In an engaging conversation, Nir Goldstein, former VP of Global Sales at Monday.com and current General Partner at Greenfield Partners, delves into his journey of scaling Monday.com’s revenue from $50 million ARR to $800 million. Sharing insights on leadership, the challenges of selling a horizontal platform, and the importance of focusing on individual growth before scaling a company, Nir offers a candid perspective on building a thriving sales organization. Here’s an excerpt of the conversation.
Omri: What were the playbooks that you guys utilized over Monday to make that jump?
Nir: There were so many, but if I had to outline the main guideline that led us while building the sales group, it was really about building a machine and mechanizing it. It may sound a bit awkward, but we focused less on chasing the next $100,000 or $1 million contract. Instead, it was more about building the framework, establishing the rhythm, and maintaining the right pace. So, every year when I reviewed my quota, knowing that it would likely triple the following year, I was more concerned with whether I was at the right run rate, hiring pace, and pipeline creation pace than just closing out the current year.
Omri: What do you think made Monday different that made it what it is today?
Nir: I think there are a few key aspects. First, I wouldn’t define Monday.com as just a productivity tool, even though that’s one way we market ourselves. What really made Monday successful, and what companies actually use it for, is managing core processes that other systems don’t address. If you consider the main processes in each department, you typically have a go-to system of record: for sales, it might be a CRM; for support, it could be something like Zendesk; and for finance, maybe ERP systems.
But there’s a long tail of processes—processes four, five, six, and eight—such as how salespeople collaborate with legal on contracts or how different departments coordinate. For these areas, there’s often no dedicated system, creating a huge white space typically filled by Excel, emails, and chats. This is where Monday.com stepped in, providing a highly flexible tool that allows departments within organizations to fill those gaps. That was a significant unmet need, and Monday became the solution to address it.
The second factor is the strength of the product itself. One reason for this is that Roy and Eran, the founders, insisted on not having a sales team for the first six years of the company—maybe longer than usual, but it created a near-perfect product-market fit. Without a sales team to explain the product, it had to be compelling, intuitive, and easy to use to convert leads into paying customers on its own.
Additionally, they built a massive, highly efficient marketing engine to capture and nurture leads. So, by the time a sales team was eventually introduced, they had a powerful product supported by a strong marketing machine, which gave them a huge advantage.
Lastly, the culture played a big role. One of the most inspiring things for me was seeing a large dashboard on a massive screen in the office that Roy had sketched out himself. It detailed their ambitious targets: $50 million ARR in the first year, 100,000 users; $200 million in the second year; and $350 million, $500 million, and eventually $1 billion ARR. It looked almost imaginary at the time, like a bold prediction. But the company moved quickly and aimed high, creating a culture that encouraged taking risks, making decisions fast, and learning from mistakes. This mindset was key to maintaining that rapid pace of growth and hitting those targets year after year.
Omri: How did you feel about transitioning to Greenfield? Why did you make that move in the first place?
Nir: Our approach at Greenfield is rooted in the belief that while there’s a significant amount of capital available for startups today—much more than a few decades ago—it’s crucial that this money comes with value. This means offering “smart money” that goes beyond just financial investment. We strive to provide a solid value proposition to our portfolio companies in two main ways.
First, we focus on being exceptionally founder-friendly. We prioritize supporting the founders we invest in and place a strong emphasis on the people behind the companies. Founders are already navigating a challenging journey, and we aim to stand alongside them, offering guidance, identifying potential pitfalls, and helping them succeed. Of course, we’re here to critique and offer constructive feedback, but we want to be partners in their growth, not just financial backers.
Second, our specific focus is on rounds B and C—crucial stages where companies transition from product-market fit and securing initial clients to full-scale expansion. At this point, they’ve often secured a sizable check and are expected to deliver significant results. This is a pivotal phase for many businesses, and a lot of them either struggle to make this shift or take a long time to do so. Our goal is to help them navigate this transition successfully and as quickly as possible, diving deep into the operational and strategic aspects of scaling.
As for my transition, it wasn’t an obvious move. If we had discussed this two years ago, I would have said that the chances of me leaving Monday were close to zero. I love the company, I love sales, and I felt Monday was still at the beginning of its journey. However, when I met the team at Greenfield, I saw many parallels to the early days at Monday—a small, promising organization with the potential to build something big.
We aim to be one of the leading funds in the early growth stage, focusing globally on rounds B and C, and I believe we have the potential to achieve that. It’s a huge challenge, but I think we’re up to it.
Omri: When you talk to founders aiming to hit that benchmark of $100 million ARR, what are some of the main challenges you see?
Nir: And by the way, the challenges don’t end at $100 million. When it comes to promising companies, especially those aiming for high valuations, their projections often go far beyond $100 million. So, the day after securing an investment, they need to deliver. They need to scale rapidly.
