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“We need to be thinking about more widespread leadership training and education for women.” with Jason Hartman & Karri Callahan

We need to be thinking about more widespread leadership training and education for women. There are challenges that are a reality for females as we advance professionally, and increased preparedness and skillsets to overcome those challenges would be beneficial. I had the pleasure to interview Karri Callahan. Karri oversees all finance, accounting, tax, treasury, investor relations, […]

We need to be thinking about more widespread leadership training and education for women. There are challenges that are a reality for females as we advance professionally, and increased preparedness and skillsets to overcome those challenges would be beneficial.


I had the pleasure to interview Karri Callahan.

Karri oversees all finance, accounting, tax, treasury, investor relations, legal, compliance and risk management functions at RE/MAX Holdings, Inc. and its affiliated companies, including RE/MAX, LLC and Motto Franchising, LLC. As part of the executive leadership team, Karri plays a key role in the development and execution of major strategic initiatives.


Thank you so much for doing this with us! Can you tell us the “backstory” about what brought you to the Real Estate industry?

Icame to RE/MAX from Ernst & Young with more than 12 years of accounting and auditing experience joining the RE/MAX team as a Senior Manager of SEC reporting. Working in the audit practice, I spent a lot of my career working with public companies. When RE/MAX was pursuing an Initial Public Offering of RE/MAX stock, I saw it as a great opportunity to join the global brand. It was around that time that I also had my second son and the RE/MAX culture and support of its employees aligned with my professional and personal goals at the time.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

One of the things I am most proud of is that I’ve been able to develop and mentor teams that can continue to run without my guidance. Some of the best advice I’ve received is that you’re in the business of replacing yourself. Being replaceable doesn’t mean that you’re going to leave or someone will be pushed out, it means that you’re going to take on different responsibilities, continue to grow and be given new opportunities. It’s a mindset I constantly try to employ in myself and it’s how I’ve been able to build a highly functioning and talented team of people across different backgrounds and diverse skillsets who have the ability to step into various roles. It’s a lesson I am proud to have learned and try to pass along to others as much as possible.

What do you think makes your company stand out? Can you share a story?

Ithink the gender diversity at RE/MAX makes us standout even more so because it is ingrained in who we are. In 1973, Dave and Gail Liniger, two young, ambitious professionals, set out to build a new company that would operate differently than competitors and ultimately disrupt the real estate industry as a whole. The company was built on the backs of people from all walks of life and backgrounds, and it’s a culture that persists at the company today. Two of our four C-Suite executives are female, 40 percent of our board is female and even at the network level — we’re close to 50/50 in terms of agents and franchise ownership. RE/MAX doesn’t talk about it being important, the company demonstrates that it’s important.

What advice would you give to other leaders to help their team to thrive?

One thing I feel is really important is to praise publicly and provide constructive feedback privately. I think it’s an incredibly important aspect of building a highly productive team. The other component is having and effectively communicating what your expectations are upfront. I have very high expectations for my team and because of that, there are often very few surprises. It’s also important to reward people for achieving those high expectations both in compensation and in opportunities for them to continue to grow and refine their skills.

Ok, here is the main question of our interview. You are a “Real Estate Insider”. If you had to advise someone about 5 non intuitive things one should know to succeed in the Real Estate industry, what would you say? Can you please give a story or an example for each?

  1. Relationships are everything. The RE/MAX foundation is rooted in entrepreneurship and relationship building is a core component of being successful. The relationship I think of most fondly is the one I have with Dave and Gail Liniger who supported my development and growth at RE/MAX to become the Chief Financial Officer in 2016 with their confidence and assurance in me guiding me forward.
  2. Never stop learning. It’s important to have confidence and take more risks because things tend to pan out in the aggregate. Following our IPO, I had the opportunity, with the support of the executive leadership team, to support the leadership team with the launch Motto Franchising, LLC (Motto Mortgage), an innovative mortgage brokerage franchise and the second member of the RE/MAX Holdings, Inc. The brand, launched in late 2016, continues to innovate the mortgage industry and garner attention for its exceptional growth. It was a fantastic learning experience and I was able to apply what I learned to the 2018 acquisition of booj, an award-winning web development and software firm, and the 2019 acquisition of data science startup, First.
  3. Don’t be afraid to do things differently. Dave and Gail deconstructed the format of a traditional brokerage, identified areas of unfairness and crafted a brand-new business model that prioritized the professional and financial well-being of the real estate agent — as well as the experience of homebuyers and sellers. I try and keep the Linigers’ vision at the forefront of my mind as I begin each day.
  4. You are the company you keep. Surround yourself with a healthy mix of like-minded individuals and people who stretch you to think beyond your own constraints. In a network with over 125,000 agents and more than 500 HQ employees, I am fortunate to meet and work alongside people who have the same core values and yet challenge each other to continuously improve and innovate.
  5. Don’t change who you are to be successful. I accepted the position at RE/MAX because it met both my professional and personal requirements when l was looking to take the next step in my career. Being adaptable is a great trait to have, but it’s important it doesn’t override what is really important to you.

Are you working on any exciting new projects now? How do you think that will help people?

Werecently launched a new RE/MAX Real Estate Search App and REMAX.com powered by booj that are designed to improve and streamline the homebuyer experience. The app is meant for the homebuyer on-the-go who craves the convenience of an app paired with real-life agent guidance every step of the way. For agents, the tool is also agent-branded so agents can better establish their business with current and prospective clients. The tools are about relationship building, sustaining and serving the customer with the best agents and technology in the business.

