In this Propel23 panel session, Rod Cherkas, author of The Chief Customer Officer Playbook and CEO of HelloCCO, spoke to Mary Poppen, Chief Business and Customer Officer, Involve.ai, Bob Block, Group VP of Professional Services and Support, Clari, and Pat Phelan, CCO at GoCardless about planning the career path from Onboarding/Implementation to CCO.
Here’s an edited version of the conversation.
Rod: What were some of the most important skills that you developed along the career path to managers/directors and customer-facing executive roles?
Mary: Two things come to mind: Understanding the operational KPIs and the financial side of the business.
As a leader in this area on the professional services and onboarding side, you get a really good look at P&L and owning revenue. This is a huge skill set as you move into the executive level, and especially to a CCO level.
Bob: For people moving from PS to CCO roles, it’s important to know that the roles are closely related, but also very different. When I think about what made me a successful PS leader, it was about getting work done, utilization, project and practice profitability, etc. You have a super myopic focus on running that business and trying to keep the wolves away – the wolves being people who wanted you to do free work to save customers.
When you make that transition to being a CS leader, you're the person who's now supposed to be saving all the customers. It takes a different mindset – it's a broader view of thinking about the customer and the end-to-end company business.
If you're able to make that shift, and think about the right thing for the customer and the business, you start to be effective in a Chief Customer Officer’s role.
Rod: Is there a particular example of a project that you led as a services leader that helped you develop that skill?
Bob: That's a great question. I've watched different consultants go about this. Some have a myopic view – you take on a task, execute it, and do a great job. Others ask broader questions about why the task is being done, what else needs to be done, etc. I was always looking around, trying to see what else was going on, and asking: What else do I see? Can I highlight some of those issues? Can I bring other solutions to the table?
There are always inflection points in the business – when something in the business changes or, or somebody gets taken out. There's an opportunity there – when the company is looking for someone with a broader view.
Pat: One of the skills that I value enormously is the ability to be balanced. You have to be able to balance a lot of things and prioritize ruthlessly. You also need to combine that with curiosity and problem-solving.
I’ve always trusted people who understand what matters to the business, align their activities around what matters to the business, and who have the confidence to be able to flag them. As a leader, you need to pick these kinds of people and entrust them with significant tasks.
Rod: Can you provide some thoughts for our audience about some of the things that they can be listening out for – to find ways to get promoted or expand their scope?
Pat: That’s an interesting one. Timing and luck have a big role to play in a career. But once timings and situations come to fruition, it’s about being in a position where you are the person that gets the nod or the tap on the shoulder.
Think about circles of impact – the first circle is the one you directly impact, say your boss. The second is your boss's boss, and so on. You need to be able to impact those circles – maybe less directly, but just as intentionally. What I’ve always tried to do is to understand what the organization values at a high level, and heavily align with that.
If you're perceived as a value-add in every scenario, that's the narrative associated with you. People speak about other people based on the experiences of multiple other folks rather than their own. That's the narrative and it usually revolves around bringing value to the table regularly and repeatedly. That's the stuff that people remember. I make that when I show up, I don't just show up to catch up – I show up to deliver. I would encourage you to think about their interactions through that lens – on a daily and weekly basis because it makes a massive difference.
Rod: Absolutely. This concept of building cross-functional relationships and understanding the role that you play and how it contributes to company strategy is super important. Any tips for individual contributors who want to get involved in things important to the company?
Mary: Leaders are going to initiate programs and projects focused on the company goals. As an individual contributor, don't be afraid to raise your hand to help out with such projects. That's a great way to show initiative and get involved in what's important. People don't necessarily know what you're interested in. They may not tap you on the shoulder unless they know you want to get involved.
Bob: Especially in SaaS, companies are looking for people that have, what I like to call, ‘extra gears’.
When I look at promotions, I look for someone who is currently operating on one gear, but has extra gears. If I give them the next job, they need to be able to do their old job, plus, their new job without missing a beat. If I pick somebody whom I need to backfill for, that’s not a promotion, it’s technically just a move.
I need someone who can build a pyramid underneath. Every time you get promoted, you get more scope underneath you. Especially on the path to CCO, you need to have those extra gears.
