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Jonathan Sousa

Founder @ Portage

Customer Success
Sales & GTM
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About Me

Jonathan Sousa has focused his career on a simple, but exceptionally important question: what does it take to deliver true value to a customer? Through his experiences over the last decade building, scaling, and leading post-sale functions at world-class startups, including Dropbox and Loom, and advising more than 50 startups while partnering with top-tier VCs, he has developed unique insight into what it takes to transform CS from an adoption and enablement function to a critical part of the revenue flywheel.

These days, Jonathan focuses his time on consulting with startups as an advisor and fractional CS leader. Along with his consulting work, his family lives outside of Lisbon, Portugal where they’re learning Portuguese, and exploring coastal villages, the epic food scene, and the occasional surf break.

Q&A with Jonathan

“The best Success teams are focused on how to drive net dollar retention as their north star metric, as it ultimately indicates a customer’s willingness to renew and deepen their relationship based on the value the product and company have delivered.”

Quick Takeaways:
  • Bringing someone on early to focus on customers — whether an experienced CSM or CS advisor — is critical to setting up initial processes to handle your first customers, reduce founder workload, and ensure you develop a perspective on customer management. 
  • A successful Customer Success function delivers product adoption among other key inputs to Customer Success, and sets net dollar retention as the key output metric — renewing and expanding the customer base, based on successful delivery of the product and its value. 
  • To ensure the success of your CS function over time, it’s important to clearly define its scope, clearly communicate this to all members of your organization, and involve all cross-functional teams in the delivery of successful customer experiences. 
  • Lead with empathy and hospitality, providing the customer with the experience they want, rather than what you think is best.
Q: Tell me about your career journey. How did you get into Customer Success? How did it bring you to where you are today?

My career journey has been centered around Customer Success. I started in management consulting, where I was the main point of contact for clients like Morgan Stanley, the Hartford Insurance Group, Citi Group, and other financial service institutions. In 2012, I saw an opportunity to pivot this experience to the tech industry and transitioned into a CS role at Birst and managed tech implementation. 

In 2013,I became a founding member of Dropbox's CS team just as Dropbox was moving upmarket and bringing on our first enterprise customers. I was tasked with figuring out the initial strategies and processes for how to deliver value with the product, and drive revenue retention and growth. My approach was to apply my consulting methodology to Customer Success, starting with understanding the customer's goals and ensuring they were getting the value they expected from the product. After three and a half years at Dropbox, I was leading our West Region CS team and managing a book of Dropbox’s largest customers, and decided it was time to take a bet on myself and go build a Customer Success function at an early-stage startup. 

I moved on to a 20-person startup called Scoop, a carpooling app that we sold to large companies and then deployed to their employees, a blended B2B SaaS and marketplace model. I had the opportunity to build and design the CS function, build a team, and develop processes that could scale as the company grew. We worked with some incredible companies like Microsoft, Amazon, Facebook, Tesla, and Cisco. 

Most recently, I was at Loom, where I led our global Customer Experience team, bringing together our customer-facing post-sale teams into one shared vision. Loom was just beginning to crack into larger enterprise customers and move upmarket, taking advantage of bottoms-up consumer momentum built during the pandemic. It was a lot of fun given the quality of the team and the constant challenge of evolving the organization to stay ahead of our rapid growth, and reminded me of my time at Dropbox. 

I left Loom to advise full-time, and now I work with early-stage companies to help them build their Customer Success motion and strategies. 

Q: What were some lessons learned from transitioning from a larger company like Dropbox to a small startup like Scoop? 

Making the transition from Dropbox to Scoop was a big decision for me. At that time, Dropbox was on the path to going public, and I had been there for a significant amount of time, longer than 93% of the company. But I felt a calling to go build something of my own, and step into a less comfortable role building and scaling up a CS function.

Joining Scoop pushed me out of my comfort zone and into this leadership role where I wore multiple hats, built processes, and managed people in a startup still figuring things out. That was a career turning point because it allowed me to develop my leadership skills and sharpen my perspective on the ability of Customer Success to be a critical, revenue-driving part of a growing startup. 

I also realized that transitioning from a larger company to a leadership role at a startup would be greatly helped by building a network in the venture and startup ecosystem through advisory and consulting. It was a great fit for where I am both personally and professionally. I often recommend that others diversify their experience and expand their network beyond just their current company, picking up ‘side hustles’ that can open doors for new opportunities like advisory roles, new positions, and deeper industry knowledge. Taking this approach broadened my network, has allowed me to make an impact and help others on their path, and has been a valuable career accelerator. 

Q: What were some key takeaways you learned from your experience working with various PLG companies? 

