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Episode #135
Sara Wilson

A Digital Content Strategy That Works For Consultants

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With almost everyone online, the digital world has undeniably become very competitive for businesses. That is why for you to stay afloat in this day and age, you need to be on people’s radar. In this episode, Michael Zipursky introduces us to Sara Wilson, the founder of SW Projects, where they craft content strategies and unique creative ideas for brands and digital publishers. Sara shares her experience and expertise with us, leading the way towards her journey of starting her own consulting business and giving out the digital content strategy that helped her reach success. She talks about the importance of writing to connect with others and nurture those relationships as well as doing speaking engagements and creating content for external publications. Start to get yourself out there strategically. Learn some key pointers on how from Sara in this conversation.

I’m here with Sara Wilson. Sara, welcome.

Thank you for having me, Michael.

Sara, I’m excited about this. You worked in a lot of managerial positions places like Huffington Post, Facebook, you’re now the Founder of SW Projects. You work with clients, well-known brands like National Geographic, the New York Times and WeWork. You’re an expert in digital content strategy, helping brands to tell their stories and to build communities. What I found interesting is your former title in a corporate role was Strategic Partnership Manager, which to many sounds like a sweet, cool gig. What was it that made you want to leave that behind and start your own consulting business?

Thank you for that lovely intro. It was a sweet gig. I would never ever represent it as anything less than a damn sweet gig. I was there for a few years. I joined when there were no partnerships teams, so I was one of the original hires. What that meant at that time was I was one of the first points of contact for anybody trying to get in touch with Facebook. You’re a public figure or a publisher. Previously, it had been working a friend contact and hoping that you would get somebody to help you take down an imposter Facebook page. They were creating this team and I was hired to run lifestyle partnerships. What that meant was I could make it up because they didn’t know. It was an amazing opportunity to say, “Here’s what I think that means.” Lifestyle typically means food, fashion, home, health, travel and all those categories, but it’s like, “Where did I see the biggest opportunity?”

For a few years, I worked almost exclusively on Instagram and fashion because I saw this insane moment happening in the fashion industry where this platform, Instagram, which had been bought by Facebook, was organically disrupting the entire industry. That’s what was exciting to me. I was able to guide that and be like, “We can make Instagram the top social platform for fashion. Here’s my strategy for doing that,” and then we went on going and executing on that. I switched over and worked on things like food just as the rise of food video came. You remember that moment when the entire Facebook Newsfeed was dominated by shot top-down food videos that were working with the best big foods of the world and Tastemade. It was a heady time and it was also a time where everybody was excited by this new technology and didn’t know how to use it, it wasn’t as sophisticated. It was an awesome educational opportunity for me because I love to teach. I also love to learn from the partner.

Don’t get me wrong, it was sweet also working for Facebook. All the stuff that you hear is true, the free food, the free this and that. It was amazing but like all good things, it had to come to an end. That was a reckoning because I was like, “This is amazing. Why would I leave?” That was about I saw a shift in two ways. The first was that brands were coming up, leading conversations that publishers used to be the exclusive arbiters or the leaders. I used to work in publishing and magazines and now, brands like Bumble or Casper. For a time, we were leading these conversations about entrepreneurship, sleep or what it means to be a woman. That whole narrative was shifting on their shoulders and yet there was no one, or at least no one that I saw, to help them navigate it. That wasn’t part of my wheelhouse at Facebook. I wasn’t working with brands. It was a cool opportunity that I saw and I was like, “I’m well-positioned to do this.”

Constantly writing externally for press outlets puts you on people’s top of mind because the worst thing is to have to sell yourself. Click To Tweet

The other thing is that I had been on Facebook longer than at a certain point, 89% of the entire company. We had these little counters on our profiles that said how long you had been there and everyone else. I thought, “I’ve been here, which means that I have more experience than 89% or even more of the company. That doesn’t feel like a place I can learn. Who am I learning from? What is culture?” That’s very typical in that growth type of company. It wasn’t for me as the company got larger. I’m much stronger in a smaller environment. That’s why I decided to leave, those two reasons.

