222: How senior MOps practitioners are navigating the 2026 job search with Ashley Langford

Ashley: what nobody talks about is the shame of a layoff. You know, even when it's a massive layoff, even when it's clearly just a business decision, even if you have every credential out there and there's every reason for them to keep you, there's still a, a quiet voice in your head that says that you've lost, that you weren't good enough to keep. And that voice is, is sneaky because it doesn't stop you from applying or networking or showing up. It just slightly changes how you show up.

You overexplain it in interviews. Um, you hedge when you should be confident, and you feel grateful just to be considered instead of walking in and knowing your worth. ​ In This Episode - Phil: What's up, everyone? Today, we have the pleasure of sitting down with Ashley Langford, marketing ops and revenue ops leader.

Ashley is a two-time Marketo champion, and at the time of recording, she was in the early stages of a job hunt, having recently been laid off from LastPass, where she was head of marketing technology. In this conversation, we cover why a layoff changes how you show up in interviews, where the marketing ops job search is actually happening right now, how to use AI to prepare for every job interview, how to evaluate remote and hybrid job offers, and how to translate MOPs work for anyone in the room.

All that and a bunch more stuff after a quick word from two of our awesome partners. Sponsor: GrowthLoop - ​ Sponsor: GrowthBench - ​ Phil: Ashley, thank you so much for your time today. I'm really excited to chat. Ashley: Yeah.

So me too. Fair warning, I'm gonna be treating this like a therapy session. So do you take Amex or insurance? Phil: I love that you're treating this as a therapy session, 'cause I feel like a lot of folks in your shoes, sometimes you don't have a ton of people helping you out with, like, how many people in marketing were also let go at the same time as you?

So maybe let's start there, Ashley. Like, we did a whole, um, MarTech Job Hunt Survival Guide, me and Daryl. Daryl kind of, like, uh, does this from his ivory tower a little bit, 60K followers on LinkedIn, massive network. I haven't had to, like, actually find a job in a couple of years now.

So I thought it'd be really cool, uh, to have someone who is in the middle of this right now, living this experience, uh, and just like tear apart the job hunt for us. Like, what was done, what wasn't done. But 1 - Why a Layoff Changes How You Show Up in Job Interviews - Phil: bring us back to, like, the day, the layoff journey. Um, I know you weren't even at, like, uh, LastPass for, for more than a year.

So, um, bring us back, Ashley. What can you share? Ashley: Yeah, I think, I think what nobody talks about is the shame of a layoff. You know, even when it's a massive layoff, even when it's clearly just a business decis- decision, even if you have every credential out there and there's every reason for them to keep you, there's still a, a quiet voice in your head that says that you've lost, that you weren't good enough to keep.

And that voice is, is sneaky because it doesn't stop you from applying or networking or showing up. It just slightly changes how you show up. You overexplain it in interviews. Um, you hedge when you should be confident, and you feel grateful just to be considered instead of walking in and knowing your worth.

I didn't fully see it in myself at first. Um, it took a few conversations before I realized I was performing confidence instead of actually having it. So I mean, that can be a really uncomfortable thing to admit when your whole brand is built on expertise and results. So I'm not fully on the other side of it, but naming it kind of helps.

Phil: Hmm. Yeah, definitely. And I feel like one of the things that's did - stands out from, uh, the, the three-part series that we did and what I'm hearing from a lot of people... Like, the whole idea of doing the, the three-part series is, like, uh, when people follow the show on LinkedIn, I reach out to everyone or almost everyone and just say, like, thank them for following the show, and I ask them, "What's keeping you up at night right now?"

Like, "What's the one thing or project keeping you up at night?" a lot of people have really cool answers, and it leads to, to episodes and content. But recently, a lot of people were just like, "Phil," like, "read the elephant in the room." Like, "Look at my LinkedIn.

I don't have a job right now, and I've been on the job hunt for almost 12 months now. The market is brutal out there." So I wanted to ask you, like, how brutal is the market out there? Daryl's experience was, like, almost, like, eight months ago.

Is it still as bad? What, what's your take there? Ashley: Oh, yeah. It's so brutal.

Um, and I say, you know, that someone from... You know, I should be insulated from it. I have credentials, I have experience, I'm active in the community, I have a network, and I've done the things that you're supposed to do, and I'm still getting auto-rejected within minutes, and I'm ghosted by companies I was really excited about. You know, I haven't been ghosted this much since I was on Tinder like 12 years ago.

And, you know, at least then I knew why I was getting ghosted, but now I don't. Um, so, you know, is, is it true? Like, you know, what's going on in the searches - search? What's different?

And, you know, the work gets you in the door. Like, it gets you in the real conversation instead of just applications in a void. But it doesn't protect you from the reality of what this market is. It just makes the, the- Brutal part slightly less brutal.

The credentials matter inside the community, but Marketo champion thing opens the door of people who actually knows what it means. But it's h- you have to still find those people, and there are d- a lot of doors that just never open regardless what's on your resume. Phil: Yeah. So we're recording this when you're what?

You've been in the job hunt for, like, less than two months, right? Like, it's, it's still pretty fresh. Ashley: Yes. Phil: Yeah.

So hopefully, maybe even, like, by the time this drops, like, we'll be changing your title and announcing the new spot that you landed at. Um, but, like, what's, what's your day-to-day look like today? Like, uh, 2 - Where the MOps Job Search Actually Happens in 2026 - Phil: one of the things Daryl said in the episode is people should stop thinking about their main KPI for the job hunt as something like the number of applications you finished in a day or in a week, and instead it should be the number of people you reach out to.

Not everyone has the network that Daryl has, and not everyone has that many people to reach out to, but you said you're part of communities. Like, what, what are your thoughts on that? Like, how are you measuring your, your day-to-day, if you will? Ashley: I think Daryl's right, you know, for the right person, and, you know, I say that as someone who's gotten jobs through my network before.

You know, it works, and I've lived it. But there's an assumption that that advice is not for everybody. You know, not everyone has a warm network. Um, not everyone has a network that's willing to move for them.

So there's a difference between people who will say, "I'll keep an eye out," and people who will actually pick up the phone and make a call on your behalf, and not everyone has that second kind of network. So yeah, conversations are a KPI, but applications are also a KPI. Um, I don't think it's either/or. I think the honest answer is you need both, and the ratio depends on your network that you've actually built, not the one that you wish you pa- you have.

