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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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Tracy Young sits down with Anastasiia Binns, Head of Revenue Operations at Semble, a patient management system for private healthcare providers in the UK. They discuss Anastasiia’s unique journey from a background in social anthropology to becoming a leader in Revenue Operations (RevOps). The conversation covers critical topics like balancing operational efficiency with empathy, transitioning roles within a company, and building RevOps functions from scratch.
Key Highlights:
Anastasiia’s Unique Path:
Anastasiia shares how her degree in social anthropology shaped her open-minded approach in RevOps, especially regarding cultural relativism and understanding how different departments or companies operate within their own context.
RevOps Foundations:
Anastasiia outlines her process for establishing RevOps functions, focusing on three key pillars:
Operational Efficiency: Ensuring processes, tools, and KPIs are well-organized.Disaster Readiness: Preparing for worst-case scenarios and ensuring continuity.Strategic Growth: Making incremental improvements after laying the groundwork.Challenges in RevOps:
Anastasiia discusses one of her toughest projects: managing 12 different CRM systems within a large organization, which she streamlined by implementing a simple, yet effective SharePoint system.
Tech Bloat and Lean RevOps:
The discussion dives into tech bloat, how startups can quickly accumulate unnecessary tools, and Anastasiia’s advice to approach tech purchasing as if it’s coming out of your own wallet. She also talks about keeping RevOps simple and lean by focusing on MVP solutions before adding complexity.
Advice for Aspiring Leaders:
Anastasiia emphasizes the importance of standing up for what you believe is right in the workplace, even if it means challenging the status quo. She also offers practical advice for handling crises, such as staying calm under pressure and leading by example.
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In this episode of Path to Growth, Tracy Young interviews Tracy Lawrence, the former co-founder and CEO of Chewse, who now works as an executive coach. Lawrence shares her entrepreneurial journey, which began with her love for food and her hometown of LA, and the personal growth that came with scaling a venture-backed business. She emphasizes the importance of inner work, vulnerability, and authenticity in leadership, revealing how personal experiences shaped her leadership style and the culture at Chewse. Now, as a coach, she helps leaders focus on self-awareness and healing to become more effective in both their personal and professional lives.
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Tracy interviews Brett Keirstead, Chief Sales Officer at Chief Outsiders. discussing Brett’s personal background, sales leadership strategies, and the evolving nature of sales, especially post-pandemic. Brett shares insights on the value of fractional sales leadership, the importance of setting realistic sales quotas, and the need for cultural fit in hiring. He also highlights the relevance of business acumen in sales roles and discusses his book, “We Are All Sales People,” which connects sales skills with life skills, particularly in enhancing communication and relationships.
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In the latest episode of “Path to Growth,” Tracy interviews Robin Daniels, the Chief Business and Product Officer at Zensai. Robin shares his personal journey of growth and resilience, deeply influenced by his father’s struggles and untimely passing. He recounts how this experience led him and his brother to adopt a “yes to life” philosophy, driving them to embrace new experiences and live life with passion and courage. Robin also delves into his professional journey, highlighting his role at Zensai, a company dedicated to empowering employees through continuous learning, performance management, and engagement. He discusses the critical role of AI in personalizing learning experiences and optimizing organizational performance.
Robin and Tracy also explore the evolving landscape of HR technology and marketing strategies. Robin emphasizes the importance of bold storytelling and community-based marketing to build strong, loyal customer bases. He contrasts the conservative go-to-market approaches of European startups with the bold, aggressive strategies often seen in Silicon Valley, advocating for a blend of both. Additionally, Robin offers valuable advice for those early in their careers, underscoring the significance of showing up with passion and taking initiative.
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This week tracy sat down with Holly Liu, co-founder of Kabam. Holly shared insights into her background, discussing her upbringing in Palmdale, California, and her journey through identity as one of the few Asian kids in her town. She recounted her path to founding Kabam, which began as a corporate social networking company before pivoting to mobile gaming. Holly detailed Kabam’s significant pivots and eventual success in the mobile gaming industry, particularly their hit game “Marvel Contest of Champions.”
Tracy and Holly also discussed effective go-to-market strategies, highlighting the importance of analytics and consumer behavior metrics in B2C markets. Holly emphasized the value of building a solid team, possessing humility, and maintaining determination, while also discussing the different stages of company growth and the types of people suited for each stage.
