AMA: Brex Senior Director, Customer Success, Ben Terrill on Developing Your Customer Success Career

I love that you’re looking to break into tech as a CSM, here are a few strategies I would recommend: 1. Internal Promotion - Some of the best CSMs I have worked with have moved up internally from other roles in the company. Customer Support and Sales Development are two internal roles that I frequently recruit from. If you’re early in your career, look for entry-level roles in Customer Success-adjacent roles at a company that prioritizes internal mobility. A benefit to both you and your employer is you’ll already have a good understanding of the product. 2. Adjacent Industries - If you have experience elsewhere and are looking to make the switch, I recommend being strategic: Focus on companies where your previous experience would give you a unique advantage in understanding the customer. (eg: if you’re an accountant today, look at companies that make software for accountants). Don’t “spray and pray” - you’re better off focusing on a smaller set of companies that you think will be a great fit. 3. Entry Level CS Roles - I think this will be the hardest path for you, but it’s possible. I frequently receive hundreds or even thousands of applicants for entry level CS positions, so it’s important to stand out from the crowd. Network and attend CS meetups or events (meetup.org is a great resource) where you can. You’ll learn a lot and you’ll also start to meet people in your local CS community who can help you.

If you enjoy what you do and why you do it, you’ll do it better and you’ll do better. Here are some questions to ask yourself when consider a new role: 1. Do I feel good about what I would be doing in this role? Do I feel good about the company I would be working for? Maybe it’s in an industry that you’re interested in, or maybe it’s something that helps shape the sort of world you want to live in - whatever it is, make sure you feel good about it. If you believe in the company you are working for, you will have much more energy at work and in your life. 2. Can you feel good about who you’re working with? What are the leaders and peers at the company like? Did you feel good during the interview cycle? Do the publicly stated values of the company align with yours? You’re going to spend a lot of time with these people and it needs to feel like a good fit. 3. What is the product like? If the product is weak, CSMs, almost more than any other role, are exposed to this. Will you be spending most of your time dealing with product issues to retain your customers, or will you have a chance to be more strategic? An early or imperfect product is fine, but I would try to validate what the short to medium term prospects are. Is the company early-stage and rapidly improving the product or is the product imperfect because it’s not being invested in properly? 4. What are the business prospects like? What is the industry or business space like? Is the industry growing or are its best days in the past? It can be very hard to retain your customers if there are macro economic issues at play.

My philosophy is that I want everyone on my team to be eligible for a raise, so it’s my job to help them understand what they need to do so that I can make the case to the business. Just as they are the advocate for our customers, I am the advocate for them. It’s not just about the quantitative - there are many qualitative things I consider when recommending a pay rise. Some of the most common pieces of advice I give to my team are: 1. Make sure you are a master of your business. Exceed your metrics or have a clear explanation of where and why you fell short. It isn’t essential that CSMs are always over 100% on everything, but you should have a clear plan that addresses why you are behind. 2. Are you having an impact outside of your specific book of business? Are you helping others when you can? Are you seeking out and taking on additional projects and opportunities when they come up? 3. Are you upholding the values of the team and organization? Are you having a net-positive effect on the morale and engagement of your peers around you?

Some of the things I would focus on to up level my CS career: Sales Skills - Developing your sales skills will really elevate you as a CSM. Your ability to influence and strategically drive a conversation to mutually beneficial outcomes is the key to your effectiveness as a CSM. Understand How You Are Measured - You need to fundamentally understand how your individual performance is measured and be able to effectively tie that into your day-to-day activities. Leadership Skills - Leadership skills are not just for formal managers! Your ability to lead others through your influence and expertise is key to your advancement in your career. Product Expertise - This goes beyond just understanding how the product works, but you should fully understand how the product solves your customer's problems. The better you understand both of these, the better you can advocate to the product team about the features or product changes you need. 

It sounds like you’re asking about how you move from being an individual contributor to being a people manager. The first thing I’ll say is that people management is not for everyone! There are plenty of career growth opportunities in Customer Success as an IC. That said, some of the reasons you might want to be a manager in CS are: 1. You want to help others grow 2. You want to expand your impact 3. You want a new challenge As a hiring manager, I would focus on internal candidates first if I’m considering a first-time CS manager. With that in mind, here are some things I consider about in CSMs who want to move into people management: 1. Are you already acting like a leader? Does the team already see you as a leader? There are many opportunities to assume informal leadership roles in most CS orgs. Maybe there’s a project you can lead? Maybe there are some more junior team members you can mentor? I would actively seek out these types of opportunities to develop your leadership abilities and gain recognition. 2. Do you have an opinion on how you can improve the business? Do you have ideas on how you can drive improvement across your team? Proactively share these with your manager if you haven’t already. 3. How have you performed as a CSM? Are you on top of your metrics? Do you XFN peers have positive feedback? 4. Can you advocate for Customer Success? Are you able to effectively advocate for your customers and team across the business?