Phil: Mm-hmm. Yeah, such a good point. So when it comes to, like, hidden jobs, uh, like one of the things we chatted about in the three-part series is LinkedIn has a bunch of job postings, Indeed, whatever. There's like the public-facing job company have, uh, companies have gone through like a six-month process to write the JD, get approval for it, post it, get it out, and like now they're overloaded with the number of people applying for it.

Hopefully, the thought was in MOPs that, you know, you're b- there's less people than like your, your average marketing job. Like it's more niche, it's more technical. Now you're probably competing with a bunch of people that don't have the MOPs experience you do, but are using AI tools to try to like tweak and, and, and trick the, uh, the application system into thinking like, "Yeah, I didn't really do marketing automation, but I did this one email that one time at that one startup, and now I'm changing my title to email marketer."

Like, what are your thoughts on, like you just said, one of the KPIs has to be applying to a certain number of jobs. Talk to us about like that hidden job market that, that we mentioned. Like we made the case that the hidden market, the hidden job market, like the roles that never make it to job boards yet, like there's a really cool opportunity for folks to like chat with people that are thinking of hiring, um, that are about to hire, haven't hired yet, like just raised a big round and you know head count's gonna come at some point.

Um, like where has your search kinda actually been happening? Is it still just mostly on LinkedIn? And, and what's been kinda the return on the visible channels versus the hidden ones that you've explored? Ashley: I, I do it all.

Like, LinkedIn first, like what my day looks like is I go through LinkedIn, I look at the new jobs that are posted, and then I scroll on LinkedIn because not necessarily like they're gonna be posting on LinkedIn, but they may be posting a job that they have, but it's not a job on LinkedIn. Um, so people will, will tag that they're hiring here. Then I look at like the niche job boards like, um, you know, the VC-backed job boards, I'll look at those. Um, and then, you know, I actually did try that Ashby hack that Daryl did mention.

Right. And no, it was, it was really cool. So I was trying a, a few keywords. Um, it was really helpful.

There were a couple jobs on there that I haven't seen anywhere else. And then there's another job board, um, or a application system, Greenhouse, and they now have a job search function that's across all of their job boards. Phil: Nice. Ashley: theirs, uh, as well, and it, it's listed o- of all their jobs.

So that's pretty awesome, and I don't think a lot of people know about that. Um, but to be honest, where my actual responses are coming from are still LinkedIn. And, you know, for all the, the talk about hidden job markets, the one that are still producing is LinkedIn. Mm-hmm.

And the thing that has changed though the most that I haven't heard people talking about is the external recruiters. Three or four or five years ago, my inbox was full of them. I mean, I don't wanna say I was beating off them with a stick, but basically was. Like every other email was either a salesperson trying to sell me something or a recruiter.

Now it's quiet. The pipeline has almost dried up completely, and I think that's a real signal about what's happening in this market that the job posting numbers just don't quite capture. Phil: Yeah, 100% agree. I probably wasn't at the volume of, uh, in- inbound recruiters that you were, but I, uh, I had some, like, there was some interest, and it's completely dry right now.

I haven't gotten one in, it has to be at least 12 months. Um, so it's cool to hear that, you know, LinkedIn is still, um, kind of the source where you're starting your day and where it is where you're seeing the most success. Are you just applying cold, like, new job posting marketing ops at this company in your city, or it's remote? Uh, like, what's the process after you find one that you apply to?

Like, are you using GPT a little bit after applying to it? Are you finding someone from the company that you have a second degree with and you're trying to get a referral? Like, what, what happens after you find one that you want to apply to? Ashley: I've done several things.

So sometimes I've just cold applied and, you know, there, done it. If there's like a really cool job - There was like this really... Or a couple really cool, interesting jobs, I'm like, "That company would be amazing to work for." I would actually go and e- either reach out to like the hiring manager, the recruiter, something, and I've never gotten a response back, like at all.

And I'm like, "Okay." And then one time there was this job, it was right after I was laid off. Um, I think the next day I saw this job, and like the job description was written for me. And I was actually first connections with this person, so it was a recruiter, like internal recruiter.

And I, I applied, and then I wrote them and I'm like, "You know, I would be perfect for this job," blah, blah, blah. "Here's my resume." Like it, it sounded better than that. And the next day, rejected, and they never reached out back to me.

I was like, "Oh." I was like rejected twice and I like, you know, laid off and then okay. Like, Phil: Yeah, what a great way to start the whole process. Ashley: Right.

I was like, "Okay, well I guess next week will be better." Phil: So what, what are your thoughts on, like, finding someone that you have a first degree with at that company? Like, we all have people on LinkedIn that we have first-degree connections with that we don't actually know, Ashley: We don't know any of these Phil: with. Right.

Ashley: Like I Phil: Majority of people I don't know either. There is though, like, a subset of people that you do know on LinkedIn, you've worked with, like you're connected with, and you feel like if you reach out to them, you won't, you won't get ghosted. Chances are, um, and there's tools for this, but like I've, I've found success like back in the day, and this is obviously like a different experience, but I've had people that are looking for jobs reach out to me saying like, "Hey Phil, I know that you're connected with so and so at this company.

I know we don't know each other super well, but I've been hunting for eight months. I'm coming up dry, like mortgage bills are piling up. Like, would you feel comfortable, uh, like look at my resume? I'm happy to like, you know, help you feel comfortable vetting for me."

But I-I've done that with a lot of people and when I do the intro, it's just like, "Hey, um, so and so listens to the podcast. They're super like curious and blah, blah, blah." And, and so like, uh, it's led to at least like that screening interview because you have the one person facilitating that intro. Sometimes I don't, I don't get a response also, but like have you tried that angle of finding someone who knows someone in that company that could at least try to get you a foot in the door?

Because companies now more than ever still have that referral bonus. When I worked in-house, like 5K if I refer a successful hire. Like, I don't care if I know this person super well or not, like I'm 100% putting their name in the ATS system and putting my name next to referral. So what are your thoughts there?

Like, have you tried that route yet? Ashley: Um, there haven't been any that I've seen. So the, the thing about MOPS is I can work in any industry. Like, that i- that's what's so different about MOPS versus working in, like, demand gen or another, you know, marketing function, is I can go from fintech to, you know, insurance to, um...

