Here at Pathlight, we’ve noticed a vibe shift around GTM meta in the age of AI. It seems as though every quarter, there’s a new company slapped onto the classic Bessemer years from $1M to $100M ARR” chart that it’s almost becoming a meme in itself.
I recently tweeted about new GTM meta that some of the fastest growing companies in the last few years have been doing, and decided that I would go straight to the source and interview the people behind the curtain of some of the fastest growing companies in this new age of AI. And of course, the first that I have to start with is Ramp :).
I had the pleasure of hiring and working with Max Freeman, VP of Sales at Ramp. Every time I catch up with Max, I learn something new because of how fast the company is growing and evolving. In our chat, we’ll cover:
Max has had an amazing journey over his past 5 years at Ramp and I’m excited to share that with you.
The goal of the series is to make this as actionable as possible, so feel free to jump to whatever section is most interesting for you and please give us comments and feedback on areas we could go deeper on next time! I’m excited to bring more convos like this with other amazing companies :).
Charley Ma:
Let’s start with the basics. Tell me more about your background and journey to Ramp. How did you end up joininng?
Max Freeman:
I started as a finance guy early in my career, but it wasn’t the right fit, so I quickly pivoted into tech sales. I went to Namely, which in hindsight, was an amazing training ground to learn how to sell. We were in a very competitive, saturated market, and we had a negative 43 NPS score and pretty bad G2 reviews. For context, we sold payroll that didn’t integrate with QuickBooks, so I had to be on top of every demo and every business case I presented to HR teams.
Charley:
And selling into HR can be notoriously difficult.
Max:
Yes, exactly. Namely had great people and leaders and I learned a lot. Before that, my first real exposure to the working world was at UBS in banking. I was tasked with spinning out deals—mostly private credit and some venture deals—and cross-selling our ultra-high-net-worth customers as wealth management was the money maker for UBS. I wasn’t closing the deals, but I was doing the analysis, and I started to understand how venture works in terms of employee equity and upside.
While I was at Namely and doing well, I always kept my eyes open for something super early-stage or pre-IPO—somewhere I felt the equity might really materialize and be meaningful. I randomly stumbled across a Ramp article on Fortune in late 2019 and first reached out to the team a bunch of times and got no response. Months went by, and finally you got hired; I pinged you via some mutual connections, and eventually got my foot in the door.
I decided to start all over again just to get a seat at the table. I went from being a top-performing mid-market account executive at a Series E company to being Ramp’s first SDR, or first SDR/AE hybrid—one of the first three salespeople.
I almost didn’t accept the offer because it was late March 2020, and the world was just about to shut down. I thought, “Do I really want to join a credit card startup in the middle of a global pandemic?” But I was 24, so if I was going to take a big swing, that was the time.
Charley:
That would have been a crazy alternative scenario if you hadn’t for both you and Ramp! So, be brutally honest: what was the state of go-to-market and sales at Ramp when you first joined? You were really on the ground floor.
Max:
The week I joined, we had just decided to move forward with Salesforce as our CRM. We basically had no structure. I was handed a laptop and a LinkedIn Premium subscription and told, “Let’s figure out who might use this product.” Around that time, we also decided we should experiment with outbound and I was the guinea pig.
We bought Apollo, started putting together sequences, and to be honest, it didn’t go great at first. I think in my first month, I booked three or four meetings. Month two, maybe seven or eight. By month three however, something clicked, and I booked around 40 or 45 meetings.
Charley:
Yes, I remember those first two months were rough. We were sending typical sequences, following the typical standard outbound playbook of an ROI-focused subject line, standard ICP-based messaging, etc but it just wasn’t landing. The market is saturated, and CFOs/finance teams are a tough buyer to crack into. So what happened in that third month?
Max:
I think it was twofold. One, we put in a ton of activity, and the sheer volume started to pay off and started to create a flywheel effect. Two, the messaging itself changed once we really started listening to the customer. We learned more about why people chose Ramp and the exact unlock they were looking for, and that influenced how we targeted and what we said.
