Redpoint Office Hours with Zendesk CTO, Adrian McDermott and Redpoint Managing Director, Jason Warner

Redpoint Ventures
Redpoint Ventures
Published in
2 min readOct 1, 2021

50 to 5,000 People: Lessons Learned from 10+ Years Scaling Zendesk’s Engineering and Product Orgs

The number one question from virtually every company we invest in starts with hiring, and most commonly, hiring engineers. It’s a war for talent, though hiring is only the tip of the iceberg. Once they’re in-seat, how do we ramp them quickly? How do we align everyone as the company goes through massive change every quarter? How do we keep everyone focused and committed through every stage of the journey from start-up to public company and beyond? This month, we get to speak with someone who has seen it all at one of the leading SaaS companies that surpassed $1 billion in revenue earlier this year.

To kick off our “Month of Scale,” Redpoint Office Hours will welcome Zendesk CTO, Adrian McDermott, on Wednesday, October 13th, at 12:00 PM PT.

When Adrian started at Zendesk as VP of Engineering in 2010, the company had 50 employees and he started managing a team of 10. Over the past 10+ years, he has been incredibly influential in the way the company has successfully scaled. He grew his team to nearly 1,500 employees as the company scaled to 5,000 and he recently stepped into the position of Chief Technology Officer (CTO) after overseeing Zendesk’s entire engineering and product orgs. Needless to say, he has experienced a lot and learned many valuable lessons along the way.

Redpoint’s newest Early-Growth partner and former GitHub CTO, Jason Warner, will join Adrian to discuss the lessons they both have learned, including:

  • The right mindset: Being comfortable making disruptive changes regularly
  • Planning for the long term
  • The balance between sales-led vs product-led growth
  • How to build trust from Day 1 with your employees, customers and partners
  • Hiring tips for engineering and product teams as you scale

Interested in attending? Please register here. This event will be interactive. We will collect questions from participants during registration and try to cover them throughout the discussion. Attendees will also have the opportunity to participate in a live Q&A at the end of the session.

We look forward to welcoming Adrian and engaging in a thoughtful conversation! Can’t make the event? Find out more about benefits available to startups through our partnership with Zendesk for Startups here.

…and stay tuned for our next Office Hours, continuing our “Month of Scale,” with Stripe’s Chief Corporate Advisor and former COO, Claire Hughes Johnson. If you would like to be notified of all future Office Hours, please subscribe here.

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Redpoint Ventures
Redpoint Ventures

Redpoint partners with visionary founders to create new markets or redefine existing ones at the seed, early and growth stages.