[Un]Churned · 12 Mar 2026 · From the week of 9 March
How CS Leaders Can Build Relationships Between Meetings to Drive Retention & Expansion ft.Darren McKee (531 Social)
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Host Josh Schachter, SVP of Strategy and Market Development at Gainsight, interviews Darren McKee, a LinkedIn social-selling practitioner who founded 531 Social and says he has posted on LinkedIn daily since March 2020. They cover how he built his following, his claim that LinkedIn and social selling sourced 81% of deals at the last company he sold, his daily engagement routine, and how companies can get employees posting. The main argument is that customer success and revenue leaders should stay visible and build personal relationships online through authentic, human content and direct outreach rather than automated, templated messaging.
For founders
- Darren says LinkedIn and social selling sourced 81% of deals at the last company he sold, which he said was around $2 million in ARR.
- Darren says authentic, human-written posts, comments and DMs stand out in the feed, and he is critical of fully automated, templated LinkedIn outreach.
- Josh says his three best-performing recent posts used real photos or screenshots containing text, and he believes these made readers stop to zoom in and read; Darren adds that real photos build trust.
- Darren says sales, product, engineering and finance leaders, including the CFO, should be posting on LinkedIn, and that buyers want to read their content more than company content.
- Darren says he would split a percentage of resulting revenue with employees whose posts generate leads, and that some form of recognition is better than nothing.
For revenue leaders
- Darren says his daily routine is five companies, three people per company and one LinkedIn action per person, which adds up to 15 engagements a day.
- Darren says prospects get 60 to 140 emails a day from sellers in his market, so he sends personalised video DMs to stand out.
- Darren says tracking social-sourced deals requires lead source data in Salesforce, and that there is not yet a good system for it, so he suggests pulling a report every two months.
- Darren says customer success leaders should aim to be the person customers call to ask what is happening in their space.
- Darren says sellers should share their quota attainment and retention results publicly, because buyers want to work with the best people.
What was said 21, most useful first
LinkedIn and social selling sourced 81% of deals at the last company he sold. Listen
He says this figure came from what he reported to the board when he was VP of sales at a company he later sold, which he described as about $2 million in ARR. He describes these deals as coming from inbound after a piece of content, from replies to comments that moved into DMs, and from persistent outreach, including emailing one contact 27 times over sixteen months. He says this result is the reason he started his own business.
“81% of our deals were from LinkedIn and social selling.”
Listen to the episode Pipeline & demand generation Link to this Report a problem
Darren McKee sends personalised video DMs to LinkedIn contacts because they are rarely contacted this way. Listen
He says he has sent thousands of video DMs to VP and C-suite leaders over the years and has sent about 50 DMs a day for the last three and a half years. His reasoning is that a deep, detailed video DM is unlikely to be matched by others, while prospects in his market get 60 to 140 emails a day from sellers. He says the purpose is to get a response rather than to tick a box.
“they're going to get anywhere between 60 to 140 emails a day from sellers in our market.”
Listen to the episode Pipeline & demand generation Link to this Report a problem
His three best-performing posts in the past three months all used real photos or screenshots containing text. Listen
Josh says his top posts were a photo of a message he wrote in the snow on the windshield of a car whose horn honked all night, a text message from a CS leader, and a Slack message from Gainsight's CEO. He says none were AI-generated or doctored, and that the text made people stop to zoom in and read. Darren adds that the photo makes people read and signals that the post is real, which builds trust for the next post.
“And those photos, I realized they all had text.”
Listen to the episode Positioning & marketing Link to this Report a problem
A company's social content effort works best when about 20% of staff create content. Listen
He says he advises clients this way, and that content from all functions, not just sales, customer success or product, is a marketing engine first and a revenue engine second. He says employees sharing content organically can replace paid spend, pointing to a comparison of millions of dollars spent for 90 million impressions. He says a company's employee posts also mean prospects see the company's people when they consider competitors.
“I talk to this a lot with all of my clients, which is 20% of your staff creating content.”
