10 Leaders Share Their Customer Success Career Paths

May 15, 2017 Mathilde Augustin

10 Leaders Share Their Customer Success Career PathsCustomer Success seems to be the new “it” job in SaaS. From new grads to established professionals with various backgrounds, there’s a growing interest in building a successful career in Customer Success. Not only can it be difficult to enter the industry, it’s also challenging to have a clear idea of what your career path should look like.

We asked 10 Customer Success Leaders who’ve built and managed thriving Customer Success organizations “How did you get started in Customer Success, and what led you to your current role?” Here’s what they said.

Stephen O'Keefe, Director of Customer Success, Hubspot

I got started in this industry back in 2004, shortly after I graduated from college. My background immediately after college was actually working in political campaigns; there, I started to observe some interesting trends with regard to how political campaigns organized and raised money. And I found some interesting software companies that did this sort of thing. This was back before SaaS companies were given that acronym -- they were called ASPs (Application Service Providers) back in the early 2000s.

I found a company called GetActive Software and they worked with large, national, non-profit political campaigns, higher ed, public broadcasting -- that kind of thing. I helped them raise money and build their membership lists. I did that for about 5 years in Washington, D.C. then I found HubSpot. So I moved back to the Boston area where I was originally from -- it seemed like a very natural transition.

What I liked about HubSpot, in addition to being a growing business, was that it was very much mission-oriented. We really want to help companies transform the way they do marketing and sales.

Stephen O'Keefe, Director of Customer Success at HubSpot 

Perry Monaco, Head of Customer Success, LinkedIn

When I first started at LinkedIn, the concept of Customer Success existed but the label did not. We’ve always wanted our customers to feel successful, see a return on their investment, and have a very positive relationship with our organization.

Customer Success has evolved over time at LinkedIn but the ultimate goal has always remained consistent. When I first started, I was primarily an educator, in terms of working with our customers and showing them how to recruit passive candidates and how to engage with our tools. We’ve evolved significantly since then.

I got involved in Customer Success because I had a particular skill set that our customers needed at that point in time. Since then, we have been able to leverage a lot of other people and get to the point where we have a more sophisticated Customer Success team.

Perry Monaco, Head of Customer Success at LinkedIn - Canada

Ellie Wilkinson, Senior Manager, Customer Success, Moz

Before becoming a Mozzer, I was an SEO Specialist providing consulting services for car dealership clients. Before being an SEO Specialist, I was actually a journalist. I got a lot of experience with writing, communicating, and talking to people! I’ve always had a passion for teaching, as well, and I was then able to bring that experience to Moz.

My career overall has been focused on communication and teaching, and I use a lot of those skills now in Customer Success to help educate our customers, connect with them, learn about their goals, and show them how they can use our tools to succeed with their marketing goals.

Ellie Wilkinson, Senior Manager of Customer Success at Moz

David Follert, Senior Manager of Customer Success, Sysomos

I’ve been with Sysomos for close to 6 years, and when I originally started here, Customer Success was still somewhat of a new thing for the company. I originally started as an account manager, which was a pretty general role. We started carving out the CSM role fairly quickly and after a year or so as an Account Manager, I became a general CSM. I then went on to becoming an enterprise/sales hybrid CSM, and I finally moved into a role that was specifically agency focused. As the role developed and due to a combination of timing and experience, I had the opportunity to manage our first internship program. This subsequently led me down this path to becoming a Manager of Customer Success, it was a very natural progression. Outside of my work at Sysomos, I’ve had a lot of different jobs, and the ones I enjoyed the most were Customer Success or Customer Service-centric. So it’s really no surprise to me that I’m doing what I’m doing today.

David Follert, Senior Manager, Customer Success at Sysomos

Monique Steele, Director of Customer Success, Vend

Coming from a retail background, I had a lot of experience in different roles and I loved the industry. I found myself looking for my next step but I wasn’t quite sure what that was.

A friend actually sent me the job posting for a Customer Success Manager (CSM) at Vend. I knew of Vend, being in the retail industry, and because of their big presence in New Zealand. It was an opportunity for me to go into something a bit different but also continue to work with retailers and actually help them be more successful. It was kind of a perfect fit for me.

I went for it and luckily they hired me!

Monique Steele, Director of Customer Success at Vend

David Apple, VP of Customer Success, Typeform

I got lucky! Before joining Typeform I was VP of Sales for another startup and I originally joined Typeform to be in charge of Sales. Acquiring new customers was never really our biggest challenge, our challenge was retaining our customers, especially since a lot of them use Typeform for short campaigns and then leave once those are over. In parallel, we weren’t really ready to build enterprise features, so the opportunity to make a big impact with sales was limited.  Because it is a lot more expensive to acquire new customers than it is to retain existing ones our CEOs decided that we needed to invest in a Customer Success department at Typeform, and they asked me if I would be interested in running that team. So I was just at the right place at the right time!

David Apple, VP of Customer Success at Typeform

Vanessa Brangwyn, VP of Customer Success, Achievers

Prior to joining Achievers, I worked at several other successful software companies in the area of customer enablement and best practices, I knew that I loved working directly with customers, and that I had the skills and the passion to stay even more closely connected to them. But during my time in customer enablement, I would only be engaged with a customer for a certain project and then have to move on. So I always wondered, “What happened with that customer? Did they hit their goals? What does success look like for them?” And I knew Customer Success was the evolution of that.

