Forgo Anything Fancy—A Conversation with Jillian Wood at Coconut Software

Chris Gillespie | April 4, 2022

Prior to running teams that marketed meeting booking or proposal software, Jill blogged about beauty. It’s one of my favorite facts about her, and reinforces an idea we subscribe to at Fenwick: The most effective content people tend to have atypical resumes.

Jill is also one of those rare B2B content marketers with actual publishing experience who knows what it takes to run an advertising-supported magazine. She has hired us four times, making her something of a Fenwick patron saint, and I can always rely on her candor.

In our interview about content operations, she discusses why building an idea pipeline is a matter of hiring obsessive collectors, content’s role in driving the right deals, and why to be your most successful, you’ll have to control things beyond your control. (Good luck.)

Jillian Wood is Director of Content Marketing at Coconut Software, a 90-person startup that builds appointment scheduling and lobby management software for banks and credit unions. This interview has been lightly edited for brevity.

Forgo anything fancy and do what works

Jillian: When I hear content operations, sometimes I just think "managing a content calendar." It could be someone’s title at a very large company—so that some people can just focus on the writing, or the many other things content marketers do.

But I’ve mostly been at startups where, if you're a content marketer, you’re doing it all: writing, strategy, creating processes, managing freelancers, and thinking about promotion (because you probably own social, too).

For me, these processes have always been pretty informal and mostly in people's brains. I’m definitely for systems, templates, and standards. But sometimes, I forgo fancy operations for the sake of production and publishing—which can definitely come back to bite you in the ass if you’re not careful. (I’ve done this to myself a lot, especially while moving from individual contributor roles into leadership roles.)

I started as an editor of two B2B print publications

Jillian: I did a postgrad in publishing after an English comms and business degree, and planned to be a book editor. But I realized I liked reading books, not making them. So I eventually ended up in magazine publishing, and I got a full-time job as the first-ever online editor for two B2B print publications, which I really enjoyed.

Read one of those publications: Salon Magazine

I discovered that I knew how to help clients tell their stories, but also add a spin our readers would like. So then I thought, “I should just be doing this for brands.” And I fell into tech because that's where the content marketing roles were. I just heard that title and thought “that's what I want to do.” And somehow, tricked some B2B software people into thinking that this B2B beauty writer could do it.

Good ideas come from good hires

Jill: How do you build a pipeline for ideas? I hate to say it, but it's always highly reliant on the people you hire. Are they the type who can look around the organization, keep their ear to the ground, pick up on stories and trends, and keep them in their back pocket? Or, know when to release that story and where? Or, gather small bits of knowledge and build them into something bigger—or take a big meaty thing and chop it down?

"It’s always highly reliant on the people you hire. Are they the type who can look around the organization and pick up on stories and trends, and keep them in their back pocket?"

I feel like the most integral thing to the whole system is, did you hire someone who's really curious and loves curating information? Because if you want a regular publishing cadence, I don't know of any system in the world that can make someone into that person. Repositories are great, but you need someone who’s a natural mental cataloger.

Is your blog a lead generator or a publication? Because those are two very different things

Jillian: What is your program’s direction? What are you hoping happens? For what audiences? What goals are you being measured on? Knowing the answers to these questions will change your operational approach. Again, I'm in B2B and beholden to more demand gen stuff than brand stuff. In my first role, we were selling advertising and it was just about eyeballs. Now I'm selling software and it’s about targeting buyers.

Starting in publishing was helpful, though. The ability to coordinate a million little pieces of information and think weekly, small picture, and then long-term, big picture about things I wanted to do—SEO projects, et cetera—taking that into B2B tech is actually really helpful. But then you need to develop a strong filter and understand how things are sold, because if a million views doesn’t become one MQL, you’ve failed.

I don’t keep a real content calendar. Nobody needs to see much more than the high level

Jill: I don't keep a very strict content calendar at all because things shift. New opportunities come up. I mark the big pillars and figure out the social posts each week. We'll figure out the blogs. Some will be for SEO. Some will be thought leadership, and some will be bones we're throwing the sales team. (Heaven help you if some of them are your CEO's less-than-stellar ideas that you simply cannot keep the f— away from.) I don't need all of those details on a calendar. I just need the big picture. No one really needs to see more than that. People think they do, but it changes so much it’s almost not helpful (outside your content team).

