Category: Entrepreneur Journey

Couchbase is on a mission to empower enterprises to develop, deploy, and maintain their mission-critical applications by delivering a high-performance, flexible and scalable modern database. Today the company listed on the Nasdaq exchange under the ticker symbol “BASE.” I sat down with Couchbase President and CEO Matt Cain to get a little more insight into how leadership and culture paved the way for Couchbase’s journey to IPO.

Congratulations on Couchbase becoming a public company! What role do you think culture plays in a company’s success?

I believe that the foundation of any leading company is its world-class team, a combination of industry leading talent and a set of values that enables those people to do the best and most fulfilling work in their careers. Culture is the product of those values in action, and leaders must be the stewards of ensuring the company is living consistently with them. When it comes to teamwork and communication, I have tried to create as many opportunities as I can to ask what’s working, what’s not working, and where the team needs help. At Couchbase our culture is a sustainable competitive advantage as we attract, develop and retain the highly-skilled talent necessary to execute on our business growth strategies. The leadership team and I work relentlessly to make Team Couchbase feel valued so they can then work together to create value for our customers, partners and shareholders.

Describe your leadership style and approach as CEO.

Several early-life experiences shaped my approach to leadership. First, my parents raised me with strong Midwestern values. I also developed a love and passion for teamwork and collective goals through competitive team sports. And going through a Jesuit education reinforced the concept of leveraging your talents to make the world a better place and act as a “person for others.” Roll all of these together and you get a servant leadership style with an emphasis on teamwork. I’m about the “extreme ownership” and “servant leadership” philosophies to drive the best results while building a culture that is durable– and wins. In this model, the leaders are ultimately responsible, but teams make the difference. My goal has always been to build, reinforce, and model a culture of openness, transparency, and trust that delivers results. And we have to have fun along the way!

Couchbase was founded in 2011 and you came on board in 2017 as a first time CEO. What was that like, stepping into a new role to lead a company?

So one of our company values is Attack Hard Problems, and that’s sort of the approach I took head on when I arrived at Couchbase. I think there’s a razor-thin edge that elite performers must balance between self-confidence, or a willingness to try new things, and humility, or knowing that you will get things wrong. With this mindset and when facing challenging times as a leader, I try to stay calm and work through things as a team. I also try to remember that I’m in service of others, like employees, customers, partners, and shareholders, to derive motivation to work through hard things. I can’t fix problems I don’t know about, so I work hard to maintain a genuine connection with as many of our team members and possible. As an example, in my first 100 days I committed to setting up at least 100 meetings with employees, customers, investors, partners, vendors and analysts to listen and learn. I’m a true believer that people can do amazing things when they work together and put the team first. I’m very proud of what we have accomplished so far as a company, and I think you can see some of that reflected in things like our Glassdoor rating and also in our business results which allowed us to become a public company today.

What advice would you give another CEO as they begin to prepare for the IPO process?

Surround yourself with a world-class team. No one person can go through this rigorous process alone– it really does take a tremendous amount of teamwork and collaboration. Invest in your people and your culture because at the end of the day, the results the team delivers are what are going to help position the business to go public. That and get ready for the grind! In all seriousness, it really does require a super talented team to pull it all off. I’m grateful for the team’s continued dedication and passion for our business, even in the face of a global health crisis. It inspires me every day.

Congratulations again to Matt and the entire Couchbase team on their IPO, which marks the latest milestone in our decade long journey – looking forward to all that is to come.

For the five years Mayfield partner Ursheet Parikh sat on Rancher Labs’ board of directors — from Mayfield’s A round investment in 2014 to the sale of the company in 2020 for over $600 million — Rancher never missed a quarterly financial target, despite two major pivots and one pandemic. Even the board meetings went smoothly, says Parikh, never exceeding the allotted two hours.

“Working with Rancher has been a delight from day one,” says Ursheet. “It’s the lowest-drama company I’ve ever seen.”

Sheng Liang, co-founder and former CEO, credits a “keep-it-simple” philosophy. “We hit our goals by laying out a plan we think we can achieve, and then finding a way to meet it. That’s it,” says Sheng, who is now president of engineering and innovation for SUSE, the German open-source giant that acquired Rancher last December.