Dropbox and Loom both required a three-pronged approach to Customer Success: leading a smooth technical implementation, building awareness among end users that the product exists (and could be valuable for them), and encouraging product usage through behavior change. The challenging and unique part of PLG companies is getting creative about how to help drive end user behavior change by pairing it closely with their existing workflows, while working closely with customer stakeholders to demonstrate the value of the product. 

At Dropbox, for example, I worked with our Marketing team to create a "Dropbox Day," for one of our customers, UnderArmour. During this event, we went on-site to build end user awareness and gain insights into where the product added value for the company. In the lead-up, we set up notifications throughout their offices to encourage employees to attend the event, and once onsite, we gathered attention by setting up a Plinko board and giving away water bottles and coffee mugs to add to the fun. As employees approached our setup, we signed them up for accounts, or, if they had them already, asked them about their work and to share a time that “Dropbox saved the day”. We left the event with hundreds of employees signed up, and dozens of enthusiastic product users with compelling stories that contributed to UnderArmour’s understanding of how Dropbox was creating value.

Loom represented a similar challenge, as the product necessitates a change in work habits from primarily relying on email, phone, and in-person communication to video messaging. As at Dropbox, a key principle is understanding where the product’s value resonates most within customer workflows, building awareness, and then leveraging user stories to convey the value to stakeholders. 

Q: What are some common mistakes that early-stage companies make when building their CS motion? 

One mistake is companies often wait too long to bring in someone who can provide perspective on customer success. Founders rightly focus on the product and establishing product market fit, and then on business development, but then often find themselves responsible for managing customer relationships once they’ve landed. Founders need to focus on scaling their businesses, versus trying to manage customer needs, but often become trapped in a pseudo-CSM role. I’d love to see early stage companies get a bit farther forward in the planning process, by investing in a CS hire or advisor who can help prepare the company with a basic CS motion to get those first customers up and running. 

Another mistake is failing to clearly identify the role and responsibilities for Customer Success, and where the organization plays within the customer journey. Customer Success should be focused on driving net dollar retention as the key output metric, renewing and expanding customers, and preventing churn. Product adoption, customer health, and customer relationships are critical inputs to customer success, of course, and a core part of the CSM’s job; but the best Success teams are ultimately focused on how to the drive net dollar retention output metric, as it indicates a customer’s willingness to renew and deepen their relationship based on the value the company and product have delivered.

Lastly, one paradigm I’d like to see change is the idea that it's necessary to bring in an AE at the end of the customer journey to handle commercial negotiations. The fear I often hear expressed is that the CSM having this conversation could jeopardize the relationship they’ve built because they’re discussing a commercial proposal. I’d argue the alternative: a CSM, who has been working with the customer for a year, is the perfect person to be running renewal and expansion conversations. They’re the person who has built a deep understanding of the customer's definition of success, delivered on the customer’s expectations, and can convey in the customer’s terms the value of continuing the relationship into the future. You can easily train a CSM to navigate a commercial cycle, but it is way harder to replace the trust built between a CSM and their customer, which is key to continuing the partnership. 

Q: How do you identify a great Customer Success organization? 

The best companies have invested the time to set clear swim lanes across Revenue teams; each team member knows what they own and how their work ladders up to achieve the company’s goals. Startups evolve rapidly, and areas of ownership change quickly too; the best companies, though, have defined and articulated the areas of ownership clearly, and in a way that is grounded in delivering the best end-to-end experience for their customers. 

To dig in a bit more deeply on this, the best companies zoom out and say, at the highest level, who is our customer — what matters to them, what are they hoping to gain from using our product? Next, they ask, how can we deliver this value, and what is the experience we want to architect for each customer? With the answers to these questions in mind, top-performing companies then allocate roles and responsibilities based on who is best-positioned to deliver the experience that would delight the customer. And then, and only then, should considerations like metrics and compensation factor in, with the best companies setting internal targets and expectations based on what their teams actually can control that add value to their customers. 

Q: What guiding principles have influenced your customer success perspective? 

Danny Meyer, the founder of Shake Shack, has a great quote on hospitality that plays on ‘the Golden Rule’: “do unto others as you believe they would want done unto them”. I subscribe to this fully, as I believe hospitality is core to the best Customer Success teams. Simply put, go a step further in designing a customer experience that meets customers where they are based on what they want and would be delighted by, versus designing an experience that you think is best for them.

In a customer-facing role, especially in tech, where there is such tough competition, delivering a great product alone is not enough. It's just not. Customer Success can and should be a key differentiator in retaining and expanding your customers. CS is not only about increasing product adoption, but also about understanding customer needs and expectations, and building a relationship based on a shared path toward achieving that customer's vision. A narrow focus on product adoption will not lead to success in the long run. 

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