How to Navigate Two Merging Companies as a Leader with Chad Estes

In this episode of the B2B Leadership podcast, best-selling author and leadership coach Nils Vinje speaks with Chad Estes, VP Customer Success at SaaSOptics & Chargify.
In this episode...

0:20 - Chad's background - Chad explains his role at SaaSOptics.
2:22 - Chad's first leadership position - He was in B2B SaaS before it was called SaaS.
5:02 - Shifting to a new department - How did Chad pivot from product management to services?
6:30 - Chad's second hire - It ended up teaching him a very important lesson.
10:02 - New, improved framework - Chad shares how previous failures helped shape new ideas.
13:54 - Lessons learned in a VP role - New leadership being brought in played a role in these lessons.
19:00 - New, unexpected leadership - What did Chad learn from his previous situation, suddenly dealing with his new leadership role?
24:52 - Navigating two merging companies - What key leadership traits are important for dealing with two different companies that come together?
28:40 - Chad's advice to himself - What advice would Chad give his younger self?

Connect with Chad Estes:

Learn more about SaaSOptics at

Learn more about your own leadership style at:


Get Notified Of Future Episodes Apple Podcasts | Google Podcasts | SpotifyRSS |

This episode was brought to you by B2B Leaders Academy

The cost of not consistently developing your leadership skills is enormous. At the B2B Leaders Academy, you can gain access to monthly leadership training and live coaching.

Being a great leader isn't hard, you just need a guide and the right set of tools. Head on over to and become the leader you have always wanted to be.

Click here to learn more about B2B Leaders Academy.

In the B2B space, mergers and acquisitions are inevitable. If you haven't been through one of these situations yet, you will.

Successfully navigating two companies coming together is no easy task, especially from a leadership perspective.

In this episode, Chad Estes will get you some incredible advice to handle this type of situation.

Chad's background

Chad Estes is the Head of Customer Success at SaaSOptics & Chargify, two complementary cloud-software platforms in the B2B SaaS subscription management space that are coming together.

Chad's first leadership position

Chad has been in the B2B SaaS industry even before it was called SaaS. One of his first leadership roles that's most notable was at a company called Vitrue where he had an opportunity to build the services team from scratch.

How did it happen?

Vitrue needed to make a major pivot at the time as their original intention wasn't working out. So the company pivoted and Chad was fortunate enough to make it through that change.

He was in product management at the time but was asked to change roles to build a services team offering around a brand new product set and a brand new industry that was just forming.

Shifting to a new department

How did Chad pivot from product management to services?

It wasn't easy. They were on the bleeding edge and it was a trial by fire. They were learning as every day went by because they were creating a brand new product. Luckily, they had some really good salespeople and executive team members that have the right connections, so they were able to land Apple as their first big account.

Everything was new but it went well and having that achievement with Apple was able to lead them to some other significant brands. They were developing their implementation and Cloud account management process while iterating with every new account that they earned.

After a few big accounts, they set out to scale their department and how they did business.

Chad's second hire

Chad learned a very important lesson when he hired the second person on his team at the time.

He realized this when the second person he hired wasn't able to fully adopt the process he developed that's been working well for the team. This person was doing a good job and had developed a really good relationship with their customer but Chad being a new manager in his role, wanted this person to adopt the process exactly the way that he had done it. He would always lean into that in their coaching sessions but it wasn't really coming through.

That person did not stay on the team that much longer and Chad regretted the way he managed that situation because that person was successful with their customer. But as things change, it's okay to evolve.

Give your team a framework to operate in but don't micromanage every single thing that they do. If it's working well with them, let your team be creative enough to work within that and be successful.

Failure is life's best teacher indeed.

New, improved framework

Chad shares about the framework he put in place for his team to help them develop new ideas.

The framework consists of a lot of product onboarding like identifying which product they're standing up and which portions of the product they are configuring. It also consists of customer management and approach, timing, frequency, and cadence. What their status updates look like, how often they're touching each customer and are all their customers the same.

Those two things might have completely different outputs, but as long as you achieve your goal, that gives people a lot more ownership of the work that's being done.

Lessons learned in a VP role

Chad shares another important lesson he learned in a VP role at a previous company.

The company he was working for at the time was being positioned for acquisition and he had no idea about it. One day, a new leader was brought in and introduced just immediately before him on the same day in the same way as the rest of his team. Everybody found out everything all at the same time and it was a surprise.