The only reason I recommend actually having a weekly calendar at all is to track promotion across channels. Like, what are we all doing to promote our messages?

You need a top-down plan and pillars

Jillian: Whether it’s yearly or quarterly, you need a strategy from your VP that ties back to company goals. Who are we trying to connect with? Where do they sit? What do they care about? That can be persona-based, that can be industry-based, that could be company size-based. There's a number of ways to slice it. But you need to start with that.

From there it’s, what do we want them to do? And dividing content by where it fits in the funnel for that persona. Usually, you’re handling the top and middle of the funnel. I don’t love when content people are assigned to do bottom-of-funnel things like brochures because they’re not experts in the product, and aren’t supposed to be. Product marketing should write that.

Right now, I’m in a bit of a pillar phase. If our team is launching a new product feature for a particular audience that requires different messaging, I’m creating a content pillar around that, so we can check that it matches what they want to hear.

Pillars won’t work if nobody else uses them

Jillian: Your plan and pillars won’t work if the rest of the company isn’t rallied around them. If I’m creating all this content but sales isn’t reaching out to those people because they’re focused elsewhere, if demand gen isn’t distributing it to those titles in their ads, if customer success doesn’t know how to help people use the product for that purpose, that content is not helping anyone.

I know we can only truly control our own distribution channels, but if nobody else is really selling what you’re saying, it likely won’t perform, and you’ll never know if you had the right approach.

Sometimes, you’re wrong about the pillar. What can you do?

Jillian: At a previous company, we launched this amazing new pillar story. Sales sold it, we got people in the door, and only later found those customers churned at a super-high rate. So even sometimes when everyone acts in concert, it can still not be the right solution. That’s not necessarily within your control as a content person, but you can combat this by spending a lot of time talking to customers, understanding the product, and knowing there’s a risk.

If customers object, sound the alarm

Jillian: If you're ever hearing from customers that a product or message is not a fit, you should be sounding the alarm. Because at the end of the day, pursuing this idea will waste your time. Sometimes leaders might kick back on that and say, “You just need to get your customers talking like you.” To which I say, sure, if you’re building a category. But you’re not always building a category, and sometimes it’s just not a fit. There’s a balance. Yes, you want to lead the market. Yes, you want to challenge people’s assumptions. But if they don’t like it, well, listen.

One of the worst situations you can be in is where the messaging gets so far away from the product that it’s not even true anymore. Great marketing and brand with a product that can’t actually deliver is a risky play.

I will do as little as I can to hit my goal

Jillian: I’m always telling people I will create as little as is necessary to hit my goals. You can often make your best content do double or triple the work by breaking it up and running helpful repeats. You should always rerun your best hits.

If someone thinks more content is always more, they probably aren’t looking at the numbers. If you rush out a bunch of mediocre content, you squander your opportunity. You’ll run out of audience mindshare.

Plus, there’s this fake belief that every buyer needs 20 pieces of content to decide to buy. In my experience, people don’t need that much to get on a demo or call. It’s more like 5-10 pieces. What they need is help deciding why you, why now, and how do I sell this internally? (Very bottom-of-the-funnel stuff.)

I love having a strong filter on what we create because if you don’t, your operational engine is quickly overwhelmed. More is not always better.

People don’t care about data as much as they say they do

Jillian: I’m not sure anyone in content marketing analyzes their data enough, and I’m certainly guilty of it. I often ask people to show me the data on their idea, but I often don’t I stop to look at whether things are effective myself. Or whether it’s time to change what we’re doing.

The idea that content data matters is kind of a lie, in my experience. We really should look at it more and use it to guide our thinking. But I often find no one in your organization will ever question you about it. They’ll ask, “When’s this thing going out?” or “Where is that press release?” And I think to myself, if only you knew the stats on that press release. But if I tell you, you won’t care. We content folks can often get a free pass on data, hilariously. But not on how much we publish.

Do it all and you’ll be well liked, but not successful

Jillian: I find that when I get fuzzy requests, or I see other teams not aligned to the same audience, or there’s a conflict between what demand gen is planning and what product is creating, I dig in my heels. You have finite resources. If you do everything everyone asks without questioning, you may be well liked, but you won’t be very strategic or successful. Obviously, that’s not entirely all on you. But if you want things to work, it sort of is.