On leaving Ramp (again)

I'm sure my younger self would find it amusing that three years after writing On leaving Ramp, I would be writing its sequel.

2023

Return to Ramp

I wrote this in my 2023 in review:

We received some press in January for the acquisition and the launch of Ramp Procurement (Fortune, Techcrunch, Ramp blog post), and I'm genuinely happy to be back at Ramp. I was a full-time IC for two months before transitioning fully into people management, and at the moment I have seven direct reports. The role change was unexpected yet necessary given some turnover & performance-related changes, but it's been a massive opportunity for me to grow. I'm excited to make the most of this through 2024 and help accelerate Ramp's growth.

To recap – I co-founded Venue, a procurement automation startup, with my longtime friends TK Kong and Kevin Chan in Fall 2022. In Fall 2023, we were acquired to build & lead the procurement team at Ramp, which is when our journey begins.

Looking back today, this was a relatively stress-free time. We were itching to build after waiting weeks for the acquisition to fully close, and I was glad to be in a more structured environment than the pure chaos of early stage. At the same time, we were given autonomy & ownership over the product roadmap, hiring plan, and timelines.

Like many teams at Ramp, we were extremely lean – TK on product, Andy on design, and six engineers including myself & Kevin. We shipped the initial version of the Procurement product in January, and publicized the acquistion then as well.

Bill Pay

Early on, it was evident that Procurement's success would hinge on Bill Pay, the Accounts Payable (AP) product at Ramp. One of Ramp's growth drivers has been the promise of a consolidated solution across the finance stack, and it was no different when selling Procurement. Given the Procurement product was nascent, we found early traction selling the Procurement + Bill Pay bundle together.

Bill Pay was Ramp's second ever product line, and had scaled to sizeable payment volume even then. Shortly before I returned though, Pavel, the then TL (tech lead) of Bill Pay, left to start Silna Health, resulting in a vacancy.

I was interested because I genuinely believed I was the best candidate – I had significant context on the codebase after building Flex during my first Ramp stint, a BNPL product embedded within Bill Pay. I also had the naivete of not knowing Bill Pay would become Ramp's fastest growing product, and the trials & tribulations of leading the team accountable. I pushed for the role, and thanks to the trust of my management chain (Max, Nik, Karim) – I was granted the privilege.

Thus, two months after my return, I became the TLM (tech lead manager) of both Procurement and Bill Pay. After Procurement's launch in January 2024, I transitioned the TLM role on Procurement to Kevin, with my primary focus shifting to Bill Pay.

2024

Bill Pay, cont.

To start 2024, not much was going well on Bill Pay. There had been further engineering attrition after Pavel's departure, the long-time PM left, and customer churn & customer escalations were both at all-time highs.

Regardless, I was excited by the challenge of turning the ship around. There's a number of decisions that we made in those early days that helped:

• To reduce the surface area of the team for customer escalations & maintenance, I proposed reducing the scope of Bill Pay to strictly the Accounts Payable product. This meant handing off ownership of Bill Accounting, the largest source of customer escalations, to the Accounting platform team. We also created the "Vendors" team at Ramp, which I eventually hired Will R to TLM.
• I hired a number of folks from my network – including William, one of the most prolific & talented ICs I've worked with.
• Max (my manager) & I found short-term help and support from other teams, leveraging the fire on Bill Pay into an opportunity to focus leadership's attention and resources. At the same time, we were significantly ramping up hiring for the team.

Looking back, this was another incredibly high-growth period in my career. I was in a true management role for the first time in my career – navigating hiring, roadmap planning, org politics, communicating with leadership, and everything in between. To learn more quickly, I read blog posts, books on engineering management, but more than anything I found my 1:1s with Max (my manager) invaluable. I eventually wrote Musings as a Manager to summarize some of my learnings.

Managing managers

A key step function change during this time for me was scaling myself from a direct line manager to someone who managed managers. I read An Elegant Puzzle around this time, and found it particularly insightful.