Additionally, the types of companies we went after evolved. Early on, I was excited to pitch Uber, Meta, Netflix, these massive tech companies, but we weren’t integrating with their systems at the time, so they didn’t care. As a team, we really started to refine our ideal customer profile, initially to series A and series B companies that were just starting to hit true scale where we actually could support their needs. It was easier to break into those accounts, and over time, as the product matured, we steadily moved upmarket.
Charley:
That makes sense. Early on, I recall how tight the feedback loop was between sales, product, engineering, design - truly a full team effort. What did you do to stay close to the voice of the customer and keep the team in sync?
Max:
One easy tactic I did was joining every call I booked—for myself and for AEs. Early on, I don’t think we even had a call-recording software, so I took notes in real time and paid attention to every objection, feature request, etc. Also, because we were only about 25 or 30 people, we had weekly stand-ups with Diego (VP of design), Geoff (CPO), and the rest of the EPD organization. I really got to understand how Ramp worked from a technical standpoint, which helped me sell more effectively. I think a lot of startups don’t foster that cohesion between sales and product, but it was critical for us at Ramp.
Charley:
Absolutely. I remember being personally excited that we had a whole-company philosophy around growth: it was the number one priority, and we wanted to empower you to scale meetings as effectively as possible. Maybe talk a bit about how you ramped up volume. Are we talking about tens of emails a day, hundreds, thousands? How did you manage that at first?
Max:
Initially, I tried to go high volume too soon. It wasn’t until we had some statistical significance in our response rates and meeting acceptance that I had the confidence to pour fuel on the fire. Once I confirmed what worked, I was sending hundreds—if not thousands—of emails every day.
I also started segmenting my approach: high volume for certain roles (like accounting managers, staff accountants, etc.), and layered on a more strategic and personalized approach for the C-suite or VP-level prospects (custom emails, LinkedIn touches, phone calls). That’s when it really took off, which gave us confidence to hire more SDRs.
Charley:
Ramp is now known for building an incredible outbound engine. How did you think about building out that sales team and integrating engineering/product resources along the way?
Max:
On the qualitative side, we were very deliberate about who we hired onto sales. We wanted a product-first sales team that would truly understand what we were selling, the competitive landscape, and the buyer personas. We didn’t look for people with typical SDR or even AE backgrounds. We wanted folks who had demonstrated raw talent, intelligence, and domain knowledge and kind of had my background. The first person I hired was my best friend Sam Buck, who was an investment banker at Goldman Sacks. We then hired Mike Weber, who joined us from Citi as well - we were paying well above market rate but we made the math work because the output of Sam, Weber, myself, and others was 5x market value - we were all booking 40-50 meetings a month and now each of them are running massive pieces of our business.
Early on, time is so scarce as an early stage company. You can’t really be teaching people how to use appropriate grammar in an email, how to navigate step by step through a cold call, etc. You want people that are going to come in, provide them tooling, and get out of their way and let them execute. On the AE side, we hired AE’s like myself - sales people that knew how to execute, had sold a product that was just okay, but knew how to win. If we could give them a 10x product, we knew we would crush quota.
At some point, I believe it was Karim (CTO) who came to us and asked, how do we make outbound an engineering challenge? I ended up spending two weeks with with two engineers who were dedicated to growth. They watched my workflow, all my manual clicks, and automated as much as possible. I can’t give away too much of the secret sauce, but at one point, I’d wake up and see replies from prospects wanting a demo— from personalized, automated emails I hadn’t even sent myself! It was incredible.
Charley:
That’s wild. I think a key factor at Ramp was treating growth and sales as first-class citizens. Karim taking two of our best engineers to focus purely on automating your process was an eye-opener. Normally, those engineers would have been coding features for the product itself, but we saw the leverage in building out sales capacity first.
Max:
Exactly. Engineers don’t normally join early-stage startups to help with Salesforce flows. But if the leadership team ties it directly to the company’s overall impact and equity value, it really motivates everyone and engineering can truly provide 10x leverage to your sales team.