Rod: There’s this concept of positioning your career turns into a series of stories that you can tell when you're looking at promotions. How does this concept play into your promotability or your ability to take on expanded roles?
Bob: If you’re someone who wants to take on more scope, but hasn’t done that part of the job before, talk about how you worked with other parts of the organization, and have already started to do the role the next job needs – even if you haven't had the title.
Mary: Too often, people think about all that they didn’t do. Instead, look at the work that you have done, and extrapolate it to what you could do. That’s how you roll right in a new project.
Think about your story and how you can take what you've learned and how you can apply it. Talk about results. People can see how you can step into a new role – even if you haven’t exactly done what they need.
Rod: What are some of the skills that you look for in a professional services leader when you hire for an executive position?
Pat: The first thing I look for is the ability to bring value to what I and the company need to achieve. I don't need somebody with a myopic, internal focus. Control is going to be part of the role, but I don’t need someone who will retreat into the services realm. I look for that ability to adapt. I also want to know that they will own a challenge they see. And that can sometimes even mean bringing a value that maybe doesn't currently exist to the table.
I also need to know if the person I hire can represent me and my org the way I would expect – beyond just doing the job at hand.
Can they be in a room on my behalf? Can I trust that they will act accordingly – in terms of what I'm trying to build? When you hire externally, it’s about prior experience. But internally, it’s about credibility – that can balance the lack of experience in some cases.
Rod: What are some of the skills that give you an indication that a service leader is going to be special and develop quickly?
Mary: Strong service leaders are curious and not okay with the status quo. This means going beyond doing their job and managing P&L to create new services, recurring revenue streams, and ask the right questions about how things are done and can be improved.
Someone in Professional Services is in the best position to share information about what's working and what's not. It’s really important to take those gaps and communicate that back within the company.
Rod: What's your advice to folks looking to transition into other functions to get the experience/value that will ultimately get them to the executive level?
Bob: When we earlier talked about the gears and the ability to do more work, it’s not just about getting more work done. It's getting more creative and transformational work done. I look for people who can ‘add more CPU’ to an issue and think: How can I transform it? How can I make it better? Always look for an opportunity to go help someone else – even if it’s not your area of expertise. Observe the organization – you’ll see places within that are starting to slow down. Maybe it’s the current leadership not getting their job done, or them not knowing what to do. If work is piling up and it’s causing frustration, that’s an opportunity for you to improve what's going on.
Rod: Should aspiring CCOs stay in the PS function up until their promotion point? Or is there value in getting exposure to other functional leadership roles?
Pat: It's exposure across the board – whether it's in a role, or tangential to it. It goes back to bringing value. Just approach everything you do with that lens. Ultimately, that's what people look for – the interactions people have, and how trusted they are, not what they do, or the roles they're in.
Rod: Any thoughts or advice for folks who want to continue to build their career, working directly with customers – without being on the management path?
Mary: I've had a few people in that situation. They’ve grown into being principals or experts within the function.
The first step is to have a conversation with your manager and let them know that you want to grow, and enable the team – without managing people, but continuing to get visibility and have customer impact. It’s possible to create that opportunity within the company, and it’s actually powerful for both the company and the employees in terms of outcomes.
Rod: What are some of the metrics that evolving leaders should think about to demonstrate their ability to have a company-level impact?
Bob: It's about how you influence the customer base as you get further up into the organization. Look at sales, renewal, and churn numbers. They start to matter as you get further up.
Pat: I agree. It’s influencing those metrics. Sometimes, that influence may even be tangential, and you need to be comfortable with that. You just need to tell a compelling story around that influence.
The second one is efficiency. Make sure to put that front and center, and verbalize it regularly.
Rod: How can mid-level leaders get exposed to the business metrics that will help them understand the inputs and levers that deliver business outcomes?
Mary: Ask your leader for the information that’s shared with the board. Find out the key metrics that the executive team is talking about every single week. Be exposed to that information and understand it.
Pat: I think that not having that exposure is a little bit of a red flag. Irrespective of what level you're at, you need to understand what the business cares about and what role your team plays in it.