Hi Ilona. Thanks for taking the time. Let's start with who you are and what you do?
Happy to be here! I’m Ilona and I head up the Content Team at AppSumo. Truth to be told, I’ve been a bit of a word nerd for as long as I can remember. This probably has to do with the fact that English is my second language (Russian is my first), so I’ve been a little bit obsessed with getting it right.
I grew up in New York, found my love for tech and startups in Seattle, and decided that there is such a thing as too much rain so I packed a U-Haul and drove to Austin, sight unseen. In what can only be described as kismet, AppSumo was the first job I applied to when I arrived. I was instantly drawn in by the punchy, irreverent copy in the job description and knew it was the place for me.
In my current role as Head of Content, I oversee our copy, design, video, email, and content marketing teams. If you’re looking at something on our site, chances are, the incredible people I work with had a hand in it.
Tell us a bit about what AppSumo does and what is the (success) story behind it?
AppSumo gives everyday entrepreneurs the tools they need to grow their business. That means deals on client-management software, social media tools, design apps — you name it. There shouldn’t be a barrier to entry when it comes to starting your side hustle (or main hustle, for that matter!) so really, our audience is anyone looking to start, grow, or streamline their business.
Here’s our backstory: Once upon a time in 2010, Noah Kagan had the idea to bundle and discount software products that he, himself, wanted to use. Turns out, a lot of people use software and not a lot of people want to pay monthly subscriptions for it. We partner with startups and match our audience of digitally savvy folks with insanely discounted access to cutting edge tools. In exchange, our audience offers founders really valuable user feedback, social proof, and capital to flesh out their roadmap or build their team.
You are an expert on outreach and outbound marketing. How do you keep your messaging natural, engaging, and not spammy?
Great question! I think the key is letting your personality shine through. Everyone has received an email that they know is just a mail-merge tag of their name and website. Frankly, those are easy to ignore. But when you take time to really understand who you’re speaking to, what their pain point is, and how you can fix it for them — that’s the kind of message you want to respond to.
Thankfully, AppSumo has always had a really distinct and funny voice. So when I took over our copy, I definitely had big shoes to fill, but I was also able to sound like me. The advice that I received was to write copy like I was speaking to a friend, and to make the conversation about them — not whatever I was selling. For instance, you could say ‘this software is intended for collaboration’ or you could say ‘never deal with miscommunication again.’ One of these focuses on the feature — the other focuses on the person and the problem you’re solving for them.
Emails sound spammy when they’re over-optimized. Instead of trying to fit in as many CTA buttons as you can, or using the word FREE in capital letters — focus on relating to your audience and solving a problem for them.
How do you work with target audiences, segmenting, and buyer personas?
There are a few ways to answer this question! At AppSumo, I think of our target audience in terms of their stage along the entrepreneurial journey: you have your wantrepreneurs (people that view starting their own business as aspirational), your side-hustlers, your full-timers, and your I’m-growing-my-own-business-and-hiring-ers (we should probably come up with a better name for them, huh?). These stages come to play when we’re thinking of how to effectively message to people, and what kind of content we want them to resonate with.
We also segment customers based on their stage in the purchaser funnel: casual buyers, super buyers, referrers, and affiliates. Identifying levers to get a customer from one bucket into the next increases our lifetime with that customer, and helps get new customers through the door. For example, celebrating milestones (e.g. a first purchase) with an incentive to repeat that action (say, offering a discount) positively reinforces the behavior amongst your audience.
When it comes to email, you should also segment based on activity. Having an active segment and inactive segment allows you to know who to send to more frequently, who you need to re-engage, and how to measure the overall health of your list. I use the size of the active segment as a pulse-check on how the rest of the list is doing, and how effective our retention tactics are.
Content is not just words, but also design. How do you make sure the marriage between the two works in your content strategy?
Design is an incredibly powerful and important part of the content umbrella, namely because:
- people learn and process information differently,
- visual media compels emotion.
I’ll use the AppSumo content strategy as an example. For a while, our design was cartoony. Our brand is informal and jokey — not to mention, software tends to be abstract (there are only so many ways you can showcase spreadsheets). But as we started to delve deeper into the AppSumo brand promises and values, we realized that at its core, our ethos was about serving and honoring the entrepreneur. Our cartoon-like images did not adequately capture the feelings we wanted to evoke. This led to our decision to tell more customer stories and partner case studies. With that comes a stronger emphasis on human-centric imagery and design.