As a leader, this wasn't the best experience to learn about a brand new boss just above you, along with your team. It doesn't allow the previous leader and new leader to develop a healthy relationship when the relationship is being introduced publicly.

It felt awkward for him, awkward for the new leader, as well as awkward for his team. Imagine having been leading a team, and then suddenly, you're not leading it anymore. You then start to question your role.

Even though that happened, Chad stayed in the organization and within a year later, they went through an acquisition and it was good for everyone. However, his relationship with that new leader was never given an opportunity to have a good grounding and good footing. They could have developed a stronger relationship if it was not introduced publicly.

New, unexpected leadership

What did Chad learn from his previous situation, suddenly dealing with his new leadership role?

Several years later, he came into a new organization and came in as a new leader who will be taking over a team that had an acting team leader. He found himself in that same situation he was in before, where the roles are just reversed. He's now the new leader coming in.

After having gone through that previous situation, he didn't want that to happen again, especially since he knew that the acting team leader was being shipped into a different role, and still would be at the company. So he requested to be introduced first with the acting team leader to establish a relationship privately before starting his new role. And it went well.

The acting team leader was very thankful for that. He was able to position things with his team in advance. And when Chad showed up, it wasn't a surprise for anybody. There wasn't that weird, awkward air in the room of what was going on and they were able to just start off clean.

Not only did it help at the beginning, but it was also helpful as they continued to work at the company. Both of them were still at the company years later, and the acting team leader at the time plays a new critical role, who handles all kinds of things that help deflect things from Chad's team. They continue to work in partnership, constantly.

Had they not built that good relationship then, who knows what would be their cross-department leadership situation. Just like the golden rule, if you were in the other person's shoes, how would you want to be treated, and even if that person isn't going to stay in the company, you never know where they go.

No matter what industry you're in, it's always a small world. That person might end up being a customer one day, and now you're the vendor and they're the customer, or in some sort of partner relationship, or just multiple companies down the line, you end up working with them again, who knows. So just play the long game.

Always remember that even though the decisions can be made out in the open, there's always somebody behind it, an advanced notice or one on one connection is always going to pay huge dividends down the line.

Navigating two merging companies

What key leadership traits are important for dealing with two different companies that come together?

As the Head of Customer Success of two different companies coming together, Chad says there's a lot of things involved as they're trying to come together as one team, one company, and one product set.

Even though everybody in the B2B SaaS world is building software, it's the people that build and support it. So just always focus on people first and make sure that you're encouraging team members to grow.

Look at it like, who's leaning forward, who's already asking for more, who's demonstrating that they're going above and beyond their specific role, and who's making other people better around them. You always need to look at the people and the process, as they're always in the constant state of iteration.

There's always a new version that you can do better but always remember that even if you can come up with a new process, if your team doesn't adopt it, it doesn't matter.

As a leader, you need to set up the framework for your team to operate well within removing obstacles but your team is also depending on you to develop the relationships and the cross-department processes that they need to be successful. So a big part of your role is to make sure you're really leaning in with other department leaders to optimize as well.

Chad's advice to himself

What advice would Chad give his younger self?

He would tell himself that how you approach things a lot of times depends upon what company you're at and at what point of maturity it is.

If you're at a mature company, you should be playing the long game, you should be making decisions that are all about scale. But if you're at a startup company, sometimes you just need to get the thing done in order to make the first few customers successful. You really need to be honest with yourself about what is that inflection point where your approach needs to be scalable at the very beginning.

If you can't make those first few customers successful, then you don't have anybody else to point to. So at the very beginning, it has to be manual and that's okay. You need to be okay with that and just look for that inflection point on when scale really does matter and not wait too long to make that decision. If you go too long manually, as a leader, it becomes a greater problem.

To find that inflection point, you should have good cross-department relationships first. So, develop good relationships with those departments that are upstream from you.

Turns Your Leadership Challenges Into Success
Leadership Success Blueprint
© 2024 LeadershipMBA. All Rights Reserved.
© 2024 LeadershipMBA. All Rights Reserved.
75% Complete
Almost there! Please complete this form and click the button below to gain instant access.
Get the PDF Transcript and Podcast Resources
Your information is safe and will Never be shared