Scaling Go-to-Market: Lessons from Building a Revenue Engine at Ramp

Alexa, CEO of Pocus, hosts Product-Led Sales (PLS) “Ask Me Anything” sessions with PLS experts to share best practices, frameworks, and insights on this emerging category. These AMAs are an opportunity to ask PLS leaders any question — ranging from hiring to sales compensation to tech stack — in a low-key, casual environment.

The PLS AMAs are for members of the Product-Led Sales community, the place to learn, discuss, and connect with go-to-market (GTM) leaders at product-led companies. The goal of the community is to bring together the most thoughtful and innovative GTM leaders to build the next generation of sales together.

Interested in joining? Request an invite here.

Meet Megan Yen, VP Customer Success and Activation at Ramp 👋

Megan Yen was one of the first 30 hires at Ramp. Megan helped build the revenue engine at Ramp as VP of Business and Revenue. She was responsible for building out what has become a 100 + person sales organization. In that time, revenue has grown by more than 100 times. Four years later and Megan now leads the VP of Customer Success and Activation.

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We recently sat down with Megan for a Pocus community AMA to hear all her lessons learned from the early days of building GTM at Ramp. Continue reading to learn more about: 

• Megan’s journey from employee #30 to now
• The early GTM engine and Ramp’s culture of experimentation
• How Megan built and scaled onboarding and adoption programs

Ramp’s early GTM experiments

“Figure out how to double revenue in 3 months. And so just do whatever you need to do.”

That was Megan’s charter when she first began at Ramp four years ago as the Head of BizOps. At the time, the GTM team was only five in sales, one in partnerships, and no one in marketing. To say they were lean would be an understatement. So how do you “double revenue in 3 months” with a scrappy team and a short timeline? For Megan and team, it was all about experimentation. 

“It took a lot of understanding of where we were at that time, where we wanted to go, and just throwing a lot of stuff at the wall to see what would stick to eventually get to where we were now.”

When Megan says throw stuff at the wall, she means everything, and it wasn’t just the GTM team. The entire company often got involved in GTM in the early days. 

Megan shared a few of the playbooks that worked (to varying degrees) early on for the team at Ramp in their experimentation phase:

Founder-led sales 

As is expected for an early stage company, founder-led sales jump started the GTM motion at Ramp. Leveraging the founders network to find warm intros into accounts. 

Operationalize the network 

Similar to founder-led sales, Megan and team experimented with extending this beyond the founders to include the entire team and even investors. This meant building prospecting lists by downloading lists from LinkedIn and  looking for overlapping connections.

Marketing stunts 

Ramp was born at the very beginning of the pandemic so the team took advantage of this odd time to try and generate PR for the company through marketing stunts. One idea that unfortunately remained just an idea was dropping cash in Times Square. The marketing stunt that did make it to primetime (years later in 2023) was highlighting Ramp’s customers on a digital billboard in Times Square, a big win for customer marketing and generating awareness for both Ramp and its customers.

Cold outbound 

All of the early experimenting led to uncovering Ramp’s very first repeatable GTM channel - cold email. Megan worked closely with Ramp’s first SDR. They would spend hours working on different email copy variations aiming to get a high volume of emails out to accelerate learning. The goal was simply to find messaging that resonated and led to a reply (or meeting). The first iterations of this motion were manual and time-consuming. Once the motion worked, the SDR team worked with operations and engineering to automate parts of the workflow to streamline the process. 

Choosing their key growth channels

What worked for Ramp may not work for all companies, but their emphasis on experimentation and scale helped them accelerate their learnings. The initial GTM experiments were largely a joint effort between growth, engineering, and the SDR team. This partnership gave the team the technical skills needed to be more data-driven with their pipe gen strategies and automate workflows once they saw repeatability. 

Megan and team ultimately chose to double down on cold email outbound as a key growth channel for a few reasons: 

1. Faster feedback cycles: With a large target market like Ramp’s, their experiments in outbound gave them the fastest feedback loop to test messaging, whereas their experiments in SEO or paid ads were longer and more expensive experiments.
2. High conversion rates: Once a reply from cold outbound turned into a meeting, the team could very quickly convert that prospect to a customer within 30 days. Given this high conversion rate, the team spent most of their effort refining the outbound engine to increase replies and meetings booked. 

