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Happy Thursday! 

There’s been a ton of talk – in ecommerce, media, SaaS, and web3 – about the importance of community. There are far fewer actual examples of building community-first in a way that translates into real metrics. Glossier comes to mind as a good example of a similar idea, content-to-commerce, and many companies build strong communities within their customer bases, but starting with the community is rare. 

The idea of starting with a community and then building products and services specifically for them is one I’ve been obsessed with for a while. When I was thinking about launching Not Boring Club pre-COVID, I wrote a memo-to-self in Notion on just this topic: 

If I’m being honest, the target customer I was thinking of for Not Boring Club would have been too diffuse to pull off a community-first business really well. They’d have too many different needs, and not enough of the same ones. 

But the idea stuck with me, and when I met Bravado’s Sahil Mansuri, I knew I’d found someone doing it right. Today, we’re going to dive into Bravado’s playbook. It hasn’t been easy to go community-first, but the effort is beginning to pay off spectacularly, and I expect it to compound for a long time to come.

This post is a Sponsored Deep Dive. I always say that I only write about companies that I’d invest in, and fortunately, we were able to invest in Bravado out of Not Boring Capital. You can read more about how I choose which companies to work with on Sponsored Deep Dives here.

This is the last essay I’m writing until September, although we have some incredible guest posts lined up. Enjoy the rest of your summer! 

Let’s get to it.

The ABCs of Bravado

ABC. Always Be Closing. 

Partially thanks to Glenngary, Glen Ross, partially thanks to those calls and emails you get, and partially thanks to cringe posts on LinkedIn, sales has developed a cartoonish reputation. 

While sales is a great way to make a lot of money, and the best path for non-technical people to get into tech, it’s not a career that most people dream of, the way they dream of becoming engineers or product managers or designers or founders. 

Sahil Mansuri, the founder and CEO of Bravado, wants to change that. “I LOVE sales. I want to turn sales into a profession that people aspire to,” he told me when we met over Zoom for his Series B pitch in February. Bravado’s homepage captures its founder’s enthusiasm: 

“Sales is the best job in the world.” 

Sahil’s enthusiasm for sales is infectious, and his pitch worked. Not Boring Capital invested in Bravado’s Series B, a $26 million round led by Tiger with participation from Redpoint, Freestyle Capital, Flow Ventures, Precursor Ventures, Mark Pincus, and my friends Lenny Rachitsky and Sahil Bloom.  

When Wander CEO John Andrew Entwistle offered to introduce me to Sahil, I was a little skeptical – another sales platform? I wasn’t sure it answered the “So what?” question I ask when I’m considering an investment, or that sales software counted as a hard startup. But I trust JAE and there were a bunch of things to love about the company and the industry it’s tackling: 

• Industry: Sales is the #1 most popular role in the country, and B2B Sales is the 3rd fastest-growing

• Grit: Sahil started Bravado five years ago, and they’ve had a product in-market for 3.5 years, but they didn’t start monetizing until last year. 

• Growth: Bravado scaled from $0 to $4 million in ARR in 9 months when it launched its Jobs product with Sahil as, ironically, the company’s only salesperson

It all clicked, though, when Sahil laid out the approach Bravado’s taken to get to where it is, and the optionality that gives the company in the future. It’s that approach that we’re going to dive into today: community-first distribution. 

In The Good Thing About Hard Things, I wrote that “Hard startups on the bits side are solving difficult technical challenges, creating new business models, or touching industries that previously didn’t make sense to touch.”

While community-first isn’t a brand new business model – every company and DAO talks about building community-first – Bravado has executed on that playbook brilliantly, building a community for years before monetizing it effectively, in a way that I haven’t seen before. 

Sahil calls it “reverse engineering a SaaS company.” Instead of building software for salespeople and then bolting on a community of customers, a brand, conferences, and the like, Sahil started by building a free professional network for salespeople, like “StackOverflow for Sales”: one place where salespeople can go to get better at their jobs.

It was a slog, and after three years in the trenches, the community didn’t really take off until last year, when the company decided to make its message boards pseudonymous so that, unlike LinkedIn, “people can ask for real advice without bloviating.” With that one shift, Bravado’s free product, the War Room, took off. Today, Bravado has over 250,000 salespeople in its network, representing 50,000 companies. And those 250k people had to go through some friction to get there; I went through the signup process, and it’s a meaty eleven steps, including connecting LinkedIn to verify your responses. 

