Developing customer onboarding career paths

Brent Claremont, Director of Customer Onboarding at Emotive shares his insights on creating an A-Team for customer onboarding functions and how the career trajectory of an onboarding professional looks like.
Shuvedha Subramaniam
June 21, 2023
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In this episode, we have Brent Claremont, Director of Customer Onboarding at Emotive. A seasoned leader with 7 years of experience in Customer Success and another 4+ years of experience in SaaS leadership, he was one of the founding CS members of the Sydney HubSpot office. He later took up the role of an Onboarding Team Manager and helped review global CSAT, launch Service Hub and build a career rotational program at HubSpot HQ. 

As the recipient of the ‘Top Manager’ award in 2020, Brent sticks to hiring for character and training for skill. He is all for having a unique perspective to challenge the status quo and improve current processes. 

In this insight-packed session, Brent gets talking about:

  1. The playbook to create your A team for onboarding functions
  2. Developing an effective career pathing program for onboarding professionals
  3. The career trajectory of a customer onboarding professional
  4. Success stories of onboarding professionals who transitioned into different roles

… and more. Tune in!

Here's how our conversation transpired.

Sri: Do you see any advantages with having that split between success and onboarding?

Brent: A lot of SaaS companies actually fraction onboarding from customer success and try to make it work. However, this might start to conjure differences between them as onboarding is a cost center, and retention, whether it is gross or net retention, is being held by the CSM team. On the contrary, I’ve also seen some really successful SaaS companies have the CSM doing both and that tends to work well for them. So, for the split between customer success and onboarding to work, I would say it depends on the industry, the complexity of the product you are offering, how long it takes for your integrations, and such.

At Hubspot APAC, we had the benefit of having a playbook that had already been built, tried, and tested in the US. But until we opened our Singapore office, where a major part of our brilliant onboarding team was built from, all of us were wearing multiple hats and there was no actual split between the teams.

The breakout between customer success and onboarding had happened a while ago  in the US and we already knew that the split was going to happen. But at Hubspot APAC, since we were the first customer success team, we had a lot of different expats who had seen the playbook come over and help us out. They had seen it happen before and they helped us in polishing the scrappy bits to suit our team better.

Sri: What are some criteria you would recommend people to think about when they are contemplating a move to onboarding?

Brent:  I have had the same kind of pivot myself. I was going from sales, account management, customer success, and then to onboarding. All through the way, I have had two great mentors to guide me. One is Tim Cormier, who's currently VP of Customer Success, and Julie Hogan, who's also a VP of Customer Success and Growth. 

They had initially hired me in Sydney, and it was very much around the philosophy of hire for character, and train for skill. That was a brilliant methodology to bring people in and that being said, the key piece was to always be organized. Especially in onboarding, you need to understand that you’ve got several moving parts, with people coming into the process, some others working with migrations and different technical issues, etc, and that makes it more important to keep an eye out for skills related to project management and timing. Technical knowledge is also doubly important, but that again is a skill that can be transferred via training. On the other side, you should also be looking for people skills that help in building strong relationships. I know this is too CSM heavy, but I think it’s a brilliant part of customer onboarding as well. One of my favorite lines that I stole from some talented people is, ‘I want you to like me as your onboarding specialist, but I want you to respect me most of all, because my job here is to challenge and push you to get results.’ As soon as you say this on a call, you can feel the relationship change. And so, relationship building, project management, and time management are some big pieces of advice for folks looking to make the shift.

Sri: With customer onboarding taking its own sort of journey now, how would you describe its evolution over the last few years?

Brent:  When I started a long time ago, I thought customer onboarding was very technical. I thought it was more preachy, getting customers through the process very quickly to make sure robust systems are integrated quickly, and you are in a really good spot. I saw this at Hubspot when I was a manager in the US and I have seen it at Emotive as well. But the core competencies for the role started to shift and the mentality started to change, from being very technical to more along project management. It now leans more on the relationship side, allowing for more direct touch with customers. Bundle these prevalent skills with a bit of technical SEO to run a project, and you can get that partnership with the customer going. And of course, it’s a two-way street and it needs that mindset shift from leadership and teams collectively to be more productive.

Sri: How would you go about building an ‘A’ Team for customer onboarding?

Brent:  In my first year in management, I learned a lot and I failed a lot. I understood that as a leader, it was important for me to go through that phase, so I could realize what worked and what didn’t. I think everyone has that trial by fire as a first time leader, and one of the main pieces to get through this phase is psychological safety. What that really means is, trust. So building that trust with your team to share and receive feedback openly as a leader is extremely essential, to become a better consultant or an onboarding specialist. 