There’s a big difference between landing contracts manually and doing it in a sustainable, scalable way. It’s possible to reach tens of millions in ARR through manual efforts, but if you don’t establish the right mechanisms and build the proper engines to maintain that momentum, you’ll eventually hit a ceiling and slow down. This is exactly what we’re trying to prevent.
I’ve seen very few startups—both in Israel and globally—put in the necessary resources and strategic focus to build a long-lasting, scalable go-to-market machine. But doing so is crucial for sustaining growth and reaching those ambitious targets.
Omri: What challenges do founders face when strategizing for growth?
Nir: The good news is that, at least in my conversations with them, I don’t hear a lot of pushback, which is a positive start. From there, I find that the companies generally divide into two groups. The first group consists of those that don’t really understand what’s ahead or what scaling truly entails. The second group recognizes what’s coming and what they need to deliver, but they often lack a clear understanding of the different mechanisms they need to establish to achieve those goals.
If you’d like, we can dive deeper into this, but essentially, there are about seven key areas where they need to start implementing the right processes to ensure sustained growth. For instance, when you look at the role of a sales leader in a company generating $10 million in ARR versus one generating $100 million, their day-to-day responsibilities differ significantly.
In a $10 million ARR company, you might have sales superstars who can step in and close deals that the team is struggling with. They might have 10, 20, or even 30 sales reps following them from one opportunity to another, and those skills are crucial for a sales leader at that stage. However, as the team grows and the company scales, leaders must begin to plan strategically. They need to analyze data, refine strategies, and adjust policies—all of which require a different skill set.
Not everyone can make this transition smoothly, and even those who can must learn new skills along the way. This shift presents a significant challenge not only for the companies but also for the leaders themselves.
Omri: Is it a healthy approach for founders to recognize that while they have a solid product and some market fit, their platform might not scale for VC backing? Can operating as a privately held business be a viable strategy? Also, is there a way for these companies to maintain a lower profile and wait for cheaper funding opportunities to arise?
Nir: First, I don’t believe that every company is meant to become a unicorn—that’s why the term “unicorn” exists in the first place. Not every company will reach the stage of going public; some will exit at a smaller scale, and that’s perfectly fine—it’s part of the business landscape.
However, if you take on a significant amount of funding and are considering transitioning to a larger scale, you’ll likely face a challenging road ahead. If your main issues revolve around efficiency and your unit economics don’t work, being a private company will be even more difficult. You risk burning cash without the necessary funding, which ultimately shortens your runway.
There’s simply no way around becoming efficient and establishing a sustainable model with healthy unit economics; that’s the baseline for any business. Unless, of course, you’re a company like WeWork, which had its unique circumstances. Once you achieve that foundational efficiency, you can navigate the balance between growth and profitability.
For instance, during times when capital is more expensive, it may be wise to slow down growth and adopt a more modest approach while conserving cash. On the flip side, there are instances where investors will push you to prioritize market share, encouraging you to grow aggressively despite the cash burn, provided your business has healthy unit economics.
Ultimately, the base of your business must make sense at the unit economic level. Without that, I don’t think it will work—whether you’re a VC-backed startup or a private company.
Omri: Do you think the industry is shifting toward more vertical solutions in the workspace, SaaS, and AI sectors, rather than continuing with a broad horizontal approach?
Nir: I believe Monday offers a horizontal solution, perhaps too horizontal at times. Without a strong marketing machine behind it, outreach and outbound efforts could be quite challenging, especially since it’s a platform that can do so many things. It’s like trying to sell Excel by saying, “I have a product that can do anything; you can calculate anything on it and solve any problem. Do you want to buy it?” The immediate response might be, “For what specific problem?”
If I were to offer advice to startups, I would recommend starting narrow, even if you have a horizontal platform. Focus on a specific target audience or ideal customer profile (ICP) within a particular industry. For instance, when we aimed to sell larger contracts at Monday, we had to immerse ourselves in our clients’ jargon and understand their daily operations. If we were targeting financial services, we needed to grasp how banks would use Monday and communicate in their language.
In general, the SaaS industry is seeing a trend towards more vertical solutions rather than horizontal ones. Vertical solutions allow companies to delve deeper into specific problems and provide tailored resolutions. I believe AI is poised to revolutionize everything in this industry, affecting both horizontal and vertical solutions. Significant changes are on the horizon for all of us.
Omri: What was your internal infrastructure like during this growth? How did you manage your day and prioritize tasks? What strategies helped you distinguish between activities that drive traction and those that become distractions?
Nir: In the beginning, particularly during the first year and a half or two, I made the mistake of taking on too much myself. Over time, I matured significantly as a leader, and it became clear to me that if I didn’t learn to teach and scale my leadership, everything would eventually crash. That realization marked a pivotal turning point for me.
