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Here’s the thing about technical product communities: they can either become your biggest support headache or your most valuable business asset.
Most companies end up with the headache. Users flood in with complex questions, support tickets pile up, and Reddit becomes another channel to monitor rather than a place that actually drives value.
Tailscale chose a different path.
With over 41,000 members asking networking questions that would make most support teams sweat, r/Tailscale could easily be a nightmare to manage. Instead, it’s become a self-sustaining ecosystem where users solve each other’s problems while Tailscale extracts invaluable product insights, all while driving 24,000 monthly referral visits.
The difference? They built systems, not just content.
Instead of treating Reddit as an afterthought, Tailscale built community infrastructure that:
- steers users toward solutions
- empowers evangelists to help newcomers
- keeps employee engagement genuine rather than promotional
Their shift from ‘founder-led community’ to ‘professionally managed subreddit’ shows exactly how technical SaaS companies can scale Reddit engagement without losing what makes it work.
Let’s break down the specific strategies that transformed r/Tailscale into a business-critical community hub.
Why Reddit is So Valuable for Technical SaaS Companies
Over the last year of analyzing Reddit strategies across B2B and SaaS companies, I’ve noticed a consistent pattern: technical SaaS brands, especially those with freemium offerings, are increasingly turning to Reddit as a channel for customer support, product feedback, and marketing.
It’s a logical move when you consider Reddit’s recent dominance in search results.
Following Reddit’s $60 million content licensing deal with Google, Reddit threads now appear in top 3 SERP positions for countless technical queries. For Tailscale specifically, searches for “Tailscale vs WireGuard,” “Tailscale setup,” and “Tailscale alternative” consistently surface Reddit discussions alongside (or instead of) official documentation.
According to Ahrefs, that’s nearly 10,000 organic visits and thousands of dollars in traffic value going to Reddit every month.
But the real value lies in what these visits represent: highly engaged users seeking honest, experience-driven conversations from people who’ve actually used the product.
It’s that dynamic that makes Reddit so valuable for technical SaaS brands:
- Organic discovery & trust: High-ranking subreddit threads double as third-party landing pages, giving prospects social proof that feels unbiased
- Crowdsourced onboarding support: Community Q&As solve free-tier setup issues quickly, cutting ticket volume and accelerating time-to-value
- Real-time product feedback loop: Up-voted pain points and feature requests surface instantly, letting teams validate and prioritize work without surveys
- Evangelist-driven expansion: Power users who master the free tier become public advocates and later champion paid plans inside their companies
All of this supports what every SaaS company is ultimately trying to do: retain customers, grow accounts, and expand usage.
That’s why Reddit has become such a valuable channel for companies like 1Password and Cloudflare who need to move users through these stages. Creating (and maintaining) their own branded subreddits helps stop the organic traffic bleed and convert high-intent searchers into engaged, owned audiences.
Tailscale has taken clear steps to own the conversation around their product.
Over the past two years, r/Tailscale has grown into a strong SEO asset, with more than 1,300 subreddit discussions appearing in search and driving over 3,200 monthly visits.
So, not only is Reddit driving traffic to the Tailscale website, but it plays a critical role in how Tailscale surfaces product insights, supports users at scale, and builds trust through open dialogue.
Here’s how the team engages inside r/Tailscale to support and scale that experience.
Exploring r/Tailscale: How to Set Up and Run a Subreddit for Highly-Technical Products
r/Tailscale is a masterclass in community management for technical products.
With over 41,000 members and a constant stream of complex networking questions, r/Tailscale could easily overwhelm a support team. Instead, it runs as a self-sustaining ecosystem where users help each other, and Tailscale gains valuable product insights in the process.
The outcome isn’t accidental.
Tailscale built systems that steer users toward solutions, enable peer support, and make employee engagement feel real and not salesy.
Here’s how Tailscale built a subreddit that actually works for a technical audience.
Make it Easy to Find Troubleshooting and Support Materials
The r/Tailscale subreddit follows a number of best practices from our own Reddit marketing guide.
For starters, the team has built the subreddit to help users find answers quickly, often without needing to start a new thread:
- Clear “Support vs. Community” boundary: An above-the-fold banner states the sub is not routinely monitored and links directly to the official support form so that newcomers know when to help themselves and when to file a ticket.
- Resource-rich sidebar: Quick-access links to the Quick-Start guide, “Common issues,” “Existing bugs,” feature-request portal, and live status page give users one-click paths to answers without posting.
- Pinned, evergreen solutions: Rotating sticky posts cover hot topics like security bulletins, new-feature explainers (like Grants), and beginner video tutorials that help people resolve common questions before starting a thread.
