Strategic Partnerships in Action: Jean Patrick, CEO and co-founder of ScaleUp Edge, with Chief of Staff Rory Hibbler

In this series, Strategic Partnerships in Action, we highlight some of the Executive and Force Multiplier duos who are doing it right. This week, we chatted with the powerful strategic partnership behind ScaleUp Edge.

Jean Patrick and Rory Hibbler began their strategic partnership about eight months ago at the start of ScaleUp Edge – an exclusive community for ScaleUp Stage C-Suite executives, advisors, and investors.

Jean is a strategic C-level executive who brings a breadth of knowledge from a variety of industries to build, scale and transform organizations from small to large public companies. She is known as a goal-driven leader who is not afraid to take on hard initiatives and has proven success in developing business strategies to drive growth and streamline processes. Jean leverages her extensive experience in strategy, operations, and client account management to transform underperforming or failing businesses into profitable performers, accelerating automation and leading through significant changes from startup to repeatable and scalable organizations.

Rory began her career as an Executive Assistant to CEOs of early-stage technology startups who are building from the ground up to raise their first institutional funding. Interested in the investment side of this ecosystem, she started working with Shelley Perry to help her set up Scalelogix Ventures, a boutique investment firm specializing in incubating companies in the ScaleUp stage of growth. As Rory learned more about the ScaleUp Stage of growth, she recognized that her skills in the early stage would be greatly beneficial to one of the companies they incubated and jumped at the chance to be a part of the ScaleUp Edge team with Jean Patrick. It was a great transition as it helped Rory to leverage her expertise in startups while continuing to learn the intricacies of SaaS ScaleUp.

Hallie Interviews Jean and Rory About Their Strategic Partnership at ScaleUp

Could you tell us about your position within the company and the primary responsibilities in each of your roles? 

Jean: I am the CEO and co-founder of ScaleUp Edge. My primary responsibility is to build the strategy, the team and set goals that align with the strategy. Additionally, “roll up my sleeves” and deliver on items as required as we build and grow. Lastly to monitor how we are doing against our strategy whether it is short-term or longer. As part of the startup, the short term is key, and the ability to quickly adjust the strategy as we find product and market fit.

Rory: I am the Chief of Staff at ScaleUp Edge. My primary responsibilities are to ensure that all of our projects on the table are moving forward. Since we’re a small team that tends to work a lot with outside contractors and within other companies, a lot of my role is coordinating with those surrounding ScaleUp Edge, making sure everything is running smoothly, and tracking resource allocation across all fronts for Jean.

What have your career paths been and how long have you been working together?

Jean: I have been part of a number of different industries and organizations. I tend to lead teams that are asked to build, fix and/or grow specific business areas. I have been part of a number of industries that include services, consulting, technology, telecommunications, education. I have had titles that included instructional designer from my very early days to general manager of a software development company, operations executive for a law firm, senior director of one of the largest outsourcing services companies, director of learning and organizational development of a start-up telecommunications company, chief of staff to chief transformation officer for a scaleup technology company and many operational focused roles. I have run over a $100M services division to a scale-up technology division where I was responsible for 30% of the company’s portfolio.

Rory: I began my career as an Executive Assistant to CEOs of early-stage startups, building from the ground up to raise their first institutional funding. Interested in the investment side of this ecosystem, I started working with Shelley Perry to help her set up ScaleLogix Ventures, a boutique investment firm specializing in incubating companies in the ScaleUp stage of growth. As I learned more about the ScaleUp stage of growth, I recognized that my skills in the early stage would be greatly beneficial to one of the companies we incubated, and jumped at the chance to be a part of the ScaleUp Edge team with Jean back in July of 2020. It was a great transition as it helped me to leverage my expertise in startups while continuing to learn the intricacies of ScaleUp.

Successful strategic partnerships look different for everyone. What is the one thing that makes the partnership between you work? 

Jean: Those strategic partnerships that have been the most successful for me is to look at these partnerships as an extension of your business and/or your team. The more open and transparent you are with these partnerships, the more successful you will be.

Rory: I think the ability to have open and honest conversations. In this early stage there’s a lot of unpredictability. I personally love getting to build and take risks in the “unknown” but I think it only works if I’m working with a leader who is willing to hear feedback and adjust as we go. There are no guarantees in early startup, so you have to have a foundation of vulnerability to hear the truth of situations in order to be able to respond quickly and effectively. 

