September 1, 2021
Podcast
BY:
Savannah Peterson

Fin.com CEO Evan Cummack on the Innovation and Leadership Podcast

Fin.com CEO Evan Cummack recently had the pleasure of joining Jess Larsen on his Innovation and Leadership podcast. Highlights include:

  • Evan elaborates on Fin’s ambition to give humans the upper hand in their working relationship with technology and describes how Fin is designed to empower users.
  • Evan discusses “middle-out” sales strategy valuable takeaways from his previous role at Twilio, where he helped shape the company’s sales strategy and product development.
  • Jess and Evan discuss how his unique combination of technical and people skills have contributed to his success as a business leader and how his personal philosophy drives his ambition.

You can also read their full conversation below:

Jess Larsen:


Today on the show, we’ve got Evan Cummack, CEO at Fin. Evan, can you talk about your previous career history before Fin?


Evan Cummack:


I joined Fin in December 2020 as CEO. Fin is a venture-funded startup software company, and it's always an interesting thing to come into an early-stage company as the CEO and non-founder. Before this, I was working as a general manager at a company called Twilio. I was at Twilio for about 10 years from right around the series B financing through the IPO. I had the pleasure and privilege of going through that whole process and then far beyond IPO; Twilio is now a very highly valued company. That was an amazing ride—I sometimes refer to it as “getting my PhD in SaaS.” I learned an amazing amount and the team there was incredible. 


Before joining Twilio, I grew up in a small town in New Zealand. Not exactly a tech hub, although there's some really great engineers and things that are coming out of there now, but when I was growing up, I had fairly limited access to technology expertise. I always had a very strong and unique obsession with software. There's a lot of people who grow up writing code and loving computers and software, but I was really obsessed with the software industry. I was obsessed with the competitiveness and with the idea that businesses could grow so quickly. The industry has such an egalitarian nature—for example, at a company like Facebook, if you have a good idea, all of a sudden you can do so many unprecedented things in just a few years on a global scale. So after I graduated in New Zealand, I came out to Silicon Valley and very quickly started at Twilio.

Larsen:


How many employees did Twilio have when you started there?


Cummack:


It was fairly small, around 30-something people. One of the interesting things about me joining Twilio was I joined at the same time as the other folks starting the sales team. So Twilio was pretty unique in the sense that we were doing about $500,000 of revenue per month with no real sales function. There was a person running “business development,” and all in one week, we basically said, “Okay, let's get an enterprise sales rep, an inside sales rep, a sales manager, and myself,” and I was essentially the first sales engineer. It was pretty interesting. 


Twilio is seen as somewhat of an icon in this bottom-up, SaaS sales model where companies adopt technology themselves. I think a lot of that is mythology; I think sales teams—especially today with SaaS being so incredibly competitive—are extremely important for most of these companies. And I do think that having a long-tail community of users is very important, and having people that will choose your technology when a project starts without you having to be in the room to sell it to them is extremely important. But when Twilio really started taking off was when we figured out how to put large contracts in front of customers, how to get them to sign, how to keep them renewing, and also how to cross the chasm into more traditional enterprises. That was when the company's revenue really started going.


Larsen:


What are a couple of the biggest takeaways from that experience at Twilio that you're now bringing to Fin?


Cummack:


The most cliché but important takeaway is just a generic customer obsession. Our Twilio CEO, Jeff, was incredibly customer-occupied; there was very little appetite for building products or features that were novel and interesting but didn't have an immediate value to either an existing customer or an imagined customer. I was always very paranoid about our business, and I was very paranoid about computers and technology life cycles and how long can certain trends last. I remember chatting with Jeff once and I asked if he was worried about Amazon. We were a big customer of Amazon and we were running on AWS, and so it seemed like if they decided to come into our turf, they would have an advantage over us. And Jeff’s immediate and clear response was that Amazon wins because while everyone else is worried about Amazon, Amazon's worried about customers. Jeff had that mentality all the time; he was just very fixated on making sure that everything we did was right for customers.


I think it's very tempting, especially as a technologist, to focus on problems that you yourself find interesting, or problems that are uniquely difficult, but the customer has to be at the center of the conversation all the time. I think even a company's vision or core mission can evolve as a result of the feedback coming from customers. I saw that at Twilio. In the early years of the company, we were very fixated on fueling the future of communications and really thinking about telecom and telecommunications a lot. As we saw how customers were really using the product—which was more about engaging with their customers at the edge of their business—the vision and mission of the company evolved to include customer experience and customer engagement. 


When you're in a consumer software company, you're making a big bet based on some intuition that you have about the world. The companies that tend to be successful are the ones where the vision happens to match up with some future trend in society. In a B2B company, it's more iterative, and more about listening to customers and evolving the product and the vision to align with what you're hearing. That’s really at the core of how I want to think about leading Fin.


Larsen:


In what ways does technology not outperform human observation? It feels like there are distinct elements of that in your business.


