Max Freeman on Building Ramp’s Sales Machine

Harry Stebbings asks Max Freeman why Ramp hired investment bankers into its early sales team. Freeman says an impressive résumé is not the only route to talent: some candidates have abilities that are undervalued by a conventional sales hiring process.

Freeman saw bankers as accustomed to hard work and equipped with business acumen. Because Ramp was selling to CFOs without an established brand, a cold caller who had just left a well-known bank for the company could get a prospect’s attention.

An early sales team also had little time to teach basics such as concise calls and good written communication. Bringing in people with those skills allowed the team to focus on execution; several bankers went on to lead substantial parts of the business, he says.

Ramp paid above the market for this talent, Freeman says, but expected substantially greater output. He describes paying roughly twice a standard sales development representative’s compensation while expecting four to six times the usual meeting volume.

The targets vary by segment, with more emphasis on quality upmarket. Freeman says some SDRs working on smaller accounts book more than 50 qualified meetings a month; a booking needs real intent and qualification, not merely a name on a calendar.

Stebbings and Freeman clarify a distinction: SDRs book meetings, while account executives take calls and close deals. Freeman says Ramp’s inside and commercial sellers may take 10 to 12 calls a day, and some account executives take more than 15.

Freeman likens recruiting to Moneyball: look for strong sellers at companies that grew substantially despite low customer satisfaction. Such sellers may have learned to create their own demand, handle poor reviews and defend a premium price in a difficult market.

A strong product can make a striking difference to a seller used to harder conditions. Freeman recalls a veteran Ramp seller being surprised when a customer volunteered a case study; he says such unsolicited enthusiasm occurs regularly at Ramp.

To distinguish a great seller from an order taker, Freeman breaks down the number. How much came from inbound, outbound, expansion, a founder’s relationship or inherited opportunities? A headline revenue figure alone cannot show what the candidate personally did.

He then asks the candidate to reconstruct a successful deal chronologically: how did they advance it, express business value and connect a workflow to an outcome? He also asks about a painful loss and whether weak qualification, missing stakeholders or a product gap caused it.

Even when an external relationship appears to explain a lost deal, Freeman expects sellers to identify the risk early and address it directly. If a prospect shares a board member with a competitor, ask how the decision will be made before mobilizing extensive internal resources.

Ramp’s interview includes a business case in which the candidate conducts a discovery call as a Ramp seller. Freeman tests knowledge of Ramp, research on the prospective customer and sales fundamentals such as executive presence, deeper questions, quantified pain and a clear value proposition.

His final test is personal: would he buy a product from this candidate? He applies a similar standard to leaders—if he would not want to work for the person, he would not make the hire.

For a seller joining an early startup, Freeman says the initial decision should turn less on title, equity or cash and more on the market, the talent, the business and its founders. A growing market can create opportunities for both company and career.

He left a mid-market account-executive role to become an SDR again at Ramp because he saw large markets in cards, expenses, payments, travel and banking. He believed the product and engineering team gave Ramp the potential to grow across them.

Talent density matters because sellers benefit from strong engineers and a product that keeps improving. Freeman also valued founders Eric Glyman and Karim Atiyeh’s previous experience building and selling a business, interpreting it as evidence of execution ability.

A technical founder need not already be a sales expert. Freeman looks for willingness to work with sellers, absorb customer feedback and give them engineering resources so the product and the sales operation can improve together.

He calls sales a data, infrastructure and mathematics problem as well as a people problem. At Ramp, engineering support helped him build an outbound automation team early, creating leverage rather than leaving every repetitive task to sellers.

Before the recent AI boom, the team studied how Freeman found signals inside accounts: a new hire, a shared university or overlapping investors. Engineers helped automate list gathering and email outreach so sellers could spend more time talking to customers and solving problems.

For a small sales team, the immediate engineering problem is coverage. A handful of people working entirely manually can reach only a limited number of accounts; automation can increase awareness and the number of prospects the company can approach.

Stebbings asks whether scaling outreach sacrifices the response rate of a carefully researched personal note. Freeman agrees this is a risk: the system needs experiments and feedback on what actually works, while sellers retain room to send highly tailored messages themselves.

Ramp maintains a growth engineering team dedicated to go-to-market tools, Freeman says. He looks beyond the raw response rate: a rejection or opt-out is still a response. The useful measure is how many messages lead to meetings; he regards just under one meeting per 100 emails as strong.

Freeman cautions against specializing sales teams by industry too early. In a large market, broad coverage may be more valuable while a company is winning share. Later, when available opportunities become more constrained, verticalization can be a lever for improving conversion.

To shorten an enterprise sales cycle, Freeman starts with qualification. Find out whether the contact can influence a decision and is reasonably committed to change within a year; a pleasant conversation with someone unable to act can waste months.

