Latest / Content, Briefly / The Writing Company: Michaela Cavallaro on Great Client Relationships
Transcript
- 0:00[on-hold music] Hey, and thanks for tuning in to another episode of Content Briefly. Very excited to have Michaela Cavallaro on the podcast today.
- 0:13She's an executive editor at The Writing Company, which is an editorial agency that's been around for thirty-plus years.
- 0:20She's been working there for nineteen years, uh, in a freelance capacity, then as an employee, and now as a partner in the business. And there's so much to unpack here.
- 0:29The Writing Company's client list is extremely impressive, like big, big names. One she mentioned was Fidelity, another was Intuit, among some others, which are very impressive.
- 0:39And I found it fascinating that, you know, the company, it's a little bit understated, I would say. It's not like a big flashy content agency.
- 0:46Like, these are former journalists for the most part doing, like, really high quality editorial work for these customers. The quality of the work is what brings them new business.
- 0:56Michaela and I talked quite a bit about how she manages the relationships with these companies.
- 1:01Like in one case, there's a company that's been with them for thirty years, and a few others she mentioned that have been with them for ten-plus years.
- 1:07So, like the types of relationships that go into, you know, a client staying on for that long become personal at some point.
- 1:14Like, these people are friends e-essentially, you know, and, and part of Michaela's job, which she describes, is finding all the ways that she can make their lives easier. Sometimes that's content. Mostly that's content.
- 1:24But just trying to like help them, you know, s-she's staying on top of like the trends that are gonna affect their work, thinking ahead on what type of content will be needed.
- 1:32Do they need to reschedule this or that based on upcoming legislation? All these types of things. So it's really interesting.
- 1:37Michaela's background as a journalist set her up perfectly for this, and then she goes into talking about how she got into the business development side of it, the relationship management side of it, and great conversation.
- 1:47It's really interesting. A little different from kind of the venture-backed B2B SaaS content that we're typically talking about, and I think there's a lot, a lot to learn in this episode.
- 1:56Before we dive in, just wanna quickly invite people to check out the Superpath Pro free trial if they haven't already. We have like fifty or fifty-five people on trials right now.
- 2:06The idea is that you can come in and kick the tires for thirty days for free, which means you'll get access to our eleven Slack channels, which are for members only, including our new AI channel, which is free right now, just popping.
- 2:17There's so much good stuff going on in there.
- 2:19Our monthly Superpath socials, which are our group calls with breakout sessions, our monthly one-on-ones where we pair you up with a peer for, for a quick chat, our weekly co-working sessions where we gather on a call and tackle some kinda like challenging project maybe we've been procrastinating on, kinda hold each other accountable to that, as well as our library of content and courses.
- 2:38So there's a lot in there. We wanna give you time to experience all of it before you decide if it's the right investment for you.
- 2:44Our goal is that the five hundred bucks you spend on Superpath Pro is the best investment you ever make in your professional development, and we wanna prove it to you first.
- 2:51So superpath.co, you can check out the link to the trial and get us s-set up there. Hopefully we'll see you in Slack. I'll get out of the way now.
- 2:59Really enjoyed this conversation with Michaela Cavallaro, and I hope you do too. Hey, everybody, Jimmy from Superpath here today with another episode of Content Briefly.
- 3:07Very happy to have Michaela Cavallaro on the show today. We met recently actually through Superpath Pro on a one-on-one call, which was awesome.
- 3:15It was great to meet, great to chat, and I thought, "We should do this for the benefit of others also," hence this podcast. So Michaela, thank you so much for being here.
- 3:23Would you mind introducing yourself and telling us a little bit about who you are and some of the work you've been up to throughout your career? Yeah. Thanks, Jimmy. I'm psyched to do this.
- 3:32So I am an executive editor and partner at The Writing Company, which is an editorial agency based in Portland, Maine.
- 3:40We have about eleven employees and I think at last count, twenty-two-ish freelancers, mostly writers and editors, a handful of proofreaders and copy editors.
- 3:50And I have been doing this for almost twenty years now, which is a little crazy. I started out freelancing for The Writing Company back in two thousand and six.
- 4:00At that point, I had left a staff job as a small business journalist and was looking to not have another full-time staff job. Portland is a small town, and I knew that The Writing Company existed.