Listen to the episode Strategy & market Link to this Report a problem
Employees whose posts generate pipeline should be paid a share of the resulting revenue. Listen
In a hypothetical, an engineer's post gets 25,000 impressions and 14 prospects engage, an SDR books four meetings, and the AE closes two of them and makes $75,000. He says a share of that should go back to the original poster, and that companies must decide the percentage. He says a spiff or recognition is better than nothing.
“Now it's up to every company to figure out like what that percentage looks like. But like something is better than nothing.”
Listen to the episode Sales team, hiring & comp Link to this Report a problem
One very large company's hiring for AE and CS roles has shifted to prioritise relationship-building skills alongside AI skills. Listen
He says a CMO of a very large company told him that over the last six months its AE and CS interviews shifted from asking how agentic a candidate is to asking whether they can host 12 dinners with 12 people in 12 cities in the next 12 months. He says AI matters, but the ability to build relationships is now the test there, and candidates who cannot do it are not wanted.
“it has pivoted now to can you host 12 dinners with 12 people in 12 cities in the next 12 months?”
Listen to the episode Hiring & team building Link to this Report a problem
Darren McKee uses a daily 531 engagement routine: five companies, three people at each, and one LinkedIn action per person. Listen
He says the routine means finding buyers, engaging with their content, sending a connection request and a video DM, and then building the relationship. He describes it as 15 engagements every day and says anyone who can't do that shouldn't be in a selling or CS seat. He calls it a methodology, distinct from his company.
“So I focus on a methodology called 531. I'm not talking about the company anymore, but 531 is five companies every single day, three people inside of said company and then one LinkedIn action to those three people inside of those five companies.”
Listen to the episode Pipeline & demand generation Link to this Report a problem
Darren McKee builds a Sales Navigator list of target accounts and uses it as his LinkedIn feed. Listen
He says the list is his ABM model, made up of prospects and the people he wants to keep close, and he imports it into Sales Navigator. He then uses that filtered feed to see who in the list is posting, who is new in role and who used to work at his past companies. He describes Sales Navigator as the greatest tool on the planet for this.
“what you do is you basically have like a list of folks that are your, that's your ABM model”
Listen to the episode Pipeline & demand generation Link to this Report a problem
Automated, templated outreach undermines relationship building on LinkedIn. Listen
He says he tells his trainees not to send a templated message to all prospects, but to study each company, how it makes money and its revenue, then write a tailored pitch. He is critical of sending that pitch through an agentic LinkedIn automation tool and pressing go. He says LinkedIn does not allow much of that automation, and that a human-written approach stands out in the feed.
“the problem with that is we've outsourced a lot of the actual effort that we do to build relationships.”
Darren McKee describes four content pillars for LinkedIn: origin story, company content, personal life and people in photos. Listen
The first pillar is a hero journey story covering where you came from, wins and losses. The second is company content that tells a story about how the product changes a prospect's life, rather than launch announcements. The third is non-work content about who you are as a person, and the fourth is photos of you with other people, which he calls the collaboration pillar.
“Yeah, so I walked through 4 pillars and the first one is that hero journey story of like where you came from.”
Listen to the episode Positioning & marketing Link to this Report a problem
His personal, non-work posts have booked him the most revenue. Listen
He describes the third pillar as posts about fishing, hunting, old Toyota Land Cruisers and family, with no lesson about work attached. Discussing Josh's draft about sumo oranges at Whole Foods, he suggests a one-line post with a photo asking 'would you pay $3.50 for this orange?'. He says people are bored on LinkedIn, so a post that makes them smile can earn engagement.
“3rd post is personal and it's probably where I've booked the most revenue.”
Listen to the episode Positioning & marketing Link to this Report a problem
Company posts that repeat launch announcements from many employees reduce the impact of each one. Listen
He says when every employee reshares the same marketing post, the company stops being unique and its reach gets burned, which he compares to a total addressable market being burned. He says company posts should instead tell a story about how the product can change the life of a prospect. He suggests using a team channel of win stories as the source for these posts.
“So really tell a story about like how you can change the life of your prospect.”
