Starting a new Customer Success leadership role can feel really overwhelming. Not only do you want to hit the ground running and show your team why they hired you. But, you also want to find the right balance so that you’re not disturbing the peace on day one.

That’s why we were so eager to sit down with Lizzy Rosen, VP of Customer Success at Vendr to learn all about her roadmap for acing the first 90 days of the job. In this interview, Lizzy shares her strategies for building trust from day one, as well as tactical questions she asks direct reports and peers to help her make informed decisions.

Eager to watch the full interview? 👇

Your First 30 Days: How to Build Trust Fast and Authentically

When you first start a new job, you’re likely operating off a lot of excitement, adrenaline, and nerves. This makes it easy to fall into the trap of “coming in hot.” But, it’s important that you don’t show up on day one trying to change anything and everything. To reduce “coming in hot” syndrome, aim to have a game plan. This typically means narrowing in on things you want to focus on, including:

• Knowing where you want to focus your attention on first
• Determining what success looks like for you and your team
• Mapping out important milestones you want to hit in your first 30 days
• Lining up the questions you’d like to ask your team, peers, and leadership to help you hit the ground running

Ultimately, you want to set the groundwork for building trust across the organization.

“The biggest quick win, no matter what company you're at or role, is quick trust. Coming into a new role, I don't want to maintain the status quo. I want to change things. I want to build things. I want to create things. You can't do that unless you have trust behind you, team members trust you, and the organization trusts you and is willing to go on that path with you. And so, I think the first thing that you have to do is build that trust. — Lizzy Rosen

When it comes to the first 30 days on the job, Lizzy Rosen breaks down her goals into four key areas: 

• Getting to know your team to set them and the team up for success
• Building personal connections with key individuals across the organization
• Analyzing data

Let’s explore these a bit more!

1. Information Gathering: Getting to Know Your Team

In your first 30 days, it’s imperative that you block time to meet with every team member, regardless of their seniority. That means you’re not just meeting with direct reports, but also making time to meet with skips too.

For some, this can feel really scary. So, it’s important to call out why you’re setting this meeting up in the first place. It’s also important that you humanize yourself and take people out of the mindset of “the new Customer Success leader wants to talk to me. Am I in trouble?”

“I like to meet with every single person on the team, no matter the level, which honestly terrifies people when you first do it. So I call out that I’m a person, I just want to meet with you and understand what your life is like and what your day-to-day is like.” — Lizzy Rosen

You’ll want to use this time to better understand their roles, challenges, and to start building trust. After all, you don’t want to come in and change everything at once, especially the things that are working. You’ll also want to make space to get to know your team on a personal level too. 

Some questions you can ask during this time include:

• What’s one thing we should start, stop, and keep?
• What’s not working? 
• What’s one thing I shouldn’t touch? Something that you love and is working great for you?
• What are your career goals? 
• How would you like to grow within our company? Beyond?
• What opportunities are you excited about within our team? 
• What’s something that’s on the Customer Success team’s roadmap that you’re most excited about?
• What team goals are you most excited about having an impact on?
• What do you think is a quick win that we could have as a team right now?
• What are your hobbies outside of work?
• What’s your preferred communication style?
• How do you like to receive feedback? 

“I think too frequently people come in and they rip up everything all at once. They sometimes forget the good stuff that people love. In my first 30 days, I try to make sure I understand what that stuff is.” — Lizzy Rosen

2. Building Cross-Functional Connections

Another thing you should aim to tackle within your first 30 days is to meet with cross-functional leaders. Customer Success works with every department, so it’s important for you to not only start building those key relationships cross-functionally, but that you understand the different dynamics you’ll need to navigate in order to succeed.

“I also like to meet with people all across the organization. I want to meet the Head of Product, the Head of Enablement. I want to meet everyone. I not only want to introduce myself, but also get a lay of the land. With every company I’ve joined, there’s always been some friction with CS, so I try to use these conversations to understand what’s not going right and mend the relationship.” — Lizzy Rosen

When you’re able to have proper sit downs with cross-functional leaders, you’ll be able to uncover what areas of friction exist, with who, and figure out a plan to reduce or remove that friction altogether.

As Lizzy puts it, “there’s no winning with customers unless all of the departments in an organization are focused on the customer, so you have to do it together to succeed.” 