- 4:14A couple of my coworkers at the business newspaper had sort of done stints at The Writing Company over time. One of them is now my partner in the business. There's three of us who own the business now.
- 4:27Yeah, so I came from a journalism background and slowly shifted into more corporate content, which is largely what we do now. Got it. So The Writing Company was in Portland, and you were in Portland.
- 4:39This wasn't like a remote thing. Are you able to talk about some of the clients you work with? Like, the logos on the website are big ones. They're very impressive. Yeah. Yeah.
- 4:46So we work with a lot of blue-chip companies.
- 4:50Fidelity is our longest-standing client, and they have been with us for our entire history, which it might actually be interesting to go into for a second, just the story of how The Writing Company was founded, because that's s- part of the story of how we ended up with these giant financial services companies as our clients.
- 5:09So Clint Willis, the founder of the company, was the Wall Street editor at Money magazine in the '80s and ear-early '90s. I'm sorry, Wall Street columnist.
- 5:19And so he was getting ready to leave New York, spent a bunch of time taking people out to lunch, like basically building his network of the people who were gonna become his freelance clients.
- 5:31And he and his wife had two little kids. They were living in Brooklyn. They were doing the, like, quit the rat race and move to Maine thing.
- 5:37And they came up here, and Clint immediately had more work than he could handle as a solo freelancer. And so he-- and one of those accounts was Fidelity. Oh, wow. This is going back to like '90s. Nineteen ninety-three.
- 5:50Wow.Yeah. And I'm not exactly sure who he knew at Fidelity, but I think, you know, c- at his time at Money Magazine, I'm sure had sources there who became clients or, you know, introduced him to clients.
- 6:03So early on, we started with this focus in financial services, and Clint was hiring young, smart kids out of the liberal arts schools up here, Bowdoin, Bates, and Colby, and basically teaching them how to be reporters.
- 6:21So he was sort of creating an editorial agency without knowing that that's what it was or that was a thing. Yeah. It was kind of well, well ahead of time. That's so interesting. Yeah.
- 6:32So over the years, the company sort of expanded and contracted for a while in line with what Clint wanted to do with the business and with the rest of his life. Sometimes, you know, a writer would say, "You know what?
- 6:45This isn't working for me anymore." Or Clint would say, "I don't wanna be the-- actually the boss of a bunch of people."
- 6:50And so he would sort of spin them off with a client or two and say, "Here, you take this client and go off and just be a solo freelancer." Oh, interesting.
- 6:58But one of the hallmarks all along was this idea of empathy for the writer and also empathy for our clients.
- 7:08It can sound a little cheesy, but we like really truly believe it, that our job as writers is to be looking out for the reader, putting ourselves in their shoes, and imagining what do they need to know, you know, how do we help them, give them just enough information, but not too much, answer the questions that we think they might have.
- 7:26And that's the approach that we've always taken with clients too, is to just try and be super empathetic.
- 7:32And in financial services, and I guess the corporate world in general, you know, people tend to leave and then go to a similar job at another company, and we have always really prioritized, you know, keeping track of those relationships.
- 7:47And often, you know, that's how we get new clients is, you know, an old client gets a new job and brings us with them. Right. So interesting.
- 7:56I feel like this is a good moment to pause and think about the arc of content marketing.
- 7:59Like I think when most people say content marketing today, they're talking about something very specific, which is a venture-backed B2B software company who hires people to do SEO content, case studies, and thought leadership.
- 8:12Like it's a pretty narrow definition. Like just thinking about it's 1993, you know, th-this is content marketing. It's just, it may-- Some of the terminology may be slightly different.
- 8:21The goals sound pretty much the same, I would guess. The mediums might be different. But really cool. I mean, h-has the writing company always pitched itself as an editorial agency, and has that- No. That's more recent.
- 8:33As content marketing has become a term that has been bandied about, we have sort of struggled to figure out how do we describe ourselves, because on the one hand, it would be really easy to describe ourselves by saying a lot of the things we don't do.
- 8:49You know, not a great sales tactic [chuckles] to be like, "Well, we don't do SEO analysis. You know, we are not marketers. Um, we are not graphic designers."
