Leading Teams in Enterprises vs. Startups: Insights from a CRO

Leaders across organizations of all sizes face a common challenge: managing the competing priorities of people and tasks. This challenge becomes particularly acute when stepping into new roles or managing large or inexperienced teams. As companies grow and market expectations increase, leaders must find ways to meet business objectives while maintaining strong team engagement and performance.

Richard Ellis, one of the managing partners at Revenue Innovations, recently sat down with Justin Barney, Chief Revenue Officer (CRO) of ThousandEyes, a Cisco company, to explore how these challenges manifest across different organizational contexts. This interview can be heard on our Some Goodness podcast - listen here.

Justin's background offers valuable perspective—beginning his career in investment banking and private equity, he transitioned to technology during the internet expansion of the late 90s. Since then, he's led teams in multiple startups (several acquired by companies like Citrix and Juniper) before taking on his current role at ThousandEyes. His experience across both emerging companies and established enterprises provides unique insights into effective leadership.

The Three Essential Elements of Revenue Leadership

Whether leading a small company or a global enterprise, Justin emphasizes three key elements that determine success: people, process, and product. Let's examine each one.

1. People: The Core of Success

"People are where it starts and ends," Justin notes. He breaks down the "people" element into three fundamental components:

Strategic Hiring

At Cisco, Justin learned that effective hiring requires more time and structure than most leaders anticipate. His approach includes:

  • Developing detailed "Ideal Candidate Profiles" (ICPs)
  • Following documented hiring processes
  • Creating diverse interview panels
  • Building diverse candidate pools
  • Implementing structured evaluation methods like candidate playbacks

Most notable is his emphasis on diversity as a business advantage. "Different perspectives lead to better decision-making and innovation," he explains.

Retention Strategies

Justin's comprehensive approach to retention includes:

  • Competitive compensation with clear earning potential
  • Using tools like TeamSpace for regular check-ins
  • Strategic in-person gatherings (2-3 times annually for leadership teams)
  • Documented career paths
  • Consistent recognition of achievements

The shift to hybrid work has changed team dynamics, making intentional connection more important. Justin's team maintains cohesion through regular video meetings and periodic in-person gatherings.

Performance Management

"A players want to work with A players," Justin notes. His performance management approach includes:

  • Clear expectations from the start
  • Documented coaching processes
  • Structured improvement plans when needed
  • Timely action on performance issues
  • Fostering a high-performance culture

2. Process: Creating Operational Excellence

Clear processes drive sustainable success in organizations of any size. Justin's team operates on a 13-week planning cycle, providing clarity and alignment across all levels of the organization.

They utilize the LAER framework (Land, Adopt, Expand, Renew), particularly important in subscription-based businesses. Justin emphasizes that success extends beyond closing deals—it requires ensuring customers see tangible value. This demands:

  • Effective team handoff processes
  • Collaborative account planning
  • Clear adoption metrics
  • Aligned compensation structures
  • Developing customer advocates

3. Product: Market Alignment

For any CRO, product-market fit is essential. Justin highlights three key aspects:

  1. Close partnership between sales and product teams
  2. Consistent customer feedback to product development
  3. Transparent communication about product direction

 

Strategic Market Expansion: The ABCD Framework

 

One of the most insightful takeaways from our conversation was Justin’s framework for market segmentation: A, B, C, and D. He likens it to how venture capitalists and private equity firms invest in markets, advising CROs to categorize markets based on the level of investment required and the potential return.

A Markets: Invest ahead of revenue (venture approach)

B Markets: Measured investment (private equity approach)

C Markets: Maintain position

D Markets: Exit or avoid

By clearly defining your market focus, you ensure that resources are allocated where they’ll have the most impact. Too often, companies try to spread themselves too thin, investing in too many markets without fully committing to any of them. This structured approach ensures a focus on the most strategic opportunities.

 

The Value of Mentorship

Throughout the conversation, one theme that kept emerging was the value of mentorship and learning from others. Justin credits many of his insights to mentors like Al Monserrat, who taught him the importance of structured market entry and operational discipline. He recommends CROs and leaders build their own “personal board of advisors,” a diverse group of mentors who can offer guidance and perspective on the complex challenges of leadership.

 

Final Thoughts

Our conversation highlighted how fundamental leadership principles remain consistent regardless of organization size. While complexity may increase with scale, success consistently depends on building strong teams, establishing clear processes, and ensuring products solve real market needs.

At Revenue Innovations, we help leaders implement these principles to optimize their sales organizations and drive sustainable growth. Connect with us to explore how these insights might strengthen your organization.

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