Cummack:


The way we think about it is this: processes are at the core of a business. Processes are executed, and they get executed by humans. So, the way that humans execute processes is very important to the overall execution of your business, and they get executed by software. It’s important to understand where software and technology are either helping or hindering your process execution. And even more importantly, processes are executed in accordance with how they are defined. If you can actually improve the definition of those processes, then there's potentially a lot of leverage you can get out of that on the human and technology side. 


Fin observes large teams of people who are working. We observe their work patterns through their web browser, and this is based on our observation that almost all enterprise applications today are running inside a web browser. From that observation, we're able to, for example, draw conclusions about things like the best methodologies that result in higher customer satisfaction, or maybe we’ll find training deficiencies. Based on what humans are doing at an individual level and at a large team level, you can figure out which patterns are the best ones to be following.


If you look at the transformation that software development had in the1990s, it was based in this flawed idea that someone in a senior position could define how everything should work, and then a bunch of people would go and build it. Then that gave way to agile software development. Now, if you look at what’s happening with teams across all industries, there's a similar transformation happening. When I was younger, I always thought “Enterprise Architect” sounded like a cool job, and that was essentially someone at the top of their business who defined the execution of processes across the company. In reality, enterprise evolves and it evolves at the edges; that's where the greatest opportunity for change lies. 

Fin’s ambition is to give humans the upper hand in their working relationship with technology. Part of that is understanding how humans and computers work together. When you achieve that, you get something really special: you end up with empowered humans.

Larsen:


Can you talk about the co-founders of Fin, Sam and Andrew?


Cummack:


Fin was founded by two accomplished consumer technology professionals: Andrew Kortina, who was the founder of Venmo, and Sam Lessin, who was a VP at Facebook. They were friends and got together to start a consumer company about five years ago and it was called Fin Assistant, which was human-assisted artificial intelligence to do more complicated things than you would expect from an AI assistant. They ended up hiring hundreds of human beings who would sit on computers and do things like book flights for people and make restaurant reservations. Coming from the consumer technology world, they were very used to having good metrics. What they found was that they just had no metrics and it was hard to understand what task types were profitable versus non-profitable, which tools were the best to use, and even how an agent’s home WiFi connection impacted their productivity. So they built another product to address this.


Sometime in 2020, I was approached by one of Fin’s lead investors about taking the company to the next level on the B2B side. Andrew and Sam’s newest product started to get traction with companies in spaces like meal delivery and vacation rentals. The next stage of the company was very clear, and there were new questions about how to maximize this, how to improve sales execution, and how to become a multi-product company. I was recruited into that role, and it's been so fun. Sam and Andrew are still involved. There’s something to be said about building a product that really solves the problem for yourself; it’s a short feedback loop when you are the customer and the developer. 


Larsen:


Can you talk about a principle of sales that not everyone with a sales background understands?


Cummack:


I use this Silicon Valley joke: it's really a middle-out sales process, not a bottom-up or top-down sales process. You can't be in the room all the time, so having a product that people can go try themselves is extremely important because you may not be there physically. As soon as you have the sense that you have a potential customer, it’s very simple to have a cross-functional sales team that can come in without being pushy and help the potential buyer to navigate their own organization. At Fin, our product is heavily integrated, so it’s important to be able to tell the customer we can help them navigate the integration. Additionally, every customer is going to try out the product at some scale before they sign a big contract; it’s not about convincing people anymore. Instead, it’s about demonstrating the value in your partnership.

Larsen:


What makes for a really great demo?


Cummack:


The demo should be tailored to the customer's business. At the end of the day, software makes difficult things easy and the more that you can show that, the more magical it is for the customer. It’s easy to have low self-esteem and it can be really tempting to think what you’re presenting isn’t interesting. But you have to remember it will be pretty awesome for the customer.

Larsen:

What are some things you have done that have led to you becoming a CEO?


Cummack:


I wanted to be really good at people and technical skills. I did public speaking training and business classes to try and understand management and leadership, but I also wanted to learn how to build and deploy software. I think I got a pretty good level of mastery over both. That enabled me to be quite useful in a start-up. Because of my New Zealand background, where the power dynamics and hierarchies in the workforce are less rigid than in the United States, I would enter into conversations with the CEO and CTO at Twilio because I had the attitude that they weren’t higher up than me. I think that attitude has helped me: you should be able to change something if it needs changing or suggest something if you have an idea. 

Larsen:


What do you think is one of the best pieces of advice you ever received?


Cummack:


This is kind of a cliché in the sales world but one that I think is exceedingly important across all different aspects of business: it’s fine to win alone but you never lose alone. There’s a really famous motto by Sir Edmund Hillary, who was a New Zealand mountaineer and the first to climb Mount Everest. The first thing he said when he got off the mountain was, “It’s not the mountain that we conquer but ourselves.” It's an affirmation that I try to remind myself of a lot. Even if something's a small challenge for someone else, if it happens to be a big challenge for me and I get it done, I'll feel good.

Larsen:


If someone wants to get their own demo of Fin, where should they go?


Cummack:


Fin.com. We’re also on most social channels—our handle is @betterwithfin. If you want to reach out to me, I’m more than happy to chat with anyone about the product or any other interesting potential conversations. My email address is ec@fin.com.