- 8:59And so that has led us to really, really lean into our strength, which is we are writers, and most of us are former journalists as well. Right.
- 9:09I'm so curious how that, your subject matter expertise, the journalism background, the editorial expectation that you set, has that insulated the writing company from some of the chaos that's been happening?
- 9:23I'm thinking specifically about AI- Yeah... and how that's affected content marketing over the last two or so years. Maybe a little bit. We had a super rough year in 2024.
- 9:35If you were to look at the year-end numbers, they look like fine, you know, like not a terrible year, not a great year.
- 9:41But the month-to-month numbers are in-- like ridiculous in terms of highs and lows, very, very bumpy.
- 9:48We think that's from a whole bunch of factors, and we're pretty sure that AI is one of them, and for a couple of reasons.
- 9:57One is, you know, as large language models got better and started, you know, use cases in content marketing started to become available, our clients sort of froze and were like, "Oh God, what do we do?"
- 10:12And there's a lot of, you know... So at this point, financial services is probably sixty, maybe fifty to sixty percent of our business. We also do a bunch in tech and also healthcare and sort of general corporate.
- 10:25Financial services in particular is really conservative, really risk-averse. And so those clients were-- a lot of them kind of froze while they were trying to figure out, what does AI mean for our business?
- 10:39Can we use it? Do we need to say we can't use it? What does that look like? Right. That's so interesting. What type of content-- Like what's your sweet spot?
- 10:47You know, like what type of content do you do for companies that like the writing company, you know, nails it every time? Yeah. I think more than a specific type of content, it's a specific relationship.
- 10:58We work best when we are sort of collaborating with someone closely as part of their team. Gotcha.
- 11:05Um, and to the point where it gets to like technically they work for the big giant company and we work for the writing company, but practically on a day-to-day level, it feels like we're all working together for the same outcome.
- 11:19We have a big bank client that's been a client for, boy, over a decade, that the relationship has ebbed and flowed, and right now we're doing everything from, you know, a landing page for a regional division based on a specific asset to big white papers, and so-- and sort of everything in between, case studies, social posts, all of that.
- 11:45And it works for a couple of reasons. One of them is-Our team can sort of expand and contract as we need to meet that client's demands.
- 11:56And also because the group of us on that project are all former journalists who are used to picking stuff up fast and a little bit knowing how to fake it when you need to on the phone with somebody who really knows their stuff, and then figure it out afterwards, we can hang with their SMEs and then create a really great piece afterwards.
- 12:20Where does AI fit in for you right now? Like, are your clients averse to it because of their subject matter, or are they like, "Go nuts, see if it saves us money or gets us better results"? No one has said go nuts.
- 12:32Other than that, we have a pretty decent range. We have some clients who have written it into their contracts that absolutely no AI is to be used at all.
- 12:42We as a company have a clear expectation with our writers that AI-produced writing, unless you are specifically told to use it for a piece, that it shouldn't appear in your work.
- 12:55At the other end of the spectrum, we have an agency client with an AI platform that they've hired us to be sort of the expert humans in the loop, so they are working with their clients to zhuzh up existing pieces, you know, running it through the tool, and then we're on board to make sure it's all still correct and also make it speak to readers in a way that AI, at least as we're seeing it, can't do yet.
- 13:28Yeah. Yeah. Okay, that makes sense. You know, I was just thinking today I was working on a piece for Superpath, and I've been doing all of my writing in a tool called Lex. Mm-hmm.
- 13:36Which is, you know, it's a document, but then the sidebar is all these AI functionalities.
- 13:41And I've gotten so used to that now that I ended up in a Google Doc later in the day, and I was like, "I sort of feel alone here." [chuckles] You know what I mean? Right. Yeah.
- 13:50I can't believe how quickly that happened, you know? Yeah.
- 13:53But I can imagine that in your world, one of the other things I was gonna ask you about is like, what constraints do you bump into working with these blue-chip companies, you know?
- 14:00Like, that sounds like that is potentially one of them, but, like, these companies are, as you mentioned, risk averse. Like, do you run into other, like, legal compliance issues?
- 14:08And how, yeah, how do you navigate all of that? So that is more of an issue with financial services content than anything else.