Sara, when you made that decision, what was the first thing that you did to build your consulting business? Where did your first client come from?

I had the good fortune to consult from within Facebook with the permission of the company. I had an amazing boss. She gave her blessing and said, “Sure, as long as it’s not interfering with your day-to-day work.” I had to go and get permission from Facebook Corporate. They were like, “Yes.” I had a bunch of clients wherein a low stakes way, figure out how to price, how to work with them. What were my offerings? What do they need? All those things that a lot of people work out in their first year, I was working out while I was employed.

How did you do that? How did you manage that? Some people would hear that and go like, “I’m busy and tired from my job, there’s no way I could do that.” What did that look like for you? Were you working evenings or weekends?

It’s all of the above. I had a busy job. Working at Facebook is not a light job. It is fuller than full-time like most jobs nowadays. I was traveling a lot. I also was able to take advantage of nights and weekends. I would get up early. I figured out how to make time. Keep in mind, I was not taking on a full client workload that you would if you were full-time. I was doing what feels a manageable amount. I had one client at a time, then a few months would go by and I have another. I had 5 to 7 over the course of a year. It wasn’t coming in every day to those companies or even at all. I would do one meeting in the morning early and then do strategy work at night. It was manageable and honestly, had it not been, I couldn’t have kept it up. What was the moment that I left? It was a growing realization that I could do this over the course of the year. It was my first or second client that Facebook said, “We think this is too much of a conflict with our own business, so we’re not going to give it our blessing.” I was like, “Okay.” I realized like, “This is my moment.” Either I can say, “Sure, no problem. I won’t work with you,” or, “This is a good opportunity to think about is this the time to leave?”

When that happened, you made that decision, “I’m going to now no longer work at Facebook, I’m going to go all in to consulting,” you had 5 to 7 or so clients that you’ve been working with so you’ve built up some experience. You have an understanding around your offerings, your messaging, who you want to be working with and the price points. What did you do to go out then and get more clients enough to make it a full-time thing to replace your income and go beyond that?

CSP 135 | Digital Content Strategy

It didn’t happen all at once. I left with two clients at that time. Those were going to last me a few months and I felt like, “Okay.” It wasn’t a perfect situation. In my head I was like, “I will have five clients when I leave.” It was somebody who told me it’s never going to be perfect. At a certain point, you need to make the leap. I was like, “This feels good.” How did I get more? It is a combination of doing many things that I am still in a constant process of tweaking. I will tell you that I will walk you through what those things are, but I don’t think I knew all of these things coming out day one. One is looking closely at the network that I have and that I’ve built over many years, whether it’s from journalism, publishing or the platform context I created for myself working with a ton of influencers and publishers. I went out to some of those key relationships and those key people that I had worked with who knew me.

Some of them came to me after I left Facebook and set my goodbye email and wanted to have coffee and discuss. I picked up a couple of clients that way. I would say first and foremost, I think of my network and the relationships in it as the reason I’m doing what I’m doing. I treat, nurture in that network like a job. I’m big on the follow-up. I consider a lot of those people friends. I nurture friendships with some of them. The ones that aren’t friends, I try to be as available and in their face as possible in a non-annoying way. I do that by writing. I write a newsletter as often as I can. I’m more constantly writing externally for press outlets to try to put myself top of mind because the worst thing is to have to sell yourself.

Sara, I want to dive deeper into the one that you said there about relationships because your background is relationships and partnerships. You clearly know what you’re doing there. As you launched your business, you leverage that even more to go out and get more clients. I want to get tactical here. How are you doing that? A lot of people will say, “I need to do a follow-up.” What does that look like for you? Are you using a CRM to do that?

No. I should be. I should have a more strategic way to do this, but I will tell you there are a few different things I do.

Walk us through to what you do and how you manage it.

I spoke about writing and it seems not to connect but it does because that nurtures a lot of relationships. Number one, I write as often as I can. That gets my name out there. It helps to show people that this is how I think.