As a leader, psychological safety or trust is my number one priority when I start a job. What's worked really well for me in my years at HubSpot is having an eclectic mix of backgrounds. This means having people on the team from not just different areas of the world, or different backgrounds, or cultures, but also from different experiences. That would give you unique perspectives on how to approach existing problems and in challenging the status quo of playbooks and processes. This is also something that I’m really looking at now in Emotive as we’ve got some brilliant people on the team.

One example from my experience at Hubspot:

In my team, just before I left, we had two to three salespeople, two brilliant support team members, people from product, and some long term Customer Success onboarding specialists too. This meant that we had the foundational knowledge from customer success and onboarding and the challenging, forecasting, and direct nature from sales. All their different strengths and weaknesses mix and match together to build that solid A Team. The sales people became more technical, while the folks with core project management and challenging characteristics formed the customer success team. All this brought about a nice blend and I believe this is what made my team better.

Sri: How do you create a culture that’s conducive for internal mobility?

Brent:  This is something that we're creating really well at Emotive now. Emotive has been around for a little over three years now and we are still in our early days, whereas Hubspot has been around for much longer. There are quite a few different pieces that are in play to build that conducive environment, and one of them is having a brilliant HRBP or Human Resource Business Partner. The HRBP is to understand where that internal mobility is available, what previous individuals have done in the role, and building out that path. For example, you might need to be in the role for one year, have a great standing with your manager, hit excellent metrics, and then you might be available for an internal opportunity. It has to be made sure by the HRBP that it’s the right thing for these individuals. The HRBP is also tasked with understanding leadership. With my team, we had some brilliant support team members come over, and I knew they were at the right time, looking for a career change. We ended up keeping those talented individuals in the company. 

Some managers shy away from all this and are not keen on mentioning another job for fear of team members losing focus on their existing jobs. I disagree with that. I think you can approach it in a way where you think about someone's longer term career, understand people may change their roles six to seven times in their lifetime, and want to be a part of that. And that's really exciting. 

I'll give you one specific example. One brilliant team member of mine, Brittany Whittington, was an excellent onboarding specialist. She was promoted to senior onboarding specialist, but she wanted to try something different. So, we had a close alignment with our sales engineering team and she was one of the first team members to make that transition. We made sure she was learning the sales methodology and was also understanding more technical stuff on how to code slightly to deal with those bigger prospects. She managed to get that opportunity not only with HubSpot, but she actually moved to Berlin to help open our Berlin office which is something really special. That's a good example of strong internal mobility leadership aligned and supporting an employee.

Sri: What's your take on people moving from CS to onboarding and vice versa?

Brent:  I wouldn’t exactly term it to be a dichotomy of skills. Infact, I believe there’s quite a bit of overlap between the two and I am a big fan of it. I always position customer onboarding to be less transactional in nature than sales. Onboarding tends to vary a lot depending on the company. And the onboarding periods vary between 14, 30, 60, or 90 days. The CSM’s role on the other hand is focused purely on relationship building.

I am all for people moving from onboarding to CS and vice versa. I’ve seen some CSMs come over to the onboarding side and do a brilliant job at it. I’ve also seen some onboarding specialists transition to CSMs and do an amazing job as well. For me, it’s just one question that helps me make the choice. And whenever I ask someone why they're looking to make a change, I'm typically not satisfied with answers like "I want more money" or "I don't like my role". What really resonates with me is when somebody says they want to build relationships, be more of a consultant, and get a better understanding of the product. It shows a commitment to growing professionally, because at Emotive, if you were to work in customer onboarding for six months, you'd gain experience with 100-150 different types of businesses. On the other side, for the CSM role, it should be about wanting to work with different businesses, and gaining a deeper understanding of the technical aspects of the product. That's an amazing opportunity for personal development and I'm all for it!

Sri: Would you recommend CSMs do onboarding first before getting into a CSM role or do you think it's not best for everyone?

