The 88th episode of Datacast is my conversation with Evan Cummack — the CEO of Fin.com.
Our wide-ranging conversation touches on his childhood in New Zealand; his 10-year stint with Twilio contributing to the incredible growth of the company from Series B through to IPO and beyond; his current journey with Fin; lessons learned as an appointed CEO redefining the product, finding customers, hiring executives; and much more.
Please enjoy my conversation with Evan!
Listen to the show on (1) Spotify, (2) Apple Podcasts, (3) Google Podcasts, (4) TuneIn, and (5) iHeartRadio
Key Takeaways
Here are the highlights from my conversation with Evan:
On Growing Up in New Zealand
I was born in New Zealand in the 80s. Growing up, I had fairly limited access to information, so I taught myself software development out of old programming books from used clothing stores on crappy old computers. I didn’t have any notion that anything I was doing was out-of-date because there was no way of knowing. I felt like I was the last generation of people to grow up without access to the open, unlimited amount of information on the Internet, which nowadays allows people to become great engineers (no matter where they are). I then studied software engineering and business in New Zealand, had a great job during college, and set my sights on coming to Silicon Valley pretty early on. I knew there are many like-minded people who sit around together and presumably build great products. As soon as I graduated, I made the pilgrimage.
My job during school was fairly instructive in non-technical ways. It’s useful to understand how to communicate technically and navigate an organization, understanding who will appreciate technical discussion and who needs things to be explained to them differently. There’s a lot to be said about navigating different levels of technicality and doing that in a way where you feel confident at each level. That means dealing with software engineers and knowing when to draw the line; but also talking to managers and not bogging them down in details that they don’t need. The job also taught me about how enterprises buy and sell technologies. We even worked with public sector customers, the ultimate example of enterprise-style software purchase and implementation. That’s an excellent exposure to the fact that the software industry isn’t just software; it’s also an industry.
On Joining Twilio
I was pretty dead set on joining a venture-funded startup. There was not much interest on my side to go to a publicly-traded company. Honestly, the decision-making at the end of the day came down to the quality of the CEO. When joining a small enough company, you tend to meet the CEO, so the quality of the CEO and the team matters a lot. It is about how well you get along with these people and how well you will be able to go in the trenches with them.
Additionally, the product also matters. I spent a lot of time playing with Twilio’s APIs, which sold me. Before that, I had had some exposure to telecommunications and understood how slow-moving the industry was. Playing with Twilio’s APIs gave me the aha moment of how this newfound capability could create value. That told me I should push hard to try and join this company.
On Sales Engineering
Sales engineering is an exciting career. Sometimes, it is called solutions architecture or solutions consulting. You work for a company that sells a relatively complicated and flexible tech product (like AWS or Salesforce). In order to accelerate the adoption cycle to get customers to buy the product and be successful with it more quickly, you will have a team of engineers who are building and shipping the product all day. They consult with customers on how to take the product, customize it, integrate it, and deliver business value with it. Success in that role comes from people who are increasingly technical.
In the 80s or 90s, sales engineering means being a product expert, understanding all the features, and being able to rattle off. Today, it is more complicated. Getting excited about the product is underrated in terms of being able to get your customers excited.
There is also more emphasis on engineering than sales. Most good sales engineers move to product management or marketing engineering rather than sales.
To me, this role is for people who love customer success and be in the motion of making money/building momentum but are not necessarily in the sales mindset of pricing, relationship-building, and closing deals.
On Learning Curves at Twilio
Twilio grew a lot in employee headcount, customer count, revenue amount, and market capitalization. For me, joining Twilio during these stages has been really good from a growth perspective. I kept looking for the next thing I was interested in and demonstrating the lower risk proposition to let me do it than to bring someone in. An extreme example is the General Manager opportunity for Twilio’s IoT and Wireless business unit. We built this entire business from scratch with a fairly large engineering team across several continents and dedicated sales/marketing teams.
As you become more senior in an organization, your mind needs to transition from feeling the need to please the people around you and do what is asked of you to focusing on what the market wants and how to get it done at what costs. It is no longer about what other people expect of you since no one expects anything. That is the nature of entrepreneurship, as you need to create expectations for yourself. I think that is one of the core components of leadership in general. There are a lot of other components in terms of getting people to follow you and believe in you, but there is undoubtedly a big mindset change. I actually envy people who get into that mindset very young. It took me a while after being out of school to understand that that was an option.