You know, I've been in biotech. I've been, you know, selling HR stuff. I've been in every industry, and I can easily, I don't wanna say hop from one industry to another, but that's what's so amazing is it doesn't matter what they're selling. It, it, it could be widgets, it could be, you know, blood, it could be anything.

It does not matter as long as the systems are, are there. I can do it. So that is what's so unique about MOPS people is it could be any product as long as the systems are there. So it's, it's kind of odd because just because I worked with someone over there doesn't mean necessarily I'll ever see them in another company.

You know? It's, it's interesting. Phil: Yeah. So you mean, like, because of that multifaceted industry-wise experience, you have less of those, like, first-degree connections who also know someone at a company that has a job posting right now?

That's, like, one of the limiting factors for you? Ashley: Yeah, 'cause it's so broad about where... 'Cause I guess the network is so spread out. Phil: Yeah.

Yeah. That is tricky. Yeah. I empathize with that one.

Um, so, like, you've been a hiring manager also, right? Like, you spent, I mean, back in your in-house days and myself as well. Like, do you feel like that, like, s- two-sided POV right now is giving you a bit of empathy in the process? Like, um, you built and hired mobs teams throughout your career.

3 - What Hiring Managers Actually Look For in a MOps Resume - Phil: A lot of job seekers right now are kinda guessing at what a hiring manager is even looking for, what they're skimming for. I was chatting with, uh, a VP of MarTech at Databricks, and she's like, "Phil, I don't even open Greenhouse anymore." Like, that tool is just littered with people writing AI slop cover letters. Every resume looks exactly the same because everyone does the same thing.

They see a job posting, they have a resume, they upload both to GPT, and they're like, "Improve my resume for this JD and write a cover letter for it," and they - maybe they tweak it a little bit, and the output is that, like, you look exactly the same as a bunch of other people in the ATS. So, like, like, I empathize with folks like you that are on the job hunt, but, like, the, the hiring managers too that, like, they have an open req, they wanna hire someone, but they have the hardest time ever right now to figure out who is really legit.

Because, like you, like, I don't fault you if that's what you do to apply to jobs because, like you said, like, one of your KPIs is number of applications. I can't just apply to one job per week and, like, spend 40 hours on that one application. Like, I have to apply, move on to the next, right? So it's like, how do you find that balance between how do I stand out from this application that I really like at this one company and balance that with there's 20 other jobs that I wanna apply to today, and tomorrow there's gonna be new ones?

Like, how do you find that balance? Ashley: Yeah. I mean, first of all, I hate cover letters. I think they are dumb and outdated because, I mean, all they say is like, "Hey, I want a job."

Like, w-what else are you supposed to put in there? Like, they're dumb. Like, I mean, even when there wasn't AI, I would have a standard cover letter, and I would just swap, you know, I'm applying for this job at this company. Like, that's it.

So they were dumb to begin with. Um, so sorry, that was my, my rant. Um, but, but knowing how it is on both sides, I think it, it changes how I present myself. Like if I'm looking at a entry-level mops role, you know, entry-level experience, you gotta know what you're looking for.

So necessarily like Marketo experience is almost irrelevant. You know, that could be taught. What I can't teach and what I'm looking for is, is found in the interview. It's curiosity.

I wanna know how you think. Are you the type of person that see... can see like a weird data discrepancy and figure out why? Do you like puzzles?

Do you dig? Are you, you know, a curious person? That's the person I'm, I'm hiring. But, you know, a senior level person is completely different.

I wanna see the numbers. I wanna see, you know, the data, not just manage an email program or own the tech stack. I wanna see what happened because of you. What did you improve, and by how much?

Over what timeframe? Results, not just responsibilities. So knowing that I'm ruthless about my own resume and how I talk about my work, I don't let myself off the hook with vague language. If I can't attach a number to it to push myself, I, I try and push myself to find one because I know how I am when I'm a hiring manager, and I s- and, you know, I skim past when I'm r-reviewing.

I know they're gonna be skimming past things, so I put results in my resume, and they're... everything is attached to a number. So, and they're actually a little highlighted in mine, so you can see that I did this to this, and it improved by this much. Um, I do not change my resume for each job and tailor it because It takes a lot of time, and if I'm spending, let's just say 30, 40 minutes tailoring a resume for one job, that is a lot of time.

And if I never hear back, not even an automatic rejection, like that is a lot of time wasted. And, and, you know, if they can't even auto-reject you or just send you a, "Sorry, we found someone else," like that's just not right. Phil: Yeah. do do you think that it's, like, lame or the output is just gonna be sloppy if you were just to take the JD, the PDF of your resume, and ask GPT or ask Claude to improve it slightly or optimize the current resume for the JD?

Like, y- you say you're not doing that today. Have you tried the output? Like, what are your thoughts Ashley: So I've tried it. So I did it with LinkedIn.

So LinkedIn has a new tool where it can - like if you apply through LinkedIn, you can tailor it to the job, and I did try it. So I actually got a reply and a phone screen from it. Phil: Hmm. Ashley: but I think that they're pushing those to the top of the pile, is what I think that they're doing.

Um, what - But you know, the job, it, the role wasn't a fit, so I can't exactly call it a win, but I did get something from it. Um, but I did think it was really interesting that, that it did it. Um, it didn't really improve my resume that much. It was just like slightly changed a bit.

Um, so I d- I don't know how much it changed. I really think it just pushed it to the top of the pile, is what I really think it did. Phil: Yeah, I didn't know LinkedIn was doing that. Ashley: Yeah.

Yeah. Phil: Maybe folks should, uh, give that, give that a try if they're Ashley: He's a little Phil: for right now. It's cool to hear your, like, hiring manager experience from the other side. Yeah.

'Cause I - Like, I think it's, um... Like, obviously, your POV, I have a, a similar POV, but, like, every hiring manager is different. I'm sure a lot of people agree with you. They hate cover letters as, like, an applicant and a hiring manager.

But there's some people that actually like them. Like, I worked with a boss who didn't look at LinkedIn, didn't look at the CV. It was all about cover letters for him. And he said exactly what you hate about them is that, like, everyone writes the same thing.

Like, "Hey, I think I'm a great fit for this one role because this is what I've done in the past." And he used it as, like, a filter to find people that were trying to, like, look different from everyone else, and I feel like that's really interesting right now with the AI slop of applications. So let's say, hypothetically, the hiring manager, or in some case, like it's - it, doesn't get to the hiring manager until it's, like, pre-selected by someone in HR, the recruiter dealing with, like, the Greenhouse applications, right?

