The Anti-Sell Strategy: How Rootly's Brutal Honesty Attracts Top Talent

Most startups spend their energy selling candidates on why they should join. JJ Tang, Co-Founder and CEO of Rootly, has built a different playbook: telling potential hires exactly why they shouldn't.

This counterintuitive "anti-sell" approach has helped Rootly, an AI-powered incident management platform, attract top talent from companies like Google, Nvidia, and major enterprises while maintaining what Tang calls "very high talent density."

In a candid conversation with Amit Matani, CEO of Wellfound, Tang revealed how brutal honesty about startup realities has become their secret weapon for building a team that genuinely wants to be there.

Watch the full conversation on YouTube below or on Spotify here

From Flashy Perks to Hard Truths

Rootly's anti-sell strategy emerged from a painful lesson. In their early days, Tang admits they tried to be "this cool, sexy startup, like an Airbnb and Shopify with all these perks and benefits and leave and all of those things."

The result? They attracted the wrong people.

"The thing that we realized was the people we were attracting wanted those things, and less so were tied to the mission and the hustle and the outcomes that they could drive here as a company. And so we got rid of all of it."

Now, Rootly does something most startups would consider career suicide:

"We tell candidates all the time how hard it is to work here, how bad it is to work here, all the difficult things and challenges that they will go through. And they're still excited. It's very self-selecting."

This approach has created what Tang calls a "very high talent density" where people self-select out if they're not genuinely committed to the mission and work style.

The Anti-Sell in Action: Connecting Candidates with Former Employees

Rootly takes their transparency to an extreme that would make most HR departments nervous. When interviewing for roles, they regularly connect candidates with people who previously held the position—including those who quit.

Tang shares a specific example:

"We're interviewing for a particular marketing role, and we're back filling that seat. And the person that we're interviewing, we put them in touch with the person that quit their job there to ask them, what did you love about working at Rootly and what did you not love?"

This level of transparency serves a crucial purpose: eliminating day-one surprises. "That level of transparency gives them a lot of confidence that they're stepping into something that wouldn't be a surprise on day one," Tang explains.

For recruiters: Consider implementing this approach selectively. While it requires confidence in your company culture, it can dramatically improve hiring quality and reduce early turnover.

For job seekers: Companies willing to connect you with former employees demonstrate confidence in their culture and leadership. This transparency often indicates a healthier work environment than companies that only show their polished side.

Beyond Anti-Selling: Radical Financial Transparency

Rootly's honesty extends far beyond the hiring process. Every two weeks, Tang shares the company's complete financial picture with all employees—something most startups guard as closely as nuclear codes.

Every two weeks, Tang shares the company's complete financial picture with all employees:

"We show our books. We show exactly how much money we have left, how much burn we're going through, our cash flow, how much money we're making, every single metric that we're tracking towards. Everything my finance team knows, my whole company knows."

This transparency, which began during the challenging post-ZIRP era when tech layoffs were rampant, has created unexpected benefits. "It gives them a greater sense of ownership. It gives them the sense that they are building this ourselves, together with us," Tang notes.

Transparency creates empowerment that extends to customer interactions. Rootly engineers directly communicate with customers at companies like Nvidia, troubleshooting issues without needing management approval. "They don't feel anxious, fearful, or the sense of needing my or their manager's approval to have that interaction."

The Results: People Who Choose to Stay

The anti-sell strategy has created what Tang considers Rootly's defining cultural characteristic:

"Everyone here, regardless of the company that we were building, would still be here today, even if we pivoted, even if we change, because they just want to see each other win."

This isn't just founder wishful thinking. The approach has practical benefits:

• Self-selection eliminates poor fits: "We've had people that have made the mistake in their first week and realize that themselves. Like, hey, this is really not a place I want to be because I'm not going to be like everyone else here. And they leave. As a business, that saves you so much time and energy as well."
• Higher talent density: By repelling people who aren't committed to the mission, Rootly maintains what Tang calls "very high talent density."
• Reduced turnover: People who join despite knowing the challenges are more likely to stick through difficult periods.

