Maya Research: The Business of Culture I 2025 I Download Now
What Outreach Discovered About the Future of Remote Teams
2025 I DEEP DIVE INSIDER PROFILES
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When we met with the leadership team at Outreach, the first impression was how steady and collaborative the environment felt. Customer success joins sales on prospect research. Engineers attend deal reviews. Managers coach emotional intelligence and communication skills as part of everyday work. The culture feels deliberate, shaped by curiosity about how teams grow and stay connected.
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During our conversations, the team described a series of questions they are working to understand. How can relationship-building stay genuine when most of it happens online? What helps people feel close when they are spread across different locations? As AI handles more of the repetitive parts of selling, which human skills continue to matter most?
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These questions guide how Outreach organizes its own sales team and how it supports the 10,000 companies that use its platform. Observing those organizations over time has revealed a clear pattern. When sales teams grow quickly, the structure and habits that worked early begin to change. Sarah Kim, Outreach’s Head of People, described this shift as familiar to anyone who has experienced rapid growth. “At 50 people, everyone knows what everyone else is working on,” she said. “Information travels easily and wins are shared. Around 150, smaller groups start forming with their own routines. By 300, performance varies across teams even when conditions look the same.”
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Founder Manny Medina has seen this evolution across many young companies. Informal systems that once helped teams move quickly become less reliable as they expand. “I have watched companies lose momentum when their ways of working stayed too informal,” he said. “Growth requires structure that supports communication and shared understanding.”
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Many of these changes appear gradually. Knowledge sharing slows, and new hires have fewer ways to absorb the unwritten parts of the job. “Our data shows that teams maintaining consistent growth establish clear systems for sharing what works before challenges appear,” Kim said. “When those systems are already in place, scale feels more manageable.”
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In recent years, Outreach has studied how shifts in buyer behavior influence sales culture. Many B2B buyers complete most of their research before meeting with sales. This change alters what a productive conversation looks like. “Five years ago, sales representatives provided most of the product information,” said Marcus Chen, VP of Sales Development. “Now prospects arrive with a detailed understanding. The most effective representatives help them see their situation from new angles.”
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Manny Medina described this as an evolution of professional focus. “Speed is no longer the primary measure,” he said. “Understanding is. Teams that learn to ask thoughtful questions create stronger relationships and more lasting results.” Jessica Torres, a senior account executive, offered an example from recent experience. “One of our representatives spent several hours studying a client’s industry before a discovery call,” she said. “The preparation led to a conversation about challenges the client had not fully defined. That type of exchange creates real progress.”
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Outreach’s approach reflects a wider movement toward intentional culture building. As work becomes more distributed and technology takes on routine tasks, organizations are paying closer attention to the systems that support learning, connection, and shared purpose. For teams focused on long-term growth, these systems form the foundation for both performance and stability.
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Looking at workforce trends and customer behavior patterns, Outreach's leadership predicts three major shifts that will reshape sales culture over the next five years. First, the rise of "Expertise-Based Selling" where sales reps become genuine subject matter experts in specific industries or business functions rather than product specialists. "We're already seeing this with our top performers," explains Kim. "They don't just understand our platform – they understand supply chain optimization or HR technology ecosystems better than many of their prospects. That expertise becomes the foundation for consultative relationships." Medina believes this trend will accelerate: "The companies that win will have sales teams that prospects actually want to talk to because they bring valuable insights, not just product pitches."
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Second, the evolution of "Collective Selling" where complex deals involve coordinated efforts from multiple specialists rather than individual account owners managing everything.
"Enterprise deals now touch so many stakeholders that no single rep can be expert in every decision criteria," notes Chen. "Our most successful teams coordinate technical specialists, industry experts, and relationship builders. The culture needs to reward team success, not just individual achievement."
Third, the emergence of "Continuous Customer Development" where sales culture extends beyond initial deals to ongoing value creation and expansion opportunities.
