SalesTechStar Interview with Allison Metcalfe, CRO at Cloudinary

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Allison Metcalfe, Chief Revenue Officer at Cloudinary chats about the common misconceptions surrounding the role of CROs with SalesTechStar.com:

 

Hi Allison, tell us about yourself and your journey through the B2B SaaS Allison Metcalfe, CRO at Cloudinary market over the years…

I’m the first chief revenue officer for Cloudinary, a company that set the new standard for image and video management and delivery. Cloudinary is unique in that it’s a fully bootstrapped SaaS business with more than $100M in revenue and both enterprise sales and product-led growth motions.

Before Cloudinary, I held CRO positions for two other companies. The latest was at Quotient, which I helped lead through a massive transformation from agency-managed service to a product-driven technology company, integrating multiple acquisitions and ultimately driving to a successful exit for the organization. Prior to that, I was the CRO at Demandbase, where I led a reacceleration of growth, including multiple acquisitions and product launches – all while the company transformed from an ABM platform to a full G2M suite with multiple cloud environments.

While many see success in net-new logo sales as the path to taking on a CRO role, that was not my experience – and I’m glad that it was not. Rather, my experiences leading a variety of functions across the revenue-generating side of various businesses has positioned me to be a more complete and effective executive.

I started my tech career in account management and helped pioneer the customer success movement. I led customer success/account management and operations for Jigsaw (acquired by Salesforce), and served as VP of customer success for LiveRamp before becoming GM for the company’s largest growth business and later the SVP of LiveRamp’s productivity, field strategy and partnerships. During my tenure, the company grew from $30M in revenue to $500M,  was acquired by Acxiom and spun out as an independent public company – which it still is today.

Through all of these experiences, I’ve gained a unique appreciation for each function and developed a holistic and collaborative approach to leading a high-performing, sustainable revenue organization.

As a CRO who has held this role for a couple of companies thus far: what are the biggest learnings you’ve come away with?

What surprises many others to hear is that being successful as a CRO has very little to do with personal sales acumen – although I am a great salesperson 🙂 . It’s a far more analytical role that requires careful planning, long-term strategic mindset and general strong leadership skills. While a sales leader needs to focus on in-quarter or in-year revenue, a CRO is regularly thinking multiple quarters and even years ahead.

I’m largely focused on broader market changes, customer needs and building processes that lead to predictable and sustainable outcomes. It’s a highly data-driven role and requires someone who can foster intense collaboration across not only go-to-market functions such as sales and marketing, but also among the CFO office, the product team, customer success and more.

In order to succeed, a CRO must be able to come into a company, think about it as a blank slate opportunity, solve a very complex puzzle that balances market expectations and sentiment, customer experience, product value, available resources, and the skills and talents of the team. It’s a highly dynamic role and one that suits my personality and love for team collaboration and data.

If I had to summarize my most important advice for other CROs, it would be:

• Have 1:1s with every executive staff member, especially the CFO and CPO, and understand how they are evaluated and what is important to them. Build empathy.
• Separate pipeline production and forecast conversations.
• Pipeline conversations should always be cross functional. Marketing should own the model but the supply chains are diverse. Everyone needs to be there.
• Drive change management with data. If sales is not adopting new methodology, show them their sales excellence metrics and what money they would make if they were on point. Manage your sales team like baseball players.
• Have an operating system. I use the V2MOM framework and OKRs.
• Anticipate what your fellow leadership team members are afraid of and address them proactively.

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What top misconceptions would you bust about the role of the modern B2B CRO?

The biggest misconception is that there is a universal definition for what a CRO does or what makes a good CRO. This is largely because the CRO role is a fairly new invention in the SaaS world. In 2015, it wasn’t a role most organizations even considered filling, but it’s become so popular now that a lot of executives have had some exposure to the role in some capacity.

It reminds me of the nascent customer success movement when Salesforce was helping redefine account management as a distinct function. As customer success started to take over a lot of responsibilities for the post-sales process, companies had to figure out what the boundaries of that shift would be. Each company had to decide exactly how their org chart and processes would evolve to adapt to this new function. And everyone did it slightly differently until best practices emerged over time.

