Kate Crane, founder of Direction Over Perfection and a former DoorDash and OpenTable exec, joins Kelly to share the job search skills no one taught you but everyone needs. They cover how Kate teaches young people to fish, the art of asking for advice instead of help, why professional development should start sophomore year of college, and how you really should be using AI in your job search. These are skills for your first job search, your fifth, and every pivot in between.
You graduated. You updated your LinkedIn. You started applying. And then silence.
Here's the thing. The job search is a skill set. Most of us were never taught it.
Kate Crane is fixing that. She's the founder of Direction Over Perfection and a former VP at OpenTable who helped scale DoorDash's drive platform from nine million to five hundred million. Now she coaches college students and early career professionals on the skills they actually need. Her philosophy is simple. Teach people to fish. In this conversation, Kate breaks down why your resume should articulate the value you bring, not just the tasks you had.
Kate explains the difference between asking for advice and asking for help, and why one gets you so much further. She walks through how to build a personal marketing plan for your job search with four priorities ranked in order: title, company size and stage, industry, and specific companies. Have clarity on what you want. Then rank it.
One of Kate's biggest reframes: think in career vectors, not career paths. A path implies you know exactly where you're going. A vector is a direction. It gives you room to explore, pivot, and find where you actually thrive.
If you were rejected within minutes of applying, a human never saw your resume. That's not a reflection of your worth. It's a system problem, and there are ways around it, starting with networking your way into the role alongside your applications.
Kate shares her honest, nuanced take on AI in the job search. Instead of asking AI to rewrite your resume for every job description, grade your resume against the job posting and let it gap check what's missing. Then decide what's a real gap versus what just isn't written down yet. AI is a tool, not a ghostwriter. Proofread everything it gives you back. It's still your resume.
Kate also makes a case for starting your professional education sophomore year of college, not after graduation. Retail jobs, nannying, restaurant work. They all build translatable value: serving others, understanding client needs, inventory management. Don't wait until you have one work experience to find out whether you actually like it.
This episode is for the new grad staring at a blank screen. It's for the mid-career professional quietly dreading another job search. And it's for anyone who has ever thought the rules of the game should have been explained before the game started.
Start with direction. Build the skills. The rest follows.
Kelly Callahan-Poe: Nobody teaches you how to find a job, but today's guest has spent her career changing that. She calls it teaching you how to fish, and the lessons apply at every stage of your career. Welcome to the Marketing Moms Podcast. I'm Kelly Callahan-Poe. Today's episode is called Job Search Skills for Life with Kate Crane. Kate is the founder of Direction Over Perfection, a career mentorship practice for college students and early career professionals, drawing on a journey that took her from a 2008 layoff at a New York art gallery to scaling DoorDash's drive platform from nine million to five hundred million and a VP role at OpenTable. Welcome, Kate. Your company is called Direction Over Perfection, which I love. Talk to me about why you named your company that and what that phrase means to you.
Kate Crane: I really passionately believe that early in your career, you just need to get going. You need momentum, and making a good next step, finding something that's going to help you build your career path. It doesn't have to be perfect. You just need to start and get going.
Kelly: So no on perfection.
Kate: No on perfection. We just need direction and momentum.
Kelly: I love it. So for students or new grads, you talk about teaching young people how to fish rather than handing them a job. Can you tell me about your philosophy on that?
Kate: I think the way I coach people is there's a balance of coaching and consulting. Sometimes I'm wearing my coaching hat, helping them explore what they're good at, what they're interested in, and trying to find some career vectors at the intersection of those two things. I like the word vector instead of path. A path implies something linear. Looking backward, sure, it's a career path. But looking forward, it's really a larger vector, a swath of opportunities. The consulting hat is teaching you how to fish. I want to help you build a set of skills that gets you this next job, but also the next four jobs. How to build a resume, which in my view is articulating the value you can bring to a company rather than a set of responsibilities you had. How to network in a way that doesn't feel icky, that feels natural. Asking for advice rather than asking for help.
Once we've gotten through the consulting bit, the final element is landing the job. We talk through what an interview looks like, what behavioral questions are likely to come up for your vector or industry. There are so many tools now for really powerful interview prep, so now you have the content. Let's work on the confidence. Feeling confident in how you're going to show up for that interview and how you're going to show up on your first day. When I started as a management consultant, I went through a very tactical three week course on expectations for how to be a good consultant. I've kind of deconstructed that. What does it mean to be good at your job on day one? That's different from what's expected of you in month four. We talk about how to dress, and I know that sounds silly and tactical, but you want to pattern match your peers. Some people know that innately, and others are really nervous about it, so let's demystify it. From an actual work point of view, what does a meeting look like? What does showing up well in a meeting look like? Taking your own notes, contributing appropriately for your level, anticipating your boss's needs, managing up. Later in your career it feels obvious, like just being a good professional. But nobody teaches it early.