I joined Achievers as a CSM in January 2011 and managed a portfolio of accounts across all industries (one of the nicest things about our solution is that it’s industry-agnostic -- all employees from all industries want to feel appreciated). As our company and customer portfolio grew, there were a lot of growth opportunities from a CS perspective, and I moved into a management role. I was able to learn a lot through that experience because by then I had been exposed to so many more customers (as opposed to just my own individual portfolio).

I continued to lead a number of other cross-functional initiatives in that role. And through that exposure, I was able to enhance some existing processes and develop some new, which led to this moment, where I’m heading up the entire Customer Success team. I’m really excited about it because I get to work with the best team in the business, every day.

Vanessa Brangwyn, VP of Customer Success at Achievers

Sam Brennand, VP of Customer Success, Uberflip\

Honestly, I kind of stumbled into the role! When I was in University I would not even have been able to tell you what Customer Success was.

I went to school for brand communications and marketing. I graduated wanting to go work as a Brand Manager for a big fortune 500 company. My first roles out of school were in consulting for a small company in the city called Venture Accelerator Partners. I worked with startups and small and medium size businesses that needed part-time help with marketing and sales. It’s fun for me to look back on that experience now. At the time, my role was to help organization's build marketing strategies, help them to execute those strategies, and to ensure their success. We were doing Customer Success without really thinking about it or calling it "customer success". I did that for a few years and as part of my role I happened to meet one of Uberflip's Co-Founders, Randy, at a marketing event in the city.

I chatted with him for around 20 minutes about what Uberflip was doing, added him on LinkedIn, followed him on Twitter, and over the next 6 to 12 months I was regularly in touch with him. He would post a great piece of content from Uberflip’s blog and I would go read it or comment on it on Linkedin. Because part of my role at Venture Accelerator Partners was to do our internal marketing, I would also regularly feature Uberflip content as part of our social media curation strategy. Over time I was able to build a relationship with Randy to the point that in 2014, just as he was looking to build out the Customer Success team, he happened to give me a call.

I think my first question to him might have been something like “what does Customer Success mean?”, to be honest. But as I learned more about the role and the idea, the more I realized it fell perfectly into what I was looking for. I still love marketing and that’s what I’m passionate about, so the idea of being able to do marketing at scale through a company that builds content marketing software was very appealing to me. I still get to work with small, medium, and large marketing teams all over the world to build marketing and sales strategies, make sure they are executing them the right way, and help them report back on whether they are achieving their goals. The most fun part for me is that I get to work with some of the smartest marketers in the world. It keeps me on my toes.

Sam Brennand, VP of Customer Success at Uberflip

Peter Armaly, Principal Transformation Advisor, Oracle Marketing Cloud

I’ve been in IT-related roles for over 30 years now, and I’ve been in the software vending business since about 1998 when I joined BMC Software. I was a pre-sales consultant and focused on helping sales land customers. Around 2007, I decided to move into the post-sales world because I wanted to get closer to the product, to the value proposition, and to the customer challenges that can be addressed through software. Soon after I was asked to build a new service and hire a new team for a fee-based offering called Technical Client Services.  We worked with customers to understand their business goals, why they bought our products, and the struggles that they faced, and then built action plans that we executed over the course of a year. Our mission was to own and manage the customer’s post-sales attempts and efforts to achieve success with our company’s solutions. That was my first formal exposure to Customer Success. I had a couple of related roles after that but it wasn’t until I joined Eloqua in 2011 that I encountered a customer success model that truly worked (editor's note: Eloqua was acquired by Oracle in 2012). The Customer Success organization deployed 1:1 and 1:many models and Customer Success Managers (CSMs) provided the right information to the customers who needed it, when they needed it. Eloqua did a great job of putting in place an approach that was proactive. That’s when I had the opportunity to work with such Customer Success luminaries as Paul Teshima, Chad Horenfeldt, Jocelyn Brown and Kia Puhm. It was a transformational period for me because I realized that with authentic engagement, intelligence, and technology you can scale this kind of thing.

Peter Armaly, Transformation Advisor at Oracle Marketing Cloud

Zakir Hemraj, Co-founder and CEO, Loopio

It was very unexpected. I started my career as a Developer, and I also worked in Sales for a couple of years. When we started Loopio, my Co-founder Matt and I were building the product, and our third Co-founder Jafar was selling and getting initial traction in the market. It wasn’t until we closed some deals that a couple of our customers started to ask about implementation, onboarding, and best practices. Being the keener that I was, I volunteered to work out an implementation plan, and that’s how Customer Success was born at Loopio. For a while, I was working in those two worlds: coding features for the product, and managing customer relationships.

A mentor once told me a terrible, but effective, analogy —“you can’t sit on two toilets at the same time.” Eventually, that’s what happened. It got to a point where nothing I was doing was at the level of quality that I wanted it to be. I did a bit of soul-searching, talked to a few mentors, and I realized that the best thing for me personally, and for the future of Loopio, was to focus on Customer Success.

In retrospect, nothing was more valuable than understanding the pains and needs of our customers. It helped us make better decisions for the business. As a CEO, having the ability to speak to customers every single day, especially in those early stages, helped us lay the foundation for a feedback-driven culture.

- Zakir Hemraj, Co-founder & Chief Executive Officer of Loopio

For more insights from Customer Success Leaders, head over to our Inside Customer Success interview series.

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About the Author

Mathilde Augustin

Mathilde is the Manager of Digital Marketing at Amity. After moving from France to complete a degree in Political Science from McGill University, she made her way to Toronto in order to pursue her passion for Marketing and Tech.

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