"The traditional handoff from sales to customer success is disappearing," observes Kim. "Our best reps stay involved throughout the customer lifecycle, continuously identifying new opportunities and ensuring success. Sales culture needs to measure lifetime value creation, not just initial contract value." With sales teams increasingly distributed, the leadership team has developed specific cultural practices that maintain connection and knowledge sharing without requiring constant meetings.
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Their "Insight Broadcasting" system enables reps to quickly share prospect intelligence through short video messages that others can consume asynchronously. When a rep discovers that prospects in manufacturing are suddenly concerned about supply chain resilience, that insight immediately becomes available to colleagues working similar deals.
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"Insight Broadcasting solved our knowledge hoarding problem," explains David Park, an SDR. "I used to keep good intelligence to myself for competitive advantage. Now I realize that when I share insights, I get better intelligence back from teammates. Everyone's more effective."
They also use "Deal Story Archives" – a searchable database of how specific deals developed, including what worked, what didn't, and why prospects ultimately bought or walked away.
"Deal Story Archives accelerated my learning curve tremendously," notes Alex Chen, who joined six months ago. "Instead of learning only from my own deals, I can study dozens of similar situations and understand which approaches typically succeed."
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Perhaps the biggest cultural shift involves what sales managers actually do day-to-day. Outreach has moved their management approach from activity oversight to strategic coaching and psychological support. "Our managers spend less time reviewing call metrics and more time developing their reps' business judgment," explains Rachel Martinez, a sales manager. "We analyze prospect psychology, discuss influence strategies, and role-play complex stakeholder situations. My job is developing consultants, not monitoring activity."
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Medina sees this as essential for future competitiveness: "AI will handle activity monitoring and basic coaching. Human managers need to develop strategic thinking, emotional intelligence, and industry expertise. The companies that make this transition will have much stronger sales teams." This shift requires different management skills and cultural expectations. Managers need deep industry knowledge and coaching abilities rather than just sales experience and motivational skills. "The best sales managers now are part business strategist, part therapist, and part teacher," observes Kim. "They help reps think through complex problems, manage the emotional challenges of long sales cycles, and develop skills that AI can't replicate."
Traditional sales metrics don't capture cultural effectiveness, so the team has developed alternative measurements that predict long-term team performance.
"Collaboration Score" tracks how frequently reps share insights, participate in team deals, and contribute to collective knowledge. Teams with higher collaboration scores consistently exceed targets and retain talent longer. "Knowledge Velocity" measures how quickly successful practices spread throughout the sales organization. Teams that rapidly adopt and adapt new approaches outperform those where best practices stay isolated.
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"Prospect Feedback Quality" analyzes what prospects say about their sales experience, regardless of whether they buy. Teams with stronger cultures receive better feedback even from prospects who don't convert. "These metrics predict future performance better than traditional activity measurements," explains Lisa Wong from sales operations. "A team with strong collaboration and knowledge sharing will eventually outperform a team with higher current activity but weaker cultural foundations."
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The leadership team's approach offers practical frameworks that any B2B organization can implement regardless of size or industry. Start with "Cultural Due Diligence" during hiring – evaluate candidates' collaboration skills and learning agility as much as sales experience. "The best individual performers often struggle in collaborative cultures, while good collaborators can develop sales skills quickly," notes Kim.
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Implement "Systematic Knowledge Capture" to preserve and share insights across your team. Whether through video messages, deal archives, or regular sharing sessions, create structures that prevent valuable intelligence from staying trapped in individual heads.
Develop "Future-Focused Coaching" that emphasizes strategic thinking, emotional intelligence, and industry expertise rather than just technique improvement.
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"Train your people for the sales environment that's coming, not the one that made them successful in the past," advises Medina. "The companies that make this transition early will have significant advantages over those that wait until they're forced to change."
For Outreach's leadership, the future of sales culture isn't about maintaining the energy and competitiveness of traditional sales environments – it's about building collaborative, learning-focused teams that can navigate increasing complexity while maintaining authentic human connections in an increasingly digital world.
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