That traction is a clear sign that Bravado fills a hole in the market for salespeople who want to get better at their jobs by learning from a community of top sellers. . Out of over 4,000 accredited universities in the US, only 50 have a major or minor in sales. There’s no Dribbble or Figma for salespeople, like there is for designers. Salespeople have made do on LinkedIn, but there’s gotta be a better way to get tips and advice, and to just celebrate a win, than doing it in view of your whole professional network. 

That’s the hole War Room fills, but War Room is just the first step in a brilliant strategy to build products for the community that Bravado has so patiently built. The reason Sahil built Bravado in the first place was to build better products for salespeople after realizing that all of the existing ones “are awful.” But in a market dominated by a giant like Salesforce, he knew he couldn’t just build a product and try to sell it the same way all of the would-be Salesforce-killers have tried.  

The community-first strategy has paid off handsomely for Bravado. Thanks to War Room, when Bravado turned on its first paid product, Jobs, it grew to $4 million in revenue in 9 months at a $4 blended Customer Acquisition Cost (CAC) with 95% organic growth. When the hiring market recently turned sour, it listened to its members in the War Room, built off of the Jobs product foundation, and quickly launched Flex. Flex, which lets sales professionals work as Freelancers, opens up new options for the future of Bravado, for who gets hired, and how salespeople leverage themselves. 

That’s what building community-first enables: optionality. With the War Room humming, Bravado’s just getting started on its quest to build better products for salespeople. In the process, it’s rewriting the playbook for bottoms-up, community-first go to market. I think that integrating this deeply with the community will become table stakes for new SaaS startups that want to build deep moats going forward.

Today, we’ll dive in to understand the ABCs of the community-first juggernaut Bravado is building, and where it might go in the future: 

• Sahil’s Sales Story 

• Meet Bravado: The Anti-SaaS SaaS Company

• From ABCs to JOBs

• Bear Market Flex 

• The Future of Sales

To understand where Bravado’s headed, you need to understand how Sahil got to Bravado. 

Sahil’s Sales Story

In May, Sahil joined me on Not Boring Founders to talk sales. In response to my first question, “What will the world look like in a decade if you’re wildly successful in your mission?”, he said: 

When kids are growing up, someone wants to be an astronaut. Someone wants to be a firefighter. These days, I think a lot of people want to be a tech founder or an engineer. I don't know a single kid that grows up and is like, man, one day, I hope I get to be a salesperson, you know? No, one's got their little GI Salesperson Jane character that they're running around with. 

His mission is to change that, to build a world in which: 

• People aspire to be in sales.

• Sales is recognized as an amazing way for non-technical people to break into tech.

• Sales is taught in high school and college as a skill that you need in order to be successful. 

It’s a mission that comes from personal experience. Growing up, Sahil said, “I was good at math, I was good at tinkering, I took every AP physics, chem, etc….” He was smart, but he had no idea what he wanted to do. But while he was in college in Washington, DC, he did what people in DC do: got involved in politics. Specifically, he joined the Obama Campaign in Field Operations. 

Field Operations is essentially sales. Going door-to-door explaining your candidate’s position, hosting events to get people excited, and lots and lots of cold calling. And Sahil loved it. He had found his calling. 

After school, Sahil joined Meltwater, a 600 person sales organization, as a Sales Manager, and quickly became the #1 sales representative in the company’s 10-year history. Within two years, he was promoted to Managing Director and sold to companies like Exxon, Prudential, Pernod Ricard, AIG, Panera Bread, and the Air Force. 

He left Meltwater in 2011 to become the 23rd employee at a little startup called Glassdoor as an Enterprise Sales Manager. Selling to companies like Google, Facebook, Microsoft, and Amazon, he was the #1 rep out of 50 in his first year with the company. 

Moving on up, Sahil got hired as the VP of Sales at a smaller startup called Virool, and there, he became the largest customer of a tiny Israeli company, SalesPredict, building a predictive AI lead scoring tool. The product wasn’t intuitive for the user, and when Sahil gave feedback to the SalesPredict team, they asked him to join them and fix it himself.

In his time in sales, Sahil had realized two things about sales software:

1. All sales tools are awful. 

2. There’s no bottoms-up sales tooling.

He wanted to understand why that was, so he took the job and joined SalesPredict to help build its product. Working with designers, engineers, and data scientists, he needed to brush up on his technical skills, so he started learning R. When he got stuck on an issue, he turned to his now co-founder Yoni Acriche to ask for help, and Yoni replied, “Oh, just Google it.”