During these meetings, here are some questions you can ask: 

• What’s your team being measured on?
• What are you being measured on?
• What are your OKRs?
• What’s your team focused on right now?
• What do you care most about right now?
• What has historically worked great between your team and CS?
• What hasn’t been working well between our teams?
• What should we start, stop, and continue doing?
• What feedback do you have about my team? 
• What are some blind spots that I might encounter with my team?

Get product demos from across the org

A great way to spend some of the time during your cross-functional syncs is to get demos of the product too. That way you’re able to learn about the product from a wide range of perspectives. After all, Sales might talk about the product differently than the Product team, so being able to understand it from multiple perspectives is a great way to deepen your knowledge, and in turn, help customers succeed.

As you’re navigating these conversations, consider getting demos from roles like:

• Onboarding Manager
• Customer Success Manager
• Support Rep
• Product Manager
• Content Marketer
• Sales Development Rep
• Account Executive

“I love getting demos from a wide range of people across the org because everyone does it a little differently and you learn a bit more about the positioning, what people are focused on, and the nuances of your product too.” — Lizzy Rosen

3. Analyzing Data

Data makes the world go round, right? And understanding how to use data to make better decisions is an important skill for Success leaders to possess. 

As a leader, it’s important that you have a deep understanding of what’s working, what’s not, and what opportunities you can take advantage of. Given that you’re coming into the organization with a fresh pair of eyes, this is one of the best times to start diving into your company’s data. 

Maybe you’re able to discover a new finding from existing data that others hadn’t been able to see because you’re analyzing it without bias. You won’t have the customer stories in the back of your mind to justify a loss. But rather, you’re coming in with a heightened sense of curiosity to challenge what we sometimes eventually come to accept as “truth.”

“I spend a lot of time with the Head of Ops. I really want to get into the data. I want to look at churn-loss reasons. I want to understand if we’re contracting more than we’re churning. I want to start getting my head around those numbers and that takes time, but it’s perfect to do at the beginning because you don’t have any bias yet.” — Lizzy Rosen

When you’re able to look at your company data with a fresh set of eyes, and work alongside ops to slice and dice the data, you’ll have a much easier time when it comes to setting your Customer Success strategy moving forward.

Your First 60 Days: Setting the Customer Success Roadmap

Now that you’ve spent a lot of time with your team and peers gathering information, hopefully you’ve got a solid understanding of the direction you want to steer your team in. Now’s the time to set your Customer Success strategy. 

“This is typically when I’ll bring the team together in person to map out what we want to create for our customers and what’s the ideal experience for them.” — Lizzy Rosen

During this time, Lizzy suggests running an exercise that she loves to run with her team to help answer questions around: 

• What do our customers need?
• What are our customers thinking?
• What are our customers feeling?
• What are customers trying to achieve?
• What problems are they having that they need help solving?
• How will we measure these things?

To run this exercise, Lizzy prompts her team to walk through months one to 12 of the customer journey. During this time, Lizzy and her team will walk through all of the different questions customers are asking at each stage of their post-purchase journey. 

For example, in the early stage post-purchase, customers might be thinking or feelings things like:

• “Oh my gosh, I just bought this new software. It better go well.” 
• “I just asked my VP of Finance for money to buy this thing. It’s my first time ever doing something like this. I hope it wasn’t a mistake.” 

Ultimately, customers at this stage are likely feeling a little overwhelmed because onboarding any new tool is a big task for anyone. Layer on the need to show value in that tool as well, it can add a lot of stress. So, how can you and your team ease that stress and help customers onboarding and get value from your product in little-to-no-time?

“Once we have an understanding of what our customers are thinking and feeling at each stage of the lifecycle, we can start getting into creation mode. Then we can start coming up with: What are the activities that we need to do to meet our customer needs? How are we going to measure these things? How are we going to build them?” — Lizzy Rosen

It’s Time to Start Building

Once you’ve aligned your team on your plan of action, and how you’ll measure success, it’s time to start building. Here you can start to map out what groups of people are responsible for bringing your plan to life. Who’s responsible for building specific content, decks, videos, Vitally Playbooks, or whatever it may be.

While you likely already have a project management and accountability framework that you’re used to, it might be a good opportunity to learn about a couple others. In particular, a great accountability framework you can lean on is the RACI Matrix. 

A RACI matrix is a chart that tracks the responsibilities of each team member across a specific project or goal. RACI stands for:

• Responsible: Someone who’s directly responsible for completing tasks within the project.
• Accountable: An individual who is ultimately responsible for the success of the project or task.
• Consulted: Someone who can provide valuable information or insights to help the project succeed, but not someone who’s necessarily doing the work. 
• Informed: Someone who just needs to be informed on progress or goals.