- 14:18And we've been doing it for so long that we can anticipate a lot of the kind of edits that compliance is gonna have. You know, you never wanna say an investment will return X. Yeah, yeah. You say it may return X.
- 14:32So a bunch of that we, we just know, and we teach our writers. And then the rest of it is just being really comfortable with slow processes. Got it. And kind of commensurate with that, slow payment sometimes. Um- Got it.
- 14:46Yeah. Yeah. That makes sense. I spent a brief period of time at Intuit working on the QuickBooks blog, and we ran into that. Yeah.
- 14:53The last job I had before that was, like, a tiny little startup, which was go as fast as you possibly can, and then I was like, "Someone has to review this? What?" Uh, it was crazy, but you get used to it. Yeah.
- 15:03They're one of our clients now, actually. Interestingly, we're doing a bunch of writing about AI, about how they're using AI internally. Oh, interesting. But we don't use AI to write about how they're using AI.
- 15:15[chuckles] AI is so complicated these days. So interesting.
- 15:18Do you find yourself tempted to go into content strategy, keyword research, reporting, all this other stuff that could potentially help you upsell your existing clients? It's a conversation we have from time to time.
- 15:32Honestly, the one we have most frequently is design, is about whether, you know, we should have in-house design.
- 15:38That's kind of the most frequent request from clients, and by frequent, I mean maybe twice a year for something more than... You know, we have a couple designers that we work with from time to time.
- 15:50You know, so it's only occasional that someone will even ask us for more than that.
- 15:56We really feel like, though, the thing we keep coming back to is that what sets us apart is our emphasis on the craft of writing and on the, on being good reporters, you know, when we're talking to SMEs.
- 16:12And so we just sort of keep coming back to that as that's the thing that sets us apart, and that's really where we focus. Yeah.
- 16:20You know, one other thing I wanted to ask you about was how to develop and maintain good relationships with your clients. So, like, you know, ten, gosh, 12, 14 years ago, I worked for an agency in DC.
- 16:31This was, like, one of my first content jobs, and it was actually called, like, custom media, not content marketing at the time.
- 16:36And we worked mostly with professional associations, and they would print magazines, and like the team that I was on was working on digitizing, you know, getting websites launched, like thinking about SEO, like, for the first time for most of these organizations.
- 16:50And it was very interesting. The company had been around at that time for probably 30 years, and observing the way that the company leadership took care of the clients was really interesting. It's a lot of- Yeah...
- 17:01coming over to my house for dinner, you know, going out to a nice restaurant.
- 17:05It's like flying to them and do-- playing golf or, you know, all, like, really, like, these relationships were incredibly important, not just to the business- Yeah... but to the people running the company as well.
- 17:15Mm-hmm. I just thought, I mean, I really respected the way that they took care of their clients.
- 17:18And I'm thinking about the writing company working with Fidelity for 30-plus years and some of these other, you know, you said one company, 10 years. Like, these are, like, real relationships.
- 17:26These are not transactional. So this is a very, very long lead-up [chuckles] to ask you about, like, what's your perspective?
- 17:31How do you go about, like, you know, forging and then keeping these strong relationships with your clients? Yeah.
- 17:37I have another cheesy answer to this, but it's another one that we really believe, is that our job is to make their lives easier.
- 17:44Like, these people have impossible jobs at, you know, marketing people at big corporations have a million people asking them for stuff. They're under-resourced. They're getting, you know, they need everything yesterday.
- 17:59Yeah. And so we try really hard to-Be a solution to their problems.
- 18:05And so that is everything from, you know, like I saw something today about the date that Canadian-- you know, that Trump is gonna announce the Canadian tariffs got pushed back a little bit, and I know that that's gonna affect an interview that I have scheduled in a couple of weeks.
- 18:22So after this call, I need to reach out to that client and say, "Hey, I don't know if you saw this, it seems like we should push that interview with the SME a couple of days."
- 18:31So it's like that kind of broad awareness, but also just like we like working with [chuckles] with these people. Yeah, yeah.
- 18:39And so each of our leader-- the folks on our leadership team has an editorial role and then also a role in managing the business, and I'm in charge of business development.
- 18:52And so, you know, it's part of my job to keep track of people and, and then encourage my colleagues to do the same. And it's something that I just have, like, I just like doing it.