So maybe you do end up with a recruiter that loves cover letters and actually reads the first paragraph of them. I think it's a cool opportunity to be creative, knowing that every single cover letter is written by GPT or Claude. Like, why isn't the first line of your cover letter, like, try out just for fun, like, "This cover letter is brought to... is not brought to you by GPT or by Claude.

This was handwritten by me." Uh, or like you write your cover letter by hand and just, like, take a picture of it and like... I don't know. I feel like it's like, it's an opportunity for you to stand out from...

And, and like you said, like how much time do you wanna spend standing out when, you know, I'm not even getting, like, responses for, for a lot of these? But I don't know, my mind goes to, like, experimentation and, like, I would test that out for a full week. Like, go all in and customize and optimize my resume and the cover letter for all of them, and have, like, the first line just be like, "This cover letter is not written by GPT and Claude. I hand wrote this.

I'm a huge fan of what the company is building for..." I saw blah, blah, blah. I don't know. Like, what are your thoughts, here?

Ashley: Well, what's - I think that would be really interesting to run experiments, 'cause I love, you know, running little experiments on, on different things just to see the results. And, you know, what's also interesting is some of these ATS systems don't even accept cover letters. So some of them don't even want them. Um, you know, and like, I mean, we could probably do a whole, a whole show on the, the hate, you know, the downfall of ATS systems and why people hate them.

Because some of them are great, some of them are horrible, and, you know, some of them just are a pain to deal with. But some of them are j- when they just want my resume and just put my information in, done. Like, those are great. But, you know, when they want, like, your blood type, your Social Security number, your address, every single thing you've done since elementary school, and you have to hand put that in, like, that's a pain.

Phil: Yeah. Yeah. No, I feel that. I - one thing I would say, like, uh, to add to your experiment list is, like, for a week or two, I would try to optimize my resume for every job that I'm posting, and not by hand.

Like, have Claude or GPT do it. And what I would say is, like, in marketing ops, there's so many buzzwords, and whether it's a, a system like an ATS deciding whether to move Ashley to the next round or not, or it's a recruiter that has no idea the technical components of marketing ops. Let's say the role is actually called GTM engineering, and, like, we could do a full episode about that. What are your thoughts there?

But, like, I'm sure you've applied to some roles that are calling themselves GTM engineers. Maybe they're, like, technical marketing. Maybe they're m- email marketing. Like, think of all, like, in that job at the Ashby search hack, like, how many keywords you throw in there that could be the job title for it.

Like, how many recruiters are looking at your resume and seeing that you're calling yourself a marketing operations person, and the JD is a technical marketing architect? That's the same thing. You and me can agree. The, the, the technical recruiter might just be like, "Ah, this person is operations.

They're, they're not an architect." Like, move, auto-reject. But, like, GPT would've changed your headline to be architect, would've changed your experience in, like, the, the first thing at LastPass to just be about architect. So I don't know.

Fun experiment, like, just riffing on Ashley: Oh, yeah. No, there's so many cool things that you can do, and, you know, 4 - How to Use AI to Prepare for Every Job Interview - Ashley: I think AI is super, super amazing. And, and what I've - what I'm using it for mainly in my job search is kind of like interview prep. That's how I've been using it heavily.

So what I do is I, I like Claude. Like I've had a subscription to OpenAI and - or I have them for OpenAI and Claude. Phil: Yeah. yeah.

same. Ashley: yeah. Like, but I, I use them for different things. I think they both have their strengths and weaknesses.

But with Claude, before every interview, I build what I call an interview packet. I put in the job description, and then I put in the LinkedIn profile of who I'm meeting with. And then I put in any other information that I have, if I've met with the HR person, if it's a second interview, if it... or whatever.

And, um, then it gives me a breakdown of their background, their career. It builds me a whole like HTML packet basically of who they are, what they're interested in based on their posts that they've posted on LinkedIn, um, things that they've commented on, their history, where they've been, and specific questions I should ask them, as well as, you know, things related to the job. It is really cool. And of course, you should always verify and do your own research, um, because, you know, AI likes to imagine things sometimes and make up stuff, because I've caught it doing that.

I'm like, "Are you sure?" And it's like, "Oh yeah, you're completely right, that - I don't know where I got that." So always verify. But it, it really helps you with, with doing some of your research.

And even for, you know, some of the, the people that are more junior in their career, it can help you with actually interview questions. So my daughter, when she was - turned 16, she's now 17, she was, um, wanting to get a job at Chick-fil-A. And Chick-fil-A is notorious for, you know, very hard interviews, apparently. I did not know that.

Phil: Interesting. Ashley: and she, you know, did not want any of my interview advice because, you know, I've never had a job before, and, you know, I know nothing about interviews. So I gave her my iPad, set up, uh, ChatGPT for her, and she actually had a voice interview as, um, a, you know, acted as a Chick-fil-A manager, and she did it several times, and it prepped her for the interview She nailed the interview and got the job, Phil: Nice. Ashley: it was awesome.

And then a year later, she wanted to go work at Starbucks, so she did the same exact thing for Starbucks. And Starbucks is apparently another hard company to get into. Um, and she's working at Starbucks now. So it's, it's crazy.

Um, it really can help you with even confidence of, of, you know, talking to somebody and not feel like you're just talking to yourself. I mean, even though you're talking to a robot. But, um, you know, it's, it's - it can... You know, maybe you could tell it to be a little bit m- not mean to you, but not so, like, nice.

Like, say, "Criticize me a little bit and, and like help me with my answers." Um, and it's - it can be super helpful in so many different ways. Sponsor: MoEngage - ​ Sponsor: Knak - ​ Phil: I l- the, the part I love the most is that you're spending a lot of time on that part, but you're doing it for active interviews, and it's not an application that could go in a dark hole and you have no idea where it went, and you spend 10 hours on... Ashley: Right.

Phil: an actual interview. Like, now is the time to go all out. It's funny that you, you talk about that. We, like, super briefly touched on it in the three-part series, but, uh, I wanted - I coulda done, like, a, a deeper dive on it, 'cause I actually do something similar for the podcast when I prep for, uh, some of the interviews that I do, and it's, um...

