In this episode of "20 minutes VC," Harry Stebings interviews Dylan Sarota, cofounder and Chief Strategy Officer at Terminal, a company that facilitates the creation of technical teams through remote operations as a service. Sarota highlights the advantages of distributed engineering teams, noting how Terminal, which recently raised a $13 million Series A, is redefining the future of work. He emphasizes the importance of market selection, leadership, and making remote teams feel like first-class citizens. Sarota also discusses career growth, advocating for gaining experience across different disciplines within a single company to build a robust foundation for future leadership roles. The episode delves into the philosophical and practical aspects of remote teamwork, the value of mentorship, and the balance between prototyping patience and operational speed, offering insights into building successful, geographically diversified teams.
You are listening to the 20 minutes vc with me, Harry Stebbings, and I'm so excited for our episode today.
Harry Stebbings expresses his excitement for the episode, setting the tone for the podcast.
However, enough of the soppy stuff and to the intro, and I'm thrilled to welcome Dylan Sarota, cofounder and chief strategy officer at Terminal.
Harry transitions from his personal reflections to introducing the guest, Dylan Serota, highlighting his current role at Terminal.
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Harry describes The League's approach to dating, emphasizing its respect for user preferences and time.
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Harry endorses Zoom as a highly regarded conferencing app, citing user reviews as evidence.
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Harry highlights Culture Amp's focus on employee feedback and culture, encouraging listeners to learn more.
Sure thing. And there were a lot of people involved and timing was so important to make this happen so quick.
Dylan acknowledges the importance of collaboration and timing in the rapid development of Terminal.
My aha moment was when I realized that there's actually an incredible opportunity to create a company that could simplify this process by thinking about providing a platform that could take on a lot of the large upfront costs of real estate and other services and complexities involved, and create basically an AWS for remote operations.
Dylan shares the pivotal realization that led to the creation of Terminal, likening it to an AWS for remote operations.
Absolutely. I think one of the biggest mistakes people make early in their career is leaving a company too soon.
Dylan advises against the common practice of leaving companies prematurely, emphasizing long-term learning and growth.
And he told me after graduating that you got to maximize experience over title and salary until your early thirty s and basically get an amazing foundation of experience to maximize what will ultimately be your highest grossing years.
Dylan relays career advice from his mentor, Dave Potruk, stressing the importance of gaining experience over immediate rewards.## Career Development in Varied Disciplines
"But if you want to build a company or be a CEO coo, I think you should focus on getting experience in different disciplines, like sales, marketing, finance."
This quote emphasizes the importance of a diverse skill set for aspiring CEOs and COOs, suggesting that experience in multiple business areas is beneficial.
"It was absolutely the right time to make a change."
Dylan Serota reflects on his personal experience of leaving Eventbrite, indicating that the timing and support he received were crucial in his decision to pursue his passion with Terminal.
"So we believe geographically diversifying or building teams across multiple markets is a muscle memory that you should start building much earlier than conventional wisdom would suggest."
Dylan Serota argues for the strategic importance of establishing geographically diverse teams early in a company's growth to enhance sustainability and talent acquisition.
"So there's many aspects here. I think, first, market selection is key."
Dylan Serota discusses the multifaceted approach to creating successful remote teams, highlighting market selection and the importance of strong leadership and product ownership for remote teams.
"One of the, I think, most important factors is time zone alignment."
Dylan Serota identifies time zone alignment as a critical element for effective communication in remote teams, emphasizing the need for synchronous communication opportunities.
"That culture should not be stagnant or overly preserved. It should evolve with the team that you build."
Dylan Serota shares insights on company culture, advocating for a dynamic approach that allows culture to grow and change with the team, especially in the context of remote teams.
"And so when you end up putting that into the engineering leadership and to juggle all of those different balls, that's definitely, I think, the biggest challenge and the commonality that we see when companies are deciding to establish a remote team."
Dylan Serota highlights the common challenges faced by companies when establishing remote offices, particularly the strain it places on engineering leadership who must manage multiple complex tasks beyond their normal scope of work.## Distributed Teams: Philosophical vs. Practical Hurdles
"Philosophically, we hear that companies know they will need a remote team at some point, but think that they're just not quite ready or not quite set up to make it successful yet."