Of course, keeping things simple doesn’t just happen. It requires some key ingredients. First among them is trust, so that executives, employees, and directors know they can rely on each other to do what they say they will. Another is transparency, so that everyone can pull together to address challenges as quickly as possible. And it requires a particular kind of pragmatism.

“To be a successful entrepreneur, you have to be ambitious and optimistic. You have to believe you can topple VMware, or Amazon,” says Sheng. “But many companies get carried away and don’t back it up with a dose of reality.”

Sheng, an engineer who had a key role in the development of Java while at Sun Microsystems in the 1990s, eschews many practices that complicate life for Silicon Valley entrepreneurs. For example, Rancher never had different sales targets for the board, the company, and the sales team. There was no sandbagged “board plan” to keep Sheng looking good for directors, and no unrealistic “stretch” plan promising soaring bonuses to salespeople who hit higher sales quotas. Instead, every salesperson at Rancher had one unchanging quota, based on the only plan that mattered: the real one.

“If you can grow 100% a year, there’s no reason to go for 120%,” says Sheng. “Heck, if you just grow at 50% for another 20 years, you’re the next Microsoft.”

Seeing the opportunity

Given its business, Rancher had little room for shenanigans. The company was founded in 2014, when companies were flocking to a new technology called “containers,” which let them deploy their software in tiny chunks that could be run on any kind of infrastructure, from a mega-data center to the server in the closet.

Rancher’s founders immediately understood the implications. Sheng, Shannon Williams, and William Chan had founded Cloud.com in 2008. It sold software for anyone that hoped to create their own cloud platform rather than use AWS or Azure.

By the time they started Rancher (Darren Shepherd, a former Cloud.com customer, was the fourth co-founder), very few people would think of competing with AWS, Microsoft, or Google. But while these companies offered their own container services, Rancher’s founders foresaw a day when companies would need “multi-cloud” tools that would work on all of the main platforms — say, to be able to shift to another cloud service or company-owned data center, if a cloud had an outage.

For the first 18 months, the team struggled with how to help customers trying to run software in such a heterogeneous world. A technology called Docker had emerged as the basic container technology. If Docker containers were like rail cars of code, customers still needed a system to organize them into trains, and to manage those trains as they moved onto different gauge rails.

Rancher built a Docker-based system, just in time for it to be rendered irrelevant by Kubernetes, an open-source technology created by Google that quickly became the standard container framework. Suddenly, the tiny company faced competition from a slew of well-funded startups offering their own implementations, or “distros,” of Kubernetes. Worse, the cloud giants themselves threw in Kubernetes management as a freebie to get companies to use their cloud offerings.

It was a scary time, says Shannon. But the level of trust was such that no one left. “We had so much confidence in each other that we didn’t face the self-doubt that brings down a lot of startups,” says Shannon. “We were able to move through a risky time pretty comfortably.”

Forging a new path forward

The easiest path would have been to crank out their own distro, with extra features or some other small advantage. But Sheng was not willing to bet the company that Rancher could do a better version of free.

“If you have an ounce of honesty, you’d have to realize that was a hopeless business model,” he says. “It was obvious to us, but I can tell you it wasn’t obvious to a lot of our competitors, and still isn’t.”

Instead, the team bore down on finding unaddressed niches in the Kubernetes ecosystem. While many distros focused on running software on a particular public cloud, Rancher’s namesake product helped customers easily move containers between competing clouds, but also on other kinds of infrastructure, such as legacy, company-owned data centers. In 2019, it added a popular miniaturized Kubernetes distro called k3s that can be squeezed into IoT devices such as wind turbines and drones, which have very limited compute capacity.

As sales rose, the founders made sure to keep their focus on market realities. At one critical juncture, Sheng and Shannon, who was Rancher’s president before the acquisition, decided to write down a list of all the reasons a customer would not buy Rancher’s products — from lack of a feature, to the fact that the company was simply too small. While many startups focus only on making their products as good as possible, “We’ve learned that the why nots are often more important than the whys,” says Shannon. Rancher’s development effort therefore focuses as much on eliminating “why-nots” as creating “whys.”

