Using Technology to Amplify Leadership with Mike Wolber

In this episode of The B2B Leadership Podcast, best-selling author and leadership coach Nils Vinje speaks with Mike Wolber, Chief Revenue Officer at Rent Dynamics.
In this episode...


0:19 - Mike's background - Mike explains his role at Rent Dynamics.
2:59 - First leadership position - What was the trajectory that landed Mike his first leadership role?
4:18 - Capitalizing on the position - Mike considers it the "best and most accidental timing ever."
5:37 - Internal evangelist - How did Mike unify the pre-sales and post-sales side of the business?
7:51 - Identifying holes - How did Mike approach a solution to fixing smaller issues based on a bigger picture vision?
10:29 - Core leadership principles - How did Mike navigate that growth both personally and with the team?
12:35 - From good to great - Mike shares advice for leaders, regardless of their roles.
14:14 - Professional love language - Mike elaborates on why he talks about this regularly.
16:24 - Major organization transitions - What was the driving force behind making the changes?
24:14 - Time auditing - How often does Mike track where his time is being spent?
27:24 - The network effect - What advice would Mike give to leaders to get more support?
29:48 - Mike's advice to himself - What advice would Mike give his younger self?

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Learn more about Rent Dynamics at

Learn more about your own leadership style at:

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Amplifying your own leadership skills is one thing.

Amplifying other people's leadership skills is another thing.

How did technology help Mike Wolber amplify his and other people's leadership skills?

Read on to find out.

Mike's background

Mike Wolber is the Chief Revenue Officer at Rent Dynamics, a property technology company focusing on real estate.

First leadership position

In 2015, Mike left Nike, a worldwide brand with a phenomenal organization and an incredible culture for G5, a start-up company in Bend, Oregon.

What made him do this?

He was at Nike for about five years and always worked in product creation technology. During his stay there, he observed that the technologies that other companies were bringing into Nike were the ones driving the change.

Mike saw this change happening so he got to the point where he wanted to be the problem solver himself. He made an intentional decision to step into a technology company so he could become that problem solver for other small and big-sized companies.

He joined G5 in April 2015 and within about 3 months, G5 transitioned from being a startup to being a scale-up. Mike happened to be at the right place at that time so he capitalized on this incredible opportunity.

Mike considers it the "best and most accidental timing ever."

He started as a sales engineer and within 18 months, he landed his first people leadership position. He became the director of a team of 2 which he scaled to a team of 12. Within three years after that, he became the second-line leader over an organization of about 80 people.

Capitalizing on the position

How did Mike capitalize on his position?

Mike's biggest core value and philosophy which he has developed over the years has been understanding how to best serve customers. If you understand your customers at scale, you will understand how to win the market. Your customers are a representation of the market.

When you're trying to grow a business, you have to keep retention in order. One of the keys to Mike's success was to identify the holes in the business and become that problem solver that has a big heart for multiplying people around him.

Be an internal evangelist for the things you could do better to positively impact revenue, internal morale, and to aid and grow the business like you wanted to.

Internal evangelist

A lot of times there can be tension between what happens on the pre-sales and post-sales side of the business. It can be a challenge to align these two.

How did Mike manage to unify these two sides of the business?

The role design played a big role for them. Instead of calling their sales engineers, "sales engineers", they call them "solutions engineers'' and they spread them across sales, implementation, and account management. This team cared just as much about winning the deal as they cared about the customer's success.

Mike has developed this heart and passion for winning on both sides of the coin, which became an opportunity to help make sure that his executive team that was senior and sometimes a little farther from the customer, could also understand some of the challenges that the business was having.

Being able to identify the holes in a business is a key element of being an internal evangelist.

Identifying holes

Mike shares an example of some holes that he saw and fixed.

Lots of technology companies struggle with this internal morale and conviction that their product is amazing and assume that their customers are going to find the value in it on their own and they're going to be raving fans and advocates.

Mike is making sure that Rent Dynamics has a plan and a strategy in place, not just for the CX organization, but for the whole business to operate under this notion that they're all in the job of turning customers into advocates and raving fans.

It's important to make sure that the few customers who become the many customers are what you take care of first.

Core leadership principles

One of the core leadership principles Mike learned from G5 that paid dividends for him and for the people he was responsible for developing was tactical and technical relevance that he had in the business and being able to multiply that.

