In this episode, Aaron Woods, Director of Strategic Post Sales with experience at LaunchDarkly, Catalyst Software, Datadog, and Fidelity, shares his journey through customer success and leadership. Aaron reflects on his transition from sales into customer success, the challenges of building post-sales teams, and how he cultivates a culture of mentorship and growth.

Aaron takes us behind the scenes of managing complex customer relationships, setting ambitious goals for teams, and the evolving role of customer success in today’s SaaS landscape. He emphasizes the importance of treating customers as people, investing in relationships, and leveraging tools like AI to streamline operations and improve customer outcomes.

Whether you’re a customer success leader, a startup professional, or someone navigating their career in SaaS, Aaron’s insights are packed with practical advice, inspiring strategies, and real-world lessons.

Key Topics Covered:

0:00 – Welcome & Introduction
Scott introduces Aaron Woods and his extensive experience leading post-sales teams at top SaaS companies.

2:30 – From Sales to Customer Success
Aaron shares how his time at Fidelity shaped his approach to delivering exceptional customer experiences.

5:00 – Breaking Assumptions About Customer Success
Aaron reflects on common misconceptions about customer success roles and why they’re often the most challenging jobs in business.

8:45 – Building Strong Customer Relationships
How understanding that “it’s just a person on the other end of the line” changes the game for customer success.

12:00 – Setting Audacious Goals for Teams
Aaron’s approach to team leadership: setting goals that inspire excellence and differentiate your team in the marketplace.

15:00 – Balancing Goals and KPIs
Why building relationships and understanding customer benchmarks can make your team stand out.

18:00 – Mentorship and Career Development
Aaron discusses his work with Catalyst Coaching Corner and his passion for helping people unpack their career goals.

21:00 – Managing Remote Teams Effectively
Insights on hiring, building culture, and curating team relationships in a remote-first world.

25:00 – The Role of AI in Customer Success
Aaron explores how AI can streamline workflows, surface insights, and allow CSMs to focus on what truly matters: building relationships.

30:00 – Pressure Is a Privilege
How Aaron embraces challenges as opportunities to grow and develop leadership skills.

35:00 – The Future of Customer Success
Aaron’s thoughts on the specialization of customer success roles and the importance of demonstrating business impact.

38:00 – Advice for Early Career Professionals
Aaron’s advice for young professionals: be patient, focus on learning, and trust the process.

Key Takeaways:

• Customer success isn’t generic: Tailor your approach based on your product, customer maturity, and company goals.
• Relationships matter most: Treating customers as people—not transactions—builds long-term trust and success.
• Pressure leads to growth: Challenging roles offer unparalleled opportunities to gain experience quickly.
• Embrace mentorship: Leadership isn’t the only path—find what works for you and seek guidance from those ahead of you.

Notable Quote:

“I set audacious goals for my team: I want us to be the customer success team that other companies say, ‘We need to hire them.” – Aaron Woods