One test is to ask the contact to bring a more senior stakeholder to the next meeting in return for the seller bringing technical resources. A willingness to make that introduction can reveal a genuine champion; refusal calls for a direct discussion of what is blocking progress.

When a prospect asks for an early discount, Freeman prefers to establish technical fit and business value first, especially in larger accounts. He wants both sides to understand the cost of ownership and the financial or operational impact before debating a small price concession.

He allows that very small businesses and one-call closes can be different. In complex sales, however, a jointly developed assessment of value gives the buyer a reason to act and can reduce the need to compete solely on price.

For the first sales hires, Freeman generally recommends paying 100% of on-target earnings for at least two quarters before imposing a formal quota. Early on, the founder may not know enough about sales cycles or achievable output to set a sound number.

An arbitrary target can fail in either direction: a seller may greatly exceed it and trigger an unexpected payout, or miss an unrealistic number despite making a solid start. Stebbings adds that a perceived failure can damage confidence even when the initial result was useful.

Once there is enough evidence of pipeline progression and the length of the sales cycle, Freeman says, set a quota that is ambitious but grounded in data. The timing depends on the segment; shorter cycles provide feedback sooner.

He advises hiring two sellers or SDRs instead of one. A pair provides a comparison, spreads the founder’s onboarding effort and gives the hires competition and companionship. One person alone is much harder to benchmark against a founder’s own selling.

A difference in performance does not automatically mean firing the lower-ranked person. If the gap is modest, examine whether one had better leads, founder introductions, product knowledge or motivation. Freeman says a pronounced outlier calls for a different conversation.

For an early business, Freeman favors building momentum around a single product and ideal customer profile. Twenty enthusiastic customers for one offering may be more valuable than a handful who are only partly served across several unfinished products.

At a later stage, a company may need special incentives to launch new products. Freeman describes offering two or three times quota credit on new offerings to create initial momentum, customer references and eventually more multi-product accounts.

Sales candidates, especially leaders, can interview very well because persuasion is their profession. Freeman says Ramp’s hiring mistakes included relying too heavily on pedigree and big-name employers without testing whether someone could solve problems independently and commit deeply to the job.

Asked about younger workers and expectations around work, Freeman says there are still many people willing to work intensely. His view is that leaders must create a culture that attracts them; he cites young Ramp sellers who choose to come in on weekends.

For onboarding, Freeman organizes the material into four areas: the product and technology, buyer personas, the competitive landscape, and the company’s internal systems. He expects sellers to know the offering well enough to answer direct technical questions rather than rely on vague claims.

Buyer knowledge requires switching context. A CFO at a venture-backed software company may care about broad business outcomes, while an accountant at a construction company may need a specific month-end workflow fixed. The seller should understand each person’s priorities and challenges.

Competitive knowledge matters in a crowded market. Freeman wants sellers to study rivals and explain differences diplomatically, positioning their product around the buyer’s actual requirements instead of merely criticizing the competition.

Ramp’s enablement leader is a former seller and sales leader. Depending on the segment, the boot camp runs 60 to 90 days, with a particularly demanding first four weeks combining practical exercises and self-guided material.

New hires must pass discovery and demo certifications before receiving accounts through the routing system. Freeman sometimes joins those assessments himself. The aim is to ensure that a seller can perform the basic work before taking on a full book of business.

Depending on the segment, new sellers may start speaking to customers on their own after two to four weeks. Before then they listen to recorded and live calls, team meetings, pipeline reviews and forecasts; a frontline manager supports them closely as they begin.

Freeman says enablement cannot substitute for frontline management. Managers still have major deals to close, but they also need to invest in new hires because future targets depend on those sellers becoming productive.

He estimates that roughly 70% of first calls impress him and 30% fall short of the standard. He reviews recordings from new and experienced sellers and brings both the seller and their leader into a conversation when a call needs work.

Asked about the ratio between a seller’s quota and compensation, Freeman says extreme efficiency can suggest a team is leaving opportunities uncovered. He describes Ramp’s ratios as roughly seven to twelve across segments, while acknowledging variation among roles.

Ramp-up periods depend on deal length. Freeman gives examples ranging from 60 days for inside sales and 90 days for commercial to four months for mid-market, five for enterprise and six for strategic enterprise.

A promising new seller is often the person asking frequent, thoughtful questions about accounts, pipeline and product. Freeman treats curiosity and initiative as positive signals; silence or questions that could easily be answered from available documentation can be weaker ones.

In interviews, he deliberately leaves time for candidates’ questions. An excellent applicant might research a leading seller’s process, explain the fit with their own experience and connect that evidence to the role—much as a seller would prepare for a prospect.