Brent:  It really depends on the type of business. From my experience in customer onboarding, I can say that the honeymoon period when a customer signs a contract and gets excited is a great opportunity to build a relationship and set expectations for CSMs. And for CSMs to know how they are coming in through the door will be really helpful in showcasing a bit of their technical side too. At Emotive, when we were going through a massive growth spurt at the end of last year, instead of just throwing bodies at the problem, we tried to be smart by combining people, process, and technology. We even trained some new CSM hires to help with onboarding for the first couple of months. And then we'd move them to their current job. And that was incredibly beneficial, not only for handling the capacity planning during the massive growth, but also for helping the CSMs develop professionally. Enablement was key and was incredibly cost-effective; instead of taking months to train them, it could be done in weeks. It did take a bit of pushing and pulling, but the perspective was really helpful.

Sri: How do you develop a programme of career pathing effectively for individuals who are currently in customer onboarding?

Brent:  I believe there are two approaches to this. First, it's important to make people aware of the opportunities that are available. For example, if someone asks me what I want to do with the rest of my career, I may not have a clear picture of what I want in the next 10 years - and that's totally normal. From a business perspective, it's smart to understand the requirements needed to move up internally when a great opportunity comes along. On the other hand, it's up to leadership to invest in professional development and help employees develop their skills to reach their goals.

Here's an example: During one of our team meetings, I brought in a former colleague, MK Getler-Porizkova who had shifted to another role. She used to be an onboarding specialist in Sydney and is now the CMO at Loop & Tie. Her career trajectory has been amazing - she started out as an onboarding specialist but has now done a stint in Sydney and worked on great things at HubSpot. It's inspiring to see how far she has come and it's something that I have found particularly helpful for everyone on the team and for me personally. This would help the team to know what’s expected of them and overall for the company to have some structures in place before internal mobility can come in.

Sri: Is there a formal career trajectory mapping that you do for your customer onboarding team?

Brent:  We absolutely do that and we have core competencies in place just for mapping. It's been that way for a long time at Hubspot - from level one all the way up to principal level. We had some amazing onboarding specialists who didn't want to manage people or move roles. And we had those career pathing levels built out for them to reach the highest possible role in onboarding. Having these levels is incredibly important for a rapidly expanding company as it facilitates growth and development and allows you the time to prepare for the shift. And once the shift had happened, at Hubspot, we changed titles to ensure they matched but they were still paired with the core competencies. 

For example, 15 people were separated into sections such as learner, developer, developing contributor and master. These categories weren't only applicable to the job they were doing, but also for personal development in areas such as methodology, communication, time management and technical skills. This process would happen twice a year, allowing individuals to work with their managers and get their opinion on what areas they are passionate about and what they want to improve. That to me was the best professional development because it is invaluable and is something that will help you throughout your entire career. So, having those rich conversations about building core competencies will be extremely beneficial.

Sri: How can a candidate evaluate if they are a good fit for a customer onboarding role?

Brent:  Like I mentioned before, we want those different perspectives for the role. There are a lot of great resources available to help you understand what customer onboarding is. So when you talk to a recruiter or anyone else, make sure to ask about the pros and cons. Don't just get the glamorous details - you want to know what could be stressful too. For instance, having multiple customers at once, dealing with customers who aren't happy with certain aspects of the product, or meeting deadlines can all cause stress. Plus, since it's a completely new process, you will have to take ownership and manage your own book of business, which can be overwhelming. And when it comes to gaining experience, there's no better way than working with 100 different businesses in six months! This is something you just can't get anywhere else. 

So here's what I suggest: first, figure out what type of role you're looking for - is it relationship building, technical, or project management related? Then, make sure that the company's mission and goals are aligned with yours, and that their culture matches your own. That's a great way to decide if a role is the right fit for you. For example, I've seen some great examples of people thriving within different roles - Kate McCaffrey started as an onboarding specialist and eventually became a manager, Brittany Winnington was in charge of sales engineering in Berlin, Ryan Jannetty became a manager from the team and Erin Woods was a talented onboarding specialist who is now a principle very early in her career. It's great to see that people from varied backgrounds can succeed and reach their goals, so don't be afraid to apply for opportunities that you think you might not tick all the boxes for - you never know where it could lead!

Sri: We have a question from our Preflight Community. What's the most interesting move in or out of onboarding that you've seen?

Brent: I’ve seen people completely change their career trajectory, while some others decided to go with the bartender approach and pivot. For instance, they've gone from onboarding to becoming a bartender, or even pivoting to selling golf equipment. But what I'm noticing more recently is that folks are choosing jobs based on culture and overall happiness instead of just salary. Of course, in the current economy, salary is still important but it's not the only priority. People are making decisions for the happiness of them and their families and that's brilliant!

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