- 19:03I like connecting to people, I like meeting new people, I like keeping in touch with people over time, and it turns out that that's a great business development skill, which, you know, was news to me [chuckles]
- 19:14in my forties. That's awesome. Yeah. Yeah. That's awesome. You know, as you think about like the top like two or three challenges you deal with on a day-to-day basis, is it evergreen problems?
- 19:25Is it like, we gotta get this article done on time, you know, or is it ki- emerging problems, uh, or opportunities, meaning like, what are we gonna do about AI? You know, how do we reposition the company if needed?
- 19:35Like that type of stuff. I think it's mostly evergreen problems of like, do we have exactly the right people we need to get X thing done next week with like a flavoring of...
- 19:49Like there's always an emergent, I wouldn't even go so far as to say crisis, you know, but a thing to keep an eye on, you know, pivot to video, for instance- Right...
- 19:58to pull one out of the, you know, the historical, you know, who's gonna take-- be the point person to pay attention to, you know, what's going on with AI tools, for instance. Like I've g- uh- Right...
- 20:09one of my partners is the designated guy to worry about AI. Right. That's cool. I like that because it's like- Yeah... something like AI is like too big for everybody to just worry about- Yeah...
- 20:19a little bit all the time, you know? Exactly. Exactly. And it gives the rest of us freedom to worry about other things. Yeah. Yeah. [chuckles] That's so interesting. And I chat with a lot of content agency folks.
- 20:28Like we have some agency customers through our marketplace, and we have agency owners on the podcast from time to time, and the agency world is pretty crazy right now.
- 20:37I mean, I feel like a lot of companies-- Well, there's different types of agencies.
- 20:39Like Th-the Writing Company, I would say the history of it, you know, kind of the niche, the niche nature of it, the editorial focus is pretty different actually than most of the folks I talk to- Yeah...
- 20:49who are like content agencies, like less than ten years old, are-- AI is all they think about, you know.
- 20:54Like how do we either get stuff done faster, you know, save money on content production and pass that on, or save money on content production and keep it, you know.
- 21:03Like there's some like, like should we launch an AI specific service? Should we just infuse it in the other stuff we do? Do they need to be separate? Like these are questions that like, I'm not envious of.
- 21:14Like they're really challenging questions to be thinking about. Like, do you have agency owner friends that you kind of commiserate about this stuff with? That is a great question. Not really agency owner friends.
- 21:26We have-- I guess there's one or two I can think of. It's more we have friends at other agencies who aren't necessarily the owner or the founder, but people we've known for a really long time. Yeah. Yeah.
- 21:39You know, sometimes they're clients, sometimes they're just people we've crossed paths with, where we will definitely, when things get squirrely, like last year we did a bunch of like, "Hey, let's just kind of make the rounds and let's find out, are other agencies having this really weird year like we're having or is there something wrong with us?"
- 22:01But it's super invaluable to have those folks out there to, as a reality check. Yeah. Yeah. Totally. That makes sense.
- 22:09I certainly haven't found anybody, at least in my experience, that just like figured it out, you know. Like m-meaning AI specifically, like what are we gonna do about this?
- 22:16How do we, whatever, find ways to monetize or pass things on or whatever. Yeah. Complicated question though.
- 22:22We're all just like, we were talking about this earlier today, you know, we're a bunch of English and History majors who were good writers and ended up also weirdly being good at this client management, corporate, you know, navigating corporate clients, like this weird hybrid skill set.
- 22:41So we're sort of always just making it up as we go along, you know, as smartly and thoughtfully as we can. But, you know, also we're just making it up. Right.
- 22:50You know, my great hope with all this AI stuff going on is that there will be a silver lining, which is that the craft of writing is appreciated more than it has been- Yeah...
- 22:59in the past, or at least certainly over the past couple of years. Yeah.
- 23:02And that an emphasis on storytelling and people and subject matter expertise will be highly, highly in demand as all of this shakes out and we have a be- little bit better understanding of, of what's going on.
- 23:16So with that said, I think you're very well positioned. Thank you. Yeah. And I think we, this time last year, I probably would have said, "I can't talk to you about this right now." [chuckles] Yeah.