Hiring early generalists to “figure it out”

Megan shared that a key to success in the early days was the ethos on her team and her early “generalist” hires. The ethos boiled down to “really do whatever you need to do to help the company out (besides things you're maybe not the best skilled at).” This ethos necessitated that Megan’s early hires needed to be comfortable with ambiguity and be biased toward figuring things out, even if not in their wheelhouse. 

“The first five hires were all what we just called ‘generalist bizops’ hires, where they would plug in and out of different special projects to help move the company forward.” 

Each of these hires would partner with others across the company to go deep and provide additional horsepower that moved the needle on specific company goals or projects. For example, BizOps would pair with product to help define a new area of the product to develop or tackle the first sales comp plans. Once any of the BizOps teams' projects or experiments became repeatable and easily operationalized, they wrote the job description to go and hire the person or persons who would then scale that motion. 

Once the company reached initial growth milestones and the GTM engine became more established the generalist BizOps team transitioned into more of  RevOps function. At this point, Megan realized customer activation and adoption were the next functions that needed attention. 

Balancing human-led and scaled onboarding

Like many other companies, Ramp began with entirely one-on-one human-led onboarding. Also, like many companies, they realized quickly that this model would not scale. As Megan shifted her focus toward activation, she noticed the strong correlation between activation and onboarding, so moving to a scaled model wasn’t as simple as “making onboarding self-serve.” There needed to be thoughtful consideration for what scaled meant at Ramp. 

As a financial product, the team found that fully self-serve with no human interaction onboarding was challenging and negatively impacted their activation and adoption metrics. So the team landed on a hybrid model:

• Implement customer segmentation rules: The first step was to delineate which customers should continue to get white glove onboarding. Aligning on the level of onboarding required for their different customer segments (SMB vs. Enterprise) allowed the team to really zero in on what activation meant for each segment and what resources they would need to activate. For smaller customers, this might mean more in-app guidance vs. larger organizations that need 1:1 support. 
• Opt-in to talk to humans: It was important the human element was not totally lost in Ramp’s scaled onboarding approach, so they provided live group onboarding sessions and created pathways for customers to talk to a human if they needed help (and/or signaled high potential).

Since onboarding touched product, customer success, marketing, and even sales this needed to be a cross-functional effort. Megan set up a cross-functional project focused on customer activation. Similar to her experience running the early days the team began running experiments to quickly land on what moved the needle for their activation metrics.

The key to getting quick learnings from their activation experiments? Keeping them simple.

When focusing on activation it was easy to overcomplicate things. For example, testing in-app video messages to guide users sounds like a great experiment to run, but in practice, there were far too many variables to track. You would never know if the video itself worked, the placement, the timing or something else entirely. 

Megan recommends defining activation experiments as granularly as possible. One of the early experiments the team focused on was trying to get new customers to create their first card quickly. They boxed their experiments to only move the needle on that one metric, choosing tightly defined experiments. In this example, they tested lifecycle emails, incentives, and directly emailing the customer to push them toward card creation. 

Rapid-fire advice

Megan’s experience at Ramp is vast so we closed out our chat with some rapid-fire questions from the community, here’s her closing advice: 

• Balance qualitative with quantitative: Ramp’s experimentation culture permeates every team but not every team tracks experiments in the same way. The growth team tracks everything in Airtable and is very quantitative. Their pipe gen experiment results tend to be more black or white. If you’re in Customer Success or focusing on activation, leave room for qualitative data and more context, not everything will be solvable with a black-or-white experiment. 
• Go beyond red, yellow, and green CS health scores: The health of a customer is not easily captured in a red, yellow, or green health score. Megan suggests choosing one North Star Metric and a few other metrics that act as leading indicators for the health of customers. This might be usage of a particular feature or other product usage signals. 
• Don’t let scaled onboarding content go stale: If your product team is developing new features faster than you can update your scaled onboarding docs or programs, don’t worry. Ramp hosts webinars every week to keep content fresh and Megan encourages the team to get scrappy with Loom videos when necessary.  

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