while I worked at the major tech company, the CEO himself said that when they rolled out their first AI product in October 2024, he wasn’t sure how to answer customers’ questions about product use cases.

Many companies know they should use AI but they’re not exactly sure how to roll it out across their organizations. While they understand that AI could replace their workers, they’re not exactly sure how to make that happen. Far too many supervisors have yet to learn how to use AI themselves, let alone teach their employees how to use AI.

Take it from my former boss May Habib, CEO of Writer: