Navigating Board Roles and CEO Paths with Cube COO Jen Grant

As a new CEO, you can suddenly find yourself sitting on a board with venture capitalists and other members offering advice. How do you prepare yourself for this situation? Strategic networking, practicing financial prudence, focusing on constructive communication, and surrounding yourself with trusted advisors can help you put your best foot forward.
In this episode, Mark had the opportunity to talk with Jen Grant, COO at Cube, a startup that helps businesses leverage their precious data by connecting all data sources with data apps and analytics tools. Their conversation sheds light on the practical and strategic steps involved in becoming a CEO or board member in the marketing industry. The discussion delves into actionable advice on networking, financial prudence, customer growth strategies, and the nuances of board interactions.
Jen Grant is an experienced go-to-market executive who, before joining Cube last year, served as CEO of Appify where she is still a board member. As CMO, she led Looker to an incredible $2.6 billion acquisition deal with Google, her old employer. Jen sits on the boards of Kyndi, Dialpad, and Pecan AI, sharing her unique insights and tech industry marketing experience.
These are the key takeaways from Jen’s interview.
One of Jen’s emphatic points was the undeniable power of networking. She shared her personal experiences to illustrate how building a strong network is imperative for securing board seats and advancing one's career. Networking isn’t merely about attending industry events; it's about nurturing genuine relationships over time.
Mark and Jen both highlighted the importance of giving back to the marketing ecosystem. This is not just altruistic but also enhances your reputation and solidifies your network.
Jen emphasized the necessity of a cost-conscious approach to company operations, particularly before scaling up spending. This involves establishing sales cycle performance and being judicious about financial commitments. Mark reinforced the importance of thorough bottom-up math calculations to justify growth strategies to investors.
Finding and vetting the right venture capitalists (VCs) is crucial. Jen advised observing how potential VCs comprehend your business model and conducting discreet interviews during the due diligence process.
Jen discussed the importance of upselling and growing current customers, particularly at the SMB level, to increase the Average Customer Value (ACV). This is often a more sustainable growth strategy compared to constantly chasing new customers.
While expanding into enterprise markets can significantly boost revenue, Jen insists on a meticulous approach. This involves a learning period of six to twelve months to build pipelines, understand procurement processes, and ensure product readiness.
Both Mark and Jen touched on the intricacies of board interactions, emphasizing the need for constructive communication. Building a supportive relationship with independent board members can help explain decisions and provide valuable guidance rather than creating friction.
Jen and Mark agreed on the significance of building an advisory board consisting of individuals with expertise in areas where the founder may lack knowledge. This can provide diverse perspectives and boost decision-making.
Role-playing different scenarios, such as changing the company’s target customer size, can prepare CEOs for effective communication and decision-making during board meetings. This helps in anticipating potential concerns and crafting well-thought-out responses.
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Note: The insights shared in this podcast were initially distilled through advanced AI summarization technologies, with subsequent refinements made by the writer and our editorial team to ensure clarity and engagement.
Every week during a season, host Mark Roberge—co-founder and Managing Director at Stage 2 Capital and a senior lecturer at the Harvard Business School—interviews some of the tech industries most successful and renown leaders and managers in the areas of sales growth and Go-to-Market strategy. This is a HubSpot for Startups original podcast, and part of HubSpot's Podcast network. It's available on Apple, Spotify, and anywhere you get podcasts.
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