By early 2020, Rancher had carved out a valuable corner of the booming Kubernetes ecosystem, and done so quickly. Sheng loves to point out that rival Red Hat had a Kubernetes distro before Rancher was even founded, but didn’t come out with a Rancher-like product until 2020. “We went from three years behind Red Hat to two years ahead.”

When SUSE approached the company about an acquisition in July, the Kubernetes market was heating up. While the pandemic had hurt overall tech spending, it had also caused many companies to accelerate their adoption of the cloud as a way to save money and accomplish their digital transformation goals. While Rancher had grown to 250 people, Shannon figured SUSE’s much larger sales and engineering teams meant Rancher could quickly reach ten times more customers than it could on its own.

“The market was developing much quicker than expected, and by combining forces with SUSE we’ll be able to build the undisputed market leader in Kubernetes,” says Sheng. “Ursheet supported us staying independent but also realized that the exit could help us realize our vision and that it made sense for our stakeholders and employees.” The SUSE offer was one of many, and the company’s value had more than doubled by the final bid.

Read also: Ursheet Parikh’s cradle-to-exit role at Rancher Labs

“We’ll never know what might have happened otherwise,” says Sheng, “but we probably did the right thing.”

Again, no drama.

Ankur Singla knows what it’s like to be an overnight success. Back in December 2012, Juniper Networks bought his first start-up, Contrail Systems, for $176 million. The company was just nine months old.

So when Ankur started Volterra in 2017 with $25 Million in Series A funding led by Mayfield, he was looking for a different kind of experience. He wanted to develop technology to tackle one of the digital economy’s knottiest problems, knowing full well it might take years to solve. He just didn’t know which problem. So while he searched, Volterra’s engineering team started work on a new kind of soup-to-nuts “edge” network that companies could use to replace scads of standalone products that weren’t designed for modern cloud applications. Whatever problem Ankur ultimately settled on, it would make use of this cloud networking platform. 

“I was on a quest to find that big application, and we ended up going on a lot of goose chases to find it,” says Ankur. “And then the pandemic hit.”

Suddenly, companies all over the world were trying to figure out how to keep employees productive from their homes, and edge-centric networks, which handle traffic closer to end users so everything doesn’t go back to overwhelmed corporate networks, were suddenly center-stage. After refocusing on a technology that was supposed to have been a means-to-an-end, the company’s sales grew at a 300% clip in 2020. To take better advantage of the sudden demand, Volterra agreed to be acquired by much larger F5 Networks for $500 million in January 2021.  

“We didn’t want to do another infrastructure company,” he says. “We created technology we could apply to a big and tangible problem, like autonomous cars or industrial robotics. In the end, we found we’d already created something that applied across many problems.”

“Founding investors have to build a zone of trust with founders as they explore the different phases of early stage company building,” says Mayfield managing partner Navin Chaddha. “It was a delight to partner with Ankur, who is a big thinker and constant learner, as he and the team guided Volterra to a great outcome for all.”

From the beginning, Volterra’s networking and security technology was designed to address the obvious weaknesses of legacy networks in a cloud-centric world. For decades, companies had built expensive, complex private networks so employees in the office could safely use applications they created or purchased from companies like Microsoft and Oracle. By comparison, the public Internet was insecure, slow, and inefficient. With little network capacity at the edge, every mouse-click generated traffic that might have to travel thousands of miles to a corporate network or cloud data center.

The public Internet was also unbalanced. Network capacity was largely architected so a few big companies (think Netflix) could push content to consumers and far less for when consumers wanted to send information back.

Read also: How Mayfield’s Navin Chaddha Supported a Founder’s Quest

Ankur realized those assumptions no longer applied. Long before the pandemic, companies were shifting rapidly from on-premises applications to cloud services that live on that same Internet they used to eschew. And overall traffic patterns were shifting as well: It wasn’t just Netflix movies sucking up the Internet’s capacity, but billions of Instagram, YouTube, and TikTok posts ricocheting across the globe.

“The Internet was built for moving data downstream. With the distributed nature of modern applications, we realized it needed to be more symmetrical,” Ankur says. “That was probably our biggest insight.”

But it wasn’t his only one. The 100-person engineering team also developed a new security model for distributed applications and a console that enabled network administrators to easily monitor and manage them all. Significantly, it was “multi-cloud,” allowing companies to securely manage apps hosted on AWS, Google Cloud, and Microsoft Azure as if they were one.

“The basic idea was, ‘We will operate the network and apps for you so you can focus on your business,’ Ankur says.

When the company came out of stealth mode and began selling in 2019, the response from customers was swift.  SoftBank, for example, signed up to use Volterra’s platform in its new 5G network in Japan, as did other companies from a wide variety of industries.

While Ankur kept drilling down on the right applications to maximize Volterra’s value-add, the company leveraged the capital it raised to staff up to about 125 employees, almost half of whom were industry veterans who had worked with Ankur at some point during the past 15 years.

When COVID hit, Ankur expected demand for the product would drop. He decided to put his quest for “the killer application” on hold, and focused on the existing product to ensure the company’s near-term survival. Instead, demand spiked as companies that had only been thinking about moving to multi-cloud and edge-centric computing suddenly had no choice. Enroute to that 300% growth in 2020, Volterra signed up customers that included two more huge phone companies and a top five carmaker.

By year end, it had become clear the company’s ten person sales and marketing team couldn’t keep up with demand. Ankur began looking for a partner with a larger sales force and established marketing programs, to help make the most of the moment. 

One of the potential partners was F5, a 25-year-old company with a broad product lineup, a well-known brand, and a long list of marquee clients that might be receptive to Volterra’s technology. The companies also shared a similar raison d’être.  Both focused less on the basic plumbing of the Internet, and more on making sure companies could run their apps as quickly and safely as possible anywhere. 

When talks escalated and F5 made its acquisition offer, it was the right decision for investors and offered the best way to drive adoption of the company’s technology. 

“I had really wanted to keep building the company,” Ankur says. But after long discussions with advisors including Navin, Volterra accepted the bid from F5.

“You’ve got to do what is right for the team,” Ankur says. “I’ve learned over my career that if you don’t, things will never work out in the long-term.”

From the outside, the brief story of NUVIA reads like a Silicon Valley fairy tale. Three semiconductor industry veterans who had worked together at Apple on the A-series chips that power millions of iPhones and iPads started the company in 2019 to create an ambitious new kind of chip for data centers. Less than two years later, on Jan. 12, Qualcomm announced its intent to acquire Nuvia for $1.4 billion plus company cash and completed the acquisition on March 16.

Easy peasy, right?

Wrong. NUVIA had raised a $53 million Series A round in Summer 2019. The founders started discussions with investors and strategic partners to raise their Series B, with expectations of closing a round within a few months.  But after COVID-19 hit, all financing discussions paused, leading to worries about future funding.  “This put some serious gray hair on our heads,” says Gerard Williams, NUVIA’s CEO, who co-founded the company with Manu Gulati and John Bruno. “We’d convinced hundreds of great people to leave cushy jobs to join us.”

Having never so much as pitched a VC before starting NUVIA, these first-time founders were fortunate to have an experienced team of advisors and board members to help them navigate the challenging times. Our own Navin Chaddha took a particularly active role, both in driving a process that led to a $240 million Series B last September, and in the decision to sell to Qualcomm a few months later.

Navin’s involvement with NUVIA dates back to early 2018, when Manu and John, then at Google had an idea for a data center start-up and then reached out to talk to Gerard, still at Apple, about joining them in this endeavor. To test their basic thesis — that data center operators needed a new kind of super-fast, low-power server chip to keep up with the soaring demands of an increasingly cloud-based economy — Manu called Navin for an informal chat.

The two had known each other since the late 1980s, when they were classmates at the Indian Institute of Technology in New Delhi. Manu knew that Navin was one of the few VCs in the Valley with experience and enthusiasm for the high-stakes game of building chips. He’d even developed a detailed thesis about a coming “silicon renaissance.” 

“Not many investors have an appetite for something as capital intensive as building silicon, and far fewer understand the big picture, or all the global trends,” says Manu. “Navin advised us to go big. Plus, Navin was the top student in our class, so we wanted him on our team.”

The admiration was mutual. Navin had followed Manu’s career as he, and later John, moved to Google to create processors for consumer devices. The two of them and Gerard have a combined 100 patents and 20 major chip architectures on their resumes.

A pandemic, and a seismic industry change

NUVIA got off to a great start. By the end of 2019, it had assembled a star staff of 100, and was well on its way to developing a server processor codenamed “Phoenix” that in tests would run up to twice as fast as competing chips from Intel and others. By February of 2020, Nuvia had lined up investors for a big Series B round to be raised around mid-year. 

Then, the pandemic hit. “Everything came to an absolute standstill,” says Gerard. “It seemed like no one wanted to jump in anymore until things got back to normal.”

That’s when Navin and other board members took a more active role. They led a plan to reach out to potential investors and run a tight fundraising process. They pitched many new entities within a few weeks, including big financial institutions (previously, they had focused on VCs and strategic partners). During this time, the board met around three times a week to discuss promising leads, but Navin often spoke with one of the founders multiple times a day. “Navin was very, very proactive in making sure all the leads were followed and making sure the spreadsheet was up to date,” says Manu.

Finally, on Sept. 24, the company announced a $240 million Series B. The round was led by Mithril Capital, and Mayfield was joined by investors including Marvell Technology Group founders Sehat Sutardja and Weili Dai, as well as funds and accounts managed by BlackRock and Fidelity Management, WRVI, Dell Technologies, Capricorn and others. 

Then, the industry was rocked by a series of headline-making announcements that reinforced new realities, including increased consolidation in the data center silicon industry, including a decision by the world’s largest consumer device company to make more of its silicon itself. In September, Nvidia announced a planned $40 billion acquisition of ARM Holdings, saying it would let big cloud companies integrate Nvidia’s AI and graphics technologies into custom-designed chips. In November, Apple unveiled its first Macs powered by its own M1 chips (rather than chips from Intel).

As they tried to think through the new market realities, the team got the kind of sober, honest counsel that Navin is known for. He explained why the changes might reduce NUVIA’s TAM if more companies moved to in-house silicon programs, but also why the new conditions might compel industry giants to want to buy NUVIA in short order.

Sure enough,there were multiple acquisition inquiries  – and the founders were prepared to consider them. Just to be sure, Navin and other directors spent time with each of the co-founders to find out if they were ready to give up on their dreams of building their own independent, public company. “The board was 100% behind us either way,” recalls Manu. “But emotion can get in the way at times like these. Navin helped us stay data-driven and objective. He plays the cards in front of him, and doesn’t mince words. I love that about him.”

When talks with Qualcomm got more serious, Navin showed another side of him that the founders hadn’t expected. “Navin really, really, really – I don’t know how to emphasize this enough – cared about our employees. Looking back on 2020, it’s clear he was trying to do what was best for them all along the way,” says Gerard.

“None of this could have been possible without the support and guidance of our early stage investors, and in particular Navin,” says John. “He took a threesome of first-time founders and stood by our side all the way through.”

When asked about the one quality that first-time founders should look for an investor, the answers come in quickly:

Gerard: Stamina;  Manu: Founder friendliness; John: Resilience

The relationship between Mayfield partner Rajeev Batra and Manny Medina, the co-founder and CEO of Outreach, started off with a big misunderstanding. Actually, two of them.

The first happened in 2012, when Manny sought Mayfield’s investment in GroupTalent, a recruiting software start-up he had co-founded. After hearing the pitch at Mayfield’s offices, Rajeev was deeply impressed with the first-time CEO’s obvious talent, curiosity and intensity. “He clearly showed many of the signs of a great entrepreneur,” says Rajeev. But all Manny heard was that Rajeev chose not to invest.

Then, two years later, Rajeev cast the deciding vote against Manny’s newly pivoted incarnation of the company in a startup competition put on by the Harvard Business School, their mutual alma mater. Manny’s antipathy hardened. “When I heard how we’d lost, I swore I’d never speak to Rajeev again,” says Manny, a former Microsoft product manager and early Amazon AWS team member. “He was dead to me.”

So a year later in April 2015, Rajeev knew he was in for a fraught conversation when a couple of mutual friends told him that GroupTalent had morphed into Outreach – and was exactly the company he’d been searching for: one that made software to help salespeople be more effective in their outreach to potential customers. When one of them urged him to give Manny a call, Rajeev thought: “Ooh, I’m not so sure he likes me very much.”

Unable to quell his intellectual fascination for anything involving sales and marketing-related technology, Rajeev overcame his hesitancy and contacted Manny. After a somewhat chilly first exchange – they laugh now about how Manny at first tried to put off the meeting for months, before inviting Rajeev to his tiny office – they quickly bonded over a shared belief that Outreach could crack one of the most obvious remaining opportunities in cloud software. Despite Salesforce.com’s dominance of the CRM market, the cloud had yet to revolutionize the daily lives of salespeople.

“The original idea behind CRM twenty five years ago was to help salespeople be more productive, but it ended up being a tool for sales managers that salespeople are forced to use, not because it helps them or they love it,” says Rajeev. What salespeople needed, they agreed, was a tool to help them boost their win rates by optimizing and streamlining their use of communications channels such as the phone, email and LinkedIn. “I’d kept close tabs on sales automation since I worked at Siebel in the late 1990s,” says Rajeev. “It was clear that Manny was approaching the problem in a truly original way that could transform how salespeople engage with customers.”

Five years later, Outreach is the leader in a thriving market called Sales Engagement. Its position in the burgeoning market, estimated to be $30B+, has turned Outreach into a unicorn. The company estimates that fewer than 10,000 companies now use sales engagement tools, compared to a million or so that use CRM to keep track of customer accounts. “This is a 100x opportunity,” says Manny.

And a relationship that began bumpily has turned into a deep bond, with Rajeev becoming a trusted advisor for Manny on everything from the company’s basic business model, to how to professionalize its own sales and marketing strategy. Meanwhile, Rajeev has come to admire Manny’s purposeful, transparent leadership style, and the way he has honed a company culture that is hard-driving yet empathetic. “The real story is about Manny’s growth as a CEO, from a guy with a twinkle-in-his-eye that wouldn’t take no for an answer, into the leader of a company that is changing the world,” says Rajeev.

The anatomy of a founder/early investor partnership

When Rajeev made that call in April 2015, Manny and his three co-founders had begun to pull their company out of a death spiral. With cash running out, they’d created workflow software to help them make better use of digital tools to identify and set up meetings with potential customers for their recruiting platform. When customers began showing more interest in the sales software, they pivoted hard and relaunched the company as Outreach.

With grit and charisma, Manny all but willed the company forward. He landed dozens of accounts by cold-pitching tech executives as they tried to enjoy a quiet latte at a San Francisco coffee shop. “It makes it very hard for people to say no when you’re standing right there,” Manny says.

When Manny first responded to Rajeev’s call, Outreach had just raised a $2.4M seed round for the newly pivoted business and was not in a rush to raise a series A. Still, Manny couldn’t resist making Rajeev sweat a bit.

“We’re a little booked up until after Memorial Day,” Manny told Rajeev. That was more than a month away, an eternity for a VC who thought he may have found the startup of his dreams. Manny ultimately agreed to meet sooner, but insisted Rajeev come up from Sand Hill Road to Manny’s tiny office in a not-so-swank section of San Francisco. “It was really just a desk, two chairs and a table with a TV that didn’t work,” Manny laughs. “I appreciated his persistence. He knew this was not going to be an easy meeting.”

By the end of the 2.5-hour meeting, things had turned around. Manny had given up his boycott of Rajeev. He started contacting the dozen or so CEOs and SaaS leaders Rajeev felt could help the first-time CEO take advantage of the opportunity Outreach had created. That August, Mayfield led Outreach’s $9 million Series A, and Rajeev joined the board.