So he copy-pasted the code he was having trouble with into Google, and voila… 

The exact issue popped up in Stack Overflow, the “public platform building the definitive collection of coding questions & answers,” with dozens of helpful answers. 

“Why doesn’t something like this exist in sales?” he wondered. 

Then, when he was interviewing a designer, she sent him a link to her portfolio in Dribbble, the community where creatives share their work. 

Once again, he wondered, “Why doesn’t something like this exist for sales?” 

The question kept coming back up as he played with the delightful software that non-salespeople got to use, right when the “consumerization of enterprise software” was in full swing, and became increasingly intent on bringing the same level of software to sales. Finally, in the summer of 2016, eBay acquired SalesPredict for $40 million, and Sahil decided it was time to scratch the itch.  

But having spent so much time in sales at early-stage startups, Sahil knew what a grind it was getting even really good software in customers’ hands via the traditional enterprise sales model, so he set out to flip the script. 

Meet Bravado: The Anti-SaaS SaaS Company

Product-led, or bottoms-up, growth has become a popular approach to customer acquisition for consumerized software startups. Give away a free version of software that a handful of employees love to use, make it really easy for them to sign up for pro features with a credit card, and then layer on sales using those early adopters as a beachhead for the company-wide deal. Product-led growth has propelled companies like Dropbox, Zoom, Figma, Notion, Slack and many more to great heights. 

That motion is standard in most enterprise SaaS verticals, but it hasn’t really hit sales. Quick: think of a sales tool that people love so much that they beg their management teams to buy it for the company. I can’t either. More often, at some point, after trying some spreadsheets, then graduating to a lightweight CRM, the VP Sales convinces the CEO: it’s time. Salesforce. 

“I’ve done this before,” they say. “It will be easy,” they say. “Three months, tops!” they promise. 

And then, inevitably and invariably, six months later, the VP Sales is breathing down the engineering team’s neck and keeping the Sales Ops person in the office late every night “until we get this damn thing implemented.” They finally do. It’s not perfect, but it works. Leadership finally has a good pulse on the company’s pipeline. They understand the funnel, and realize that there’s a big leak between “MQL” and “Closed-Won.” They re-jigger the flow; SDRs are now to call MQLs twice, email twice, and then call a third time. The sales team, of course, doesn’t love this new system. Their boss is on them for not making enough calls. Every night, after they’re done doing their real job, they sit there and update Salesforce because those automatic integrations they were promised are broken and the engineering team is focused on customer-facing work and they’ll fix it in a few months. The company misses revenue targets. The VP Sales is fired (VP Sales, incidentally, have the shortest tenure of any executive position at 19 months). The new Chief Revenue Officer (she has 25 years experience, she’s not settling for “VP Sales”) comes in and says she can turn it around, no problem, “We just need to set up our Salesforce the right way so I’m properly instrumented.” And on it goes. 

Whew. Where was I? 

Right, for some reason, bottoms-up software hasn’t taken off in sales like it has in other verticals, so companies end up buying clunky, hard-to-implement old software. While “No one ever got fired for buying Salesforce” certainly isn’t true in the long-run, it sounds right in the short-term. 

Given his decade-plus in sales, Sahil knew that he wasn’t going to win the sales tools category with a traditional enterprise sales approach, or even with a bottoms-up approach. “The push to the first few million in ARR is really hard and expensive,” he explained, “until you build a brand, get reviews, write case studies, earn trust, host conferences, and build momentum.” 

Instead, Sahil decided to take a different tact. He calls Bravado an “Anti-SaaS SaaS Company.” It’s an inverted approach: start by building a community of sales professionals, listen to what they need, build products to fill those needs, get feedback from the community, and iterate.

By building community-first, Bravado was building a brand, getting access to a pool of customer insights, and actually developing its own distributed sales team for its eventual products. 

Think of it this way. Software companies typically generate high margins by building products with high fixed costs (typically R&D) and low marginal costs (it costs practically nothing to make copies of the software). Build once, sell millions of times, profit. Of course, there are still marginal customer acquisition costs – it takes some amount of money to convince each customer to use or buy the product. What Bravado is doing has a similar logic. It spent high upfront costs building a community of its target customers, and now, it should be able to distribute new products to them and through them at low marginal customer acquisition costs.

So Bravado started simple, with a community for salespeople. 

People joined, but growth was slow. Bravado experimented with new formats. In one iteration, it let sales leaders start their own communities, like #Live-Better-Sell-Better and #Other-Side-of-Sales and invite members. At the time, all profiles on Bravado were attached to real people with their real names, and Sahil told me that while people were finding value, there was still a lot of LinkedIn-esque posturing. 