Strategic Market Entry Through Focus

Rootly's honesty extends to their business strategy. Instead of trying to compete head-on with established players like PagerDuty in the crowded incident management space, they found an underserved niche.

Tang explains their differentiation:

"We focused on the collaboration niche where people were, how were they orchestrating and responding to incidents and not the on-call copies, which is really well defined by companies already like PagerDuty."

Using a compelling analogy, Tang describes their positioning:

"The way to kind of think about a tool like PagerDuty is this single player game that allows on-call engineers to wake up in the middle of the night and be alerted that something's wrong... They're the smoke detector. They're really good at telling you when something smells funny. But once you wake up and you realize, hey, my kitchen is on fire. What should I do next?"

This strategic focus allowed them to build credibility before expanding scope—a "Trojan horse play" that helped them eventually compete for the broader market.

For founders: When entering crowded markets, find a specific underserved niche rather than competing on every feature. Establish credibility in your niche, then expand.

Hiring Leaders Who Can Do the Work

Rootly's anti-sell philosophy extends to leadership hiring, where they challenge conventional wisdom about executive roles. Tang believes the best leaders are also the best operators.

Tang challenges conventional wisdom about executive roles:

"My VP of engineering that has been with me for the last two years, when he came here, he did the coding take-home exercise. I think the vast, vast majority of engineering leaders would strongly disagree with that."

This extends across all leadership roles: "My sales leader on my team, my director of sales, he can confidently run our biggest deals by himself without any help. And he's able to guide his team through that journey as well."

The philosophy is simple: leaders who can't do the work struggle to guide teams effectively.

For job seekers: Look for leadership opportunities where you can maintain hands-on involvement. Companies that value operator-leaders often provide better learning and growth opportunities.

The Don't Get Cute Principle

Central to Rootly's culture is a value Tang calls "don't get too cute about it"—avoiding overthinking when action is needed.

Tang explains this focus principle with an example:

"When we were building out, we were doing this sprint recently around our mobile app. We were trying to figure out of these six features, which one should we do first? And we were getting stuck in this paralysis... And after two meetings, we realized, hey, we could have finished half of this list by the time we got there."

This principle helps them maintain focus and avoid the analysis paralysis that can slow growing companies.

Key Takeaways: Why Anti-Selling Works

Tang's approach offers several counterintuitive lessons for modern hiring:

1. Honesty attracts commitment - People who join despite knowing the challenges are more likely to persevere through difficult periods.
2. Transparency builds ownership - When employees understand the business deeply, they make better decisions and feel more invested.
3. Self-selection improves quality - Repelling the wrong people is as valuable as attracting the right ones.
4. Former employees are your best recruiters - Companies confident enough to connect candidates with former employees demonstrate cultural strength.
5. Leaders should be doers - The best managers can still execute the fundamental work, not just delegate it.

Rootly's anti-sell strategy offers a refreshing alternative to the typical startup sales pitch. Instead of promising unrealistic work-life balance or flashy perks, they promise something more valuable: transparency, ownership, and the chance to work with people who genuinely chose to be there.

"The default motion is to talk to our customers," Tang explains, describing how they've maintained this honest, direct approach as they've scaled. "And I think had we not done that, we would have been far too removed from what the reality was."

In a world full of startup promises, sometimes the most compelling pitch is simply telling the truth.

For Job Seekers: Navigating Anti-Sell Companies

1. Ask about challenges - "What are the downsides of this role?" Transparent companies appreciate directness.
2. Consider requesting former employee contacts - Confident cultures will connect you with previous role holders.
3. Show mission alignment - Research their customers and problems, not just perks.
4. Own your outcomes - Share examples of taking initiative and responsibility, even for failures.
5. Demonstrate ownership - Share examples of taking initiative and responsibility, even for failures.

Remember: If a company's honesty about challenges scares you off, you probably weren't the right fit anyway.

JJ Tang is the Co-Founder and CEO of Rootly, an AI-powered incident management platform trusted by companies like NVIDIA, Figma, and Elastic. Prior to Rootly, he led enterprise growth at Instacart.