HRTech Interview with Jonathan Leaf, CRO at BambooHR

Jonathan Leaf, Chief Revenue Officer at BambooHR catches up with us at HRTech Series to talk about a few top sales-revenue and business growth misconceptions:


Tell us about yourself and more about your time in the B2B SaaS market…

My name is Jonathan Leaf. I grew up in Minnesota but have lived in lots of different places throughout my career working at four different SaaS tech companies. I started in the reseller business channel, which meant I supported customers end-to-end for any of their IT needs be it software licensing, hardware procurement, data center builds, or professional or manage services. I gained a deep understanding of companies’ infrastructure and IT stacks across customer segment types and did that for 18 years.

I then had the incredible opportunity to build AWS’ first commercial/SMB business in the Central United States. And as we all likely know, AWS was very influential as the first to market on the public cloud. So we built that organization from the ground up, helping thousands of customers build their cloud infrastructure, including everything from storage, computing, security, and networking, to machine learning, AI, big data, you name it.

That led me to RingCentral, where I had global segment responsibility for what we termed commercial sales, which was a group of about 600 or so individuals that supported the acquisition, upsell, cross-sell,  expansion, and retention of a customer base of about 300,000. So an incredible experience when you think about velocity and volume, managing a $800 million business. And what we did for those customers spanned the unified communications as a service, as well as the contact center as a service. So certainly SaaS and SaaS are at the forefront of this AI revolution, thinking about employee experience and how to better serve your customers.

And now as the CRO at BambooHR, I’ll get to take the experiences from my channels, AWS, and RingCentral to lead Bamboo through its next wave of growth, focusing on creating efficiencies in how we support our customers, and how our people can engage their customers.

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As a B2B SaaS CRO: what do you feel revenue leaders especially when in a segment like HRTech need to do to drive growth goals for their brand?

I center on two things primarily as a leader of any revenue business.

One is: how do we benefit the experience of our customers? The decisions we make, the products we build, and the go-to-market strategies we implement, all have to benefit the customer.

The second thing I think about often is: how do you ensure the employee experience is world-class?

And when I think about employees, I certainly think about the revenue organization that I support.

How do I ensure all members of that organization are focused on the right activities and they’re very, very efficient in their ability to do those every day?

So centering around employee experience and customer experience are the two North stars that allow you to make smart impactful decisions that benefit the workforce and certainly the experience of the customer.

I also think as we think about the future of BambooHR, customers want more with less. Because we’re primarily SMB-focused, these customers aren’t in the business of tech, and most aren’t in the business of HR. What they want is an easy company to work with, that offers easy technology to help run their business, that will help them solve for one that one thing. SMBs are looking to manage fewer vendors and how to be more efficient with their capital, so they can focus on their business, employees, and customers.

So as BambooHR continues its multi-product journey, I think we have a very unique opportunity to support those needs with our customers and help them to be more efficient. 

Take us through some of the revenue strategies and revtech you’ve often used to power processes and goals?

At the highest level, people need context, communication, and alignment. Coming into a role like this, the first couple of things I want to do is build trust, relationships, and credibility. First and foremost, the workforce needs to know I’m here as an ally, I’m here to help and I am here for the right reasons, to ultimately drive outcomes for our customers and our employees.

So the initial stages are focused on listening to our employees, understanding the company’s strengths, and understanding the company’s opportunities. I lead with our mission, vision, and values, to ensure that people are still connected to the fabric and the culture of the company. And that they’re very, very clear as to our priorities, and get into why the priorities are what they are. Why is it that we’re doing the things that we intend to do?

We coach, enable, make plans, and be accountable for how we’re going to bring those priorities to life.

Creating accountability and educating our teams to be able to do exactly what it is we’re setting out to do creates momentum. I firmly believe if you’ve given people context on the why and the how you earn the right to drive accountability.

So once you’ve laid down that plumbing and you’re very, very clear as to where it is we need to go, i.e. spanning each of the respective segments, functions, etc, you next need to mechanize and build instrumentation. It creates consistency in what you measure, and the frequency of how you do it, which facilitates training and coaching where there are areas of opportunity for teams and individuals. And you start to just drive accountability in how you go about engaging.

Pervasive to all this is how you engage the cross-functional team. Oftentimes, especially when a company hasn’t had a CRO, the company can be quite segmented and fragmented and isn’t as cross-functionally aligned as it could be. I firmly believe everyone needs a seat at the table to keep ourselves centered in the customer journey. End-to-end, from when a customer raises their hand to when a customer is 5 years into the relationship. How do we create efficiencies in that journey? Ultimately the job for a CRO is how to go about doing that, and how to ensure everyone has a seat at the table to inform that and to create ownership in the process.

How can modern HRTech CROs build better sales-marketing alignment and also align on creating better customer experiences in your view?

Sales and marketing alignment is dependent on everyone having a seat at the table. The more complex the revenue org—acquisition, expansion, customer success, implementation, and adoption—it’s all the more important those groups again have a seat at the table.

