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

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/

Radical Candor by Kim Scott: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375

Michael Koenig on LinkedIn: https://www.linkedin.com/in/michael-koenig514/