Charley:
So once you nailed your approach, how did the SDR team evolve? How did you start thinking about the next hires and scaling out that outbound approach?
Max:
We continued hiring carefully, looking for the “figure-it-out” factor. I’d rather hire someone with hustle and intelligence than someone who’s done exactly this job at a big company like Salesforce or LinkedIn. Those big-company sellers sometimes rely on brand recognition, whereas at an early-stage startup, you have to be fully self-sufficient.
We also iterated on our incentive structure. Initially, we only compensated SDRs on meetings booked, which didn’t solve for quality. Eventually, we tied SDR comp to both SQLs and closed-won deals (or deals that reached a certain stage for enterprise). That forced everyone to care about quality as well as volume.
We also created transparency around what was working. We had a Slack channel called #outbound-meetings—any time someone booked a meeting, the entire company saw the message, who the prospect was, and the exact outreach that worked. That real-time visibility and accountability was huge.
Charley:
What about interviewing SDRs? Early on, how did you vet them, and what sort of exercises or questions did you use to figure out if someone was a good fit?
Max:
This one I stole from you a bit! I didn’t rely on a typical “mock cold call” approach. Someone who’s good at smooth-talking might ace that but not have the problem-solving or business acumen. Instead, we had a business-case exercise. It was intentionally vague, asking candidates to break into three accounts and explain how they’d do it. We’d poke holes in their reasoning to see how they handled objections and how much structure they brought to the table.
For account executives, we do a hybrid of that plus a mock call to check if they have a structured process—like MEDDPICC or another methodology. But primarily, we want problem-solvers who can handle ambiguity.
Charley:
Looking back at the early Ramp days, is there anything you’d do differently?
Max:
Two main things:
Charley:
Moving to the present: we now live in a post LLM world. There’s a debate in sales land about whether the SDR role is dying. Do you think SDR roles will still exist in five to ten years?
Max:
I think the SDR role will vanish for anyone who’s average or below average—those who just load contacts into sequences and hit “send.” But for great sellers, AI is going to make them better.
For instance, we use AI to parse signals from Salesforce notes, call transcripts, or triggers like, “This account’s expense management contract expires in four months.” AI helps us quickly find those leads and generate relevant emails. That frees humans to focus on having great conversations and calls. So the good SDRs will remain indispensable; the rest might get replaced by automation.
Charley:
Any advice for founders or sales leaders on how best to integrate AI tools into their outbound and sales motions today?
Max:
For early-stage companies, AI is fantastic for research, list building, and picking the right time to reach out. It can also help identify who to contact and when, based on triggers from calls or notes. The key is letting AI handle repetitive tasks so your SDRs can focus on strategic outreach and relationship-building.
Charley:
Final question: you went from being an SDR—one of the most junior salespeople at the company—to running a massive best-in-class sales org. How did you manage to scale with the company so effectively?
Max:
I made Ramp my life. I never asked for promotions or scope. I just tackled every problem I saw and never hesitated to ask for help. There’s so much I don’t know, and I’m comfortable being honest about that.
Another big piece is hiring. I spent a ton of time recruiting, and I made a point of hiring people better than me. For example, I hired someone recently and he’s much stronger than me analytically. We have a large-accounts lead who is far more experienced than I am. A lot of people fear hiring folks who might outshine them, but for me, it’s been crucial. The better they are, the better we all do.
Charley:
That’s fantastic perspective. What would you say to a younger leader who finds themselves having to manage more experienced members on their team? What advice would you give?
Max:
I’m super transparent. I tell them I won’t always have the answers, but I’ll remove blockers so they can be successful. I’ll give them all the product context, the buyer persona knowledge, and the resources to thrive. If they come in and excel, the scope, equity, and progression will follow. That honesty is usually well-received.
Charley:
Awesome. I know we’re at time, but I’m sure we’ll have more to learn the next time we catch up. And for anyone that’s looking for a best in class financial suite, we’ll make sure to send em your way.