Kelly: Is there anything that surprises you when you talk to young professionals? Things that seem obvious, like bringing a pen and paper to work, or how they take notes and listen. What are people just not prepared for?
Kate: Simplifying it, there are two archetypes. One thinks, I'm fine, I got it, I don't need the advice. Great, I love that confidence, I hope you actually got it. Because I and a lot of my friends have been on the other side, watching somebody walk in with great confidence and thinking, I have to teach this person everything. I've had peers come to me and say, love what you're teaching, please add: don't chew gum in an interview. Real tactical things to add to the list. The other archetype comes to me with less confidence, asking, how do I actually do this? You say talk my way into it, but what does that mean? And I'm happy to break it down. Confidence is the hardest thing to build, so I'm excited when people have it. But having it doesn't mean you know everything. It's still worth a conversation.
Kelly: It's funny. A professor I've worked with at my alma mater always asks me to teach some entry level tips, and he said his biggest challenge with students taking summer classes is they don't understand basic professionalism. Starting with an internship. Don't wear a baseball cap. Don't wear sandals or tennis shoes to work.
Kate: I'm guessing we both started in a business casual environment and graduated toward jeans and an elevated top, then maybe further to jeans and a t-shirt. That's definitely been my experience. In an art gallery, how you showed up mattered. It didn't have to be fancy, but you had to hit a minimum bar of hip. As a consultant, we were literally taught to pattern match. My first day on a client site, I was told not a suit, so I wore a more casual business outfit, a skirt and top, but I was working with an oil and gas startup where my male peers were in steel toe boots, jeans or khakis, and a polo or button down. I was never going to wear that, but I pattern matched my own version of something more casual. At DoorDash there were no baseball caps, but our CEO and COO wore jeans and a button down. I had a boss who wore the same five t-shirts every week, a day of the week rotation. This is going to date me, but this was 2017, and the whole company wore Allbirds because they were the hip sneakers in San Francisco. I stopped wearing silk shirts to work because that was too elevated for that environment. That's something I was taught, and I don't think we teach it now, especially without a real training program.
Kelly: I'll date myself even more. When I started my first job, pantyhose were required. Women were told to wear them. We've evolved since then, thank goodness. That was also back when people smoked in their offices. And then there's the smaller stuff, like your phone. We didn't have phones when we started. We barely had the internet.
Kate: Thank God for Spanx.
Kelly: Are you leaving your phone on the desk in a meeting? Those things need to be taught. And where you take notes.
Kate: I think that's cultural, honestly. Some companies are laptop closed for meetings, so if you're laptop closed, phone face up might be appropriate to keep an eye out for something important. It really depends on the company's meeting protocols. Especially early in your career, you're probably a taskmaster. You're given a set of things to do. You're not autonomous yet, and you're looking for the next project, which is exactly what you should be doing. But a great early career move is: you finish the tasks, you go to your boss and say, these are done, what's next, please review this. The reality is your boss doesn't have time to review it right away. There's a gap between finishing and getting reviewed, and probably a gap before the next task is ready. So what do you do with that idle time? Don't get on your phone, don't scroll social media unless that's literally your job. Have something relevant to your industry up. Learning something, researching something, working on a model. If someone walks by and you've got ESPN open, that's a problem. I actually remember that happening with someone I managed back in 2012. But if you have the New York Times or an industry publication open, that shows you're learning, and it helps you grow while also shaping how people perceive you.
Kelly: In advertising and marketing, we focus on the customer. Learn everything you can about the customer, and there are so many ways to do that. But also the industry. Are you getting Google alerts? Do you know what's coming across the wire that could impact your industry? There's so much you can do with that idle time, then bring it to your boss: hey, this just happened, how does it affect what we're doing? Let's shift to AI, because in terms of the job search, how does someone actually stand out when it's nearly impossible to get past an AI resume screener? Where does AI help you in a job search, and where does it hurt you?
Kate: I have mixed feelings on using AI to adjust your resume for every single job description. That was the guidance a year or two ago. Scrape the job description, scrape your resume, ask AI to make it fit, so you have the right keywords for the applicant tracking system. Let me start with the ATS itself. In my opinion, the ATS and job boards like LinkedIn and Indeed are working in the best interest of the employer, not the applicant. There are simply too many applications for a human to read each one, so appropriately, they use AI to filter. A great recruiter builds multiple filter sets for multiple archetypes, and hopefully you fit one of them. A less good recruiter has one filter, looking for one archetype, and if you're a rich, layered candidate, it won't understand that richness. It just looks for keywords. If you've been rejected within minutes or within 24 hours, you weren't rejected by a human. You were rejected by the system, and I coach people not to be disheartened by that. The way to work around it is to network your way into the role alongside applying.
