Mission:
Transform Founder into Industry Leader

When a rapidly scaling startup reaches 120 employees across three countries while actively fundraising for Series B, executive bandwidth becomes the most critical constraint. I joined this late-stage PropTech company to build the operational infrastructure that would free their CEO to focus on what actually mattered: securing funding, building strategic partnerships, and positioning the company for scale. What I found was a brilliant founder drowning in operational chaos, spending 80% of his time managing fires instead of building the future.

BACKGROUND

This late-stage PropTech startup had successfully raised $15 million in Series A funding and was scaling rapidly across three offices spanning two countries, with approximately 120 employees managing operations in San Diego (administrative, sales, accounting, finance, marketing), Tijuana (architectural design, 3D rendering, platform development), and Monterrey (tech innovation hub creating platform integrations). The company was actively pursuing Series B funding to scale further, but faced significant operational challenges that threatened its ability to execute on its growth strategy. The CEO was drowning in day-to-day operational decisions, managing his own calendar, and spending roughly 80% of his time putting out fires rather than focusing on the strategic priorities that would drive the company forward. There were no standardized communication systems, no executive brand presence despite active fundraising efforts, and no infrastructure to support the kind of executive leadership the company needed at this critical growth stage.

THE JOURNEY

Challenges

When I joined as Chief of Staff, the operational chaos was immediately apparent. The CEO managed every aspect of his schedule personally, fielded requests from across all three offices without any filtering system, and was constantly pulled into operational decisions that should have been handled at lower levels. This meant he had minimal time for the activities that actually mattered at this stage: securing Series B funding, building strategic partnerships, and positioning the company for scale. The organization suffered from constant redundant information requests because there was no clear communication structure or escalation path. Department leads would come to executives with the same questions repeatedly because no one had documented answers or established protocols. The marketing team, while talented, lacked the strategic communication skills and confidence needed to interface with high-level investors and industry figures. Cross-functional coordination across the three offices was informal at best, with different teams operating in silos and duplicating efforts. Additionally, despite the CEO's expertise and the company's momentum, there was zero executive brand presence. In an industry where thought leadership and visibility directly impact fundraising success, the CEO was essentially invisible to the investor community he was trying to court.

Solution

My approach centered on building comprehensive executive operations infrastructure while simultaneously establishing the CEO's industry presence. I designed and implemented company-wide communication policies that created clear escalation paths and information flow, ensuring that the right information reached the right people at the right time without overwhelming leadership. I became the CEO's strategic proxy, serving as the gateway between him and the organization. Rather than allowing every issue to land on his desk, I filtered operational problems, coordinated solutions across departments, and only escalated decisions that truly required CEO-level strategic input. For C-suite meetings, I restructured the entire format with formal agendas distributed in advance, strict time limits to maintain focus, and documented minutes that captured clear action items with specific ownership and deadlines. This transformed meetings from rambling discussions into efficient decision-making forums. On the brand-building side, I developed a comprehensive content strategy that positioned the CEO as an industry thought leader. I managed a creative team including a videographer, editor, graphic designer, and content scheduler to produce consistent, high-quality content for LinkedIn and Instagram. I wrote scripts and developed trigger questions for video content that showcased his expertise in ways that would resonate with target investors. We incorporated meaningful visual elements, including the bamboo motif that represented his personal philosophy around growth and persistence. Beyond content creation, I coordinated all cross-functional strategic initiatives, serving as the liaison across the San Diego, Tijuana, and Monterrey offices to ensure alignment and eliminate redundant work.

Implementation

The transformation began with immediate operational changes. I took over management of the CEO's complex calendar and strategic initiatives, implementing systems that reduced his prep time by 25% while simultaneously increasing meeting effectiveness by 40%. The communication policies I established eliminated 30% of redundant information requests within the first quarter, freeing up bandwidth across the leadership team. For the brand-building initiative, we moved quickly and strategically. Within two weeks of launching his social media presence, the CEO's follower count grew from zero to 500, with content consistently achieving engagement rates between 8% and 12%, well above industry benchmarks for executive content. More importantly, the visibility created tangible opportunities. He connected with tier-1 investors including L'ATTITUDE Ventures, which led to serious investment discussions. He was invited to Chip Conley's exclusive retreat in Cabo, initiated active partnership discussions with Blake Mycoskie of TOMS, and gained access to high-level events hosted by Irwin Jacobs where he met government officials and other influential figures. The strategic positioning work culminated in an invitation to Reid Hoffman's exclusive Masters of Scale event, a significant validation of his emerging thought leadership. On the operations side, I orchestrated high-stakes events including investor keynotes attended by government officials, quarterly all-hands meetings across all three offices, and team-building activities that achieved 95% satisfaction rates. When I transitioned from building the Customer Success department to the Chief of Staff role, I trained three people to sustain the systems I had created, ensuring continuity. That department continued operating successfully using the frameworks I established until the company's closure in 2024.

THE RESULTS

The operational infrastructure established during this engagement yielded transformative results. By redirecting the CEO's focus from operational firefighting to strategic priorities, we fundamentally changed how the company functioned at the executive level. The structured meeting protocols, clear communication systems, and strategic filtering meant that leadership could focus on activities that actually moved the business forward rather than constantly responding to internal chaos. The CEO's time allocation shifted dramatically, with the majority of his hours now devoted to fundraising conversations, strategic partnerships, and growth planning rather than administrative tasks and operational problem-solving. The brand-building work delivered visibility and access that directly supported fundraising efforts. Consistent 8-12% engagement rates on social content created an active, engaged audience of potential investors and industry leaders. The connections forged through this visibility opened doors that would have been difficult to access otherwise. Securing an invitation to Masters of Scale represented a significant milestone in establishing industry credibility. The operational foundation built during this period positioned the company to manage its distributed workforce effectively, with clear systems for coordination across 120+ employees in three offices spanning two countries. The 95% satisfaction rates on company-wide events demonstrated that despite the operational challenges, we could create experiences that strengthened culture and investor relations when it mattered most.

This project reinforced my belief that standardizing processes, communications, and workflows is essential for operational excellence and consistent results, particularly when coordinating specialized remote teams. The experience of building operational systems for a neurodivergent-focused business provided valuable insights into creating inclusive frameworks that accommodate diverse thinking and learning styles. I discovered the importance of balancing structure with flexibility when developing systems that must serve both internal team needs and external customer experiences. Creating clear, visual documentation proved particularly effective for aligning distributed teams across different disciplines and time zones. This engagement demonstrated how thoughtful operational design can transform an expert's knowledge into a scalable business model, even with limited founder bandwidth. The satisfaction of helping bring financial education to an underserved neurodivergent audience made this project particularly meaningful from both an operational and social impact perspective.

Since implementing Anna's strategies, my brand has become more aligned with my goals, and my online presence has opened up new opportunities. I've been invited to events in the Bay Area, Los Angeles, San Diego, and Tijuana, and even had the chance to be a speaker at some of them.

Anna's ability to empathize and convey emotion within written communications is a rare talent. She's confident, knowledgeable, and has a knack for getting things done. I would highly recommend her to anyone looking to enhance their digital communications."

Mission: Transform Founder into Industry Leader