As a content strategist, you need to worry not just about the textual message, but also how it looks. How does your content department work with the design team?
We’re blessed to work with some of the best designers in the game, who can visually translate even the most complex concepts. That said, designers aren’t mind-readers, so it’s important to have clear examples of what we’re looking for. Recently, we got into the habit of creating mood-boards via Pinterest and Really Good Emails to draw inspiration and be able to accurately communicate what we want.
This might sound really basic, but one thing we’ve only recently started doing is creating a strong visual style guide, both for internal and external use. Keeping an up-to-date repository of our colors, logos, fonts, etc. has allowed us to become more streamlined and consistent. And this goes without saying but as a team grows, documentation is everything!
At AppSumo, the design team is an integral part of the content team — and we work closely on just about every project. Jeir, our amazing Creative Director, sets the tone and direction for a campaign. For example, we’re cooking up something. 🔥
for our Black Friday event this year. Jeir and I met to discuss potential themes and landed on a visual identity we were excited about. From there, his team works with the video, ads, and affiliate teams to create assets that match for each channel. Our copy team then brings it over the finish line with choice words that match the look we’re going for.
The start-off point is important here: for a campaign like Black Friday, we led with design. Other campaigns, like say, a Back-to-School Giveaway, start with an idea or a feeling expressed by copy. Then it’s the design team’s job to translate that into a visual. Collaboration is key here. Having a team that feeds on each other’s energy and wants to supplement and improve what’s already there is the missing ingredient between good and great.
Many people nowadays think that humanity has stopped reading and that the average attention span is shortening. What do you think? Do you think people don’t read online?
People definitely don’t read as much as you want them to, but I also don’t think the situation is as dire as it seems. We actually polled our audience about this last year and the results were about what you’d expect (picture on the left). While there were many "skimmers", we did have some customers tell us that the copy is an integral part of the experience for them (picture on the right).
But we did have some customers tell us that the copy is an integral part of the experience for them:
Words definitely matter — that’s why newsletters like Morning Brew have seen a resurgence recently! Ultimately, there are many different kinds of people, all with their own preferences and proclivities. So my answer is: repurpose the same kind of content in every medium so each visitor can choose their own adventure. We have fun, engaging copy if you care to read it; a high-energy video if you prefer to watch; and screenshots and GIFs sprinkled throughout the page for those that need to visualize. Instead of lamenting that audiences have shorter attention spans, ask yourself: How do I get a piece of that attention pie?
I’m sure that at AppSumo, you are often talking to various audiences. What’s your take on localisation?
Lucky for us, entrepreneurship exists worldwide. Add the secondary layer that we sell software tools to grow online businesses, and our target market is the entire world. (No big deal, right?)
That being said, we are definitely experimenting with localization. For example, we created a task force to translate one of our deal pages into Spanish — including copy, video, and a webinar. We then ran ads exclusively to a Spanish-speaking audience. Our main learning from this experience is that it is not easy to do!
There are tools that can help, however! We recently featured Alugha on AppSumo, which allows you to translate video content into the language of your viewer.
I would recommend using insights from tools like this to better understand who your audience is, and what opportunities are your biggest levers before making massive time/resource investments.
You are very passionate about e-mail marketing. To make sure you send the most compelling e-mails with good frequency and timing, you need to have some sort of framework or calendar. What do you use?
You’re so right, I AM very passionate about e-mail marketing! This is a tough question to answer because it really depends on who your audience is, what product you’re marketing to them, and how frequently you’ve been sending emails in the past. We started by sending two emails per week. Then, as our deal calendar grew, we experimented by slowly adding more emails to the week and monitoring how our audience responded to them. Now, we send closer to five emails per week — many of them digest-style featuring multiple tools in one.
I don’t think there’s a magic cadence, but I would keep this framework in mind:
Provide value every time by being entertaining, giving something away for free, or solving a problem
Don’t send an email just to send an email (see point #1)
Monitor how your audience is reacting to what you’re sending them. A/B test length, copy, subject lines, etc. Keep your lists smaller but more engaged. Know your key metrics, like unsubscribe rate, and course correct when your leading indicators tell you to.
What’s your take on simply textual vs visual templates? Which works best and when?
I love a plain-text template! Our Chief Sumo, Noah Kagan, sends mainly text-based emails for his YouTube channel and they have great engagement!
Plain text emails make more sense when they’re coming from a person, rather than a company. Visual emails really let your brand shine!
