Nathan Barry: Everything We Learned Growing ConvertKit to $40M (and What We'd Do Differently)
Jun 18, 2024
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Join Nathan Barry, Founder of ConvertKit, and Barrett as they discuss building a $40M company, leadership growth, the importance of clear communication, feedback culture, strategies for team relationships, brand differentiation, and personal growth.
Balancing safety and performance is crucial in company culture to avoid creating internal tensions.
Nathan Barry's journey from $5,000 side project to $40M company showcases key decision points and growth.
Leadership transitions within ConvertKit highlight pivotal decision-making moments and strategic shifts.
Cultivating feedback culture through practices like listening walks fosters trust, empathy, and strong relationships.
ConvertKit's approach to compensation includes equitable and performance-based incentives for sustainable growth.
Deep dives
Building High-Performance Culture vs. Caring for Employees
Struggling with the balance between building a culture focused on safety and performance, the podcast discusses creating strife by emphasizing softer aspects while silently prioritizing winning. The tension between these priorities led to a need to reevaluate the approach to fostering a healthy company culture.
Founding of ConvertKit and Growth Strategies
The episode delves into the inception and growth of ConvertKit, highlighting Nathan Berry's journey from a side project earning $5,000 monthly to a $40 million annual recurring revenue company with 80 team members. Insights into key decision points, team expansion, and revenue growth demonstrate the evolution of the company.
Transition of Roles from COO to CEO
Detailed reflections on leadership transitions within ConvertKit, from Barrett Brooks evolving from COO to CEO, showcase pivotal moments in decision-making, mentorship influences, and the collaborative journey of leading a company. The narrative captures the dynamics of succession planning and strategic shifts in leadership roles.
Cultivating Feedback Culture and Meaningful Connections
The podcast emphasizes cultivating feedback culture through practices like listening walks and unsolicited feedback. These practices foster strong relationships, deepen understanding among team members, and create a foundation of trust and empathy. The value of knowing each other's stories and building connections emerges as a cornerstone of a healthy work environment.
Hosted Retreats for Extended Collaborative Problem-Solving
The podcast discusses organized retreats where participants engage in extended problem-solving sessions. These retreats involve group discussions focusing on strategic business issues. Innovative practices like discussing absent members' strengths and areas for growth are highlighted. Participants provide constructive feedback, emphasizing each individual's potential for growth.
Company-Wide Feedback Practice for Growth
The episode explores an internal feedback practice within ConvertKit that spans across teams. This practice involves candid feedback sessions, from the entire company to executive teams. The feedback is direct, encouraging growth and personal development. Participants initially feel nervous but find the experience valuable, receiving insights unattainable through regular channels.
Balancing Compensation Structures for Long-Term Growth
The podcast delves into ConvertKit's approach to compensation structures, emphasizing equitable and performance-based incentives. The discussion highlights a standardized salary system, profit-sharing, stock grants, and benefits packages. The strategic alignment of short-term versus long-term, and performance-based versus guaranteed compensation is underscored. ConvertKit's unique approach aims to balance incentives for sustainable growth and value creation.
Reflects on Departure and Transition Process
The conversation reflects on Barrett's departure from ConvertKit, focusing on the transparent and thoughtful transition process. Discussions revolved around aligning career goals, transparent communication, and setting clear timelines. The departure process aimed at mutual understanding and effective transition planning. The reflection emphasizes the importance of open dialogue, strategic planning, and respectful handling of personnel transitions.
Career Growth and Leadership Transition
The podcast episode delves into the speaker's experience with career growth and leadership transition. It discusses how the speaker and a colleague managed their company, reflecting on past decisions about handling personnel and performance. The episode explores the challenges of transitioning from a co-leadership model to more independent decision-making, emphasizing the importance of clarity in leadership roles and decision-making processes.
Podcast Strategy and Differentiation
Additionally, the podcast episode highlights the speaker's strategic approach to podcast content and differentiation. It details the shift towards in-person episodes for higher quality conversations and better audience engagement. The speaker shares insights into guest selection based on uniqueness and asking questions that prompt fresh stories. Moreover, the episode explores the speaker's effort to stand out through artwork and naming conventions, aiming for distinctiveness in presentation and content delivery.
Nathan Barry is the Founder and CEO of ConvertKit. In previous careers, Nathan has been a designer, author, and blogger. After learning the power of email marketing, he gave up a successful blogging career to go all-in on ConvertKit. Outside of work, Nathan spends his time playing soccer, woodworking, and chasing after his three boys.
This week, Barrett and Nathan sit down for a candid conversation about the ups and downs of building a $40M company, and what they wish they had done differently. They also dive into their strategies for growing personal brands, the power of clear roles and communication in projects, building strong team relationships, creating a supportive yet high-performance company culture, and much more.
In this episode:
[00:00] - Intro
[04:20] - Why Barrett left ConvertKit
[15:18] - Building confidence as a leader
[22:59] - "We should have fired more people"
[37:57] - Creating a healthy feedback culture
[44:13] - Strategies for better communication
[58:14] - Designing comp and benefits
[01:07:46] - What we nailed on the growth side (and what we could have done differently)
[01:23:10] - Lessons learned from Barrett's departure
