Scaling the CEO with David Ulevitch, formerly CEO of OpenDNS (acquired by Cisco)

Since the startup (and founder) journey doesn’t go neatly linear from technical to product to sales, tightening one knob (whether engineering or marketing or pricing & packaging) creates slack in one of the other knobs, which demands turning to yet another knob. So how do you know what knob to focus on and when? How do you build the right team for the right play and at the right time?

It all depends on “What time is it”: where are you on the journey, and where do you want to go… In this episode of the a16z Podcast, general partner David Ulevitch (in conversation with Sonal Chokshi) shares hard-earned lessons on these top-of-mind questions for founders; as well as advice on other tricky topics, such as pricing and packaging, balancing between product visionary vs. product manager, how to manage your own time (and psychology!) as your company grows, and more. Much of this is based on his own up-and-down, inside-outside, big-small-big-small, long journey as CEO (and CTO) for the company he co-founded, OpenDNS.

The company was later acquired by Cisco after it pivoted from consumer to enterprise. Speaking of, what are the latest shifts and nuances in selling and buying enterprise products, beyond the phrase “consumerization of enterprise”? Or beyond the cliché of “design thinking” — how does one go beyond user experience and beyond things like fun gifs (which are pronounced, ahem, “jifs”) to focusing on the whole customer experience, and earning the right to be complicated?

My Notes:

  • Product experiences are evolving to Customer Lifecycle Experiences due to SaaS being a recurring revenue model.  Having to think about keeping your customers continually happy and satisfied rather than a traditional enterprise sale (which is a one timer up front) changes the role of the sales rep and also the role of the product manager.  The product role becomes even more important but the focus must stay on customer experience throughout the end to end customer lifecycle not just the on boarding/pre-sale.
  • Mid market focused products can’t support an enterprise sales team. Sales motion must align with customer lifecycle experience.  Things like developer evangelism, freemium products, product/market led sales motion – they are in fact a strategic alternative to having a field sales team.  However to get the elephants you need to have elephant hunters.
  • Pricing and packaging aim for Power Users – power user hurdle, Fewer packages is better, 2-3 max.  When developing packages, focus on the power users as the ones who would be willing to pay extra.  What are the features that power users would really need as opposed to buckets of features that are necessary.  Things like notifications, auth, audit, size limits, etc.
  • “Horses for courses” hire the right leader now for the right problem now – don’t think too far ahead about whether your Director-level hire can operate as a VP.  Success is contextual – what you need from your leaders in one stage of the company is not what you need in the next stage.
  • Product visionary vs product manager – these are different roles. CTO/ product CEO can still be a visionary but needs to offload the “ground war” of tactical decision making to a execution focused PM/VP Product.  In my own experience this is usually the stage that experienced PMs who aren’t domain experts are hired into.  The downside is that once you are hired into this role it is very challenging to grow into the next “visionary” role.
  • Trust – if you cannot trust one of your leaders to tell you accurate information about what is happening on the ground that is a huge problem that needs to be resolved ASAP.  (Typically, the leader needs to be replaced.)