From startup to “real” company

From the very beginning Manny was tapping Rajeev’s insights about how to scale a SaaS company and expertise in CRM. The Mayfield partner had been an early investor in Marketo, a leading marketing automation software company that had done for digital marketers what Outreach was trying to do for salespeople.

The most obvious place where Outreach needed help was ironically, in finding true product market fit and aligning its go to market (GTM) motion and putting basic financial controls like collecting cash before paying commissions. Manny had cobbled together a less-than-traditional team for a company aspiring to sell to the world’s most sophisticated companies. It consisted of a small group of gung-ho recent graduates willing to work on commission alone–more Glengarry Glen Ross than Silicon Valley. Manny let them set up a sales office amid the shut-down steel mills near Penn State. The average deal size they were closing was just $1,200 and less than two seats per customer.

“You know you can’t build a big company this way, right?” Rajeev told Manny the day after Mayfield became an investor in Outreach. “He told me ‘You’re running this place like a drug dealer,’” says Manny. That was on a Friday. On Monday, after a weekend of worry, Manny called an all-hands meeting. From then on, he announced, Outreach wouldn’t do deals for fewer than 10 licenses.

When sales began to soar, Manny’s instinct was to keep his foot on the gas. But when he told the board of his plan to grow annual recurring revenues for 2016 six-fold, from $2.7 million to $17 million, Rajeev urged him to first ensure the company could give itself the room to learn and build its teams and processes to nail product market fit and understand levers of growth. “What are you trying to prove, Manny?” After much debate, Manny changed the target to “only” $10 million. “As a systems thinker, Manny relies on both data and instinct,” says Rajeev. “There is an obsession with the numbers and not the “why” of the numbers. You want to create a culture of setting lofty yet achievable goals, not impossible ones. This creates a possibility of winning, not one of despair & losing no matter what.”

Building a world-class team & equitable culture

The Outreach culture has always been “team first” and deeply rooted in its values of GRIT, having “each other’s back”, accountability, and customer centricity. To that end Manny has been obsessed with surrounding himself with a great team and advisors he can learn from and be an excellent leader & CEO. From the early days, upon Rajeev’s recommendation, he joined 10XCEO, a peer based CEO coaching group and now counts many world class SaaS Entrepreneurs and CEOs on his speed dial and many who reach out to him for counsel. The company has won numerous awards for being one of the best companies to work for.

Working closely with Rajeev, Tejas Maniar, Mayfield’s head of talent, has helped Manny and Outreach CRO, Anna Baird recruit its CTO, CFO, chief people officer and other key people. Gamiel Gran, Mayfield’s vice president of business development, leverages the firm’s CXO network to connect Outreach executives with people who can supply everything from messaging feedback to customer introductions. Kamini Ramani, Mayfield’s VP of Marketing, secured an invite for Manny to attend an exclusive retreat of enterprise software leaders, at which he met Aneel Bhusri, co-founder and CEO of Workday, who became an investor and advisor to Manny.

While he’s a sponge for learning from others, Manny has an uncanny instinct for talent and people, an important quality in a CEO which is worthy of honing. Most importantly, as an immigrant of Latin/Russian descent he understands what it means to not be from “central casting” and to be overlooked for otherwise suitable opportunities.  When Outreach was preparing to hit the gas on its growth plans, Manny insisted the company hire Matt Millen, who had run sales for motivational speaker Tony Robbins before selling business telephone services for T-Mobile. Rajeev was surprised given Millen’s lack of SaaS experience but shared Manny’s belief that Millen’s empathic, emotional style would resonate. Millen ended up taking sales from $5 million to $50 million before Manny promoted another “non-obvious” choice: former CFO/COO Anna Baird into the CRO role.

Vision, mission and purpose

While there has been an incredible focus on establishing and owning the Sales Engagement category, Manny is always thinking bigger, strategically about the future of the market and most importantly what is the purpose of Outreach.  Why should it exist and why does it matter and to whom?