Writing nurtures a lot of relationships. Click To Tweet

Where does the writing go? I know we’ll talk a little bit later about some of the external outlets but you’re putting this mainly what’s your blog or to LinkedIn.

When I started, it was a newsletter. I thought about what is the thing that’s going to bring the most value to the people that I want to reach, CMOs, founders and people in marketing. I did a lot of marketing newsletters. I thought it’s got to be concise. It’s got to deliver value. I came up with something called the short of it, which is my take on one digital content trend or moment that’s popping. What is it? Why should you care? I had to leverage it for your own business.

How often is that being published? 

When I started, it was great ambitions to do it every other week. I realized, “I shouldn’t work hard on these.” It started to be monthly. I’ve switched my strategy entirely where I take a topic, pitch it out and place a story in an external outlet so that it has that press kit and then rounded up and give it extra value in the newsletter. This happened where I placed a piece in Harvard Business Review about digital campfire, which is a term that I came up with for this new moment that is happening across the social landscape which is younger audiences leaving social or retreating from social media and moving into more small communities. I named it, pitched it, that piece ran, then I ran into that up in my newsletter. I added extra content and pushed that.

That strategy going forward is the best. How that connects to relationships is I sent that out and many people who I had met over the last few years got in touch with me to reignite conversations and potentially down the road, hire me or not. I do think of it as an essential ingredient. Another big thing is I seek out and accept opportunities to speak or do interviews. I do love working with early-stage founders but that’s not my bread and butter because they can’t afford me. I love hearing what they’re up to. I love bringing value to them in other ways. I host a series at a VC Fund here in LA, which is a Female Founders Dinner Series where they organize it all and bring in fabulous, top, amazing guests.

I get to show up and with a little prep, interview them and I have that relationship now. I’ve met them in a non-business context that I’m not selling them but it’s a relationship. A lot of stuff has come out of that. I would say I go to key conferences and events but not all. I’m strategic where I know there’s going to be high-value groups of people and I hate what that term means. It’s a little vague but you can tell by the organizers and who’s doing it. I don’t think it makes sense for me to run myself ragged going to everything but I go to them, try to make genuine connections, then I follow-up. I’m making the connection with something more than just, “Here’s who I am selling.” You’re going to get to know me like, “Am I bringing value to your life at this moment?” We have a relationship. The way I stay in touch with them is through newsletters.

CSP 135 | Digital Content Strategy

When you say in terms of the follow-up, is the majority of your follow-up done through your newsletter? Are you doing a lot of one-to-one emails or text messages?

A lot of emails. If I need you, we’ve had a conversation, I’ll always follow-up unless something has gone terribly awry and I’m completely too busy. I make a point to follow-up with an email. I’ll often send a card on holiday time. Something that’s personal to them and keeps them in mind if they’ve helped me or if I’ve been in the mix with them. That can be helpful.

How do you follow up because you’re not using a CRM? How do you remember who to follow-up with?

I come home for a conference, I have business cards, I place them on my table, I look at them, email those people, then I put them into a Google Doc like Rolodex. That’s how I keep my Rolodex. That’s not efficient. I want to change to something that’s better, but I haven’t prioritized it. I have so much other stuff going on.

Have you heard of a tool called Boomerang by any chance? 

I use Boomerang all the time. I consider it to be my little remote assistant. It’s funny because I use it to Boomerang my husband sometimes and he’s like, “Are you doing a gym class?” I Boomeranged it. I use it for many purposes that crossover both work and life.

A good pitch has a very strong point of view. Click To Tweet

For anyone who’s wondering, “What are these guys talking about, Boomerang?” It’s a little extension for Gmail or even Outlook that allows you to schedule when you want to send messages into the future. Another feature that I like is that if you send an email to someone and you don’t get a response within the defined period that you want, let’s say one day, one week, one month or whatever, it will remind you. It will come back and say, “You need to follow with that person.” That’s not a full-on CRM by any means, but as a way to ensure that you don’t let things fall through the cracks, it’s a great tool.