This quote emphasizes the mental barrier companies face when considering remote work, suggesting it's a matter of perception rather than actual preparedness.
"And part of the reason that they were a very desirable acquisition target was purely because they had that team in place in Waterloo that had already been established, the operations were set up."
Dylan Serota explains that having a distributed team can make a company more attractive to acquirers, as it demonstrates established operations and potentially lowers integration costs.
"So as a company, you don't want to be a jack of all trades master of none. But with early stage employees, I actually think that those who are less expert but exhibit more interdisciplinary skills can show a higher upper cap on their learning and adaptability."
Dylan Serota advocates for hiring versatile employees at early stages who can adapt and grow with the company, rather than hiring specialized experts right away.
"Everyone doesn't scale at the same linear rate. But I think it's important for leadership to find the people who have that aptitude and continue to give them opportunity and resources to learn and grow."
Dylan Serota stresses the importance of recognizing employees' varying capacities for growth and providing them with opportunities to evolve alongside the company.
"So this is probably the biggest area of my own development. I've had to work on transitioning into founding terminal. But as a leadership team, we examine and scrutinize our decisions weekly, not just based on the outcomes of the decisions, but how quickly we were able to make those decisions, and how could we speed up that process in the future?"
Dylan Serota discusses the importance of not only the outcomes of decisions but also the speed at which they are made, suggesting regular introspection to enhance decision-making processes.
"So when we go back on a weekly basis and look at some of those decisions, we're trying to separate outcomes from process and then speed up the process or clarify ownership across the team to make those decisions happen faster."
Dylan Serota explains the process of assessing decision-making effectiveness, highlighting the distinction between outcomes and the decision-making process itself.
"So I think the prototyping phase is critical to test quickly, but not rush to market. Until you really believe you have the right signals that the product and the business model are right."
Dylan Serota discusses the importance of balancing the need for speed in prototyping with the necessity of ensuring product and business model viability before scaling up operations.
"I don't love that phrase. I will say, I think that what you need is really clear goals of what you want to accomplish. You need clear ownership and accountability. And then you got to trust in your team to make decisions which might not always be right."
Dylan Serota expresses his distaste for the "move fast and break things" philosophy, advocating for a more considered approach to decision making with clear goals and ownership.## Speed and Decision Making
I do believe in speed and decision making, being hypercritical in.
The quote underlines the speaker's belief in the importance of swift decision-making and critical analysis in the product development process, suggesting that perfection may not always be the primary goal.
I think that really comes down to the type of business you're pursuing and what signals you agree on with your investors are the right ones to indicate you're ready.
This quote explains that the decision to raise venture funding should be based on the specific business type and mutually agreed-upon success indicators with investors.
Looking at it purely as a process and not using the investors that are currently in the room and those out there as people who can help be a barometer for where you're tracking.
The speaker suggests that startups often mistakenly view fundraising as a mere process rather than an opportunity to leverage investor insights to assess business performance.
I think marketing is really challenging to work in a distributed model.
This quote points out the specific difficulties of managing marketing efforts within distributed teams, particularly concerning brand and product alignment.
I think it's right. And market dynamics will inevitably prevail, whether that changes up or down.
The speaker expresses the opinion that compensation for remote teams should be determined by market forces, implying a flexible approach to compensation based on location and market conditions.
The biggest myth, I think, is that although we have all this communication technology, that virtual communication is sufficient to build relationships with remote workers and face to face, I think still matters so much.
This quote challenges the assumption that technology can fully replace in-person interactions, emphasizing the enduring value of face-to-face contact in building team relationships.
Be the one that hires the lawyer, don't be the lawyer.
The speaker recounts a pivotal moment when advice from his father prompted a reevaluation of his career path, steering him away from law and towards business.
Kind of like finding and sticking with a great general doctor.
The analogy illustrates the speaker's belief in the importance of developing a lasting relationship with a mentor who can provide tailored advice over time.
In five years I see terminal being a global brand that's foundational for how the next wave of great companies will scale.
This quote reveals the speaker's ambitious vision for Terminal's growth and its potential impact on the global business landscape.
Every single touch point I've had with the team members at Atomic, from Chester to Jack to Andrew to you, it's just been exceptional.
The speaker conveys appreciation for the collaboration and shared vision within the Atomic team, highlighting positive interactions and a strong team dynamic.