Q&A with Timothy Daley: My Journey Back to Affirm

Meet Timothy Daley, a Senior Machine Learning Engineer and an Affirm Boomerang, who left the company in October 2020 and returned in April 2024. We recently sat down with him to learn more about what prompted his decision to leave and ultimately return, and what he’s most looking forward to as his career with Affirm continues.

What initially drew you to Affirm, and what prompted your decision to leave?

Timothy: Lockdown prompted my departure from Affirm. When Affirm went fully remote, I was dealing with some personal issues and saw an opportunity to join another company in person. Biotech, which was exempt from remote work mandates, provided that opportunity. It was a bandaid fix for a personal problem, not an Affirm problem. Additionally, I took an opportunity to lead a team and gain leadership experience. Based on advice I was later given, and what I've personally learned in the meantime is, if you're on a rocketship, just hang on.

What motivated your decision to return to Affirm?

Timothy: I had been interested in returning for well over a year and I kept in close touch with team members at Affirm. Once it was the right time, I decided to re-apply. The people at Affirm were the biggest draw for my return. I had worked with my current manager, Chuan He, and my former colleagues, Kevin DelRosso, and Kelli-Jean Chun and many team members during my first stint. I also have a lot of trust in Nitesh (Head of Decisions Foundations) and his leadership. Now that I'm back, I see a lot of opportunities to tackle bigger and more challenging issues in terms of Machine Learning models and infrastructure.

How has your perspective on career growth and development evolved throughout your journey as a boomerang employee?

Timothy: Coming straight out of academia, I didn't fully understand how growth in the industry really works. Now, I have a much better perspective. I've learned that opportunities don't just happen; you have to drive them.

What advice would you offer to other former employees considering returning to Affirm?

Timothy: Stay proactive about looking for opportunities instead of just reacting to what's happening around you. I kept in touch with several people at Affirm, allowing me to monitor the company's progress. The leadership team has done a great job navigating through challenges, and now we're back to focusing on growth. So, my advice is to stay connected, be patient, and look for the right moment to make your move.

How do you envision your long-term career trajectory within the organization now that you've returned?

Timothy: I want to see where my new journey at Affirm takes me. When I rejoined, I knew the team and the opportunities and trusted the company enough to take a similar position to the one I had previously had at Affirm. My team leaders and I worked out a plan for my growth and advancement. My growth depends on what new opportunities we can find for Machine Learning and whether we need to create new teams for new products. It also depends on what new verticals will come up as we expand the scope of the business. While I enjoyed management and would love to have those opportunities again, I also like building things. So, my career trajectory will be shaped by the new challenges and opportunities that arise.