It’s been a game-changer. The other one I would say and I don’t use it but I’ve heard it recommended many times is Mailtrack. Are people opening your emails? Are they forwarding them? I haven’t done it yet for a variety of reasons, but I’ve heard that like Boomerang, it can be game-changing.

Let’s talk and dive into what you’re doing with your content specifically around the external publications. You got a piece put into HBR, Harvard Business Review. I believe the title is The Era of Antisocial Social Media, which I love because people who know me know I am on social media but it’s not where I spend a ton of time. I prefer to interact through in-person meals or meeting people or higher touchpoints and not just on the social channels but there’s a lot of value in there. Many people use it a lot better than I do. Regardless, that’s a well-known brand, one that can add a lot of caches. It’s something that you can leverage for future publications. Some people even go as far as saying it’s hard to get into HBR and once you do, there are not many publications that you can’t get into. You’ve done that. Spill the beans. How did you make that happen? The bigger thing is not so much about HBR itself, but the principles, the ideas that you use that you felt were critical in getting you in there. The few can then apply to other publications that they would want to get into as well.

First of all, I have a background as an editor, so I have a sensibility of how to pitch a piece and how to frame a piece that an editor would care about. That said, I’ve pitched many pieces that have not been placed or found at home. The genesis of this piece was from a newsletter. I was writing it as a newsletter and I came up with the term Digital Campfires. I happened to be doing a workday with a founder friend of mine. I mentioned it to him and he goes, “You should pitch that. Don’t put it in your newsletter, pitch it.” I was like, “That’s so much work.” I’m already done and ready to send this thing. I was like, “You’re right.”

I spent a month trying to track down and find the name of an editor and I’m part of a Listserv group called Women in Tech or It’s Rachel Sklar’s brainchild. I’ve known her for years. She’s from Toronto as well. It consists of a lot of different women and usually through tech media and marketing worlds. I made an ask to, “Does anyone know anybody at HBR? I have a pitch. Does anyone want to share an email?” I was able to procure that. From there, I got an intro to the editor. The pitch was the thing that might’ve gotten me in the door, but the pitch was the thing that got me past like, “Thanks but no thanks.”

Break it down for us because someone may not have that email for the right person or they might be going, “That’s why this worked for you, Sara, because you had an end.” There’s a lot more to it if you didn’t have a good pitch. They wouldn’t have accepted it. When you say your background is in journalism and editing, what does a good pitch look like for people? 

CSP 135 | Digital Content Strategy

A good pitch has a strong point of view. It varies for publication to publication. You have to know what the audience is for the specific publication. I do read Harvard Business Review, but I read a bunch of different articles to get a sense of, “How do I frame this so it makes sense?” I knew that my piece was for a business audience whereas there are other pieces I’ve written that are more for a typical consumer-phasing audience. This was not that. This was a specific actionable takeaway for marketers, “What is the trend?” and then specific takeaways. Knowing that’s the framing, I was clear. First, I up top identified clearly what this was about. I also made it extremely research-heavy. I did a paragraph of, “Here’s what we’re seeing in the landscape which is Gen Z and Millennials are thawing a little bit on their assignment around social. There’s not a flood or an accident but this is a small thing that we see and this is an interesting trend.”

Linking to that hard data that I had found and then going, “Where are they going instead?” They’re going to Digital Campfires, which was an original concept and then identifying clearly what those campfires are. I was able to break them down into three different types that I then put one line explaining each. At the end of the pitch, I said, “In this, I will talk through actionable takeaways for marketers of how to navigate each of these Campfires with a ton of specific examples.” It was a combination of establishing the trend using data and insights, showing my original approach, how I would tackle it, then explaining how I would make this relevant to marketers.

How much of that did you communicate in your initial outreach to the editor? Do you send the article?

No. I sent a pitch. The pitch had all of those elements. It was 200 words explaining what this was in my approach with bullets of what I would tackle. It depends on the publication. I wrote a piece for Ad Age and I sent the entire piece. A lot of publications won’t even consider that. I’m always a big fan of doing the pitch first so you don’t have to. For Ad Age, I knew that I would run that on my newsletter or something anyway if they didn’t accept it. I didn’t mind.