The team kept listening to its members, and kept iterating. In 2020, inspired by Dribbble, they launched Bravado Portfolio, profiles with verified information including which companies a salesperson had sold to, awards they received, performance against quota, work history, and testimonials. Bravado verifies the information using member-submitted information like paystubs and contracts. 

Portfolio was helpful in that it gave salespeople something they could bring to potential employers to showcase real accomplishments. It was a useful building block, but it wasn’t the magical community unlock the team was seeking. 

They also provided tools for salespeople to learn, level up their careers, find mentorship, and develop skills they’d need to enter sales, or advance, from SDR to AE, from AE to Director, from Director to VP Sales. Again, these were useful building blocks and a good way to build trust with the community, but they weren’t the unlock. 

Then, in August 2021, they hit it: the War Room.

The War Room is like Stack Overflow for Salespeople, a place where sales professionals can pseudonymously submit questions, provide answers, and just talk shop. 

Pseudonymity was the key. Freed from trying to impress others in their industry, and from worrying about their boss seeing, Bravado’s members were able to ask the questions they would have otherwise kept in. Some are general – How worried should we be about the recession? – and some are tactical – How could I have said this better to a potential client? 

War Room became the hub for B2B salespeople, and the fastest-growing community in sales. 

It took four years for Bravado to hit 10k members. By the time I first met Sahil in February, Bravado had 175k members. Today, it has 250k members, from 50k companies, including roughly ⅕ in sales leadership roles. 

Four years into the company’s life, the community was finally humming, and Sahil was ready to prove out the Anti-SaaS SaaS thesis by turning on the revenue jets.

From ABCs to JOBs

Last October, Sahil decided it was time. Bravado had built up a captive audience of salespeople who trusted the community, and by extension, the company. VPs of Sales, the people responsible for hiring, had been using Bravado for two years and trusted it. 

Bravado announced its newest product: Jobs, a way for companies to hire salespeople. 

With one email to the community and one post in the War Room, and with Sahil as the company’s only salesperson, Bravado acquired almost 300 customers in nine months, all through inbound. 

Jobs builds on everything that Bravado has built to date. The War Room is full of both salespeople looking to get hired, and sales leaders at companies looking to hire. Bravado Portfolio provides a source of truth that hiring companies can trust to more quickly screen and verify potential hires. And by helping to train up salespeople, Bravado has increased the quality of the talent pool. 

Hiring companies pay a subscription fee to access Bravado’s talent, and 20% of base salary per hire. From $0 in September 2021, Bravado hit a $4M ARR run rate by March 2022. 

Jobs seemed like the perfect product at the perfect time, when every company was looking to grow their sales teams in order to turbocharge top line revenue.

Then, the market crashed. 

Bear Market Flex

On March 12th, Sahil hit publish on what would prove to be his most controversial LinkedIn post ever (and he posts on LinkedIn a lot).

He predicted that 20-40% of sales reps would be out of a job within weeks. Commenters replied that he was fear mongering. 

Almost five months later, it unfortunately looks like he was directionally correct. Layoffs are happening throughout the tech industry. Just this week, Robinhood announced that it was laying off 23% of its staff. And even companies who haven’t announced layoffs have frozen hiring. All of a sudden, the hot jobs market that propelled Bravado Jobs chilled, and many people in the War Room were looking for work at exactly the wrong time. 

Getting insights from its community in real-time, the same insights that inspired Sahil’s post, the company realized that we were entering a world in which very few companies would be hiring full-time employees and in which there would be a surge of sales reps looking for new jobs. Those insights gave it a head start. 

So Bravado moved quickly to start preparing its newest product: Flex, which lets employers contract with salespeople on a commission-only basis. Companies can increase revenue without increasing burn. Salespeople have the freedom to control their destiny and work as Freelancers. It’s announcing the product for the first time here.  

Sometimes, Flex means 100% commission, other times it’s part-time with a base salary or stipends, and even offers contract-to hire, where reps prove themselves over 2-3 months with an opportunity to convert to a full-time role. Like a Deel for sales (plus the talent network), Bravado handles everything: sourcing, contracts, payments, training and compliance. Companies just select the right people and start growing revenue.

Born out of bear market necessity, I think that Flex has the potential to reshape both Bravado and the way that salespeople work. It makes sense on a few different levels. 

