3 ways to keep a community engaged

(4 min read) How one Creator built a lucrative six-figure community by scaling herself to 600+ members

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Tl;dr

  • Jessy Grossman has 39,000 cross-platform followers

  • 600 members pay $500+ per year to be in Jessy’s community, Women in Influencer Marketing. You do the math. And that’s just 40% of her business

  • Jessy suggests three (3) ways to increase engagement and retention in a community:

    • Customize onboarding so new members feel welcomed and guided

    • DM people at scale to increase engagement

    • Be a matchmaker between your members

  • Jessy’s Stack includes:

    • Slack to engage her professional audience where they already spend time

    • CommonRoom.io to automate Slack community direct messaging

    • Zapier to automate between Slack, email, and other tools

600 professionals pay her $500+/year

Rising tides lift all ships: we all work on this together, we all support each other, and it will really elevate the entire industry, which elevates us all. It's a very different way of thinking.

Jessy Grossman is the founder of Women in Influencer Marketing (WIIM), a paid community of 600 people that most Creators probably want to know.

How did Jessy, previously a Creator manager and influencer marketer herself, build a community so many execs are willing to pay $500+ a year to be a part of?

Let’s get into it!

The Business

If you read last week’s essay, you understand what makes a community valuable:

For Creators, community is a fandom that has consistent value-adding interactions with each other regardless of the Creator’s engagement.

But how does one actually create a community that self-sustains and spends money because of how much value members are providing to each other?

Jessy accomplished this through WIIM, where she generates multiple six-figures in annual revenue (600 member x $500+ annual fees). 

Her total reach is roughly 39,000. 

What’s more, Jessy’s community directly drives just 40% of her revenue (though it certainly contributes to driving her other sources as well):

While Jessy has a diverse and lucrative business, I was most interested in its super-engaged core - her community.

I asked Jessy the tough question I personally have about all successful communities:

The biggest challenge for Creator communities: Busy Creators find it difficult to be super involved in a community, and members disengage and churn without them. 

How do you solve that?

She offered three (3) tips for how she scales herself to keep the community feeling active and alive — without spending all day sending messages herself…and they’re pretty brilliant:

  1. Customize onboarding so new members feel welcomed and guided

I personally send them a giant welcome note with a ton of emojis that makes them feel really welcomed, and include a checklist: 

- Go to the introductions channel

- Introduce yourself

- Check out our events page

- Register for an event

- DM me if you have any questions

Then I have it set so that if they don't respond within X number of days, I will send them a follow up message. 

People often decide how they feel about something immediately - that’s why first impressions matter. By investing in her onboarding process and coaxing new members to get active, Jessy is giving her subscribers a positive first impression, getting them invested in the community, and likely earning more of their long-term retention.

  1. DM people at scale to increase engagement.

We have sponsored content that companies want us to share in Slack, and what's been most effective for us is framing them as conversation-starters that people can weigh in on. That gets traction. 

I'll post the predetermined content approved by the brand in our #Conversations channel, then I'll copy the link and DM everybody individually, saying: 

“Hey, I posted this in #Conversations and I'd love to get your two cents on it.”

And instead of people being like, “Oh, just another thing in #Conversations,” they're like, “Oh, she personally reached out to me because she wants to hear my opinions on this.” 

I'll always say that it's sponsored, I never hide that fact.

People find it hard to resist a personal invitation - as long as it feels personal and relevant. The beauty of communities is that most topics are relevant to most members; asking directly for an opinion feels appropriate, and is a great way to get otherwise shy members to engage.

  1. Be a matchmaker between your members.

We send out monthly emails where we pull four people each month and say, “We've selected these people that we think you should connect with.” 

We offer a list of recommended topics and ice breakers, we share their LinkedIn and suggest they connect there…it's another way that we keep the engagement going. 

Positive 1:1 interactions are where the biggest value in a community are, but can be hard to come by for more introverted members. By creating a system to matchmake at scale while providing discussion topics to make conversation easy, Jessy is maximizing the possibility that her community members make truly meaningful connections. 

Now, you might be thinking, “Avi, this level of engagement seems like a lot of effort (or money).” 

Jessy’s figured out the hacks. For example, when matchmaking members:

I'll give you a little glimpse behind the scenes on how we scale this:

We send one group of four people to 98% of our members each month, but to the four selected people that month, we send another four people because we don't want them to get themselves.

What really lets her scale, though, is her set of tools that automate the messaging and emails from the moment a new member signs up.

Let’s talk about what that looks like in The Stack below!

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The Stack

These are three (3) of the tools Jessy swears by:

Jessy uses Slack for her community for one simple reason every great marketer knows: you should always try to be where your customer is.

We chose Slack not because it's the most superior tool, but because it's where most of our community already was. When you talk about the challenges of getting people engaged, it was going to be an even bigger challenge if we made them download a whole new platform that they don't even know or care about. 

Common Room is how Jessy automates her community engagement within Slack.

I link up my Slack and then I can send mass messages in the form of a DM, instead of in a channel. 

It feels more personal, and I can use field templates to say “Hey {first name}” and it fills in Avi, it fills in Jessy, etc. 

Jessy uses Common Room to make community members feel personally engaged. It powers her:

  • Custom welcome messages

  • Requests to engage with channel content

  • Direct follow-ups on inactive members

I wish I had something like this for LinkedIn!

Zapier lets Jessy automate community engagement outside of Slack.

Zapier is connected to MemberPress, which is the WordPress plugin that we use for our membership. When a member signup is completed, that triggers Zapier automations. It connects to Mailerlite, the email marketing system that we use, then adds the new member into a special email sequence.

For the next eight days, the new member gets a daily email that says, “Hey, check out this element of the membership. Tomorrow you're going to get another email showing you about something else.” 

We hired someone to write those emails and to structure them in a more engaging way because with membership, you have a really small window to really hook someone.

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Written by Avi Gandhi, edited by Melody Song,
powered by TheFutureParty

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