Like, in Claude I have a setup that is just like a, I call it, like, a mock interview with the person. And so, like, Claude helps me set up with, like, a bunch of suggested questions based on, like you, like I, I feed it a bunch of context on their profile, stuff Ashley: Oh, nice. Phil: And so, like, spits out, like, a bunch of potential questions and helps me pick, like, an angle for the main episode. And once we have, like, a good list of 20-ish questions or whatever, Claude does a three-pass simulated interview with itself on, like, a dynamic persona of that person, and it fine-tunes the initial questions based on feedback.

But it's so funny you call that hallucinations, 'cause I've caught it too. Like, the end output is this, like, nice interview prep, and I, I start getting into it and I review it, and one part is just like, um, "So and so, you said this, uh, and, like, I'd love to ask you about this," blah, blah, blah. And then, like, I always verify those with Claude and I'm like, "Where did this person say this?" And you're like - A-and Claude's always like, "They, they said that in, like, round two of the simulated interview.

Good call. They didn't actually say that. I'll add that to memory." And, like, I caught it doing that so many times, and it's in, like, the context file, it's in the prompt, it's in the memory folder now, and it still does it all the damn time.

But yeah, it's such a cool call-out at the, the hallucination. Ashley: Yeah. It's really interesting. Like, it can do really cool things.

But, you know, what I wanna try next, though, I haven't done it, is I wanna record one of my interviews and then feed it into Claude and say- Analyze this, you know, how do you think I did? Can you, can you tell me how I did? And, and then see what happens after it. You know, did I overexplain?

You know, a feedback loop I think would be really helpful because there are some times where you think you did amazing, and then they're like, "Nah, no, you're done." So I think that would be helpful. Phil: Yeah, 100%, and yeah. This isn't legal advice or anything, but you probably don't even need to, like, give the disclaimer to someone.

Just, like, start recording it on your phone. Just have Ashley: in Georgia. We're a one-party state, so... Phil: you go.

Um, yeah, those - the, like, I, I feel like there's a whole bunch of stuff we can unpack on, on AI tools. Like, one thing I wrestled with when we were doing, um, like, one of the, the second part of things is, like, I went down this rabbit hole about people just building AI tools for folks in the job application area. Like, I was, like, on the fence about actually, like, telling folks to do the Ashby job search hack because, like, we're using Google to search for something, and I'm like, "Should, should people be using Perplexity?

Should there be, like, a script for that? Is there probably, like, an, a web app that I can create with CloudCode that, like, does that for me automatically?" And I actually tried to do it, 'cause, like, for the newsletter, I do a newsletter every week for, for every episode, and one of the sections of it is, like, highlighting people that are open to work, as you know, but also highlighting recent job posts. And I use the Ashby search hack for those, and I tried to automate it with, with Cowork first.

It was, like, my first project with Cowork, and it was crap. Like, it was so bad cause, like, I have to do so many filters. I only highlight global remote work or at least North America and, like, global only. And just, like, that filter, like, Claude having to go through every posting and decipher whether it's actually global remote or US remote or US/hybrid.

Like, it was just really bad. There's, like, that missing semantic layer between like, the job posting. Um, but I wanted to ask you about the whole, like, remote part of this. So I don't know if you were remote at LastPass or not and, and how big of a fan you are of remote.

5 - How Senior MOps Practitioners Evaluate Remote and Hybrid Job Offers - Phil: But something that Daryl said that really made me ponder during the current job market is that, like, stop looking for just remote. Like, if you're only interested in remote, cool. It's fine. It could be, like, something you strive for and include in your job search.

But you gotta include local roles. Like, you gotta include hybrid. You gotta include local roles. You have to be open to, like, getting some of those roles and, like, you try it out.

You see how it is. You talked a lot in, in, our conversation before starting this about still being picky despite how crazy the market is right now. Talk to us about that. Like, riff on that a little bit.

Like, why are you still picky despite, you know, how some people have been in a job for so long and some of the negative things you've said about the current hunt? Why are you still picky, Ashley? Ashley: Yeah, so I, I mean, I've been remote since 2019, and it... I, I have to have a remote job.

It's not just a comfort for me, it's, you know, value. And, you know, it's something that I, I just need in my life. So my dad, uh, worked remotely for my entire, entire childhood. We're talking in like the '80s, '90s and early 2000s.

And it was called, you know, before anyone called it remote work. So I grew up seeing what it actually looked like, and when somebody had autonomy over their time and their environment, it actually works. And my husband is a CPA. His firm is based in California, and he works from home here in Georgia and has for four years now.

And tax season for a CPA is brutal, and the crazy hours, the pressure, and it was so much worse when he actually had to commute about 40 minutes. It was horrible. The driving alone is just so bad. But now it just, not having to drive and being able to just go into his home office is just so much more of a relief.

And when I would commute into Atlanta, I was losing three hours a day just sitting in traffic. Three hours. Like, that's just not a small thing. That's, that's time I'm never getting back.

I mean, I do miss, you know, the social part, the lunch with colleagues, the face-to-face. You know, that's real and I don't wanna pretend it isn't. But I'm so much more productive at home. But I, I have noticed that hybrid is becoming so much more common and, you know, these San Francisco companies, they are pushing full in-person again.

A lot of these companies are in-person only. And I get it, it's, it's a real trend, but I also think that these companies are making a talent decision whether they realize it or not. When you open a role to remote, you're not just getting more applicants, you're getting talent from places that nobody thinks to look. So some small town somewhere has an incredibly skilled mops person who would never relocate but would actually, you know, really crush that job.

You just have to be willing to find them. Yeah. Phil: have you kinda changed your tune a little bit? You said you're 100% remote, all in on remote, but are you looking at certain local roles, hybrid Ashley: looked at some of 'em.

Um, some of them that are a little bit closer, definitely not Atlanta. Um, but sometimes I think... I, I looked at some of the hybrid ones and, you know, if the salary makes sense and then how hybrid it is. Um, there was one that was in Atlanta and they said hybrid and, you know, I think hybrid, at least three days in office is what I think.

This was every day in office basically, except for you get like one Friday a month off and I'm like How is that hybrid? Like, you get one Friday work from home, like a month. That's not a hybrid role. So it was, it was really interesting to see what some people's definitions are.

