Caldwell, Chief of Staff at Mesh: Advize Career Interview
A career journey from mechanical engineering to founding a startup assisting gaming content creators, Caldwell's path to Chief of Staff at Mesh is anything but typical.
This interview reveals the dynamic nature of a Chief of Staff role in a small startup, juggling operational tasks like product documentation and engineering standups with high-level strategic conversations and external communications.
The ability to adapt, communicate effectively, and prioritize amidst limited resources are highlighted as essential skills.
A passion for the positive impact of the creator economy and a proactive, "do the whole thing" mentality are key traits for success in this high-risk, high-reward industry, along with the importance of self-care.
The interview underscores the value of teamwork, problem-solving skills, and understanding the power of buffering between teams.
Caldwell's story inspires exploration of unconventional career paths, highlighting the benefits of engaging with interesting companies and focusing on contributing valuable skills, rather than solely chasing titles.
The interview concludes by emphasizing a commitment to using privilege to advocate for others and highlighting the importance of self-care.
Advizer Information
Name
Job Title
Company
Undergrad
Grad Programs
Caldwell Clarke
Chief of Staff
Mesh
University of Maryland
UCLA Anderson School of Management - MBA
Majors
Industries
Job Functions
Traits
Engineering - Mechanical
Gaming
Product / Service / Software Development and Management
None Applicable
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Career Path Of A Chief Of Staff At Mesh
Caldwell, a Chief of Staff at Mesh, initially pursued mechanical engineering but quickly transitioned to the startup world, "immediately left the field and went straight into startups," founding a company to help gaming content creators monetize their audiences. After further experiences in sales and online community monetization, Caldwell's career demonstrates a dynamic shift from engineering to entrepreneurial ventures focused on digital content and community building.
Main Responsibilities of a Chief of Staff at Mesh
Caldwell's Chief of Staff role at Mesh, a smaller company of 10-20 people, involved "executive management things," participating in strategic conversations directly under the CEO, and also operational responsibilities; they even "functioned almost like a product manager" for a significant portion of their time, managing product and engineering organizations.
A Day in the Life of a Chief of Staff at Mesh
Caldwell, Mesh's Chief of Staff, spends "60 to 70% of [their] day" on operational tasks such as "writing product documentation" and daily standups with engineering teams. The remaining time is dedicated to strategic initiatives, including "guiding some of the Strategic conversations" and external communications.
Most Important Skills For A Chief Of Staff At Mesh
Caldwell, Mesh's Chief of Staff, highlights the importance of adaptability ("be able and willing to learn basically anything") and clear communication in their role, acting as a translator between executive strategy and operational execution while shifting between broad strategic thinking and detailed tactical problem-solving.
Favorite Parts of Being a Chief of Staff at Mesh
Caldwell, Mesh's Chief of Staff, most enjoys the "fluidity or flexibility" of the role, allowing involvement in diverse tasks ranging from high-level strategy to detailed code reviews. This provides significant agency to "shape something and then go build it," offering a broad view of company operations.
Biggest Challenges Faced by a Chief of Staff at Mesh
Caldwell's biggest challenge as Chief of Staff at Mesh, a small startup with "an average engineering team of like three or four people," was prioritizing tasks: balancing "highest impact" projects with limited resources and aligning executive vision with engineering execution to stay focused across the organization.
Favorite Parts of Working in the Online Communities Industry as a Chief of Staff
Caldwell's favorite aspect of the creator economy and online communities industry is the positive impact; the work directly benefited communities Caldwell personally valued, allowing them to "do something that I thought was actually good".
What Type Of Person Thrives In Early-Stage Startups, Says Mesh's Chief Of Staff
Caldwell, Mesh's Chief of Staff, highlights three key traits for success in early-stage startups: optimism in the face of "high risk, high reward" and constant challenges, a willingness to embrace uncertainty and make decisions with incomplete information ("I think this is right. I don't really know but we're gonna...do the best possible job"), and a proactive, "do the whole thing" mentality, accepting responsibility for all aspects of a project.
What a Chief of Staff at Mesh Wishes They Had Known Before Working in Tech
Caldwell, a Chief of Staff at Mesh, learned the crucial role of "buffering" between executive and operational teams, tempering feedback to protect operational teams' capacity for focused work. This experience highlights the importance of effective communication and strategic management in a leadership support role, a skill valuable beyond the Chief of Staff position itself.
Entry-Level Positions For Aspiring Chiefs of Staff
Caldwell's unconventional path to Chief of Staff highlights the atypical nature of entry-level roles in startups; the advice offered is to "just start working for companies that [one] thought were interesting," actively engaging in early-stage startup communities and focusing on contributing valuable skills rather than seeking a specific title.
Significant Career Lesson From a Chief of Staff at Mesh
Caldwell, Mesh's Chief of Staff, reflects that a crucial career lesson, though not fully mastered, is prioritizing self-care amidst the demanding "hustle culture" of startups. Maintaining well-being is vital for long-term success, as "working 80-hour weeks for a year straight is not a good recipe for a good second year."
College Experiences That Helped a Chief of Staff at Mesh Succeed
Caldwell, a Chief of Staff at Mesh with a mechanical engineering background, emphasizes two key takeaways from their undergraduate experience: the development of "a sense of how to...figure things out, solve things with whatever tools are available," and the crucial importance of teamwork experience from "Team projects," particularly for aspiring startup leaders.
How Identity Has Influenced a Chief of Staff at Mesh's Career
Caldwell, a Chief of Staff at Mesh, recognizes the privilege inherent in their career, stating it allows them to "use that privilege to help focus that aren't in the same position". This involves acting as a shield for less advantaged colleagues against those who may be unaware of their own privilege and its impact.
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