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Tracy sits down with Jin Chang, CEO and co-founder of Fieldguide. They discuss Jin’s background, including his upbringing as an immigrant from South Korea and how his parents’ struggles influenced his values and work ethic. Jin shares his journey from working at Ernst & Young and founding a cryptocurrency company to co-founding FieldGuide in 2020.
Fieldguide, an AI platform for CPA firms, automates tedious tasks in accounting and auditing, helping alleviate burnout and improve efficiency. Jin explains the significant talent shortage in the CPA industry and how Fieldguide addresses this by automating manual processes, such as auditing financial statements.
They also discuss Fieldguide’s recent Series B funding, which will be used to enhance AI capabilities, expand into new practice areas, and increase marketing efforts. Jin emphasizes the importance of understanding customer workflows and building products that genuinely meet their needs, a lesson he learned from his previous experience at Atrium.
The conversation highlights the challenges and opportunities in the accounting industry and the role of AI in transforming traditional workflows.
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Tracy sits down with Taylor Young, Chief Strategy Officer at CoLab Software. They discuss Taylor's experience at CoLab, a company that develops collaboration software for the manufacturing industry, helping teams work on 3D designs and other complex mechanical projects.
Taylor shares insights into the origins and impact of CoLab, highlighting how it fills a critical gap in collaboration tools for the manufacturing sector. The discussion also covers Taylor's childhood in St. John's, Newfoundland and Labrador, where she grew up in an entrepreneurial family, which influenced her career path and values.
Significant parts of the conversation delve into how CoLab is adapting to advancements in AI and the importance of review processes in AI-assisted environments. Taylor emphasizes the evolution of CoLab’s team culture, the strategic hiring practices, and the company's hybrid remote work model, which combines the benefits of remote work with occasional in-person interactions.
Overall, the episode paints a detailed picture of Taylor's journey with CoLab, the company's innovative approach to collaboration in manufacturing, and the broader implications of their work on the industry and workplace culture.
Key TakeawaysInnovative Collaboration Tools for Manufacturing: Taylor discusses how CoLab developed much-needed collaboration software for the manufacturing industry, enabling teams to efficiently work together on complex 3D designs and mechanical projects. This innovation addresses a longstanding gap in the industry, providing tools that were absent but necessary for modern manufacturing processes.Adaptation to AI and Strategic Growth: Taylor elaborates on how CoLab is adapting to rapid advancements in artificial intelligence, using AI to enhance their software capabilities. She emphasizes the strategic importance of review processes in AI-assisted environments and discusses the company's growth and scaling strategies, highlighting the role of AI in shaping the future of work.Remote Work and Company Culture: The conversation also covers CoLab’s remote-first approach and the hybrid model they use, blending remote work with biannual in-person team weeks in Newfoundland. Taylor reflects on the significance of company culture, noting how CoLab has adapted its culture and values as the company has grown, stressing the importance of maintaining a strong alignment between company values and its leadership. -
Tracy Young, co-founder and CEO of TigerEye, talks with Allison Whalen, CEO of Parentally. The discussion explores the intricate balance between personal growth, family life, and career development, offering a wealth of insights for individuals and companies navigating the challenges of parenthood in the professional world.
From Minnesota to Parentally: Allison Whalen's Journey
Allison Whalen's narrative begins with her childhood in Minnesota, a place she once vowed to leave but returned to with her own family for its community and educational opportunities. This reflection on her roots sets the stage for discussing the impact of upbringing on personal and professional growth. Allison's stories about her parents, particularly her mother's part-time career as a speech pathologist, highlight the subtle yet profound influence of parental role models on our perceptions of work-life balance.The Genesis of Parentally
They transition to discussing the inception of Parentally reveals Allison's deep commitment to addressing the disconnect between parental leave policies and their practical implementation. She shares her own tumultuous return-to-work experience post-parenthood, which led her to question and eventually redefine how companies approach parental leave. By focusing on meaningful work, intentional planning, and supportive re-onboarding, Parentally aims to transform parental leave from a potential career setback to a strategic advantage for companies and employees alike.Leadership, Culture, and Change
Beyond the specifics of parental leave, the conversation delves into broader themes of leadership, corporate culture, and societal change. Allison underscores the importance of empathy, mentorship, and continuous improvement within organizational leadership. She advocates for a culture that values quick iteration alongside sophistication in work, a balance that nurtures innovation and growth.Marketing strategies and the significance of LinkedIn as a tool for engagement and thought leadership are discussed, showcasing how Parentally leverages digital platforms to foster connections and support within the HR community.