Um, I mean, if, if it is, like, the perfect job opportunity, you know, right salary. I mean, the salary has to be really, really, really high for me to consider a... You know, killing three hours of my day. Um, I mean, and or if you, you know, get me a helicopter and fly me to the city every day, like, that's, that's also another thing.

But, you know, I've always said, like, I will fly, you know, to a, a office, but I won't drive to one. Like, I will hop on a plane any time and, you know, do an offsite or, or do anything like that, but just flying every day. I mean, not flying. Driving every day is just a killer.

Phil: Especially driving. Like, I feel like at least the bus or, like, local commute, there's this idea that, like, you can kinda be productive and you can listen to a podcast while you drive. But yeah, I'm 100% aligned. Um, my mind goes to, like, i- if I was in your shoes and, and the market was, like, really, really weird right now, I think I...

Like you, like, I, I'd look at the salary. I'd be kind of open to it if the company is really exciting and it's not, like, a three-hour Ashley: Yeah. Phil: I wanted to ask you about, like, what are your thoughts about taking, like, not settling, but taking something where you're not 100% sure it's gonna be a fit for the next five years, but you're taking something to pay the bills, and you're, like, just taking that job for now, but you're continuing the search? It's like a means to an end.

Like, I don't know. It's, it's kinda weird 'cause, like, y- you, go through all this work and, and setup and process and onboarding, and you're still kinda like looking for something else. Like, you said that you're still being picky right now, and it feels like you're not really considering that the next role is gonna be something you're going all in on. You're not taking something that you're just kind of okay for now and is gonna help you pay the bills.

Ashley: I mean, I'm, I'm trusting my gut. I don't think I'm gonna do that. Um, you know, I, I'm- Been in interview processes so far where something has felt off and the energy was weird, and the conversation felt forced, and it's just like two people, you know, reading a script and, uh, at each other. And in the past, I'd talk myself out of it and be like, "Oh, well, you know, the role looks good on paper.

The comp is right. Let's just not be difficult." And then, you know, you take the job and six months in you remember exactly why something felt off. And, you know, what I'm looking for now is harder to put on a checklist, but, you know, I know when it feels right.

It's when you get a call, you get on a call with somebody and you're 20 minutes in and it feels like you've known them forever. And the conversation flows, they're finishing your thoughts, you're finishing theirs. There's no performance on, on, happening on either side. That's just something that I'm just not willing to compromise on this time because I've learned that the chemistry, if the chemistry isn't there in the interview when someone is on their best behavior, it's definitely not gonna be there on a random Tuesday when, you know, things are getting hard.

Phil: Such a good point. I love that, that, that call-out of just getting like the, the vibes in the interview, let alone like... And, and there's like vibe checks from multiple different people in the interview process, not just the hiring manager coming from the, the start with HR. Yeah, really cool point.

Um, okay, so I wanna give you a bit of time, Ashley, to kinda like share about, um, you know, what makes Ashley awesome. Like, the g- good, good chunk of like the three-part series that we did is like how to stand out from the crowd, and like how to talk about your marketing ops technical work to people that maybe are at the VP level and, you know, are super far removed from what the heck like a marketing automation workflow even means today. Um, so maybe chat a bit about like how you're communi- communicating that technical work in interviews, maybe even like, uh, your resume.

You said you're like everything is tied to a number. Uh, but 6 - How to Translate MOps Work for Anyone in the Room - Phil: I wanna get into like how you're actually presenting some of that work, uh, because like y- you're kind of an example here. You said like two times Marketo champion. You've built mop- MOPS functions from scratch, bunch of different industries, like industry agnostic, if you will.

Like, there's a real translation problem in this community, especially for folks that are far removed from the work. Sometimes you're interviewing at a small company, and there's no MOPS person right now. Maybe the MOPS person left, uh, and like no one has MOPS experience in the company. Like, who is to like vet that MOPS experience?

How do you communicate deeply technical work to someone who like doesn't share that same reference? Um, give us examples. Ashley: Yeah. So I think it's just about translation, not simplification, and there's a, you know, a big difference between those things.

A lot about what we do in MOPS is really complex under the hood, but the mistake most techni- technical people make is explaining how in- Uh, explaining the how instead of the impact, and h- the how means nothing to somebody who doesn't live in the platform. So for example, once I, I rearchitected the Marketo and a Salesforce sync that went from taking days to minutes. Um, to a technical person, that's a conversation about sync backlogs, API limits, field mappings. But when I walked into the exec meeting, I said, "We r- reduced lead response time from same day to near real time, which directly improves conversion and protects pipeline."

Same work, completely different story. And then with sales leadership, it's the same thing. I don't talk about campaign triggers or data volume. I say, "Leads are getting to your sales reps faster and cleaner, so you're not working stale records anymore."

They care about that. They don't care about architecture, um, behind it. You know, I think it's about being bilingual. You have to be fluent in the technical language, and then you have to be fluent in the business language, and you have to know which one you're speaking at any given moment.

The goal is to never prove how complex the work is. The goal is to make sure the people understand why it matters and what happens next. Phil: I love it. Um, m- c- can you chat about, like, the, um, Marketo Champion certification?

Like, there was a time in the MOPS community where it, it was the gold standard. Like, Marketo was the dominant platform. No one really considered other tools. Like, HubSpot was kinda kicking around, but, like, was seen as more of a tool for SMBs.

10 years later, this space is completely different, and not to dunk on Marketo, but there's so many other alternatives. Um, a lot of the arguments often are just like, the alternatives have better UIs, and now we're moving to, like, the, uh, the death of SaaS and no automation platform even caring about UI. It's all about the CLI. And so what, what are your thoughts on that?

Like, out- outside of the MOPS community, like, those credentials, the certification, like, it doesn't land the same nowadays, especially in this market. How are you presenting yourself and, and your creds right now? Like, and maybe chat about, like, how that pitch has kind of evolved throughout your search. Ashley: I mean, it used to land so much better than it does now.

Um, but it's, it's again, it's a translation gap, and I learned pretty quickly that leading with the credential in this job search- Wasn't working outside of our community, so I flipped it. I don't open with Marketo Champion anymore, I open with outcome. S- so something like, "I build and scale go-to-market systems that improve pipeline efficiency, conversion, and visibility for leadership." That lands with anyone, regardless of whether they know what Marketo is.

Then I layer in the credential with context. I'll say, "I'm a two-time Marketo Champion, which is a program where Adobe selects around 40 practitioners globally each year." Now, even if you've never heard of it, you understand how selective it is, and it means something. So the pitch has definitely evolved.

