The Human Side of Fin

Sam Lessin, 9 Nov 2017

People in the technology community frequently ask me ‘how long will it take to replace the Fin operations team with pure AI?’*

This question assumes we adhere to popular Silicon Valley rhetoric around topics like AI and self driving cars, viewing pure automation as a goal in and of itself and the employment of people as only a stop gap solution.

At Fin, however, our mission is not automation for its own sake. Our guiding principle is providing the best experience for users of Fin.

We want Fin to be dramatically higher quality, more available, and more efficient than any human personal assistant you could hire directly.

In the pursuit of that pure goal, there are places where sophisticated software and machine learning plays a big role. Technology is clearly part of the equation.

But people are also a critical part of the system that results in the best possible customer experience. And the role of technology at Fin is largely to empower our operations team to focus their time and effort on the work that requires decidedly human intelligence, creativity, and empathy.

The Operations Role

The operations team members at Fin touch each and every task that users ask Fin for help with. There are three key areas of responsibility.

First, the ops team members are responsible for the ultimate quality of service for users. This is the most important thing ops does. They are the front lines doing research, taking action on user’s behalf, and providing the voice and empathy of the service. A lot of this part of the role is like working as a traditional assistant, but instead of being alone in an office, team members collaborate as a group and work with powerful technology and tools.

The second priority is, in a sense, teaching Fin as a system. This isn’t some abstract machine learning concept. This means very concretely curating the knowledge that Fin has about the world in our private knowledge graph, and programming preferences for users into workflows that other agents can re-use. In some sense, this is a natural language programming job, and in another sense it is almost like curating Wikipedia or being a librarian. To do this well, operations agents learn our internal language and system. Being excellent at this work means that operations agents don’t need to repeat tasks, but can instead focus on new and important work — and let machines take care of the mundane.

The third priority is working to improve the tools that the engineering team itself builds. For the last 18+ months we have all worked in the same room in San Francisco. Because so much of the technology we build is directly designed to make operations agents more efficient and help them provide high quality answers, they are intimately involved in the feedback cycle on the product.

Provide better service for users. Drive better understanding and encoding of knowledge and process. Inform better tools from engineering. These are the three pillars of the operations role.

Operating Principles

Of course, as an operations team, it isn’t just about what you do — it is also about how you do it. As a company, we have a series of principles which define our culture externally and internally. They all apply to our operations team, but in particular if you want to understand our operations culture you need look no further than these:

  1. Everyone Can Benefit From Help. Getting help enables you to focus on what matters most to you and doing your best work — whatever that may be → For the operations team at Fin, this help comes from collaborating with teammates and from leveraging powerful technology and tools.
  2. Always Know Your Goals. You can’t make progress unless you know where you are going. Don’t get trapped in local maxima or use tools misaligned with your goals. → We are laser-focused on measuring and sharing goals for members of our operations team. We are transparent about goals, we celebrate when we hit them, and we look for opportunities to improve where we don’t.
  3. Always Be Collaborative. Your team can fundamentally do more than you can alone, so invest in making your team better. → While each operations team member is responsible for certain metrics and goals on their own, we only succeed for users as a full team. Teaching others and identifying ways the entire team can improve process or operate more efficiently / at higher quality are critical components of the ops role.
  4. Always Be Improving. You should always be operating in a way that you get better the more you do something. → Doing the work well is necessary, but not sufficient. The ops team is always looking to to the work well, and set the team and company up to do a better job the next time.
  5. Celebrate Service. Helping others is deeply rewarding and dignified work. → Perhaps the most important principle of all. The ops team is fundamentally a team designed to help our users live better and get more done. Not everyone is motivated by helping others, but many many people are and find it deeply satisfying. We know that the people who join our ops team and have the best experience are the people that are fundamentally committed to helping others, and enjoy being part of a team where that is the ultimate shared goal.

The Challenges

Our operations team helps us move fast and do things far beyond the reach of pure technology for our users… but it is not without its challenges.

The first challenge is scheduling. We staff 24x7 because our users travel all over the world in all time-zones, and we need to be there for them. While many jobs staff around the clock, we are the first to admit that it is hard to do sustainably — which is our goal.

Even more broadly, we have to be very careful trying to manage supply and demand because we believe in always having people in the loop. With pure software, in 2017, it is reasonably easy to get access on the fly to more and more server resources — but not so with people. In the past there have been times when we have made mistakes, and ended up with more demand from users for help than we can reasonably fulfill.

We are working on getting better at measuring for this and hiring for it — so we don’t get behind, but small differences between forecasted demand and actual demand can put our operations team far behind where they need to be to provide the best service (see I Love Lucy).


We have had great success bringing truly excellent people to the Fin team in operations roles. The next step is to scale up so that we can provide better service to even more people. To do this, we are working to open operations centers in several locations in the coming months.

We won’t be lowering our hiring bar in the least. So far, members of our team have come from a truly diverse background — nurses, paralegals, lawyers, child care professionals, and more. What they have in common is a focus on helping others, great attention to detail and focus, and a real interest in helping us bring something new to the world.

Working on the operations team requires mastering expert tools and technology, and helping evolve our process and product.

It is hard, and it isn’t for everyone — but if this type of role appeals to you (or perhaps someone you know), we are actively hiring in several locations and would love to hear from you. (ps, there is a $500 referral bonus.)