I also think that if your product is visual, then that should be conveyed in your emails. An important call-out for visual emails is accessibility. Make sure that you leverage alt-text where your images are in the event that someone is visually impaired and leans on apps to translate your messages, or even if someone has the HTML turned off on their ESP. The last thing you want to do is send an email that’s basically null because you didn’t consider accessibility!
How do you test the quality of design and code in your emails and generally your content strategy?
When I first started at AppSumo, I introduced a completely new email layout. In order to effectively do this, I rolled it out in stages to make sure that I didn’t completely confuse and alienate our audience. That’s why I started with A/B testing to our newest customers, and when I saw that my variation was equal to or better, I moved on to the rest of the list.
For example here is the progress of one of our emails:
- Added our logo and a nav bar so it’s clear that we are the brand behind the email;
- Added a live timer to capitalize on the FOMO component of the time sensitive deal;
- Shortened up our copy considerably with more focus on a call-to-action
Social media apps. We all use them. They steal our time and we can’t help it. As a content strategist, which are the best social media channels to deliver your message?
So full disclosure: I’m terrible at Instagram—at least when it comes to my personal page. No one’s made me a brand ambassador yet (holler at your girl, @Madewell). But when it comes to content strategy, I think IG is still king for visual brands.
For a company like ours, YouTube is probably the channel I have the most faith in. Its algorithm is scary-good, and it’s free to host! We’ve seen a lot of success when we started taking it seriously — more so than on any other platform. (If you want to give our channel a follow, you can find us here.)
I also wouldn’t underestimate the value of a Facebook group — doing the grunt work upfront to find relevant groups that have high engagement can seriously pay off! I would recommend doing your research and putting time into crafting a post (here’s how I recommend you do that).
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Every successful design or tech driven company ends up with building a sales team. What’s your take on cold e-mailing and generally outbound marketing? How can you do it to break the ice, build relationships instead of bothering people?
Ok, so here’s the thing: no one likes receiving emails from a robot. And while I’m sure a lot of people will tell you it’s a numbers game, I say it’s always better to start with your warmest leads (aka your personal and secondary network) and write real messages, even if it takes longer. I would also definitely recommend my friends over at lemlist, whose software is killing the personalized outreach game.
Here are some fast and loose tips for outreach:
- Act like you know the person! Say something like, "I see you’re based in Austin! I love the al pastor tacos at Veracruz!" (Related side note: Make sure you don’t spell someone’s name wrong! This happens to me all the time and it’s an instant dealbreaker.)
- Don’t say generic things like: "I hope this email finds you well during these unprecedented times." (And if you do, make a joke acknowledging how generic that is.)
- Follow up! I often respond to the second or third email. But please, don’t make your follow-ups sound like a lyric from Eminem’s “Stan.” Instead, give people a kind way out. Say "Hey I’m a big fan and I’d love to collaborate with you - but no pressure." The relationship shouldn’t feel contingent on them taking your preferred action. Who knows? Maybe there will be a door open in the future if isn’t right now.
If this topic really gets you going (I respect that, you weirdo), I’d also recommend checking out this Outreach 101 blog series we put together!
Can you share your favorite resources?
- https://reallygoodemails.com - The best place to find inspo for an email campaign! They just came out with an SMS version of this and it’s also awesome. Plus, their emails are…really good.
- https://www.figma.com/community - I’ve been loving Figma as a collaborator and am really impressed with the community posts!
- https://open.spotify.com/playlist (Yes, I made this playlist. No, I’m not embarrassed. #FallOutBoy4Ever)
- https://www.nytimes.com/crossword - Best yearly subscription money can buy! Helps with writers block, word association, and cultural references.
What’s your greatest worry when it comes to the content strategy as a profession in 2020?
I’m always concerned with balancing SEO-led content with strong, community-driven stories. Ultimately, I think you need both: a way for new people to find you, and high-quality content to keep them engaged and subscribed. Marketing of any kind is always easier when you’re selling a good product, so creating read/watch/shareworthy content will always be priority #1.
Where is the best place for people to connect with you online?
Hit me up on LinkedIn! I’ll be quizzing you on your outreach skills. 😂
Bonus Question: What's your favorite way to eat avocado?
On toasted sourdough, with EVOO and Za’atar.
What is Avocode?
It’s an all-in-one tool for teams that want to code and collaborate on UI design files 2x faster.