Latest / The Resume Room with Fexingo: Resume Writing, Cover Letters, and Application Strategy / Why Your Resume Looks Expensive When It Should Look Cheap
Transcript
- Lucas: There is a very specific reason why a senior product manager from Apple gets rejected by a Series B startup for a director role, even though they are technically perfect on paper. It has nothing to do with skills, and everything to do with what the hiring manager perceives as the price tag attached to that person's presence. Luna: Right, so you're talking about the premium associated with brand name? The idea that if you came from Goldman Sachs or Big Tech, you're automatically going to demand a salary they can't afford? Lucas: Exactly. And it goes deeper than just salary. It's about retention risk. If you put 'Apple Product Management' in bold at the top of your resume for a smaller company, you aren't just signaling competence; you are signaling that you are used to certain resources, certain pace, and certainly certain compensation bands that might be two hundred thousand dollars higher than their budget. You have made yourself look expensive before they even read your bullet points. Luna: So the solution isn't to hide your experience, but to actively de-emphasize the prestige markers that trigger those assumptions? Lucas: Precisely. We call this 'resume cheapening.' It is not about lying. It is about strategic positioning. Think about a recent example we saw in the tech sector where a former lead engineer from a major cloud provider applied for a staff engineering role at a fintech firm. Their resume was pristine, listing millions in infrastructure savings and leading teams of fifty people. But they got zero interviews. Why? Because the hiring team assumed they would want a VP title, or at least a six-figure base plus massive equity, which didn't match the internal band for a Staff Engineer. Luna: That is such a frustrating gap between actual capability and perceived fit. How do you actually fix the document to change that narrative? Lucas: You start by changing the visual hierarchy. On a standard resume, your most recent and most impressive title usually sits at the very top, in the largest font. For someone trying to move down-market or sideways into a smaller organization, that needs to shift. You don't list the company name in all caps or use a heavy sans-serif font that screams corporate power. You use a softer serif font, slightly smaller point size, and you place the focus squarely on the scope of the problem you solved, not the scale of the organization you managed. Luna: So you're essentially asking the reader to infer the prestige rather than shouting it? That feels counterintuitive when you're proud of that track record. Lucas: It is counterintuitive, but necessary. Let's look at the bullet points themselves. A typical resume from a big firm says 'Led cross-functional team of forty engineers to deploy AI model across global infrastructure.' That sounds amazing, but it also sounds like you only know how to operate in a massive ecosystem. A cheaper, more attractive version for a mid-sized company says 'Built automated deployment pipeline reducing latency by thirty percent using existing open source tools.' Do you see the difference? Luna: Yes. One implies dependency on enterprise budgets and headcount, while the other implies resourcefulness and immediate impact with leaner resources. That speaks directly to what a smaller company values. Lucas: It does. And it lowers the perceived risk. When I review applications for my own network, I am looking for someone who will stay for three years, not six months. If your resume screams 'I'm used to free coffee, unlimited PTO, and an executive assistant,' I worry you will leave as soon as something better comes along. By stripping away those signals, you are telling me you are ready to roll up your sleeves and build things with limited resources. Luna: But what about the keywords? If you tone down the language, won't you fail the automated tracking systems that scan for specific enterprise terminology? Lucas: That is a valid concern, but keyword stuffing is mostly dead now. Modern applicant tracking systems are smarter than they were five years ago. They look for semantic relevance, not just exact matches. However, you can still include the necessary jargon without the flair. Instead of saying 'Orchestrated synergistic enterprise-wide rollout,' you say 'Deployed software update to ten thousand users.' It is boring, yes, but it is also clear, concise, and doesn't trigger any red flags about your adaptability. Luna: I love that distinction. Clarity over cleverness. It forces you to prove you can communicate simply, which is actually a highly valued skill in leadership roles. Lucas: Exactly. Simplicity is a proxy for efficiency. Now, let's talk about the summary section, because that is often where people make the biggest mistake. High achievers tend to write summaries that sound like press releases. 