In many cases, you may find yourself sitting between “Consulted” or “Informed,” depending on the level of involvement you want across each project or task.

Kick Off Your “Customer Success Roadshow”

Now that you’ve got a strategy and plan in place, it’s time to make it known to others. It’s also a great opportunity to talk about how and why your team is so amazing and garner excitement around the things your department’s working on. Ideally, they’re so excited that they’re able to help when you need it too.

“You can build a bunch of cool stuff, but if people don’t know about it, they’re always going to be confused," Lizzy says. "So that’s why I love roadshows. It gives me the opportunity to go to Product meetings, our company-wide All Hands, all of these different meetings to share:

• What we’re building
• What we want to accomplish
• Where we need help”

Your First 90 Days: Achieving Quick Wins and Building Trust

You’re officially two months down into your new role. Congratulations! 

Now it’s time to start showing your impact and expertise. The best way to do that? Quick wins.

Identifying and tackling quick wins can help you achieve two key things:

1. Building trust: You’re able to show your team and also your peers just why you were hired for the job. 
2. Building confidence: Being able to gain some traction early on gives you the chance to dispel any imposter syndrome you may be facing in the beginning days of a new job.

“I reflect on the leaders I've worked with in the past — those who inspired and motivated me, as well as those who didn’t. I strive to emulate the qualities of the leaders who inspired me and avoid the traits of those who didn’t. As leaders, it’s incredibly important that we continue to fine tune and build on our leadership style and methodology. I believe it’s an essential part of our craft as leaders.” — Lizzy Rosen

Building Trust Quickly With Your Team During 1:1 Meetings

One of the best ways to build trust across your team is to nail your 1:1 meetings and you can do that by ultimately achieving three things:

‍

1. Aim for psychological safety to be high 

Do your employees feel comfortable being themselves around you? Do they feel comfortable with being a little vulnerable? 

The best way to build a psychologically safe environment? Take the lead and be vulnerable first.

"I build trust in my 1:1s by being personal, sharing about my life and family, and staying authentic. I'm also open and vulnerable, especially in the early meetings. For example, I acknowledge to my team that they know Vendr better than I do — they're the experts. I'm here to learn from them, guide them, help with internal challenges, and take tasks off their plate." — Lizzy Rosen

2. Make opening up or sharing feedback beneficial 

Your employees have likely spent time thinking through how to deliver feedback to you, whether it’s about your leadership style or things that aren’t working on the team. Now it’s time to make sure that it was worth their time and effort. 

This doesn’t necessarily mean that you need to agree to everything they say. Instead, it could be as simple as agreeing to think about it, take a week, and actually follow up with your thoughts.

Ultimately, if your employees are asked, “was sharing that feedback worth it?”, your goal is for the answer to be “yes.” 

3. Make sure that it doesn’t take a lot of effort for employees to open up

Sharing feedback isn’t always easy. And sharing feedback with your boss? Even harder.

That’s why it’s important that you, as a leader, are creating an environment where sharing feedback feels less daunting, scary, and like a second job for your team. Because, if they feel like the effort it requires to share feedback with you is too high, chances are you won’t receive it. 

One way to ensure that you’re keeping the effort low is how you react to feedback. If you’re immediately defensive, unwilling to listen, and also combative… well I’m sure you’ve been there before. You don’t leave that conversation feeling great or excited to share feedback with that individual ever again.

Building Trust Through Low-Hanging Fruit

As you’re learning more about the people and team, it’s likely that you’ll identify a lot of quick wins that you can tackle. These are small changes that could make life easier for someone or have a quick lift on a specific metric. They don’t need to be tool overhauls or big changes in strategy, but small, incremental changes to get your feet wet.

“I find that sometimes there's things that haven’t been solved for. Not because people can’t solve for them, but because they don’t have that outsider’s perspective of ‘oh we can fix that.’ So, in those conversations I’m trying to find those low-hanging fruit and try and solve for them as much as I can. If it’s low-effort, high impact, I try to tackle those first.” — Lizzy Rosen

Less Stress, More Success in Your First 90 days

Starting any new role can be overwhelming. But, when you’re able to lay out a roadmap of key milestones you want to achieve, it can take some of the stress away. It’s also a great way to prevent you from diving straight into shiny object syndrome (at least from day one).

If you’re keen to learn more about how to be a great Customer Success leader, check out the Success/ful podcast to learn directly from incredible industry leaders and their experiences.