On Twilio’s “Middle-Out” Sales Strategy
When I joined Twilio, there was this notion that enterprise sales had been top-down historically, and companies like Twilio were flipping on its head by making them bottom-up. Neither of those two things is true. I used the term “middle-out” as a joke, but it really means that if you look at successful enterprise software companies today, they have a product that can be adopted bottom-up as people can experiment with the product and figure out what it is all about. But increasingly quickly, they have available sales resources to help individuals looking at the product from a buyer’s perspective to navigate their own organization. You will have very well-defined security and privacy reviews whenever you sell an enterprise product. These things have evolved over the last 10–15 years due to the number of companies that buy cloud products.
As things have become more competitive, enterprise buyers have become more sophisticated, and as different privacy regulations have come around the world, it is challenging to be entirely product-oriented. Even when you start with the product, you need to be quick in terms of coming in with a go-to-market team that can diffuse the complications around buying a product and help the buyers get things pushed through their own teams / explore other opportunities around the product (called “land-and-expand”). Sometimes, you even want to expand an opportunity before you land — someone is playing with the product, and you want to highlight to them that there is more that they could do with it. That is where sales engineering comes in and shows them demos.
So I believe in this hybrid approach where the product needs to be immediately adoptable, and you need to capture immediate value from it. But soon after that, you want to have go-to-market teams that are actually useful to the customer. That would be the difference between the old top-down selling and the proposed bottom-up approaches.
On Becoming the CEO of Fin
Fin was founded by two accomplished consumer technology people: Sam Lessin (who was early Facebook’s product lead) and Andrew Kortina (who started Venmo). They initially started out trying to build a consumer product and realized at a certain point on their journey that one of the tools they had built to run the company was actually a more interesting business. That is the product we now sell. Essentially, we pivoted the company and raised the money at the end of 2020. Now we are focused on building a B2B company.
When I started talking to Sam about the CEO role, I found a great product with amazing customers. When you are building an enterprise software company or thinking about joining an enterprise software company even, it is this idea of vision versus short-term execution. They do not have to be at odds with one another, but sometimes they are: when the company gets swept up in a long-term vision and is unable to build a business in the short term in order to create a self-sustaining entity. Sometimes people will build a business and cannot figure out how that becomes a vision — a version of the future that has not existed yet. Often, those companies will get acquired by another company with a vision compatible with the business they have built.
One of the things I liked about Fin was a vision of how we could apply all the modern data collection and data analysis techniques available to knowledge work. That could extend to a million different ways that play out in the future. They also had a product that was making money: looking for queue-based workers (like customer support, inside sales, financial offices), it shows exactly what those teams are spending their time on, where the inefficiencies are, what processes should be redefined, and what trainings should be modified (all via a browser extension). That enables us to see the human interactions that are occurring across different enterprise applications. That, to me, was a very compatible-forward version of the vision.
I also met with the team and the sphere of people around the company (investors, board members, etc.). Everyone was impressive, aligned, and supportive. I also felt that building a leadership team was an exciting challenge and not one that I had been able to take on before. I was able to go out and find great leaders for marketing/product/sales. That was a super interesting challenge for me, and I am happy with how that panned out.
On Fin’s Product
There is a standardized way of interfacing with business applications through the browser for the first time in history. The browser has a uniform language (HTML, CSS, Javascript) and a uniform place where things get done (the DOM). We are able to show teams: here is how your team is completing certain tasks, issuing a refund, moving from one tool to another, etc. We can tell you the 5% of cases where activities take too long. There is a tendency for the worker to use Google Translate or get lost in the knowledge base or whatever it is. So we can actually quantify that human work execution and turn it into data. We know precisely how the servers and software systems are performing, as well as the customer journey — in which what customers are doing is fairly well-instrumented.
We invest a ton on both sides of this equation where the rubber meets the road. Fin’s solution essentially sits there, observes these interactions, sends that data to the cloud, processes the data, and reveals insights and improvements. Essentially for things that would be very hard to detect at a micro level or an individual level, we can reveal them at a macro level (at the level of teams of hundreds or thousands of people even).