Similarly, marketing has demand generation, brand, product marketing, customer marketing, and all those functions that need to be bridged across the customer lifecycle. How do we make sure all the right people are in the room and how do we map out from when a customer raises their hand through to the experience they receive when they’re many years into their journey, considering other products with the company?

There is shared accountability: Sales has every right to be a voice of the customer back to marketing, letting them know what the customer is saying, what the customer wants, what our opportunities might be to inform the product messaging and to inform the campaigns that help bring that to life. And marketing has every right to push back on sales to say, hey, we are doing our part, you need to do your part on conversions.

Both teams should constantly be iterating and working to drive shared accountability that comes from a cadence and operating rhythm where all are working in the same direction. At the end of the day, I think the customer certainly benefits from that. We’re on message, we’re very prepared for incoming demand from the standpoint of sales capacity, and from the standpoint of messaging because we’re aligned on exactly what marketing is doing to support us.

Five misconceptions around the role of the typical B2B CRO before we wrap up?

I think I’ll speak to mistakes a CRO might make when they step into the role.

The first being admittedly, as a first-time CRO, for me to think I am coming in the door with all the answers and I’m going to implement some sort of playbook that’s gonna solve all our woes would be foolish. There’s many that have built this business. It’s an incredibly bright workforce that has grown BambooHR—culturally and revenue-wise—to where it is. I’d be doing the company a huge disservice if I frankly just didn’t listen and learn and leverage the expertise that is within the company. So first and foremost, I think a misconception and or a problem is coming in heavy-handed thinking you have all the answers and immediately implementing your playbook.

Number two. I think accessibility to executives is really important. I’ve seen new executives come into the office but never heard from them. That’s concerning. I think it’s really important that leaders be visible, that we communicate,  be transparent, and in some ways be vulnerable. It’s crucial for new leaders to be visible and build relationships, and build trust and credibility to earn the right to do what it is they want to do and bring the organization along with them in their plans. So being accessible and visible is a huge opportunity and something that perhaps some haven’t done well.

The third thing I’d say is it’s not a top-down effort. It is a team effort. It is a bottom-up organizational effort to drive meaningful change. We have incredible teams spanning many different functions who just want to do amazing work and want to contribute. How do you tap into that potential? How do you get these people to the table to want to contribute, to ideate, and to be change agents? It’s super important for a CRO to create an environment and a culture where people are heard, people have a seat at the table and feel empowered to be change agents. If the expectation is I lead all change initiatives or I lead all efforts pointed at our priorities, that’s a huge miss. There are so many in the company that can do that, that want to do that, and want that development, and by enlisting others to lead, you can grow and change at scale.

Fourth: CRO is a loosely used term. I think oftentimes when CROs are hired, they are sales leaders, they are not revenue leaders, which is critical to be clear on who owns the customer journey? Owning sales doesn’t necessarily mean you own the customer journey, owning the customer journey means you essentially own every team that might have any interaction with a customer throughout their experience and journey with the company. And I would just say not all CRO roles are created equal; many of which truly are not if you just frame it from the standpoint of the customer journey, owning that end to end.

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Jonathan is a seasoned global revenue leader with over 20 years of expertise in driving customer acquisition, retention, and growth strategies. His expertise spans multiple functions and market segments having led large sales operations and marketing organizations as well as sales organizations that span small business customers through to enterprise.

As a leader, he takes pride in the critical role he plays in creating a culture that allows his team to thrive. To do this, Jonathan centers his leadership style on work being purposeful, meaning employees in his organization are connected to a shared vision, have clarity on what success is in their role, and have confidence in their leadership team’s ability to develop them to be successful in their current assignment, while developing them for what might be ahead. He leads his teams with passion and enthusiasm, delivering strong business results and a distinguished pipeline of future leaders.

Prior to BambooHR, Jonathan was the Senior VP of Commercial Sales at RingCentral, an organization helping SMBs create efficiencies through AI-led global enterprise cloud communications and contact center solutions. Jonathan led a global team of 600 employees supporting 1.2B annual revenue.

Prior to RingCentral, Jonathan spent 4 years at Amazon Web Services and 18 years at Softchoice. During his time at AWS, he built the company’s first SMB-focused sales organization from the ground up. While at Softchoice, Jonathan held VP and Director roles spanning inside sales, field sales, sales operations, and marketing.

Jonathan, now based in Denver after relocating from Chicago, has lived in six cities pursuing his career. Married for 10 years with a 5-year-old son, he enjoys exploring Colorado with his family and rescue pup, Petey. An avid reader and fan of Minnesota sports, Jonathan loves to travel and has a keen interest in music, people leadership and financial markets.


bamboohrBambooHR is a leading provider of cloud-based HR software solutions that empower HR professionals to manage, support, and grow what matters most—their people. As a company, BambooHR’s mission is to set people free to do great work by automating, centralizing, and connecting employee data all in one place to support better decisions. The platform’s intuitive and intentionally designed payroll, time tracking, benefits, performance, and reporting solutions support the full repertoire of HR responsibilities—all backed by award-winning customer service. Over the past 15 years, BambooHR has been the trusted partner of HR professionals at 32 thousand companies with employees in over 190 countries and 50 industries, supporting millions of users throughout their employee experience.