Because of this, CEOs today need to define exactly what they’re looking for when they think they want a CRO. As I mentioned previously, many assume that an impressive career in net-new logo sales is the best path to becoming a qualified CRO. While sales experience certainly is beneficial, leading a revenue team is about much more than customer acquisition. Customer retention and upsell growth are also crucial to a recurring revenue business. Understanding the power of brand, pipeline development, and partnership ecosystems is key, too. Executive and financial leadership helps improve alignment with the CEO and CFO. And the best way to have that knowledge is to have done that work at a high level and been exposed to those dynamics.

Further, every company’s needs are very different and affect the skills needed for the role tremendously. A company with a culture of growth at all costs is going to want a different CRO than a company more focused on sustainable, profitable growth. Public and private companies will experience the same split, as will bootstrapped vs VC-backed orgs.

Just like in a SaaS business, it’s about finding product-market fit. And that requires deep introspection and a lot of conversations from both the executive team and the prospective CRO to identify.

Take us through some of the salestech and revtech you’ve relied on over the years to drive revenue goals?

I’m a big believer in intent data and an account-based go-to-market approach. I believe in having a strong understanding of your ideal customer profile (ICP), driven by prospect data well beyond just revenue and number of employees. In particular, I think insight on technographic data is critical to help identify the best fits for a given product or solution. Intent data is also incredibly powerful, especially when it can be viewed in the context of a holistic buyer journey.

I also respect the power of predictive analytics around forecasting and there are some wonderful tools for this available today. Importantly, sales recording tools with AI on top have been transformative for not only helping the sales team operate, but also to inform our entire go to market strategy. It used to be that a company would launch new content or messaging to the sales team and rely on their anecdotal feedback. Now, we know exactly which messages and content are useful and resonating.

How can CROs today use better tactics to centralize and align different connected teams (sales-marketing-customer success- others)?

The biggest thing is to be intentional about the fact that outcomes are everyone’s responsibility. My teams don’t operate in silos, as nearly everything we focus on at a strategic level requires cross-functional collaboration and alignment. We take a team-centric approach because the diverse perspectives and points of view that different individuals and groups bring to the table are incredibly valuable since each group feeds off and influences the others. If nothing else, it’s critical to create a culture where everyone feels invested, has the chance to be heard, and to hear from others.

For example, when we think about pipeline development, that’s not just an SDR team. The entire marketing function, along with the GTM operations team, sales enablement teams, and others are critical to make it successful. When preventing churn and promoting upsells, that’s not just a customer success challenge. It’s also heavily reliant on product and pricing, as well as partnerships, especially as composable tech stacks and integrations become increasingly critical to delivering customer value.

If you had to talk about the things that keep CROs up at night: what would you highlight?

1. Customer value – Are we barking up the right tree in terms of positioning and pricing the solutions and aligning that exactly to what customers want and need? And even if we are today, those wants and needs are always changing, and where are they headed? Competitors are always gaining new competencies, markets change quickly, price sensitivity fluctuates, etc. The conditions are always changing and while that’s half the fun, it’s also most of the stress. The key is to trust the process and make sure you know exactly how your customers perceive the value of their investment.
2. Pipeline development – How do we bring in new prospects that are the right fit for what we do? We know we have unbelievable products that have incredible benefits for our customers. But not everyone is the best fit, and not everyone should be. How do we make sure we’re being as efficient as possible in bringing value to the people who need us most?
3. Team Success – I coach youth basketball and volleyball. If my kids come back and play the next season, I did a good job. If not, I failed. I think about creating the same sense of excitement and reward for my teams at work. Frankly, it can be stressful working in go-to-market roles, from entry level to executive level. We are the one group in any organization whose performance is hyper-objectively measured and visible. I’m constantly thinking about how I can help my team grow, feel valued, find balance, and take pride in their work while enjoying their lives.

A few thoughts on the future of salestech and revtech before we wrap up?

The tech landscape can be overwhelming. There are so many tools and technologies available, and so many promise to achieve the same thing or have overlapping functionalities. At the end of the day, the sales process is more science than art, but art is the most valuable and often the most significant differentiator.

As tools continue to get smarter and more capable, AI won’t replace people skills, the power of relationships, and the knowledge of what each customer feels and wants. That has to come from conversation and empathy. It’s a truly human skill.

While it’s important to ensure the supporting tech stack is robust and empowers teams to do great work, don’t over index on AI. People still make purchasing decisions, and they know when selling experiences aren’t genuine and authentic. A big part of the CRO job is to drive business outcomes and efficiencies, but we can’t lose sight of the fact that people do business with people.

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