On Hiring
Number one: It is more effective to find the people you want and spend your personal time getting them. For example, I have not really used recruiters for our leadership team. I would rather find 10 people who I really like for a certain role and focus a ton of my personal energy on understanding them — their career and where they are now (versus having a recruiter speak to 100 people and hoping that one of them responds and having a deeper conversation with that person). I think this is true for sales as well. As a CEO, you want to lean in and use your personal energy/time to get high-value deals done at the early stage.
Number two: It is worth keeping in mind that hiring great people is a self-fulfilling prophecy, in the sense that you are out there convincing people that this thing is going to be successful and that this is a great beat that they should make. Having them on board with that vision actually increases the chance of being true. The only rational way to behave in that scenario is to be 100% convicted. This is a difficult mindset to get into if you are not there already.
On Finding Customers
Most enterprise software companies do not have great marketing when they start out. They do not have a great way of articulating the problems they were solving in a few words. Fin did not have that initially. Thanks to conversations with our successful customers, we are working on it now. In lieu of that, it is a lot about putting yourself on the line, making personal connections with people you think might be great buyers, convincing them to spend some time with you on it, and listening a lot.
There is a book I was reading called “Startup CXO” that talks about what a startup CXO should be doing. He/she should go from whiteboard selling (being in a room with a customer and brainstorming on a whiteboard), to presentation selling (presenting a PowerPoint and listening to feedback), to PDF selling (providing the detail of what your product does and tightening your message to generate buyers). It is essential to understand that early stage where it is whiteboard selling: Can we spend time together? Can we talk about your problems? It will be hard to find a salesperson who can make that motion very well (not impossible but hard), so you, as a CEO, must reach out to people on LinkedIn with highly personalized messages: “Here is what I know about your business. Here is what I would assume we can solve them. Can we have a conversation about it?” Furthermore, be prepared to have that kind of whiteboard-style discussion basically.
Show Notes
(02:00) Evan shared his upbringing, born and raised in a small coastal town on New Zealand’s North Island and later studied Software Engineering and Business.
(03:55) Evan recalled working as a software solution architect at NEC Corporation back in New Zealand.
(06:17) Evan talked about his decision to join Twilio in 2011 as one of the company’s early employees right after its Series B financing.
(08:40) Evan shared his perspectives on joining startups and big companies as a new grad.
(13:01) Evan provided insights on attributes of exceptional sales engineers, given his time building the first iteration of Twilio’s global pre-sales team.
(17:30) Evan unpacked the evolution of his career at Twilio — working as a product manager, a director of product & engineering, and a general manager of IoT & wireless.
(22:51) Evan dissected Twilio’s unique “middle-out” sales strategy, which has hugely impacted the company’s incredible growth from Series B through to IPO and beyond.
(29:03) Evan went over the untapped opportunity being enabled by new cellular IoT technologies.
(33:25) Evan explained his decision to embark on a new journey as the CEO of Fin.com after a decade at Twilio.
(37:26) Evan talked about the need for workflow automation and how Fin’s product features are built to address that.
(40:35) Evan went over Fin’s remote performance optimization capabilities that help teams thrive in a remote-first environment.
(42:56) Evan shared valuable hiring lessons to attract the right leaders who are excited about Fin’s mission.
(45:38) Evan shared the hurdles his team has to go through while finding early customers for Fin (as it pivoted to building a SaaS product).
(48:02) Evan talked about the qualities of Jeff Lawson that made him such a great CEO.
(50:41) Closing segment.
Evan’s Contact Info
Fin’s Resources
“Fin.com Raises $20M from Coatue” (Sep 2021)
“Customers Operations Benchmarks for 2022” (Nov 2021)
Mentioned Content
People
Book
About the show
Datacast features long-form, in-depth conversations with practitioners and researchers in the data community to walk through their professional journeys and unpack the lessons learned along the way. I invite guests coming from a wide range of career paths — from scientists and analysts to founders and investors — to analyze the case for using data in the real world and extract their mental models (“the WHY and the HOW”) behind their pursuits. Hopefully, these conversations can serve as valuable tools for early-stage data professionals as they navigate their own careers in the exciting data universe.
Datacast is produced and edited by James Le. Get in touch with feedback or guest suggestions by emailing khanhle.1013@gmail.com.
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