In December 2019, RE/MAX acquired data science startup, First, which is a company that leverages data science, machine learning and human interaction to help real estate professionals better leverage the value of their personal network. I believe this is a game-changing service for our already-productive agents and I can’t wait to see the impact the First platform has in helping to grow individual agents’ businesses.

We are ‘Customer Obsessed’ at RE/MAX and these two tools will help us better serve homebuyers and sellers as well as our vast network of self-starters and business owners.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Prior to joining RE/MAX, one of my most impactful mentors was a partner at the firm that I worked for. He always pushed me to take on new opportunities and when my gut reaction was to say no, he encouraged me to say yes. I think, especially as a female leader, that is a really important lesson. From what I’ve seen, there is more of a bias to say no, and not take as much risks, and having people surround you, who will encourage you to step outside of your comfort zone and take risks, that’s crucial.

At RE/MAX, without a doubt it was Dave and Gail Liniger. Dave approached me with the opportunity to rise to the role I am in and he basically said, “you can do this — and we will support you every step of the way.” Without a shadow of doubt, his encouragement and support has been everything.

The Real Estate industry, like the Veterinarian, Nursing and Public Relations fields, is a women dominated industry. Yet despite this, less than 20 percent of senior positions in Real Estate companies are held by women. In your opinion or experience, what do you think is the cause of this imbalance?

Fortunately, RE/MAX was co-founded by Gail and historically, this imbalance is not something we’ve seen at this company. Outside of RE/MAX, I think this imbalance is rooted, for better or worse, in life choices. I very much made a life choice when I first came to RE/MAX to take a more horizontal career move because I had just had my second child. I was able to grow and continue my professional development here which led me to the path of becoming Chief Financial Officer, but at the time, I needed to prioritize my family. I think female career paths tend to look more like a flight of stairs whereas male career paths tend to have a more linear trajectory. I think we have to all think about what opportunities are out there and how we can help equalize the balance for males and females.

What 3 things can be done by a) individuals b) companies and/or c) society to support greater gender balance going forward?

  1. Improved maternity benefits are a big deal to me and something I am extraordinarily passionate about. We’ve made steps in the right direction, but I don’t think it’s as good as it can be yet.
  2. Continued flexibility in terms of where and how people work is important. Being cognizant of how those work policies impact peoples’ families will help companies continue to move in the right direction for employees.
  3. We need to be thinking about more widespread leadership training and education for women. There are challenges that are a reality for females as we advance professionally, and increased preparedness and skillsets to overcome those challenges would be beneficial.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

The biggest challenges faced by women executives that I don’t believe our male counterparts face as often is the balancing act and guilt associated with an advancing career. I think male counterparts face this at times, but not in the same way.

I also think that at times, there is a stigma and lack of credibility associated with women leaders. I feel super fortunate that I haven’t experienced this in my current role, but I am always intentional about establishing myself and my credibility because I know it’s something other female leaders have had to overcome in their workplaces.

Can you share 3 things that most excite you about the Real Estate industry?

  1. The pace of change is extremely exciting in this industry. We have a term at RE/MAX: CI/CD — Continuous Innovation and Continuous Development. We are constantly innovating, providing new tools, training and technology to our network to prepare them for today and tomorrow.
  2. Building on the pace of change in the industry, I think we’re about to see a wave of new entrants who join the profession and as that population continues to grow, I think we’ll see increased innovation and news perspectives on how to improve the experience for the customer.
  3. Technology cannot and will not replace the human interaction needed in a real estate transaction but our theory that it can make good agents great is really exciting for business owners and entrepreneurs in the field. The continuous advancement of technology is not only beneficial to those in the profession, but also for the homebuyers and sellers who want to communicate on their preferred channels. Technology is also an important vehicle for improving transparency in the transaction and when we embrace transparency, good things happen.

Can you share 3 things that most concern you about the industry? If you had the ability to implement 3 ways to reform or improve the industry, what would you suggest?

  1. Increasing the barriers to entry for the profession would be a productive step in building business for the dedicated full-time agents in the field and would greatly benefit the homebuyers and homesellers who are seeking a dedicated and experienced professional to manage the most complex transaction in their lifetime.
  2. Because the real estate transaction can be so complex, there are oftentimes a lot of dependencies on technology solutions and task management software. At RE/MAX, we wanted to address the need for a holistic real estate technology solution as a better option to the siloed, one-off third-party solutions, which is why we acquired booj and worked with their developers to build custom technology products tailored to RE/MAX agents’ needs.
  3. We need to keep improving training, talking about and raising awareness of bias and unequal treatment in housing. People need to be educated on unconscious bias. Every year, my team at HQ gathers and learns about unconscious bias through guest speakers, which we make mandatory. I want to suggest we make this a less scary topic to talk about. Let’s drive personal growth in people and take steps to raise the level of honesty, inclusivity and professionalism in real estate.

Because of your position, you are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

Ithink creating technologies and fostering an environment for ongoing training and professional development to enable consumers to have the most seamless homebuying and selling transaction possible, should remain our north star. We are ‘Customer-Obsessed’ at RE/MAX and constantly striving towards perfecting the agent/client relationship so the dream of homeownership is attainable for everyone.

How can our readers follow you online?

LinkedIn: https://www.linkedin.com/in/karri-callahan-5219676a and for the latest news about RE/MAX, please visit news.remax.com

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