Between Two COO's with Michael Koenig

Productboard COO Greg Strickland on how to balance growth and innovation, collecting mentors and personal development, managing through change, SMB to enterprise shift, and the competitive advantage of startups

Jan 24, 2024

COO of Productboard, Greg Strickland, discusses embracing new opportunities, mentorship in early-stage companies, continuous learning, innovation with AI, scaling up to enterprise market, fostering empathy and collaboration, and personal anecdotes of executives fighting over candidates.

52:01

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Greg Strickland

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Quick takeaways

Saying yes to new opportunities, even outside of comfort zones, is crucial for personal growth in the startup environment.

Gaining valuable experience across different departments and disciplines is more important than focusing solely on career advancement.

Empathy and collaboration across departments are essential for effective decision-making and the success of a company.

Deep dives

Embracing New Opportunities

Greg Strickland, COO of Product Board, emphasizes the importance of saying yes to new opportunities, even if they may seem out of your comfort zone or beyond your capabilities. He believes that prioritizing the needs of the business and having the passion and drive to push forward are crucial factors in determining what to say yes to. By taking on new challenges, individuals can learn and grow at an accelerated rate, particularly in the startup environment where the learning curve is steep.

Introduction

2min

The Power of Saying Yes

4min

The Value of Seeking out Mentors and Learning from Experienced Individuals

16min

Leveraging Customer Data, Beta Programs, and Operational Efficiency

5min

Adoption of Salesforce and LinearDB: Increasing Visibility and Data-Driven Decision-Making

2min

Prioritization, Vision, and Alignment

16min

Developing Empathy and Understanding Across Roles

3min

Learning Product and Appreciating Support, Executive Fighting Over a Candidate, Navigating a Difficult Decision

4min

Join us as Greg Strickland, COO of Productboard, and I explore the power of embracing new opportunities and the crucial balance between business outcomes and personal advancement. Greg shares his journey of growth through accepting challenges that push boundaries, and we reflect on the times when a strategic 'no' can pave the way for others' development and align with company goals. Listen in for an insightful discussion on the mentorship gap in early-stage companies and the trial-and-error learning that COOs like Greg navigate in the startup landscape.

As the startup ecosystem continues to evolve, we dissect the influence of continuous learning on company culture, inspired by industry pioneers. I open up about the enriching experience of partnering with product and engineering-driven founders and how passion plays a decisive role in a startup's trajectory. We consider how startups like Productboard are innovating in operations and product management with the use of AI, highlighting the agility required to manage rapid change and the ethical considerations of handling customer data.

In our conversation, we delve into the challenges of scaling up to the enterprise market and the importance of building a culture that can gracefully manage internal friction points. I share my approach to fostering empathy and collaboration across departments, revealing personal anecdotes and strategies for aligning diverse perspectives within a company. Tune in for a rich discussion full of practical insights, memorable moments, and tips for nurturing a successful startup environment. Follow Productboard on LinkedIn and check out their blog for more engaging content that can help steer your company towards growth and innovation.

(00:06) Saying Yes to New Opportunities

(08:14) Startups' Impact on Learning Culture

(17:25) AI for Operations and Product Management

(31:34) Navigating Enterprise Market Challenges and Feedback

(37:07) Friction and Empathy in Customer Relations

(45:25) Developing Empathy and Cross-Departmental Collaboration

Links

Greg Strickland on LinkedIn: https://www.linkedin.com/in/gregstrickland/

Episode Link: https://www.betweentwocoos.com/productboard-coo-greg-strickland

Matt Blumberg: https://startupceo.com/

The Hard Things About Hard Things by Ben Horowitz: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205

Amp It Up by Frank Slootman: https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115/