A Call for Inclusivity and Support
One of the most poignant aspects of the interview is Allison's call for a more inclusive and supportive approach to parenthood in the workplace. She emphasizes the need for societal and policy changes to ensure that parental leave is not just a privilege but a right accessible to all. Through her insights, Allison invites companies, leaders, and individuals to reflect on how they can contribute to a culture that supports working parents, enabling them to thrive in both their personal and professional lives. -
Meghan Gill, SVP of SalesOps and Sales Development at MongoDB, joins Tracy Young to discuss her early influences and the adaptation needed to thrive across the journey from startup to IPO.
Meghan shares her background, including growing up in Flushing, Queens, with a teacher mother and an entrepreneur father, which inspired her to join startups, including MongoDB as one of its early employees. Her parents initially questioned her decision to join a small company but eventually supported her, especially when MongoDB went public.
Meghan discusses her role at MongoDB, her transition from marketing to sales operations, and the importance of adaptability and learning in her career. She highlights MongoDB's evolution, including its IPO and shift towards a cloud and consumption-based business model. Meghan emphasizes the value of humility, continuous learning, and resilience in facing career challenges.
The conversation also touches on effective collaboration between marketing and sales, the significance of recruiting and developing the right talent, and the challenges of balancing a demanding career with motherhood. Meghan and Tracy share insights on building a supportive work environment, especially for working parents, and the potential impact of remote and hybrid work models.
Meghan reflects on a personal setback in sixth grade that shifted her mindset towards growth and resilience, underscoring the importance of facing adversity. She also discusses MongoDB's future, especially in enabling AI applications, and the interview concludes with a mutual appreciation for women's representation in leadership and entrepreneurship.
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In this interview, Alina Vandenberghe, co-founder and co-CEO of Chili Piper, shares her journey from Romania to the US, her upbringing during communism, and the lessons in perseverance and collaboration she learned. She discusses the challenges and rewards of founding Chili Piper with her husband, emphasizing the importance of mutual respect and the ability to handle conflicts in such partnerships. Alina highlights her passion for innovation and culture, and the complexities of roles like marketing in a dynamic environment. She also shares her approach to handling competition, emphasizing collaboration over confrontation, and provides insights on personal growth, stress management, and maintaining company culture during expansion.
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Tracy Young speaks with Shirin Oshidari, an experienced sales leader with a background in companies like OpenSpace, Streetlight Data, and Autodesk. Shirin shares her unique life journey, starting with her upbringing in Tehran, Iran, during the revolution, which led her to move to the U.S. as a teenager. She talks about growing up mostly alone, as her siblings were abroad and she was much younger than them, which cultivated her independence and resilience.
Shirin attributes her character and approach to life significantly to her father, describing him as a no-nonsense, positive person. She discusses how the challenges of losing everything at a young age and being refugees shaped her outlook on life, teaching her to make the best out of difficult situations and to focus on education and moving forward.
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Toby Corey chats with Tracy Young about his journey, mixing personal stories and business insights. He dives into how his parents' values shaped him, especially his dad's creativity and his mom's compassion. Toby reflects on his career, from software to leading startups, emphasizing how he loves learning new stuff and tackling big challenges. He talks about the ups and downs of startup life, the importance of a tight-knit team culture, and making smart, forward-thinking decisions. Big on sustainability, Toby's really into making a positive impact for future generations, and he's all about personal growth, always pushing himself to learn and do better.
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Tracy Young, co-founder and CEO of TigerEye, interviews Joanna Riley, CEO at Censia, about founder-led sales and leadership. Joanna Riley shares her journey from being inspired by her parents and growing up in San Francisco, her experiences working for the FBI and realizing her entrepreneurial aspirations. She discusses her various ventures, including building companies in China and her current role at Censia, an AI platform for talent. Jo emphasizes the importance of diverse hiring and how Censia’s platform addresses biases in recruitment.