First and most obviously, at a time when companies are simultaneously facing hiring freezes and lofty revenue targets, easily hiring salespeople on 100% commission lets companies fill empty seats or give another option to employees they’d otherwise need to let go, without locking themselves into full-time hires. Among Flex’s ten pilot customers, a handful have used the product to transition full-time employees to commission-only for the time being to maintain continuity for both the employee and the company, in the hope that they’ll be able to re-hire them seamlessly when the market turns back up. 

Second, because it’s lower commitment, Flex gives companies the opportunity to widen the net on their hiring pipelines. Prior to the downturn, Sahil told me, there were a lot of people who wanted to switch from B2C sales at a company like Verizon to B2B sales at a company like Salesforce, but Salesforce would only hire people with backgrounds in B2B sales. Flex gives companies like Salesforce the opportunity to give those people a shot, and let them build their resume for the next B2B sales job they apply for. Sahil also believes that the same dynamics will help improve diversity in sales, which is stereotypically very white and very male, by giving people from underrepresented backgrounds a foot in the door and a chance to prove themselves. 

The third level is the most fascinating, and hints at why a product like Flex might change the way that salespeople work. 

“As a salesperson,” Sahil told me, “It’s hard to build a relationship with a customer, but once you have that relationship, it’s very valuable and can be worth a lot of money for a long time.” He points to Salesforce poaching the best Oracle reps to bring over their enterprise customers in the early days as an example. 

Traditionally, though, salespeople haven’t had the ability to maximize the value of their rolodex. If a top rep at Salesforce has a great relationship with a company like Google, she’s only able to sell Salesforce to Google, until another company poaches her away in part for that relationship. 

But with Flex, the salespeople with the best relationships might be able to maximize the value of those relationships by working part-time, commission-only with a number of companies whose products they feel good about selling. Each relationship might yield five sales instead of one. The company gets the benefit of flexibility and new accounts, and the salesperson is able to leverage their most valuable asset more fully. 

While independent sales agents have existed in channel sales, they’re not mainstream in B2B SaaS because B2B software sales has become so technical and specific that companies have wanted people fully trained on their product. By shifting the focus from the product – which salespeople will of course still need to understand – to the relationship, Flex might remove friction, increase liquidity, and modernize sales. 

With their Bravado Portfolio, a salesperson would be able to easily prove that he’s sold to Tesla three times, McDonald’s four times, and LVMH six times, and let companies essentially bid for those relationships. The best salespeople will make more money, and companies will be able to more efficiently grow their revenue through additional logos. 

This vision, too, came out of conversations in the War Room, where people discussed ways to better capture the value that they create through the very human act of relationship-building. More than Flex itself, Bravado’s potential lies in its ability to find signal in those conversations, build products to address them, and sell them to its engaged community of members. 

The Future of Sales

While Jobs and Flex have proven that Bravado is able to launch products that generate revenue and help its community quickly, what the company has really built is a distribution machine with a moat, a captive bottoms-up channel through which to sell sales tools. 

Bravado’s first two hit products, Portfolio and War Room, came from insights that Sahil had gleaned himself, by seeing products like Stack Overflow and Dribble that other professions had access to, but that salespeople didn’t. Its next two, Jobs and Flex, came from insights generated in the War Room, and built on top of both War Room and Portfolio.

But Sahil’s original a-ha was bigger than any one product; it was that no one was building great software for salespeople. That’s Bravado’s big opportunity. 

It can listen to its members’ issues with the tools that they have to use, probe for more detail, and then spin out products that address those issues. When it creates new products, it can train its community on how to use those products, and then distribute them bottoms-up, community-first into the 50,000 companies for which its reps work. 

Instead of building a product and grinding for the first couple of years to find buyers, it’s grinded for the past four years building a community so that whenever it launches a new product, it does so to a waiting audience of exactly the people who would use and buy those products. 

In a May interview with TechCrunch, Sahil summarized why he thinks sales is so crucial: “There’s basically two really important jobs in any company, which is that you either build the product or you sell the product.”

Bravado has painstakingly created a community-first cheat code to sell the products. Just how big it gets will come down to its ability to build the products that that community needs. 

If you’re interested in learning more about Bravado, including the new Flex product for companies to hire salespeople on a 100% commission basis, or generally want to nerd out about how to grow revenue during the downturn, you can reach Sahil directly at [email protected].

Thanks to Sahil for working with me, and to Dan for editing!

That’s all for today, we’ll see you tomorrow morning for a Weekly Dose of Optimism!

Thanks for reading,

Packy