- 23:26Because it w- it was just so strange, but now I think we're starting to see that, that companies are not seeming so paralyzed and are seeing like, "Okay, no, we do still need to communicate to our audiences, and we need to do it in ways that maybe AI can help with around the outer edges, you know, for research or brainstorming, but can't get to the storytelling and the, you know, putting yourself in the shoes of the human being who's gonna read this and understand what they're looking for."
- 23:57Right.
- 23:58Do you have any advice maybe for agency folks, maybe for freelancers, maybe for ac- really any content marketer, you know, based on what you've been doing at The Writing Company for the past, I guess-Closing in on 20 years, right?
- 24:092006. You know, it's a different style than, I think, at, at least what we primarily are seeing in Superhave, which is, like I said, venture-backed B2B SaaS.
- 24:18Like, are there things that folks who are not in this editorial world should learn and borrow from folks like you and The Writing Company? I mean,
- 24:27I really think our approach to the way that we work with clients is-- and which extends to the way that we work with each other internally, is just, like, we try to be a good community, you know, a community of people who enjoy working together, like, take the work pretty darn seriously, but don't take ourselves that seriously, and try to extend that ease both to each other and to our clients.
- 24:54Feel like that's what makes the business successful ultimately, and it's why I wanna come to work every day- Yeah... is because of that vibe. That's awesome. Yeah. I love it. Mikala, thank you so much.
- 25:05So we did this a couple weeks ago. Now we get to do it again and record it. So thank you for taking the time twice now. I really appreciate it, and I'm glad other folks will- This was so fun... get to hear this now.
- 25:13Where can we send folks? We'll send them to The Writing Company website, of course, which I think is just thewritingcompany.com, right? Yep.
- 25:18And also, you're publishing content there too, which we should direct people to. I mean, you know, it's the cobbler's kids have no shoes. Yeah.
- 25:28[laughs] Uh, perpetually on my to-do list for two weeks now has been rolling over, figure out next blog. [laughs] Yeah, yeah. So, so we do put content up there.
- 25:38Um, it's almost all-- or, you know, it's all focused on our writing principles and the way that we think about writing.
- 25:45The big hit of that, of the blog and our semi-occasional marketing email is an annual list we make of the best things that our team has read in that calendar year.
- 25:57So it's not things that have necessarily been published that year, just, like, what's your favorite thing that you read this year. So that one is up on the blog. Uh, okay. Well, people should go check that out.
- 26:07I'm gonna go check that out because you know what? It's actually really hard to find good stuff to read nowadays because all the social networks don't want you to share links, so nobody shares links anymore. Right.
- 26:15You know, that used to be the fun part of Twitter, and now it's just everybody- Yeah... or just telling them. Yeah. Yeah, whatever. And we, we now have clients asking us, "When is that email gonna come out?"
- 26:26Oh, interesting. And we're planning actually this year of inviting clients to like, if you read something great, you know, tell us and submit to it. So it's like, you know, born out of, "Oh my God.
- 26:40W-what can we say in a year-end email?" Yeah, yeah. It's not just like, "Have a restful end of the year. Thank you for your business."
- 26:47Out of desperation came this idea that turns out to do all the stuff that we are trying to do as a business, like, you know, share love of good writing, build community. Love it. I will check that out.
- 26:58Actually, and one last side note. In our-- we have a reading list channel on Slack, which-- and the idea is if you find something you like, post it, so other people can read it.
- 27:06And I recently used Claude to create a Slack app that would scrape the channel and pull all the links out.
- 27:12So there's like eight hundred and fifty something links that got pulled out, and people were loving it, and I was thinking like, "Why is it so hard to find stuff?"
- 27:19You know, like, I think to, like, look at-- read a, a blog, which now seems almost like a novelty because it's not a LinkedIn post, which is, like, perfectly optimized for the algorithm.
- 27:28You know, and you can actually go read, like, great, like, great writing, like, really, like, truly great writing, like, mostly is still on blogs. So anyways, a side note, but people can check that out too. Yeah.
- 27:37We'll have links to all that in the show notes. Mikala, again, thank you so much. Really appreciate your time, and we'll see you in Slack. All right. Thanks, Jimmy. Take care. Take care. [outro music]