Early in the search, I was still leaning on the inside language, lifecycle models, system architec- architecture, platform experience, and I could see people's eyes glass over. Now it's less of, "I'm great at Marketo," and more of, "I solve revenue problems." The credential backs it up, and it, it doesn't carry the story anymore. Yeah.

7 - How to Recognize When a Take-Home Project Is Free Consulting - Phil: Do you have a portfolio, Ashley? Like, one of the pieces of feedback that I got from the episode was from folks that are in the enterprise world that were just like, "Phil, your portfolio idea was amazing if you work in startups, but, like, none of the work I do can be documented outside of current systems. I can chat about the fact that we have a CRM and I connected it to our automation tool, but I can't talk about the how, the why, the tools, the language.

Like, none of that stuff can be public. It's super confidential. There's PII involved," blah, blah, blah, blah, blah. And so for them, like, they're just pushing back on that portfolio idea entirely.

Where do you kinda land on that? Like, do you have a portfolio? Ashley: I'm gonna be honest, I don't have a portfolio, and I also have a hard line against unpaid work. So early in my career, I did one of those take-home projects.

I spent hours on it. I built out a whole strategy presentation. I gave them real thinking, real ideas, and they ghosted me, and I've never heard, I never heard another word. And, you know, I've talked to other senior directors recently that were in their job search, um, who've gone through the exact same thing, hours of work, real intellectual property, handed it over, silence.

And then you wonder, like, did any of those ideas end up in their deck somewhere? So, you know, I won't do it anymore. If you wanna know how I think, talk to me, ask me hard questions, give me a real problem to work through in a room, and I'll show you exactly how I operate. But I'm not gonna build out your next year of strategy on the hope that you turn it into an offer, because that's not an audition, that's free consulting.

I think the portfolio equivalent for mops people is the conversation itself. The way that you translate technical work or the questions that you ask, the problems you solved, and how you talk about them, that's the work, and you don't need a deck to see it Phil: I love it. I, I love your heart's dance on, on take home projects. I totally agree.

I was talking more like you thinking about the, sum of the work that you've done, right? Like that you just talked about the Marketo to Salesforce sync. Um, like I'm sure the company, you know, everyone can figure out that they're using Marketo and Salesforce. So, like, just someone, like, saying it in an interview, like, "This is the speed that we improved.

This is the dollars that it led to," it'd be pretty easy for you to put that in a slide somewhere. Like, show the before and the after, and the outcome of some of the after. Like, somewhat visually throwing that in your cover letter somewhere. Like, I don't know.

I, I think that, like, there's a non-creative element that people just assume mop's work is, and you think of all these, like, diagrams of, of the stuff that we do, and sometimes it's confidential or not. But yeah, I totally agree with the, the take home project. Ashley: Yeah. Phil: I feel like some folks in, in, in this weird job market right now have your strong feelings about it and, and share mine, and would just kinda concede this time around.

Like, I'm applying to 50 jobs every week, and I'm getting one interview request, and that one interview request says that there is gonna be a take home project, and it is unpaid. As long As it's kind of, like, not too crazy and it's not something that's obviously trying to extract free work for me. I've seen some companies pay for it. Some companies are even crazy.

Like, uh, one of my last bigger, uh, in-house roles was at WordPress and Automattic, and they have, like, a one-week trial period. Every single hire goes through this. And so for you right now, it'd be tough 'cause you're, like, on the job hunt. You have, like, a full-time job almost.

But it's like you get invited to their Slack, and you work on this hypothetical project, and you get to, like, Slack asynchronously with the people you would work with. You Ashley: Oh, that's cool. Phil: You go back. You make the changes.

So it's kinda like a two-way street, and they pay you for it. Like, the whole time is paid. It's not crazy hourly rate, but they respect the fact that they're asking work for you. And, and, and so I don't know.

But yeah, I totally agree that, um, you know, it is so uncool to just, like, demand someone to just, like, fix a, a bunch of their problems or come up with, like, free solutions, put it in a slide deck, present it to us, and then you never hear from them again. Like, so uncool. Ashley: It happened to my - one of my old coworkers that was laid off, and I'm like... And she was complaining about it.

She was like, "And then I've never heard about it." I'm like, "This is why I've told you, you don't do free work. We don't work for free." And she's like, "I know, but I really liked them."

And I'm like, "This is why." Phil: Yeah. Ashley: she was demand generation too, so she gave, like, strategy on what they should do and researched everything, and I, I know her work and, and I know how many hours she put into it, and I'm just like, "Ugh, I feel so bad." Phil: Yeah.

Ashley: But she found a job, so not with that company, but another one. Phil: Yeah. No, awesome. Uh, couple last questions for you, Ashley.

Like, you're, um... maybe folks listening are, like, a bit earlier in their career than, than yourself. Like, you're a bit more on the senior level side. Uh, like, you've had director level titles before.

Most of the job hunt content out there is kind of written for people that are earlier in their careers. A lot of, like, the stuff out of our, uh, job hunt survival guide was geared toward, like, mid-level folks. Um, the senior level search is a different problem set for me. Like, there's different competition, different timeline.

You are often asked to, like, submit a deck for strategy type work, and some of the conventional wisdom doesn't actively, like, help you that much. 8 - What Director-Level MOps Job Searches Actually Look Like in 2026 - Phil: So curious to ask you, like, what's the specific friction of being director level practitioner in this market that no one kinda warned you about because of how crazy things are right now? Um, something you didn't really see coming? Anything jump out to you?

Ashley: Yeah, the thing that nobody warns you about at the director level is that the job description stops reflecting the actual job. You know, in MOPS, you already wear every hat. I'm a strategist, I'm a therapist, I'm a plumber, I'm a janitor, I'm a hostage negotiator, you know, and that's just a Tuesday. But, you know, at a senior level, the job description gets more ambish- ambitious.

You know, they want someone who can build strategy, run the platform, manage the team, repeat, report to the C-suite, and then somehow do all the execution work. That's not one job, that's three. And then you look at the comp range and it's like they want a unicorn, but they have budgeted for a pony. You know, the overqualification thing has come up too.

