Navigating Board Roles and CEO Paths with Cube COO Jen Grant

Summary

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.

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Key Takeaways and Calls to Action

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.

Networking: The Keystone of Career Progression

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.

Actionable Takeaways

• Leverage LinkedIn: Regularly engage with industry leaders, participate in discussions, and share valuable content.
• Mentorship: Find mentors who can provide guidance and advocate for you when opportunities arise.
• Networking Groups: Join professional organizations and groups related to your field to meet like-minded individuals.

The Importance of Giving Back

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.

Actionable Takeaways

• Volunteer for Speaking Engagements: Share your knowledge at workshops, webinars, and panels.
• Mentor Up-and-Coming Professionals: Offer to guide newer professionals in their career journeys.
• Publish Content: Write articles and blogs or create videos to educate others in the industry.

Navigating Financial Prudence and Growth

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.

Actionable Takeaways

• Establish Performance Metrics: Before increasing spend, ensure you have clear metrics to gauge ROI.
• Prepare Financial Scenarios: Present detailed financial calculations to your board to support growth plans.
• Quarterly Reviews: Conduct regular financial health checks to adjust your strategies based on market signals.

Vet Your Investors Wisely

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.

Actionable Takeaways

• Interview VCs: Treat your initial meetings with VCs as interviews. Understand their vision and approach.
• Seek CEO Insights: Speak to other founders who have worked with the VCs you are considering.
• Evaluate Fit: Assess if their feedback and approach align with your business goals.

Growing and Upselling Current Customers

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.

Actionable Takeaways

• Customer Segmentation: Identify which customers have the potential to be upsold or require additional services.
• Loyalty Programs: Implement loyalty programs to incentivize current customers to increase their spend.
• Customer Success: Focus on customer success initiatives to ensure sustained satisfaction and upselling opportunities.

Testing Enterprise Markets Carefully

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.

Actionable Takeaways

• Pilot Programs: Start with pilot programs to test your product in the enterprise space.
• Hire Wisely: Consider hiring experienced enterprise sales reps and invest in proper training and coaching.
• Patience: Allow sufficient time for learning and adapting to the enterprise sales cycle.

Constructive Board Interactions

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.

Actionable Takeaways

• Build Trust: Foster transparent and honest relationships with your board members.
• Seek Diverse Opinions: Engage board members who bring a variety of perspectives and experiences.
• Regular Updates: Provide regular and comprehensive updates to your board to keep them informed and aligned.

Creating an Advisory Board

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.

Actionable Takeaways

• Identify Gaps: Determine the areas where your team lacks expertise and seek advisors accordingly.
• Trust and Experience: Select advisors who have experience relevant to your current business stage and trustworthiness.
• Define Roles: Clearly define each advisor’s role and expectations to ensure they contribute effectively.

Role-Playing Scenarios for Effective Board Communication

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.

Actionable Takeaways

• Scenario Planning: Regularly conduct role-playing exercises for various strategic decisions.
• Feedback Sessions: Encourage board members to provide constructive feedback during these sessions.
• Consensus Building: Aim to build consensus and support for major decisions through collaborative discussions.

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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.

About "The Science of Scaling" Podcast

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.