'Visionary leader with twenty years of experience driving innovation in the financial services sector.' That is noise. For a candidate trying to appear accessible and grounded, the summary should be functional. Luna: So what does a functional summary look like for someone coming from a prestigious background? Lucas: It looks like a job description written in first person. 'Experienced project manager focused on reducing operational costs and improving team velocity. Proven track record of delivering complex initiatives on time and under budget.' See? No buzzwords. No claims of being a 'guru' or 'rockstar.' Just plain facts about what you do and how well you do it. It removes the ego from the equation, which makes you seem safer to hire. Luna: It definitely shifts the tone from 'look at me' to 'here is how I can help you.' Does this apply equally to cover letters, or is that where you can afford to be a bit more expressive? Lucas: The cover letter is actually the most important place to address the elephant in the room. If you are moving from a large corporation to a smaller one, you must explicitly state why. Not in a defensive way, but in a proactive way. You might say, 'After spending five years optimizing processes at a global scale, I am eager to apply those frameworks to a more agile environment where I can see the direct impact of my work on the bottom line.' Luna: That is brilliant because it turns the potential negative—being too big for the role—into a positive desire for autonomy and tangible results. It frames the move as intentional, not accidental. Lucas: It does. And it preempts the question about flight risk. Hiring managers hate guessing why someone is applying. If you tell them upfront that you are seeking a different kind of challenge, you remove that anxiety. You are giving them a narrative they can use to sell you to the rest of the team. You are doing their PR for them. Luna: I think many professionals struggle with this because they feel like they are selling themselves short. They worry that if they don't highlight every single achievement, they won't stand out. Lucas: Standing out is not the goal in the early stages. Being hireable is the goal. You can always show off your brilliance in the interview. The resume is just the ticket to get through the door. If the ticket looks like it belongs to a first-class passenger trying to sit in economy, they might just not let you on the plane. Keep it simple, keep it relevant, and keep it affordable. Luna: So the takeaway is really about empathy for the hiring manager. Understanding their constraints and designing your application to fit within those boundaries rather than challenging them. Lucas: Spot on. It is about lowering the friction. Every time you add a layer of complexity or prestige that doesn't directly serve the job requirements, you are adding friction. Remove the friction, and the decision becomes easy. Luna: Before we wrap up, I want to mention that if these strategies have helped you think through a career move or decision, the way this show stays ad-free is through listener support. You can buy me a coffee dot com slash fexingo — that's F. E. X. I. N. G. O. Lucas: Yeah, and that support allows us to keep digging into these nuanced topics that aren't covered in the mainstream career advice columns. It helps us bring you these detailed breakdowns every week. Luna: Thanks for keeping the content free and valuable. Now, back to the topic, do you think this approach works for executives moving laterally, or is it mostly for mid-level pivots? Lucas: It works for executives, but the stakes are higher. An executive resume is already a delicate balance of authority and approachability. When an executive tries to 'cheapen' their resume, they have to be careful not to lose the signal of their seniority entirely. It is a tightrope walk between appearing too junior and appearing too costly. Luna: So for a VP level, maybe the key is to emphasize mentorship and culture building rather than just hard metrics? To show they are investing in the team rather than just extracting value? Lucas: Exactly. At that level, the narrative shifts from 'I built this thing' to 'I built the team that builds these things.' It shows you are scalable and sustainable, which is exactly what a growing company wants in a leader. They want someone who multiplies their output, not someone who adds to their overhead. Luna: It really changes the entire framing of the conversation. Instead of negotiating a salary based on past prestige, you are negotiating based on future potential and cultural fit. Lucas: And that is a much healthier place to be for both parties. You are entering the relationship as a partner, not as a transaction. It sets the tone for a longer, more successful tenure. Luna: I think that is a powerful way to end the discussion. It reminds us that a resume is not just a history of what we did, but a proposal for what we can do together next. Lucas: Right. So the next time you update your resume, ask yourself: does this make me look like the best candidate for the job, or does it make me look like the most expensive option? Choose the former, and watch your response rate change.