Mike has a heart for helping people get to great and become better than him. He wanted to have an army of people that are technically relevant and understand how they win and retain in the business.

From good to great

Mike shares advice for leaders who are not sure how to help their team get from good to great.

One piece of advice he has for any leader is to seek feedback early and often.

If you're stepping into a role for the first time, be specific but intentional about seeking feedback, and reduce your ego as much as possible, so that you can incorporate that feedback, because it's one thing to ask, and it's a whole nother thing to take action.

Professional love language

Mike talks about professional love language all the time.

Back in 2013, before he got married to his wife, they read this book called The Five Love Languages. It's all about understanding how you and your partner give and receive love. The way you want to be loved may not be the same way she wants to be loved.

Mike has the same kind of analogy in the workplace which is that he knows what his career aspirations are and he knows how his bucket feels full at the end of the day. He's also aware that the people around him may have different kinds of bucket inputs.

To understand your people, recognize that the way you approach a situation is not the way that somebody else approaches the situation and the way you like to receive recognition or feedback is not the same way that everybody else does.

Ask the people you work with. However you do it, be intentional. Be courageous and vulnerable. If you do this, you can cater your leadership style to how people want to be managed, which goes a long way.

Major organization transitions

What was the driving force behind the major organization transitions Mike had?

One of Mike's mentors shared that his career philosophy had been built around this notion of designing himself out of his job. Making the people around him capable of doing more than everything, removing his ego, and believing that when he designs himself out of his role, the next role will be there.

This idea became Mike's obsession. He started owning it. He wanted people to do better than him and they did. He hired his successor and then was offered the CRO position at Rent Dynamics because they had seen the growth of G5.

If you want to design yourself out of your job but you are not sure how to go about it, just do the work that's expected of you first and spend the rest of your time doing the fun stuff.

It may get a little scary at first but once the system is running, there may not be enough other things to focus on in your organization. So you have to supplement with other growth areas outside of your core role.

As a leader, you have to foster that belief within your team and the people that work for you because you don't want to create a group of individuals who are in their roles and think that they're the only people who can fill their roles. That's just not true because people leave organizations all the time.

Time auditing

Mike doesn't do time auditing because he is a goal-driven person. On top of that, he also works for a CEO who's helping him realize where he should be investing his time to get the lift that Rent Dynamics needs out of him, and also how he can raise the boats of the people that he's responsible for.

His CEO guides him through questions and doesn't tell him what to do. He's helping Mike do it on his own because he knows that Mike wants to feel like it's his own fingerprint, even if it's his CEO's fingerprints, to begin with.

The network effect

As you grow and progress through leading various leadership positions, it can be hard to find an appropriate outlet or find others in your organization that you can lean on, where you can openly share the challenges that you're going through without fear of either sharing too much, or sharing something that's inappropriate.

Mike shares advice for leaders at any level to help them with the network effect whether it's coaching or peer group.

As a C-level officer himself, it's his peer group. If he's not connected to his peer group, unable to disagree, commit, and talk through the things that matter, then he's on an island.

It's important to have a highly functioning executive team.

One of Mike's biggest personal goals was helping shape the dynamic in their executive team. He does daily touchpoints with his executive team and it is the biggest reason that his job satisfaction is high right now. Even though they have different opinions, directions, and feelings about what is going on, they have that common bond that plays a huge role in wanting to stick around.

This applies to any leader regardless of if you're talking about your peers or your executive team.

Mike's advice to himself

If Mike could go back to the earlier stage of his leadership journey, he would tell his 27-year-old self this core belief to embrace this internal mantra that everyone around you is making it up as they go.

When you join a new company, or you step into a new role, you feel intimidated because you assume that all the people around you have the answers, or they've been there before, or if you speak up, it's not going to be well received.

There may be a lot of people who have experience at bigger companies or they've done the playbook before. But, for this exact problem that you're trying to solve right now, there's a good chance, it's their first time dealing with it too.

There is no playbook for that. You have to do the right thing. You have to be the first or the second person that raises your hand. That neutralizes the intimidation factor of stepping into a new company or new role.

People who have high convictions can have higher confidence. If you think everyone's making it up as they go, you can step into any situation with a good peer group, find a mentor, and take action to make things happen.

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