In your experience, how common is it to need to do a lot of follow-up after you do the pitch?

It’s very common. You could have some major self-esteem issues if you didn’t assume that you have to do a lot of follow-ups. It comes with the territory. I’ve had to follow-up 2 or 3 times in some cases with editors who have then gotten back to me. I do think that persistence pays off. You don’t want to shoot emails at them every other day, but you do want to follow up. That’s where Boomerang can be helpful because there’s a feature where you click follow-up and you write the email and it says, “If they have not replied.” If they do reply, the email will not go out. I do think that persistence is key. I don’t think that pitching is for the faint of heart because it makes you feel like crap if they don’t get back to you with all your hard work. At the same time, it is worth it, at least it has been for me.

Pitching is not for the faint-hearted because it makes you feel crap if people don't get back to you with all your hard work. Click To Tweet

The other thing to remind people is that even if your idea is not accepted by one publication, it doesn’t mean that a different publication won’t accept it. In the worst-case scenario, there are still many ways to leverage that content, your own website, LinkedIn, lots of things that you can even still do with it. It’s not a failure because your target or ideal publication says no to you.

I pitched campfires to 10 or 7 different publications and it wasn’t right for them. That’s okay.

It sounds like a lot of your business and opportunities are coming from the relationships that you’ve established, the follow-up, the newsletter, but what’s the impact that you are seeing from having your content in these external publications? These days some people might try and judge their success or failure in that short of a time span, which is a big mistake. What have you seen overall? How much has publishing in other publications supported and helped your business?

There are two ways that I took in my head and measure it because I do think it’s a little hard to measure concretely. The first is obvious, a direct correlation between me placing something and somebody coming to me. The Ad Age piece had a bunch of that and I had people wanting to take calls with me. I’ve done a couple of proposals out of that. Has anything come of it? I don’t know. I also had a piece like that in Quartzy. Quartzy is Quartz’s sister publication about lifestyle and it was about the wellness industry. I believe I had a piece of business come out of that. That’s direct and that doesn’t seem a lot like 1 or 2. However, what I do think is even more valuable for is legitimizing me to somebody’s boss or to themselves, “I’m a CMO or I’m a founder and I come across Sara, she’s introduced to me through a friend of a friend or I see her on LinkedIn.” “She’s written for these publications. Here’s how she thinks. This is her approach.”

It legitimizes me to them in a way that no introduction ever could and that I never could, that I never want to be walking into a meeting without that legitimization. That is where it’s more valuable. The third way is when I walk into a meeting, they’ve already read a lot of that stuff. It makes my job a lot easier because I don’t have to explain as much. They get it already and it helps me. They’re a fit for me as well. It’s hard to measure. All of this could be fuzzy because you’re going to spend so much time doing this but I know that it does drive my own business since I’ve seen it and because people constantly email me and talk about it and ask me questions about it and pass it on.

Elliot Vegan, who’s a peer coach in our coaching program, describes this as confirmational marketing. I’ve always loved that term because many consultants’ websites, they don’t necessarily generate a ton of business directly through the website, but the website if done properly, still helps you to win business. The first thing when someone does when they want to engage you or before they do is they’re going to go to your website, they’re going to your LinkedIn profile. All of these materials, the messaging that you have on these things, the case studies, the results, all that is confirmational. That’s exactly what you’re saying as well, Sara. I want to thank you for coming on, sharing a bit of your journey and lessons learned along the way here. I also want to make sure that people can learn more about you and firsthand see an example of your newsletter, so that they could think about how to deconstruct that and apply some of those best practices to their own business. Where’s the best place for people to go?

CSP 135 | Digital Content Strategy

You can go to my website, You can also find me on LinkedIn, SaraEWilson. I’m also on Instagram as that as well. I’m the verified account, @SaraWilson, so you should see me. That’s the best place. You can sign up for my newsletter at the bottom of my website.

Sara, thanks so much.

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