Eric Gilpin’s career spans some of the most transformative phases in tech. From scaling Upwork’s enterprise business from zero to $650M to driving G2’s global revenue organization, Eric has been at the forefront of leading revenue teams through significant growth and transformation. His unique perspective combines deep operational experience with a clear focus on creating alignment and driving enterprise value.
In our conversation, Eric unpacked critical strategies for evolving from sales execution to executive revenue leadership, designing frameworks for team alignment, building and implementing leadership values, and navigating the complexities of go-to-market planning.
Listen to Eric's episode on Apple and Spotify.
1. From Sales Leader to Revenue Executive
Eric describes a clear progression in leadership responsibilities as one moves from managing a sales team to becoming a revenue executive. Early in your career, he says, it’s about execution—running plays given from above. But as you grow, it shifts to strategy, and at the highest levels, it’s about alignment and ensuring the right people are in the right seats.
A pivotal concept Eric emphasizes is the transition from focusing on “what” and “how” to mastering “why” and “who.” Revenue executives must spend less time in tactical execution and more time aligning cross-functional teams on the organization’s broader goals. This shift requires delegating effectively and building trust in your team to execute the “what,” while you focus on aligning the organization on the “why.”Eric’s “who are we chasing” framework was one of my favourite takeaways. He shared how at G2 they narrowed their freemium customer base of 200,000 down to clusters of 3000 to target with the GTM team. “Not at categories or revenue are created equal.”
2. Team 1 Alignment: Driving Cross-Functional Collaboration
A recurring theme in Eric’s leadership philosophy is the importance of “First Team” alignment—ensuring that the executive team operates as a cohesive unit. Drawing inspiration from Patrick Lencioni’s framework, Eric highlights the necessity of treating your peers in other functions (e.g., product, marketing, finance) as your primary team. When the leadership team isn’t aligned, it creates downstream friction across the organization.
At G2, alignment starts with clarity around the ideal customer profile (“who are we chasing”), resource allocation, and shared metrics. Eric stresses the importance of “being a student of the functions you partner with” and to deeply understand how they go about serving the customer. Time is an important factor here. Eric spends roughly 50% of his time with his executive partners.
3. Designing for Adaptability: Why Systems Matter More Than Tactics
Eric’s success scaling Upwork’s enterprise business stemmed from building adaptable systems that could evolve as the market shifted. He emphasizes that processes have a shelf life; what worked yesterday won’t necessarily work tomorrow. This was evident at G2, where narrowing the ICP from 200,000 product listings to a focused target of 3,000 accounts allowed the company to prioritize high-impact customers and allocate resources more effectively.
Regularly revisiting systems and processes is critical for staying relevant in a rapidly changing market. Eric advises leaders to constantly question whether their current strategies still align with buyer behavior. This discipline of reassessment prevents stagnation and ensures the organization remains agile in the face of change.
4. Friction as Fuel: The Role of Healthy Tension
Rather than avoiding friction, Eric believes it should be embraced as a source of growth. Accountability creates pressure, and pressure inevitably creates friction. But within a healthy culture, this friction becomes productive rather than destructive. I couldn’t agree more with his view here.
Eric shared how fostering healthy tension involves assuming positive intent and focusing on the work rather than the individual. At G2, encouraging difficult conversations and maintaining clear expectations helped the team uncover hidden opportunities and solve systemic challenges. By normalizing these discussions, leaders can turn friction into fuel for innovation and improved execution.
5. Operationalizing the “Why”: Balancing Mission with Metrics
Eric ties every decision back to the company’s core purpose. At G2, the mission to empower business professionals to achieve peak potential informs every aspect of the go-to-market strategy. But he balances this with a disciplined focus on metrics, knowing that inspiration without data-driven action lacks impact.
For example, G2 tracks not just revenue but leading indicators like customer ROI and pipeline velocity. These metrics provide early signals, allowing the team to pivot long before issues materialize in the P&L. By connecting daily actions to the overarching mission, Eric ensures alignment at all levels of the organization while maintaining operational precision.
6. Planning for Agility: Build Flexibility Into Annual Goals
For Eric, annual planning isn’t about rigid execution but building a framework that can adapt to change. He emphasizes that plans are living documents, meant to evolve with both internal and external dynamics. At G2, this includes creating upside and contingency plans that allow the team to respond nimbly to unexpected challenges or opportunities.
This approach ensures the team remains aligned but flexible, capable of reallocating resources or shifting priorities as needed. By treating the annual plan as a starting point rather than a fixed roadmap, leaders can balance structure with adaptability. Given everything we’ve all experienced the last 4 years, this makes a ton of sense. 😅
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