Finding the right people to work with, teach, and empower was essential. I was fortunate to have some truly amazing directors and team members under me. Once I focused on developing their independence and skills, I was able to lift my head from day-to-day tasks and start planning initiatives that could genuinely move the needle.
If you look at my time allocation, I spent only about 10% to 20% of my time focused on the current quarter, which is quite unusual for a sales leader. The remaining 80% was dedicated to planning for the next quarter and even looking ahead to the following year. Managing a large organization requires time for significant changes, so I needed to plan ahead, run experiments to validate my assumptions, and then implement changes accordingly.
Even small successful changes made a substantial difference for my team. The key enablers of this process were the strong infrastructure around me, including an effective HR business partner, capable sales leaders, and a robust revenue operations team. Their insights and analyses were instrumental in facilitating the changes we needed to make.
Omri: How do you manage your day? Are you more of a to-do list person, or do you rely entirely on your calendar? What does your productivity routine look like?
Nir: I’m trying to be a to-do list person, but it often ends up just staying in my notebook. I get pulled into meetings and other tasks, which makes it hard to keep up. For me, WhatsApp is the best tool for staying on track; I find it much more efficient for delivery and immediate communication. I don’t pay much attention to Slack, and emails feel way too slow. If someone needs me to approve a deal or jump into something, they just WhatsApp me, and I’m on it right away.
Omri: When you compare the pace at Monday to how it is now at Greenfield, do you feel there’s a difference in terms of hustle and intensity?
Nir: Everyone promised me that transitioning would slow down my life and make things easier—suggesting I’d have time to visit cafes, enjoy coffee, and meet new people. But I don’t know if it’s specific to Greenfield, but we’re moving fast here. It’s a pretty intense business.
Is it as intense as managing 200 people with all the context switching and challenges that come with it? Probably not; that was really tough at Monday. However, we’re still working hard and running at a fast pace. I’m currently engaged with around 14 or 15 companies on their sales strategies, interviewing about 50 to 60 candidates each quarter, and participating in four or five forecast meetings a week. It’s quite a whirlwind!
I may love it or not, but I think I’m addicted to this level of activity.
Omri: Is there a book, podcast, movie, or any other resource that has significantly influenced you—something you think about almost daily that shapes your mindset?
Nir: When I started my transition into sales, I read two influential books that really helped shape my approach. The first one was The Challenger Sale, which provided valuable insights into effective sales strategies. The second book, although not strictly a sales book, was Never Split the Difference. This book focuses on how to interact with people, motivate them, and drive them to take action.
I believe these are great starting points for anyone, whether they’re founders or individuals looking to enhance their sales skills. These two books were instrumental in helping me take my first steps in sales and gain confidence in my abilities.
Omri: Are you a family man? How do you feel about the role of family as a support system in your career?
Nir: I draw a lot of energy from my family. There were two long periods where I struggled to set clear boundaries between work and home life. Working extensively with my U.S. partner—my VP of Sales at Monday—and attending C-level meetings meant that my schedule was often packed. With only four or five hours of available U.S. time, it wasn’t uncommon to have meetings that stretched until 7 or 7:30 PM.
The commute from the office could take another 40 minutes, and for far too long, I neglected to prioritize time with my family. I’ve learned this lesson, perhaps too late: it’s essential to carve out family time. You need to step away from work, even if it means returning later after the kids are asleep. Establishing that boundary between work and home is crucial for maintaining balance in your life.
Omri: What’s next for Greenfield?
Nir: We’re currently finalizing the fundraising for Fund III, which is set to be one of the largest funds in Israel. We feel fortunate to have strong backing from our LPs, especially during these non-trivial times. In our first fund, we made three initial investments in promising companies, and our pace is robust.
We are also expanding into the U.S. market, growing our New York office with the aspiration of becoming increasingly global. Overall, things are progressing well for us. However, our focus remains on supporting our existing portfolio companies and staying ahead in identifying the next promising startups for investment.
Omri: This is my last question for you. Is there a specific investor you look up to in the industry—someone outside your own venture firm—who you think has something special?
Nir: My transition into the investment world has definitely been eye-opening, especially considering how new I am to this space. Initially, I didn’t have a deep respect for bankers or investors in general. You always have those thoughts in mind: “Hey, you didn’t do it; you didn’t walk that way; you don’t know how it really is. You’re mainly reading the numbers, but you don’t really understand deeply.”
However, after a year of working alongside our incredible partners, my perspective has changed significantly. I’ve developed immense respect for their expertise and the depth of their understanding. For instance, one of our partners, who has a background in investment banking, leads our investments in the cybersecurity sector. He possesses a profound knowledge of the industry that goes beyond mere numbers.
This experience has revealed to me the complexity of their roles, particularly in how they support founders in making crucial business decisions. They act as a thoughtful and supportive board, guiding entrepreneurs through significant challenges. As someone with an operational background, I now appreciate the value investors bring to the table far more than I did before.
