Transitioning from Startup to Enterprise in Community
In a recent Talk About Your Community livestream, I sat down with Max Pete, a community manager at Square, to discuss the transition from managing community teams in startups to working in a large enterprise. Max’s career path, filled with unexpected opportunities and strategic decisions, offers a roadmap for community professionals navigating similar transitions.
From Startups to Square: The Journey
Max began his community career working with startups like Freelance Founders and SuperHi. He often found himself as the sole community manager, handling everything from engagement programs to event management. His first big break came through a proactive approach: when he reached out directly to the CEO of SuperHi via Slack, expressing interest in a community role, even though the position hadn't been posted. That bold move led to two years of building and refining SuperHi’s community before the company was impacted by layoffs.
Max’s story serves as a reminder for professionals: taking initiative and "shooting your shot" can open doors you never knew existed. As he transitioned to his role at Square, Max shared how his startup experience—where he was often a one-man team—helped him develop essential project management and problem-solving skills.
Overcoming Imposter Syndrome and Thriving in Enterprise
When Max joined Square, he shared that he experienced imposter syndrome, a challenge many professionals face when moving into larger, more complex environments. Despite his wealth of experience, Max initially felt overwhelmed by the sheer scale of Square’s operations and the size of his new team. With a team of 13 other community builders, and more cross-functional collaboration than ever before, Max quickly learned that working in an enterprise didn’t mean a slower pace.
Max noted that adapting to enterprise work required a shift in mindset. He could no longer move as quickly or independently as he had in startups. Instead, projects, such as Square’s gamification revamp, required collaboration with design teams, copywriters, and marketing professionals to ensure consistency with Square’s branding. This slower but more thorough process taught Max the importance of cross-functional relationships, as each department brought a new perspective to the table.
Building on Past Experience
Max’s past experience as a solo community manager gave him a unique advantage when working with a larger team. His ability to wear multiple hats and manage end-to-end community programs helped him stand out. He emphasizes that professionals transitioning from smaller companies to larger enterprises should focus on how their past experiences, even if in leaner environments, translate into valuable skills in larger, more structured settings.
He also shared an important reminder for job seekers: don’t disqualify yourself from an opportunity because of a lack of direct experience. Max landed his role at Square by framing his startup experiences in a way that resonated with the needs of an enterprise. His adaptability and willingness to take initiative were critical to his success.
Career Advice for Community Professionals
Max's journey offers valuable lessons for those aspiring to move from startups to enterprise-level roles:
Shoot Your Shot: Don’t wait for job openings. Take the initiative to reach out to companies you're passionate about, even if they haven’t posted a role yet.
Imposter Syndrome is Normal: It’s natural to feel overwhelmed in new environments. Give yourself time to learn and adapt, especially when moving into a larger organization.
Leverage Your Experience: Your startup experience, where you’ve had to be resourceful and work independently, is highly valuable in larger settings where structure and cross-team collaboration are crucial.
Network Relentlessly: Max emphasized the importance of networking with colleagues, both within and outside your immediate team. Building strong relationships across departments can improve collaboration and open up future opportunities.
Conclusion
Max Pete’s journey highlights a career path for community professionals, from startup roles to managing enterprise-level responsibilities. His adaptability, relentless pursuit of opportunities, and ability to translate experiences across different scales of organizations exemplify the resilience required in today’s job market. Whether you’re building a community in a startup or navigating the complexities of a large enterprise, Max’s story is a reminder to stay open to learning, remain persistent in your goals, and embrace every step of the journey.
If you’re a community professional seeking new opportunities or facing similar career transitions, take Max’s advice: shoot your shot, build relationships, and never hesitate to reach out. Success is often the result of consistent networking and believing in your capacity to grow within any role. Keep moving forward, even when challenges arise, because the next opportunity might be just around the corner. If you’re a community professional looking for guidance and career path ideas, I’d be happy to schedule a time to talk.
About Max Pete
Max is a Community Builder who currently helps run community at Square. After nearly a decade in marketing and advertising, working with music labels, agencies, and running his own freelance venture, he found himself at a crossroads due to job burnout and a desire for more meaningful connections. This transition led him to uncover his true calling within the community space.
Affectionately known as the "community cheerleader," Max embraces this nickname as it reflects his commitment to being a supportive and encouraging presence. In addition to his work as a community builder, Max is an avid writer and speaker. He also indulges in his passion for music as an amateur DJ and playlist curator.
Advocating for limb different individuals is another significant aspect of his life. Max proudly serves on the board of the non-profit organization Design With Us and volunteers as a coach with Nubability.
Show Notes
Authenticity in Connection (0:00): Max Pete joins Todd Nilson to share what he’s been working on at Square, as part of a 13-member team. There is an aim to bring authenticity to connection via Substack, rather than the posturing and constant stream of ‘successes’ brought to social media.
From Startups to Square (9:05): Starting with a focus on startups, Pete explains how he secured a job by messaging a CEO out of the blue rather than a traditional application. The dots are connected on how he ended up in a role at Square and the applicable skills. Being on a large team has actually been work for Pete rather than working by himself in a slower pace.
Past Lessons and Future Goals (21:40): Improving the experience, making the process more simpler, and erasing tech debt are a few of the projects up and coming for the Square team’s focus. It is a slower process working with multiple teams, such as marketing, copywriting, etc, where a project needs multiple approvals. Moving from a startup to enterprise requires new tools, new communication, and time to get acclimated.
The Market for Community Senior Roles (33:32): Pete covers the team structure within the larger company and various roles. Consuming content from other community professionals is valuable in terms of inspiration, knowledge, and energy. Parting thoughts encompass a recommendation of ‘shooting your shot’ and not simply waiting for opportunities to land.