I do think there's a better way to use AI on your resume now. I'll scrape a job description, and I have a few versions of my own resume. You don't need four versions, a master version works too. Take the job description and your resume and say, grade my resume against this job description. It'll gap assess what's missing, and then you can say, help me fix that, or interview me, because maybe those are real gaps, or maybe they're not real gaps, just not written down yet. Then ask it to help optimize your resume for that job description. I think that's a better approach. AI is still a tool, but if you're asking it to rewrite your resume, give it clear guidelines: maintain the level of detail, use a STAR format, situation, task, action, result, don't oversimplify my work. Whatever you want out of it, tell it clearly, and then when it gives you something back, proofread it. Tell it not to exaggerate, not to make things up. That might sound obvious, but don't assume it'll do it correctly. It's still your resume. It's still you. You're ultimately accountable for it.
Kelly: One of the things you talk about is the distinction between academic education and professional education, and that the professional piece should really start sophomore year, not after your diploma. What should nineteen and twenty year olds be doing right now that no one is telling them to do?
Kate: From my own hiring experience, it's genuinely difficult to hire someone straight out of undergrad. Not because they're not smart or don't have the right education. It's because they've never worked before, and I have to teach them how to take notes in a meeting. The way to mitigate that is to start building professional education through work experience in college. That doesn't have to mean an office job or a full time job. It can be working in a retail shop, nannying, working in a restaurant. Your responsibilities might be sales, inventory, childcare, serving tables, but the value you're creating is serving others, understanding client needs, managing inventory. Those translate into real value adds a hiring manager is looking for. And internships in an actual office environment are a great way to test whether you really want to do the thing you think you want to do, or whether you don't, and that's just as valuable to learn. You have to start early so you're not walking into graduation with only one work experience. What if that one thing you tried, you didn't like?
Kelly: Great advice. Now talk to me about the idea of separating the work from the person.
Kate: That's core to my people management philosophy, and it comes from consulting. As a management consultant, I managed a project team, and separately I was a people manager, sometimes for people on my project, sometimes for people elsewhere in the organization. I physically separated managing the work from managing the person. How did you do that work product, how do I keep you motivated, and where do you want to move in your career. That's also why I focus my practice on young people. When I joined DoorDash I was 31 and felt like an old lady. It was a young company, full of people between 24 and 30 who hadn't managed anyone before. They liked being at a cool tech startup, the work was hard and fun, but they didn't know what they wanted to do next. So I'd ask: do you want to be a chief product officer, a chief operating officer, or a chief revenue officer? Answering that question, or struggling to answer it, helped us tease out where they might go next. Maybe a stretch project in sales, or one focused on customer requirements for a new product, to help them explore what's next.
Kelly: That's related to this idea you have about creating a marketing plan for yourself.
Kate: Yes. I love how these questions jump around my career chronologically but are so interrelated. One of the best pieces of advice a friend gave me on how to conduct my own job search: get clarity on what you want. Don't just search for strategy roles or chief of staff roles or sales roles broadly. There are three or four concepts within this marketing plan, and you rank them by priority. What position or title are you looking for? What kind of company, public, big, small? What industry? And are there specific companies you want to work for? The last time I went through a search, title was my top priority, VP or above, in go to market or operations. After that, food tech or marketplace, because that's where I had value, with CPG a loose third. My second priority was actually company size and stage, Series B to E, because I knew my sweet spot. Company itself was agnostic, because I don't always know who the new companies are in those stages. Other people flip it. I really want to work at Nestle, I live in DC, I want to be in CPG, but really I want to work at Nestle specifically. Beyond that, they're agnostic about marketing versus strategy. Have a point of view, and don't have too many plans. Simplify as much as you can. The reason this matters is that when you start your networking plan, in addition to applying through the ATS, you say, hey friend, I'm looking for a job, I've built a marketing plan for myself, I'd love your advice on how I'm taking myself to market. You're asking for advice, not help. And nine times out of ten, when I asked friends for advice on my marketing plan, they didn't just say you should talk to so and so. They said, give me thirty minutes, I'll connect you. That, to me, is the answer to the test.
Kelly: I love it. Any final advice for people handling their job search at any stage of their career?
Kate: Be able to articulate your value to somebody in person. Find a friend, find a partner to talk it through with and get it on paper. It can be an AI partner, it can be an in person partner. But I hope you can see the value you already have in yourself.
Kelly: Perfect. Thank you so much for sharing your insights today, Kate. We're going to provide links to your website, your podcast, and your contact information in the transcript. Don't forget to subscribe and share. Thanks for joining.
Stay curious enough to keep growing, brave enough to follow your calling, bold enough to build the career you actually want, not the one you settled for.