Some learnings I had through this process:

• Being a competent IC requires a completely different skillset from being a competent manager.
• Ease folks into management gently – test the waters with 1-2 reports, collect recurring feedback, and be prepared to rollback if necessary.
• I found this article by Saumil Metha incredibly insightful.
• Rather than split time equally between teams, spend 80-90% of your focus on one area at a time before moving onto the next.

Promotion to director

I adequately captured how I felt in my 2024 in review post, which I'll quote below.

As mentioned in last year's review, to close 2023 I was the Tech Lead Manager of both Procurement and Bill Pay, managing a total of seven people. Procurement was still a month away from its public launch, and Bill Pay was drowning in customer escalations and bandwidth constrained by recent turnover. Much has changed over the last year – Bill Pay has stabilized and its TPV (total payment volume) has grown 4x YoY, Procurement has grown to a sizeable customer base, and we've spun up a third team for Vendor Management. I manage a team of fourteen engineers now, and expect that it'll grow to twenty by the end of next year.

Looking back, it's been a remarkable year. I'm still coming to terms with the knowledge that decisions I make can cause a meaningful delta in Ramp's potential outcome, and I've seen this play out over the last year. From recommendations for team leadership, performance related feedback (both positive and negative), and architectural design decisions, I feel a burden to make correct decisions over and over again. In hindsight, it becomes apparent what the right choice was, but in the moment it's incredibly ambiguous. This pressure is also isolating – no one has the full context that I possess, and although I can seek advice, ultimately the decisions are mine to own.

2025

Growing into the role

I spent 2024 growing into my role at Ramp, and by 2025 I had a much better understanding of what success meant. I still spent time reading and learning about engineering leadership, I learned how to pace myself through days of back-to-back meetings, and by the end of the year I was managing an org of close to 40 engineers.

I also had the opportunity to champion and drive broader Engineering initiatives. I co-led a revamp to Ramp's performance cycle process, a subject I'd long been passionate about. I also co-led improvements to our backend hiring process – leading Hiring Manager / Engineering Leadership interviews, auditing our interview questions, sending outreach on LinkedIn to improve our top-of-funnel, and helping close candidates across the board.

A new manager

I'd been reporting to Max since 2023, the longest I'd reported to anyone in my career. However, Max wanted to shift back to an IC role, and did so in March of 2025.

In my career thus far, I had 7 managers – three at Meta, four at Ramp – and by that point I generally believed I could succeed with any manager pairing. With Max moving away from people management, I was faced with the choice of the two most senior engineering leaders at Ramp, and I didn't pay it much mind. Leaders at that level, understandably, have their attention split between an innummerable number of fires, and by this time I felt confident in being able to run the engineering org I managed independently.

However, I underestimated the value of the relationship that I had with Max. Throughout our time working together, we'd built up significant context and trust working together. Shortly after the change, I realized that adjusting to a new manager would be significantly more challenging than I had originally imagined.

Farewell, again

I'll refrain from publicly going into detail for the reasons of my departure. I found this framing from Will Larson apt (and the article as a whole):

There’s the dream that originally convinced you to join, still recognizable but frayed. There’s dozens of little frustrations, miscommunications, and disagreements. ... There’s also a huge reservoir of things that have gone well: people you love working with, teams that you’ve helped build, and company successes you were part of. For many, being [at company] is an important pillar of their identity, and that’s hard to walk away from.

Closing thoughts

I recognize that I was incredibly lucky to be at Ramp again – Ramp is and will be a generational company, and it was certainly bittersweet to leave. There's also so many people that I attribute my success over the last 2+ years, but I'd like to share special thanks to a few.

• Elena (Bill Pay PM): Elena and I started on Bill Pay at the same time, and we went through all the highs and lows together. Elena is one of the best PMs I've worked with, and an unsung hero at Ramp.
• Sam (director, product): Sam was the first PM I worked with at Ramp, and another Ramp boomerang who came back in 2025 to lead P2P on product. Sam is brilliant.
• Max (former manager): I look up to Max both as an IC and a manager – he's humble, thoughtful, eloquent, and level-headed.

Finally, to everyone who I had the privilege to manage and lead – I'm incredibly grateful to have the opportunity to learn from all of you.