It was 2008 when Jeb Dasteel was named Chief Customer Officer at Oracle, after leadership roles in Sales, Consulting, and “Customer Programs” at the company for 10 years. “I didn’t know a single other CCO at the time,” he recalls. “Everything we did, we had to make up as we went. Trial and error. We did some smart things and some dumb things, but by and large, we were successful and learned a lot along the way.” 


Jeb left Oracle in 2019 and now advises CCOs on how to refine their customer strategy. He notes that especially in the past two years, he’s impressed with the quality of modern CCOs — but CS leaders still have gaps to fill to become an established member of every executive team. 


Nuffsaid co-founder, Nick Paranomos and I interviewed Jeb on how Customer Success leaders can become more influential executives. Here’s an excerpt from our conversation. (You can also read the full interview here.)



Chris: Here’s a controversial statement that I’d love for you to react to: The CCO will never be a strategic member of the executive team unless they own a number that matters for the business.  


Jeb: I agree with that in a lot of ways. I've talked to so many people who would argue that the CCO has to report to the CEO and they cannot have a quota responsibility. I tend to agree on the CCO needing to report to the CEO, but I don't think it's absolutely essential. If you are a great leader by influence you can be under the CMO, the CRO, or the head of Service delivery and still be highly effective depending on the culture of the organization. The worst thing you can do is create the perception that the CCO’s job is somehow apart from the day-to-day objectives of the rest of the company.


I disagree with the idea that CSMs cannot be responsible for renewal revenue. For many organizations, it works really well. I don't buy into the idea that CCOs should be disconnected from the business in not having some of those strains and pressures. There is a middle ground. 


When I was the CCO at Oracle, I had the latitude to fail fast—to take risks that I knew were iffy, but to keep it under the radar and completely screw up and try it again. I would not have been able to do that had I had quarterly quota attainments. However, I did feel tremendous responsibility to help Sales sell. I was deeply involved with the Sales teams every single day.


Chris: So in a world where you're a head of CS, and your Sales peer is a dictator, your Product peers or Engineering peers are egotistical maniacs, your Marketing person’s head is always in the clouds, and somehow you're supposed to drive the resources of the organization, how does one level up their influence on the executive team with those peers?

Jeb: Here’s what I did. I managed by influence rather than trying to have line authority over everyone. Of course I had my own team, but the whole purpose of the team was to influence the rest of the organization, drive change, experiment and try things out and then deploy them where they best fit. But the purpose was never to own—and definitely never to be in competition with the rest of the organization


I found that the single best thing to do as a CCO was to build street cred—particularly with Sales and Engineering at Oracle. And building street cred meant getting engaged with deals. I would not have been successful at Oracle doing anything as a CCO had I not actively engaged with the Sales organization to close deals. 


There shouldn’t be a CS leader anywhere in existence that doesn't spend a significant part of their day being an executive sponsor for important accounts and being very actively involved in deals and issue resolution. We have a responsibility to help drive revenue for the company.


If your job really is to run focus groups and do journey mapping, I just don't think that you'll be able to make a real impact on the business and you won't be taken seriously as a real strategic leader.


Chris: That might be the best advice I've heard in a month, which is if you want to drive influence at the executive level, help close the deals.

Jeb: Exactly. Get off your ass and get on an airplane. And I'll tell you what, this was by far the most rewarding part of my job. Even after essentially 100% of Oracle's products became available as a cloud service and we had CHROs, CMOs, and CFOs as customers, the principal person I worked with for 21 years when I was at Oracle was the customer’s CIO. If I knew 100 CIOs around the world, I always felt a responsibility to maintain those relationships, advocate for those customers, and help drive business because of those relationships.


So I made it my job to be, and I know this term dates me, the human Rolodex for the top 100 CIOs in the world. Because my job was to know them and have a relationship with them so I could call them and have a conversation. There were so many times where the rep or the strategic account manager requested that I call the CIO because they didn’t have that relationship. I would also become an executive sponsor for many of those customers. 


Now, I couldn’t be an executive sponsor for every account, but I could get on airplanes four or five days a week, cover a lot of area, and be a valuable resource by putting myself in the position of doing a warm handoff and setting the relationship up for success. 


I believe every CCO should operate that way. There's literally no substitute for engaging with customers.


Chris: How can a CS leader know if they’re too tactical and not strategic enough? Are there any common pitfalls that would reveal a leader is being too tactical?

Jeb: There are two dimensions here. There's tactical versus strategic and process versus results. I think you're too tactical if you're more process-oriented than you are results-oriented. And the symptom that reveals being too process-oriented is that you're not focused on the results for your own organization by focusing on your customer's results. 


To me, there are two litmus tests to understand if you are an effective CS leader:

1) Whether you are actively engaged with the Sales organization to drive business.

2) Whether all the customer feedback being collected and analyzed is being actioned upon.


If it's a “no” to either of those two, if for example feedback is just fodder for interesting conversation, it’s a complete waste of time. And actually, it’s worse than a waste of time—it's counterproductive. You will be labeled as a person who does some “interesting stuff,” but never delivers any real outcomes or results.


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