Just below the subreddit rules, they’ve set up an “Additional Information” section that provides helpful direction and links to key support documents:
- A quick start guide for new users that includes a YouTube walkthrough video
- A note explaining that employees (Tailscalars) and trusted community members (Tailscale Insiders) have their own flair
- Self-service resource links including shortcuts to “Common issues,” the public “Existing bugs” board, a “Have a feature request?” portal, and the live “Tailscale status” page
- A support fallback note reminding Redditors that if the above doesn’t solve their problem, they should contact the official support team
Pro Tip: Investing in Support Content Makes Your Life a Lot Easier
In case it isn’t clear yet, creating high-quality content that supports product use is one of the best investments a brand like Tailscale can make. It decreases barriers to product adoption and makes it easier for them to get value out of it.
And if they’re getting value, that ROI usually isn’t far behind.
Don’t believe me? Just look at the comments in this thread about how Tailscale is pretty ****ing great.
Now, this doesn’t mean that a superior product or content is going to make Reddit a breeze. For starters, not every Redditor will take the time to search for it (or read it).
This is where building a supportive community comes into play. To do this at scale, you need moderators, employee accounts, and product evangelists.
Recognizing this, Tailscale invested early in building a moderator team that could grow with the community.
Build an Extensive Moderator team
r/Tailscale has come a long way in its five-and-a-half year existence.
The subreddit was created in early 2020, with the co-founders Brad Fitzpatrick and David Carney serving as moderators. The leadership team is still engaged on the platform, especially during major events (more on that later), but they’ve expanded the team significantly since then.
Starting in 2023, the company began formalizing its Reddit presence by adding a handful of employee accounts and an official brand account (though it’s yet to post anything). But as the company’s user base and subreddit continued to grow, Tailscale ramped up their presence on the platform.
Since the start of 2025, r/Tailscale has brought on a dozen new moderators, the majority of which appear to be Tailscalar (employee) accounts.
Overall, the moderation team has grown from a small founding group to a strong mix of company representatives and active community contributors.
Here are some of the most prominent Tailscalars leading the charge on the subreddit:
- Sam Linville, Group Product Manager: Requests diagnostics, invites feature-interest emails, troubleshoots ACL/SSH issues, clarifies docs, redirects to support, encourages feedback, provides patient, thorough answers to user questions.
- Alex Kretzschmar, Lead Developer Advocate: Answers technical questions, shares guides, links videos, offers clarifications, encourages follow-up, and engages conversationally across Tailscale and self-hosted subs.
- Natasha Sawires, Senior Community Manager: Serves as the front face of Tailscale, solicits feedback, asks probing questions, encourages dialogue, brainstorms future channels, replies individually, and celebrates user stories.
Just like with Mint Mobile’s semi-official approach to Reddit, Tailscale’s presence on the platform extends well beyond the profiles in their moderator team. While digging through different threads, I came across a number of other “Tailscalar” accounts engaging with Redditors.
With a team of this size, it’s clear that Tailscale is extracting much more value than just the 24,000 monthly web referrals.
How r/Tailscale Provides Valuable Insights for the Entire Company
As said, r/Tailscale has over 41,000 members. This represents more than one-third of their total monthly active user base of 100,000.
No wonder they invested in having more boots on the ground on Reddit. The insights shared in r/Tailscale support teams across product, marketing, sales, and support.
Product and Development
A growing number of people use Reddit to get information on products and services (remember all those Tailscale queries we saw earlier?)
Comparison and alternative pages on brand and third party sites are incredibly valuable from an SEO perspective, but there’s bias built into them. And people can usually smell it.
Reddit is a different animal.
People are brutally honest about products and services here, branded subreddit or not.
While this is a scary proposition for companies on Reddit, it’s important to remember that this type of feedback is incredibly valuable for your product and developer teams.
Some of the top posts in r/Tailscale from the last year show why Reddit is so valuable for them:
Competitive Intelligence
Reddit discussions reveal what Tailscale users value in competing tools, offering clear product positioning insights and business intelligence most companies have to pay for. For example, a recent post about Netbird highlights users’ desire for fully open-source infrastructure, indicating potential market share risks if this gap isn’t addressed.
These discussions also reveal technical pain points in competitors (like battery drain issues in Netbird’s Android app or latency problems), giving Tailscale developers insights into areas where they can strengthen their own offerings.
Voice of Customer Feedback
Getting a post that calls your product onboarding experience “*really* confusing” may be scary at first, but it’s another instance of incredibly valuable product-related feedback.
In this case, a detailed description of the challenges users experience when first joining or inviting users to a tailnet (aka: a private Tailscale network).
The detailed post includes concrete examples and screenshots of the exact points within the user journey that cause problems:
- Onboarding friction: A hidden “Switch Tailnet” and mis-labeled “Add account” button leave invitees stranded, showing significant bumps in the first-time journey.
- Navigation/visibility gap: Users can’t see the network they’ve joined inside the app, proving device lists and Tailnet status need clearer in-app surfacing.
