Summary:
In this episode, Tracy speaks with Caroline McCloskey, a seasoned go-to-market leader, currently working with startups at OpenAI. Caroline shares her unique career journey, leadership lessons, and practical advice on scaling, hiring, and navigating the tech world’s complexities. Her experience across companies like AWS, LinkedIn, and WeWork provides invaluable lessons for startups and leaders at any stage.
Key Topics Covered:
1. Career Influences
Caroline reflects on how her parents’ careers influenced her path – her mother’s drive for learning and travel and her father’s career in law – shaping her broad skillset and interest in leadership.
2. Early Career and Growth in International Sales
Caroline shares her formative experience in LinkedIn’s leadership program and her evolution as a generalist, which helped her build versatile skills in various roles and industries. Her experience setting up sales teams in Mexico and Brazil at WeWork highlights the challenges and rewards of scaling in diverse cultural contexts.
3. Lessons in Hypergrowth and Hiring
Caroline discusses the rapid growth challenges at WeWork, particularly the complexities of building and scaling teams quickly. She talks about the struggles and lessons learned from the necessity to downsize after aggressive scaling and stresses the importance of paced, thoughtful hiring.
4. Building Culture and Team Alignment
With real examples, Caroline emphasizes the role of transparent communication and community in aligning sales, marketing, and product teams. She credits a former manager for showing her the value of regular, inclusive team meetings to create a sense of belonging and shared purpose.
5. Managing in a Crisis
Caroline recounts the turmoil during WeWork’s failed IPO, noting the importance of remaining calm as a leader. She describes how a leader’s demeanor mirrors through the team and the responsibility to shield them from unnecessary stress while maintaining morale.
6. Metrics and Go-To-Market Essentials
Caroline shares her favorite GTM metrics, though she emphasizes that KPIs should be tailored to each company’s specific needs. From her perspective, productivity metrics and pipeline structure are crucial for junior sales teams to build strong foundations in their roles.
7. Advice for Startups Implementing AI
Caroline advises startups implementing LLMs to consider a long-term view. She warns against AI as an afterthought and encourages businesses to anticipate future advancements in AI technology to ensure sustainable product value.
8. Networking and Career Development
For early-career professionals, Caroline recommends prioritizing relationships over resume submissions. Building genuine connections can be a key to unlocking future job opportunities and forming long-term mentorships and partnerships.
Final Thoughts:
Caroline’s journey offers inspiration and practical insights into building resilient teams and effective GTM strategies in a high-growth environment. Whether you’re a startup founder or a young professional, her emphasis on relationship-building and adaptability provides essential takeaways for anyone navigating a rapidly evolving tech landscape.
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