Communication is a common challenge between leaders and their Chiefs of Staff. What communication failures have you had, what lessons have you learned, and what systems have you developed for communicating effectively? 

Jean: I think I tend to learn about communication both what works and what doesn’t work well every day. There are times that I think people understand or recognize what I am trying to communicate or accomplish but we move so fast in a startup that assuming the message is understood is a big downfall for me. I hold myself accountable for these assumptions and work to make sure there is clarity in the message. Having a daily standup, one-on-ones, and sharing the ‘why’ is important for clarity and understanding.

Rory: While not necessarily a failure, the fact that we are remote-only is a huge challenge. We’ve had a few outdoor working sessions at Jean’s home in Colorado but for the most part, we’ve been building this company as a dispersed team. This has created missed opportunities for the ability to brainstorm together or have those deep discussions on moving forward that I think are so crucial when you’re working in the ‘unknowns’ in the early stage. 

I’ve learned the importance of continual communication when there’s the absence of in-person. Even if it feels repetitive at times, having daily standups and at least weekly one-on-ones to ensure everyone is on the same page has become crucial for us and our team. Putting in place these regular meetings and making it a daily habit to check in with each other has been the best system we’ve found for effective communication. 

What are the biggest challenges you have working together? 

Jean: One of my biggest challenges is related to prioritizations. There’s so much to do in a startup but what is the biggest “rock” to focus on to keep momentum? Focus is always a challenge. Between Rory and I, I believe my biggest challenge is communication. Being remote and new to the company and working with Rory, we have had to create an understanding of each other in a remote environment. Rory is a great person, driven, and an incredible professional and I am so fortunate to have her on the team. She is not afraid to speak up when she doesn’t understand or more often to make sure I provide clarity or another point of view.  

Rory: For me, the biggest challenge has been managing the balancing act of startup start/go with projects. In these first few months of a company, it’s a constant juggle between starting new projects to see if they are the ‘golden ticket’, executing other projects already started, and knowing how to stop or say no to projects that might not be taking the company in the direction it needs to go. ScaleUp Edge also has multiple stakeholders involved and there are many directions we can take things within the company, and I think getting alignment sometimes on what to start, what to move forward with, and what to stop can be difficult. Since it’s all somewhat in the ‘unknown’ of what will thrive and what will grind, there are oftentimes no right answers. I think overall Jean is an amazing leader to work with in this environment, but when mixed with remote-only work and the unprecedented global challenges we are facing, we’ve had to learn to be comfortable with being uncomfortable.   

What’s one thing that comes easy to you both when it comes to working together?

Jean: Working on the ‘hard’ items… things aren’t always easy, but Rory has such a knack and a creative mind that she isn’t afraid to take on the big challenges in working together.

Rory: I think our ability to have fun and be relaxed with each other. We’ve built a great relationship and she truly is one of the best bosses I’ve ever had. I feel comfortable being vulnerable or honest when I need to, as well as that I have a lot of independence and trust in my role to make decisions. Even when things are stressful I’ve always walked away from our meetings with a smile on my face and felt like I was heard and respected, and that’s one of the greatest things about working with Jean. 

What is one of your proudest moments or achievements while working together? 

Jean: There are many in the short time I have been part of the company and working with Rory. From working together on a solution for a CEO that is scaling and helping drive results for him to supporting a larger client of ours that is needing to transition into successful scale-ups.  

Rory: A few weeks ago we did an all-hands meeting and I had put together a deck of what we accomplished since August. It was pretty eye-opening to see the amalgamation of what our small but mighty team had built in just a few short months. Looking at the sum of it all, from content created, community built, contracts signed, and foundations set for a company that interrupts such an established industry, I felt this huge sense of pride. It was a massive amount of work done by just a few people and with Jean’s amazing orchestration. 

What’s one thing that others would be surprised to learn about the both of you and/or your partnership?

Jean: How well we work together. There are a “few” years between us but the experiences, patience and ability to push each other to grow is so refreshing to me.  