- Role and permission confusion: Asymmetry between admin console and member view (“no analogue of login.tailscale.com/admin for members”) points to unifying UI patterns for both roles.
- Docs and messaging fix: Misleading “Download Tailscale” prompt after an invite highlights copy that should instead direct users to join or switch tailnets.
The post received 88 upvotes and another 38 on the top comment that “100% agrees” with the OP is a huge signal that the onboarding and sharing processes are a challenge—one that could potentially lead to customer churn.
The product team also uses Reddit to recruit users for more structured feedback sessions and research pools.
In short, Reddit provides ongoing, high-quality, real-world user insights that directly inform and improve product development, ensuring that Tailscale evolves in alignment with user needs and expectations.
Marketing and Sales
People don’t just search Google for product reviews anymore. They go straight to Reddit to ask “Is Tailscale worth it?” or “What VPN should my start-up pick?”
When those conversations happen in r/Tailscale, the Sales and Marketing teams get a front-row seat to real purchasing intent they would never see in a polished case-study or a paid comparison page.
Bottom-up Growth in Action
One of the most overlooked benefits of product-focused subreddits is how clearly they show the path from freemium user to paying customer and, in some cases, enterprise user.
With the right product and a large enough subreddit, it’s not uncommon to find Redditors voluntarily sharing information like this:
A free user becomes a power user who then becomes a product champion in the workplace.
No doubt familiar with this journey, Tailscale has incentive programs that offer free access to paid tiers for users who introduce the product to their workplace. Reddit is the perfect platform to distribute their bring Tailscale to work program as it’s a popular forum among freemium users.
This is a great example of why companies like Tailscale can make such gains on Reddit: it’s the perfect space to drive bottom-up adoption by nurturing personal users into product champions.
Community-led Advocacy
A few months ago, Tailscale’s community manager Natasha announced the launch of their new Insiders program to help reward some of the most engaged users. It included the typical perks of branded merch and access to free plans, but also outlined how Insiders would help influence product development.
The post generated 120+ upvotes and dozens of enthusiastic comments. Though there were a few who were skeptical about becoming “influencers”, Tailscale has clearly built up a community of users who are passionate enough about the product to both advocate for it and influence the direction it takes in the future.
Reddit reveals how and why real people adopt, champion, or churn, turning comment threads into live-fire testing grounds for positioning, pricing, and community based marketing programs.
Customer Support and Public Relations
On Reddit, users don’t submit support tickets. They broadcast frustrations in public for the whole internet to see.
When companies stay silent, threads grow, trust erodes, and these moments can spiral into lasting reputation damage.
But when handled well, these incidents become trust-building moments that no private help-desk interaction can match.
Tailscale’s customer support and crisis comms faced the ultimate stress test just over a month ago when a major security issue was uncovered and quickly escalated in their subreddit.
Essentially, a user uncovered a significant loophole that allowed users with specific domains to join the Tailnet of other users and potentially access their information (and even devices). That’s a huge blow to any security-driven company.
The post quickly blew up, with over 750 upvotes and nearly 250 comments (and likely many more customer support requests). Users weren’t happy.
To help calm the masses and explain the situation, multiple Tailscalars jumped into the thread to acknowledge the issue and communicate their actions. The co-founder himself, u/bradfitz, even weighed in with a response explaining the oversight and what the team was doing to rectify the issue.
Tailscale responded with clarity and context, walking users through both the root cause and the decisions that led to it. That approach helped defuse frustration and turn a tense moment into a trust-building one.
Over the following week, the Tailscale team initiated more conversations in the community to explain further actions the company was taking and to build back trust.
This kind of approach turns Reddit into a real customer support asset. It enables faster issue detection, direct engagement through transparent communication, and community-driven insights that improve overall service.
For technical SaaS companies considering Reddit as a strategic channel, Tailscale’s experience offers a clear roadmap: start with authentic engagement, invest in proper community infrastructure, and treat Reddit as a cross-functional business tool rather than just another marketing channel.
The companies that embrace this long-term perspective will build sustainable competitive advantages that compound year over year.
Unlocking Reddit is a Long-Term Investment: Get Started Today
Tailscale didn’t stumble into Reddit success. They earned it by treating the platform like a long-term asset—something worth building, managing, and investing in.
The results speak for themselves: faster support, deeper product feedback, stronger community loyalty, and a direct line to high-intent users.
Most brands treat Reddit like an afterthought. The smart ones treat it like infrastructure.
If you’re ready to build a subreddit that actually drives growth, Foundation can help. We work with B2B companies to turn Reddit into a real strategic lever, not just another publishing surface.
Get in touch with the original Reddit marketing agency today to discuss how we can help you replicate Tailscale’s success and build your own competitive advantage on Reddit.