Listen to the episode Positioning & marketing Link to this Report a problem
Long-form teaching posts keep readers dwelling, which LinkedIn measures through sends and saves. Listen
He describes dwell time as readers staying on a post to learn steps, analyse photos or screenshots and come back to later steps. He says LinkedIn's analytics now show sends and saves, which it uses to judge whether content teaches people. He says teaching posts cannot be made on every post without burning out.
“People are staying on that post for a long time, which tells LinkedIn that it's a real good post because people are learning from it, right?”
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He posted every day for about 15 months before he felt he had figured it out, and that most people quit around day nine. Listen
He says he started posting daily on March 3, 2020; Josh notes he has about 146,000 followers and calls followership a vanity metric. Darren says it takes time, effort, study and a willingness to fail a lot, and that most people quit at about day nine.
“it took me probably 15 months of posting content every single day to get to the point where I was like, okay, I think, I think I figured this out a little bit, but the majority of people quit at like day 9.”
Listen to the episode Positioning & marketing Link to this Report a problem
C-suite and technical leaders such as the CFO, product and engineering heads should be posting on LinkedIn. Listen
He says a CFO should be posting and that the company's CFO, who had just joined from a banking background, should be on LinkedIn. He says product and engineering leaders should be active too, because buyers want to read their posts more than the company's. He says C-suite posts are part of their role.
“Those are people that are deeply like, quite frankly, our buyers really want to read their stuff more than they want to read our stuff.”
Listen to the episode Leadership & culture Link to this Report a problem
Social-sourced deals can be tracked by pulling a report every two months, but there is not yet a good Salesforce system for it. Listen
He says lead source data in Salesforce is needed and that the team must know how to enter it, including next-step actions in social selling sequences. He says he built his tool 531 Social partly for this problem, and that there is not a great system yet. He says the report should show a number of deals coming from social.
“at the end of every two months, look back, pull a report and you'll see a bunch of deals coming through from from social.”
Listen to the episode Metrics & finance Link to this Report a problem
Sellers should talk openly about their own results, such as quota attainment and retention, because buyers want the best person. Listen
He describes a room of 140 enterprise AEs where people said they did not want to mention their accomplishments because it felt self-serving. He says buyers such as VPs of product and data want the best rep and will trust someone who has been killing it. When Josh says this grates against humility, Darren says it took a lot of coaching for him to do it freely.
“don't you think that VPs of product and data who these people sell to want to work with the best person?”
Listen to the episode Positioning & marketing Link to this Report a problem
A founder or leader's origin story has to be repeated, because people do not remember the first telling. Listen
He says he recycles his origin story a lot and that it is worth doing repeatedly. He points to Gary Vaynerchuk, Alex Ohanian, Sara Blakely and Jesse Itzler as people who tell their stories again and again. He says prospects in final-stage enterprise deals bring up the mailroom post and say it led them to his business posts.
“But you have to do it a lot, because nobody's gonna remember the first one.”
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A single content type will only attract one kind of reader, so content must be mixed for everyone. Listen
He says he learned this from a fifth-grade social studies teacher, who told him that posting only one type of content would reach only one type of person, such as someone who loves video. He reviews his posts from weak months to check whether he was on the platform less, engaging less, or using pictures, videos or long-form text. He says he has to pivot his content mix and that this takes study and coaching.
“you have to create content for everyone or you're only going to get that one type of human that loves video.”
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Digital trust depends on people knowing the whole person behind a profile. Listen
He says people used to do business with people they knew, liked and trusted, and that doing this digitally requires knowing the person's hero story, journey, work and life outside work. He gives the example of a dog photo that creates commonality with a CS leader. He says that once you know someone in that way, it is hard not to do business with them.
“And so the only way to know like and trust someone digitally is to actually know the whole person of that human being.”
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Customer success leaders should aim to be the person customers call to learn what is happening in their space. Listen
He says he has never been a CS leader and is assuming this goal, and that CS leaders should aim to be the person their contact calls for industry news. Josh notes that Gainsight is going through change and wants its team seen as leaders and guides. Darren agrees that the team should be teachers rather than only telling customers about new features.
“I want to be the person that my contact calls and says, hey, what's happening in the space?”
Listen to the episode Retention & customer success Link to this Report a problem