Rory: Probably our sense of humor. The two of us have a very similar but unique sense of humor. I remember one time we were in a meeting with a third party and there was something Jean and I found really funny but nobody else seemed to notice, and we managed to exchange one of those ‘Jim from the Office’ knowing types of glances through Zoom at one another and smile, which I didn’t think was even possible to do in a fully remote meeting, but there you go. 

What’s one piece of advice you would give to leaders/CEOs? 

Jean: Understand your individual challenges and strengths and your individual team’s strengths and areas of opportunity. Once you understand that, fill in each other’s gaps with the other’s strengths. The team will be so much stronger. When the team is so much stronger than individuals, you can accomplish so much more.

Rory: The power in vulnerability. Jean is one of the most impressive CEOs I’ve worked with, but she also is the most humble. Her ability to let go of any ego and be open with the team makes it an environment that you want to contribute to and give it your all. Working with someone who takes a ‘servitude leadership’ approach allows you the space to contribute and take ownership alongside them, which I believe makes the entire organization more successful. She never wants me to come to her with a question but rather with a recommendation to then have a conversation off of which is really empowering as well as effective for moving things forward. 

What’s one piece of advice you would give to Force Multipliers/Chiefs of Staff? 

Jean: I have two, focus on the results and listen. The role needs to be focused on what the company or executives need to deliver on the strategy and results. Listen to the needs of the company and the team members. CoS is a role that is the glue that will pull together the needs of the moving parts of the company. Your role is more about how you can help to impact results for the company rather than YOU.

Rory: To learn as much as you possibly can. On the job, off the job, everywhere, all the time. This role is so uniquely positioned, as oftentimes you bridge the gap from the highest decision makers to the boots on the ground executors. I approach every moment in my work as a learning opportunity, as I get to interact with so many incredible people in the ScaleUp/SaaS ecosystem. I also try to use my spare time to network and learn from other Chiefs of Staff or those in similar positions, to bring additional learnings into my job. 

What books have had the biggest impact on your personal or professional life? 

Jean: Getting Naked: A business fable about shedding the three fears that sabotage client loyalty, written by Patrick Lencioni. His books are so easy to read and very practical. This book speaks to me about being a person and “solving” problems for your clients rather than “selling”. It is all about the relationship you build with your clients and how you can help each other.

Rory: How to Win Friends and Influence People has had a major impact on both. While I don’t believe in a book telling you to ‘be a good person’ (I think that’s something you should pursue innately), re-reading it every so often I’ve found is just a great reminder of how you can positively impact those around you. Whenever I dedicate time to read through it again, the message becomes top of mind for me. 

What other CEOs, EAs/Chiefs of Staff, or strategic partnerships do you admire?

Jean: I have worked for a couple of incredible CEOs in my time but the one that I would call out more than others is Sam Gilliland. He is the CEO of Cherwell. His approach is that he gets to know his team and people within the company, is easy to approach, super smart, caring, and has an incredible business mind.  I also admire Rory in her role in a startup CoS.  She is incredibly quick to deliver results and recognizes the need to connect the pieces together in support of the strategy.  She is not afraid to speak up when there are gaps. 

Rory: I admire Brian Rumao, Chief of Staff to the CEO of LinkedIn, Jeff Weiner, a lot. He’s published some really honest articles about his role, his career development, and their relationship. I like that they have the type of partnership that is focused on strategic objectives, meeting results, and helping each other and the company grow. It seems like there’s a lot of trust and independence between the two of them, which is crucial as well for CEOs and Chiefs of Staff to be as effective as possible.

What’s next for you both? 

Jean: Grow ScaleUp Edge to a recognized company within the ScaleUp ecosystem that provides executives whether new or existing to scale up the opportunity to expand into areas they didn’t have the opportunities prior to engaging with our platform or network.  

Rory: While we’re both quite heads down on building ScaleUp Edge at the moment, and loving it, I think next I would like to finally move beyond the early stage. Spending the first years of my career here has given me invaluable opportunities to learn and grow very quickly, but now that I’m working in the growth stage more and more I find myself excited to work in a company that is further along the ‘Scaling Up Process’ so to speak. I would love to have a bigger team to work with and I think it will be great to get to help a larger organization function in lock-step.  

To learn more about ScaleUp Edge and to connect with Jean and Rory, please visit their LinkedIn pages. You can connect with Jean here and Rory here.

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