Interns to Enterprise: How Cresta's CRO Built a Category Leader

Winning your first enterprise deals and scaling enterprise teams

Most revenue leaders believe that scaling sales teams is primarily about creating comprehensive playbooks, systematizing processes, and building repeatable motions. That’s certainly my approach at Owner.

The truth is that enterprise sales resists standardization in ways that mid-market and SMB motions don't. As it turns out, the very thing that makes enterprise sales difficult to scale (its inherent complexity and political dynamics) is precisely what creates its enduring competitive moat.

I recently sat down with Alex Cramer, Chief Revenue Officer at Cresta, for a fascinating conversation about how to win your first deals as an enterprise oriented startup and scale enterprise teams. Alex has spent his entire career in enterprise sales, which is a rarity, starting as the first rep at Extol in 2008, then moving into leadership at Dynamic Signal (now FirstUp), serving as VP of Enterprise Sales at Gong, and now leading revenue at Cresta as CRO.

Our conversation revealed counterintuitive insights about cold-starting enterprise motions and building truly scalable enterprise teams; lessons that apply whether you're scaling from $0M to $5M to $50M or $50M to $500M.

1. The Cold Start Advantage: Why Enterprise Difficulty Creates Defensibility

Most founders avoid starting with enterprise customers for good reason; the sales cycles are brutal, the political landscapes treacherous, and the security requirements daunting. But this challenge creates an unexpected advantage.

Alex shared how Cresta (a contact center AI company founded by Stanford AI lab researchers) cold-started directly into enterprise:

"The way the company started was the CEO and CTO became interns at Intuit. They rented an Airbnb in Arizona outside where the Intuit contact center is located. Every day they showed up to work in the Intuit contact center as interns, studying what behaviors could be automated or augmented with AI."

This extreme dedication to understanding customer problems led to Intuit becoming their first customer. That reference case then unlocked their second customer, Cox Communications, creating momentum.

The brutal reality? This approach is nearly impossible to replicate for competitors. As organizational psychologist Adam Grant's research suggests, successful innovation requires both originality and execution capability. The difficulty of cold-starting enterprise creates what Seth Godin calls "the dip,” which is a painful period of effort that ultimately becomes your competitive moat.

The learning: The hard work of building enterprise credibility becomes your sustainable advantage. This is why so many enterprise-focused startups started with almost unbelievable levels of customer obsession and adaptation.

2. The Enterprise Playbook Myth: Focus on Frameworks, Not Scripts

I asked Alex the question that keeps many revenue leaders awake at night: Can you truly playbook enterprise sales?

His answer was refreshingly honest:

"We don't think we can do that. We certainly have a sales process, and when I train the team, everybody follows this process, but you do have the ability to deviate. If you deviate, you have to have a good reason why. We have plays that are proven, but I'm very hesitant to map out a very specific playbook."

This aligns with research from McKinsey that shows high-performing enterprise sales organizations emphasize adaptability over rigid processes. The most successful teams focus on frameworks that provide structure while allowing for judgment.

At Cresta, their sales process framework includes:

• Qualification criteria (identifying a solvable problem, securing a champion, and mapping executive decision-makers)

• Discovery meetings (technical and business discovery)

• Custom demonstrations

• Parallel technical and business tracks

But unlike SMB sales, where you can optimize minute details like exactly how many minutes to wait before calling an inbound lead, enterprise requires flexibility within structure.

The learning: Build frameworks that guide rather than playbooks that dictate. As Alex puts it: "You need to hire smart people that come in and can assess the situation and be nimble. Otherwise, you're going to have a playbook with 450 chapters."

3. The Enterprise Talent Equation: Hunting in Pockets

One of my favourite takeaways was Alex's deliberate strategy for acquiring enterprise talent, which is one of the biggest challenges in scaling.

The conventional wisdom says to look for lone-wolf hunters with rolodexes of C-level contacts. Alex instead focuses on what he calls "pockets" of talent:

"We very rarely hire just through recruiters or cold outreach. We try to hit these pockets where we get referred to one person who was a top rep at this company. Then we're pushing them to share who are the top three reps you ever worked with? We've been really successful hitting pockets: we had the Medallia pocket, the Qualtrics pocket, the Yext pocket, the Sprinklr pocket."