Um, you know, but you feel it. You can sense when the comp range isn't gonna work and anyone says a number out loud and it's like there's this weird tension where you spent, you know, 15 plus years building expertise and now that expertise is being used against you. So the other thing that surprised me is how much relationship ca- capital man- matters at this point and how hard it is to demonstrate in an interview process. Like in every role I've built, I built real relationships with legal, IT, HR, sales, finance.

That cross-functional trust is actually what makes MOPS work. But, you know, it doesn't fit on a resume and it's really hard to prove that to a stranger in 45 minutes. Phil: Yeah. Such a good point, Ashley.

Uh, one thing that I did wanna let you riff on a little bit is networking. Like, it's a big part of part one of the series that we did. Uh, we tried to, like, make this as wide-reaching as possible. Like, not just if you're looking for a job, because sometimes there's a lot of stuff you can do when you're still in a role, and we tried to, like, gear this to people that were in a role that they didn't love right now.

Even though the market is crazy, it doesn't mean that you can't change jobs. And so, like, one of the thesis elements there was that, you know, it's always a better time to network when you don't need something from your network, and you're actually offering and, and giving people stuff. For a lot of folks that get laid off and it's a bit of a surprise and they didn't invest a ton in their network, y- you have that feeling of, like, awkwardness a little bit. Like, "Hey, can we grab a coffee?

I just got let go. Yes, obviously, I want you to, like, give me a heads-up or put in a good word for me if you hear from somewhere or whatever." What are your thoughts on, like, the whole networking thing? Like, how has your network kinda shown up for you when you needed it to deliver?

What do you - What advice do you have for folks that maybe have a job right now or are early in that layoff journey, um, when it comes to networking? Ashley: Yeah, so I have, um, you know, some really great people in my network and, you know, it's, it's - they've shown up in ways that matter to me and, you know, not just in ways of like, "I'm going to help you find a job." You know? It's, it's ways of, of different support.

So I have some people in my network that would do anything for me. Like one of my friends, I call a friend, she was a previous coworker, she is one of the best rev ops people I've, I've known. I have known her for so long, like we worked together so many years ago and, you know, she... I remember when, when her kids, she has twin boys, they were in elementary school, and they would sneak into the office and play hide and seek under our desks, and now those boys are going to be sophomores in h- in college.

So I mean, that's how long I've known her for, and I haven't worked with her in years. And, you know, she also married my husband and I. She was the officiant at our wedding. So it's like these people you, you have relationships with that you meet as coworkers can be lifelong friends and, you know, she would do anything for me.

That's j-just not a network contact, that's a person, and these are the relationships that actually show up when things get hard. But I have... To be honest, I'm not the best at keeping my entire network warm. I invest deeply in certain people, and those are the people that would do anything for me, and I would do the same for them.

But the broader network, the hundreds of LinkedIn connections that I have, you know, the people I've crossed paths with, I'm not great at maintaining, um, all of that with consistency. But I need to be, you know, more intentional about that middle tier. Um, not the inner circle because, you know, I've got that. Not the cold network, you know, that's a different strategy.

But the people I generally like and respect who I've just let drift, those relationships deserve more than an occasional like on a LinkedIn post, so I need to be more intentional about those. And then when I did post my, um, LinkedIn that I did get laid off, I did get a lot of reach out from the, the warm network saying like, "I will keep an eye out," you know- And, and all of that. So it is still good that, that they, you know, still have thought of me and, and, you know, some of those connections did come up.

Phil: Awesome. That's a really cool story to hear. Yeah, like uh, I got so many old bosses and, and coworkers that are just like lifelong friends now, and I know that i- if, if, if I was in a position where I needed stuff and, and vice versa. So yeah, the...

it's, it's more than a network sometimes and, uh, I appreciate your, your thoughts there, Ashley. Thanks so much for sitting down with me today and, uh, being open to, you know, breaking some of the stigma around getting laid off. I know, you know, it mustn't have been easy in the early days, but it sounds like, you know, you've, you've got your principles and you're holding dear to them and, uh, yeah, um, uh, look up to you for, for doing that. Thanks so much for sharing your time today.

Got one last question for you. We ask this, uh, everyone that comes on the show. You're obviously a marketing ops leader, Marketo champion, probably a GTM engineer, if you will, for anyone listening to the job applications. Uh, but you're also a mom, like you said.

9 - What Senior Practitioners Learn About Themselves During a Job Search Pause - Phil: One question we ask everyone is: how do you decide what deserves your energy at any given time, and what's your personal system for staying aligned with what actually makes you happy? Ashley: That's a great question. Um, I don't really have a system. I think I have a gut feeling, and I've learned to listen to it more.

Um, what f- actually fills me up is pretty simple when I say it out loud. Uh, traveling with my husband and daughter, good travel. Um, I like experience that feels special and intentional. Um, I love exploring, seeing new things, being somewhere, being present with the people that I love.

And animals, I have, uh, two corgis, Cheddar and Mac and Cheese, and uh, two cats, Jeff and Lester. And we are actually meeting a Saint Bernard puppy this weekend named Olive. Phil: Full house. Ashley: yeah, so that's potentially gonna hap- happen.

And my daughter is going to college this August, so the puppy is going to be replacing her. Uh, so we're, we're gonna replace my child with a, with a puppy. Uh, but I think the deeper answer to your question is, you know, the job search has taught me something about energy that I didn't fully understand before. You know, I spent years going from one job straight into the next one without ever stopping to ask, you know, "What do I really want?"

I just kept moving because that's what you do. And now I've had to force this pause, and I've gone for walks in the middle of the day. I've finished Buffy the Vampire Slayer for, like, the 15th time. Uh, and I started tearing apart my bathroom with some power tools that I just bought, and I'm adding some- molding and color drenching it in my, my office bathroom.

And I feel like myself, you know, more than I have in a long time. So I think my system is paying attention to what feels like me and protecting that, and not just with when I'm on vacation, but, you know, as a standard. Phil: Actually, I'm, I'm mad that we didn't start with the, the Buffy bit there because it would've been a great way to coin the visual analogy, uh, for this episode here. We could have done a whole, like, uh, vampire Ashley: that, Buffy.

Phil: I love it, Ashley. Really appreciate your time. Thanks so much for doing this. And, uh, yeah, we'll keep in touch.

Um, uh, I, I know that it's just a matter of time for you out there just about how crazy things are. Hopefully this, um, help folks feel a bit less lonely and, uh, yeah, thank you so much for, for being here and doing this.