What do you love most about Customer Success?

I love thinking through human behavior, how people perceive value (soft vs hard ROI), what drives value, what are activities you can drive to increase value. All of that is fun for me. I also enjoy helping CSMs build out their own careers and form their “CS identities”. Different things motivate different people and if you can get at the core of what motivates someone, there's so much you can do with them to help them on their journey. 

You’ve led multiple CS teams at Hellosign, RentLEVER, Pared, and now Swiftly. How has your leadership style changed as you’ve gone from Hellosign to now Swiftly? 

How hasn’t it changed? I’ve learned so much over the years. Real talk here. At one point, I would’ve classified myself as a micromanager. I wanted to know every detail of what was going on at every point. Now, I know that not only is that not scalable, but it also isn’t sustainable nor is it healthy for me or for my team members. It’s amazing the things you can get done when you are enabling and empowering your teams to do what they need to do without you getting in their way. 

I’ve also learned a lot about how to build out teams, when to hire (earlier… always earlier), who to hire, when to put tools in, and just the overall process around creating CS from scratch. I have now been building teams from scratch for over 10 years.

How do you think about career progression for someone in Customer Success? What opportunities are there as an individual contributor vs. moving into management?

I recently read an article that said something along the lines of not only is CS one of the most in-demand jobs, it also has the fastest growth in regards to a career trajectory. 

For those that are hungry and want to grow, the sky is really the limit. I see CS professionals not only move around their company into departments like marketing and product, but I am also seeing new opportunities pop up within the CS organization. Opportunities like Customer Success Ops, Customer Success Marketing, Customer Success Enablement, and CS roles with more strategic customer bases. The opportunities will greatly depend on the business need but as CS continues to grow and become more important in the role of a company's success more opportunities will open up. 

Rav Dhaliwal recently posted an article saying Customer Success is at-risk of being ‘The Everything Department’. How have you established clear role responsibilities for members in Customer Success and other ancillary departments when working with customers? 

This is important to do early when building out CS. In early-stage startups, it’s not uncommon to have a very generalist take on how to support customers. 

As companies grow and evolve, it’s important to introduce segmentation of responsibilities to allow Customer Success to be laser-focused on the success of the customers. 

What helps with boundaries is documenting responsibilities in a system like Notion and making sure everyone in the company has access to it. Create a list of “service offerings” so others in the team can see what CS does and more importantly, what they do not do. Lastly, know that responsibilities will change and evolve as the company does.

What is one thing you are excited to implement as part of the ‘future of CS’?

I am excited to see how Customer Success Operations will become a much bigger role in the Customer Success Organization.

There is a continued pressure to work smarter or do more with less which can be very counterintuitive in a high-touch B2B Enterprise CS model. But even high-touch customer success teams are going to have to get creative on how to leverage tools and data to drive customer outcomes. I think this push alone is going to result in a bigger focus on Customer Success Operations earlier.

I am already starting to see this in some companies, but CS Operations are guiding decisions, giving us insights into what the quantitative data is saying, and helping CSMs marry that with the qualitative data to formulate an engagement strategy. This will have to become more prevalent not just in the larger organizations (which is where I see it now) but also in the small and mid-size startups.

CSM enablement is important for CS career growth. What enablement is a must-have for CS departments and how have you structured your enablement for the highest impact with your CSMs? 

I am a huge fan of Practical CSM. It’s very well done and relevant for what we do. We have goals on our company level OKRs to complete training in Practical CSM. Putting this front and center hopefully makes it a priority for everyone. 

You oversee both the people department and customer success -- tell us a little bit about the experience leading both departments. 

It’s been a lot of work, but also very rewarding. In theory, everyone in the company is a customer of HR. So if we approach People Ops through that lens, it makes it less different than what I do in CS every single day. 

I am currently hiring someone to take the People side of the work off of my plate so I can be more focused on CS but am forever thankful for my time I spent doing this dual role.

What advice would you give to someone looking to get into a CSM role? What about someone who’s currently in Customer Success who’s looking to stake out a career in CS leadership? 

I’d give the same advice to both. Dig in on your main motivators. Why do you want to be a CSM? Why do you want to be a leader? Make sure your “why” is true to who you are and you’re doing it for the right reasons. Both positions have pros and cons, make sure you look into both and have a strong understanding of the journey you are about to start. 

Knowing what you know now about building and leading CS teams, what would you change about leading CS. What would you keep the same? 

Things I’d change or have changed: 

• I will say what I have changed based on previous learnings is advocating for more resources earlier. CS often struggles to get the resources we need. I have learned over the past few companies that this ultimately hurts the bottom line (think less upsells, renewals, team morale). Of course, you have to balance growth, revenue, and all of those factors, but CS should never be an afterthought. 

• Hire a team that has a balance of domain and CS expertise. Having a strong balance in the team is always important. 

• What I would keep the same, is being heavily focused on my team’s career paths and opportunities. I genuinely care about this and other leaders should as well. It’s easy to put those discussions on the back burner when things get busy, but you have to make time. It’s crucial. 

What’s unique about career development for Customer Success professionals & CSMs? 

In my opinion, the unique thing around career development in CS is the sheer amount of options CS professionals have. They touch so much in an organization so the opportunities they have for movement within the company is pretty impressive. CS fits in marketing, sales, product, professional services, and much more. There are not many other roles in an organization that you can say that about.