This approach offers three powerful advantages:

1. Back-channeled validation: You know exactly what you're getting

2. Built-in support systems: Reps arrive with buddies and champions

3. Cultural cohesion: Shared values and working styles transfer over

This aligns with fascinating research on psychological safety. According to Amy Edmondson of Harvard Business School, teams with higher psychological safety perform better, especially in complex tasks. By bringing in groups of people who already work well together, you kickstart this dynamic.

Even in my SMB-focused world at Owner.com, we've used this approach, pulling talent pockets of 3-6 people from 4 different companies, with consistently excellent results.

The learning: When hiring enterprise talent, target ecosystems rather than individuals. The network effect of talent acquisition becomes a strategic advantage most leaders miss entirely.

4. The Enterprise Time Horizon: Playing the Long Game

Enterprise selling requires a fundamentally different time orientation than other sales motions.

Alex dropped an important truth that reveals why many enterprise sellers struggle:

"When I'm looking at resumes in the strat space, I can totally understand the more SMB rep moving around to different companies every year and a half, two years. But if you're a strat rep, doing that doesn't make a lot of sense because it doesn't really get good until 18 or 24 months in. So if you're leaving every 18 months, it's brutal."

Most enterprise reps see their biggest paydays in year three (the mythical seven-figure W2) where major multi-year deals finally close after years of nurturing.

This creates an interesting strategic challenge for building enterprise teams. At Cresta, Alex structures account loads to match this reality:

"For a strat seller, you're going to start with 15 to 20 of those ICP accounts. You're going to tier them into your top five or 10, and you're going to be laser-focused on getting one of those to convert in the first year. Let's say you close a Wells Fargo. Now your job changes—we trim your account book down from 15 or 20 to eight or 10. Then you close Marriott. Now you have Wells Fargo, Marriott, and four others, and you work your way into a strategic account manager business."

The learning: Structure your enterprise team around the three-year value creation curve. Most leaders optimize for short-term results, missing the exponential value that comes from patient account penetration.

5. The Leadership Factor: What Sets Great CROs Apart

When I asked Alex what separates good CROs from truly exceptional ones, his answer was refreshingly authentic:

"I think some of it is luck. You have the right CEO, you have the right company in the right moment. There are incredible CROs that I know who were at not-great companies, but had they just been at MongoDB at the right time, they'd be known as the greatest."

Beyond luck, Alex highlighted three factors:

1. Motor: "It's a job that never stops...the best CROs have that motor, that fire."

2. Support system: "I could not do my job if it weren't for my wife being supportive."

3. Balance: "Great CROs have balance and aren't fluctuating between 10 and zero in terms of their temper."

This aligns with research from Jim Collins' "Good to Great" on Level 5 Leadership, which identifies a paradoxical blend of personal humility and professional will as the hallmark of transformative leaders.

For emerging leaders, Alex offered perhaps the most important advice of our conversation:

"Be yourself. Early when I was a leader, I would look at other leaders and struggle because I don't know how to be like that. They give the great rah-rah speech every morning at 7 a.m., getting everybody fired up. But eventually I realized that you don't have to be that. There's lots of different ways to inspire people."

The learning: Leadership effectiveness isn't about mimicking others' styles but finding authentic expression of your natural strengths. Psychological research on authenticity shows it correlates strongly with trust—the foundation of influence.

Making Enterprise Work For You

The implications of these insights are clear: building an enterprise motion requires a fundamentally different approach than scaling transactional sales.

1. Embrace the difficulty as advantage: The cold-start challenge in enterprise becomes your competitive moat once conquered.

2. Build frameworks, not playbooks: Your sales process should guide rather than dictate, allowing for the judgment of talented sellers.

3. Hunt in talent pockets: Hire connected clusters of proven performers rather than isolated individuals.

4. Structure for the long game: Acknowledge and optimize for the multi-year value creation cycle in enterprise.

5. Lead authentically: Find your unique leadership voice rather than mimicking others' styles.

Building an enterprise motion is undeniably challenging, but for companies with the right approach, it creates sustainable, defensible value that compounds over time.

And that's a lesson worth remembering next time you're frustrated by the complexities of enterprise sales.