Freeman believes strongly in customer success as an outcome and has made it a distinct function at Ramp. Some team members have accounting and ERP expertise, allowing them to act as an extension of a customer’s finance operation; he says Ramp’s economics support that investment.

He views customer success as an engine for retention and expansion. Successful deployment and financial or operational value earn the right to introduce additional products later; a poor initial implementation makes that subsequent conversation harder.

On forecasting, Freeman credits a finance counterpart who built models he says consistently land within five percent across the business. He cautions that earlier, less disciplined forecasts could diverge considerably when sales alone handled the process.

His management lever is to make forecast accuracy part of performance reviews, one-on-ones and quarterly business reviews, even though sellers are not paid directly on it. Otherwise emotion can override evidence: being named the preferred vendor does not mean legal and security reviews are complete.

Ramp holds weekly pipeline reviews but has removed separate forecast calls that Freeman considered duplicative. Segment and frontline leaders, with a rotating set of individual contributors, focus on large opportunities at risk and what the team can do to advance them.

The team also examines lost deals: was the cause a product gap, price or something controllable? Freeman says Ramp often loses to the status quo. In his view, the seller has not connected the purchase strongly enough to an urgent business problem and a motivated internal champion.

Freeman believes Ramp’s brand marketing helps outbound and customer conversations, although he says precise attribution is difficult. Events, dinners and other experiences give sellers ways to engage prospects; he associates broader awareness with shorter cycles and greater willingness to expand.

Freeman describes the work before an initial call: researching the prospect across its website, LinkedIn and other sources. He estimates this could take 15 to 30 minutes per meeting, a substantial amount of time when multiplied across hundreds of sellers.

Ramp built an internal tool called Ramp Revenue to assemble pre-call research. Freeman says it can surface a product launch, a financing change or a contact’s past experience with Ramp—details that a highly prepared seller might otherwise find manually.

In his account, the tool can reduce preparation to around 90 seconds and make useful context available to more of the team. He sees the time saved as additional selling capacity that can eventually support higher quotas and revenue.

Could Ramp sell this internal system externally? Freeman says he can imagine taking additional products to market, but does not announce a launch. The decision depends on timing and whether the go-to-market organization can handle the change.

Stebbings emphasizes that an enterprise product needs more than a switch turned on: it needs sellers, implementation, marketing and customer success. Both speakers treat organizational readiness as part of the product decision, not an afterthought.

Freeman identifies a leadership weakness: the impulse to jump into every important deal or customer problem. Hands-on involvement helped him advance, but at scale it can prevent others from developing and teach the team to wait for him to take over.

The answer is not to disappear from frontline work. Freeman wants leaders who can operate strategically and still understand the trenches. He says he continues making cold calls and sending at least five cold emails a day to stay close to customers and sellers.

Stebbings asks how Ramp gave Freeman a founder-like outlook. Freeman points to exposure: when he joined, he worked closely with Eric Glyman, saw sales and investor conversations and even operated from the founder’s inbox. He describes the first nine months as an intense education.

Mentors and experienced leaders also helped him grow, he says. At the same time, the founders held him accountable for performance. Freeman describes a productive pressure to keep learning and delivering rather than assuming his role is guaranteed.

Freeman recalls a mentor’s blunt joke about sales rankings: there are people who are exceptional, people about whom it is too early to know, and people who need to leave. He uses the line to illustrate a direct style of evaluating performance.

Asked which tool he could not give up, Freeman names Inspect, Ramp’s internal coding agent and harness. He says it helps sellers create custom demonstrations and analyze customer configurations, giving them access to capabilities that once required more direct engineering support.

In hiring, he looks for people who may be about to accelerate rather than only established stars. He names sales leaders he admires and returns to his broader theme of finding talent before the market fully recognizes it.

His advice to a new rep is to commit to the craft and solve problems rather than merely point them out. New hires have fresh eyes: they may spot a broken process or bring a useful practice from a previous employer. They should also take onboarding, certification and building pipeline seriously.

When asking for feedback, Freeman prefers a specific observation and proposed course correction to a broad request for an opinion. For example, a seller can identify a pattern in two recent deals, explain what they plan to change and ask a leader whether the reasoning is sound.

The same principle applies to introduction requests, Stebbings and Freeman agree. Name the person, explain why the meeting matters and supply a concise forwardable message. Making the request easy to evaluate and pass along respects the intermediary’s time.

Asked about the kindest thing anyone has done for him, Freeman credits his wife. Early in his time at Ramp he warned that pursuing the opportunity would involve sacrifices and less time for their social life; he says she supported him then and continues to do so.

Freeman closes with a personal connection to the show: as a Ramp SDR, he listened to 20VC, took notes by hand and contacted founders who appeared as guests. Years later, he is sitting across from Stebbings discussing how that early sales effort evolved.