The basic thesis behind Outreach – that existing sales tools such as Salesforce.com’s CRM was beloved by sales managers, but not by actual salespeople – was bearing out. Rather than position Outreach as an app that could fit into those CRM platforms, the company has set out to create an entirely new AI driven platform for sales and customer engagement addressing a completely different paradigm.  One, where buyers are in control and users of technology are digital natives and remote selling is the norm. It is like providing autonomous cars in a world of horse drawn carriages.  That has meant making huge investments in everything from engineering, which is 40% of revenue, to positioning and branding, and it meant “tickling the dragon” that is Salesforce.com.

Above all, Outreach is about using technology to enable salespeople, the true unsung heroes, to solve their customer’s problems, drive revenue for their business and earn a living.  When sales people can be empathetic to their customers’ needs, the top line improves efficiently for a company, which in turn allows it to invest and innovate and improve the world.  The mission and the “why” of Outreach is simply that and as Manny puts it most people have one big idea and this is it for him!

The pandemic has only served to accelerate the company’s mission with more than 4500 companies running on Outreach.  With $289M in total venture funding, the last round even included Salesforce.com’s internal venture group, a nod of acknowledgement from the biggest player in SaaS.

Thinking back on what went right, Manny and Rajeev agree on a few key lessons.

You should choose your investors – not get chosen by them.

Besides Rajeev’s willingness to change his mind and hustle, Manny was impressed that the Mayfield partner truly shared, and understood, his vision. “After working with Mayfield, we never engage with a firm that doesn’t come in understanding the market. If a VC says ‘alright, pitch me your market’, I’ll say ‘no, you pitch me my market’,” says Manny.

If you’re creating a category, don’t try to be too cute. Enter it, embrace it, most importantly own it and lead it.

Outreach began evangelizing the idea of sales engagement software in 2015, but the concept didn’t immediately resonate with influencers and the media. Concerned, the company spent several months and too much effort trying to establish other labels, such as “revenue intelligence management”. Rajeev, who’d seen Marketo go through a similar process before coming back to the original “marketing automation” idea that ultimately led to its acquisition by Adobe in 2018 for $4.75 billion, was among the voices urging Manny to stick with the original plan. “The lesson was to be extremely intentional about owning and leading the category,” says Rajeev.  “Especially when your customers and all the players in the market start embracing your original pitch.”

“The first rule of building a category is don’t call it something stupid,” says Manny. More seriously, stick to your guns on the strategic value, and try to create a vocabulary that establishes you as the leader. “Suddenly, after a year, all our competitors are talking about ‘sequences’,’’ which is a key element of Outreach’s product and has been prominent in Outreach’s marketing.

Helping people and cultivating friendships helps cultivate sales.

One thing Manny learned while selling to strangers in coffee shops is that selling is still a very human activity. “If I could get someone to watch our demo, I had a 100% hit rate in getting them to do the trial,” Manny says. And often, those people became personal friends that turned into long-term supporters for the company, as well.  Which in turn fueled a grassroots movement for the category and Outreach.

It’s not what you know, it’s what you’re able to learn.

Manny says he was not a natural salesman. In fact, he wasn’t born much of a capitalist. He grew up in Ecuador, where his grandfather was a leader in the Communist Party. He credits his ability to continually adapt to an insatiable curiosity. “My superpower, if I have one, is that I’m unnaturally curious about your business. I’m almost voyeuristic, but it tends to lead to a lot of great discovery calls,” he says.

Rajeev credits Manny for his ability to grow from the hustling first-time founder pitching potential buyers at coffee shops, into a seasoned leader and CEO who combines competitiveness with an insistence on doing what’s right. Whether it comes to hitting revenue goals or on revamping a basic human activity – selling – “he simply doesn’t take no for an answer.”

Of course, Rajeev and Manny don’t agree on everything. Manny still doesn’t seem persuaded by Rajeev’s convoluted explanation about why he wasn’t actually the deciding vote in that HBS contest five years ago.

But they’ve settled into a fruitful partnership in which Rajeev, who has seen some version of whatever Manny’s latest challenge happens to be, provides a patient ear. “When you’re growing as fast as we are, you’re always operating way out in front of yourself so there’s going to be some self-doubt,” Manny says. “But Rajeev is a great sounding board, so those doubts don’t become debilitating.”