The Primitive Podcast - Chief of Staff Edition: Renee Weber

Posted by Buffy the Bison | June 28, 2021

Gravy Chief of Staff Renee Weber

Does the chief of staff role have tight guidelines? Do you need specific strengths? How do you even get there?

As Primitive’s Chief of Staff, Annie, discusses the up-and-coming role with Renee Weber of Gravy, you might be surprised at how unique, and necessary, this position truly is. 

Connect with the folks behind the episode: Renee Weber and Annie Gilbert 

Annie Gilbert: Thanks for joining us for this special episode of The Primitive Podcast. I'm Annie Gilbert, chief of staff at Primitive and back again as the guest host. And we have Renee Webber, chief of staff at Gravy. Renee is a connection that I met through LinkedIn, and I've learned so much from her over the past month. And I know that you'll learn a lot as well about the chief of staff role and what it looks like at Gravy.

Renee Weber: Every 90 days within Gravy, we lead our team through something called decade of destiny, and it helps us focus on 90 day chunks. And so we say, "What do you want your life to look like 10 years from now?" And you paint just a really vivid picture of what that looks like in your relationships financially, health, mentally, and walk through the whole exercise, and then you break it down. And so every 90 days is 2% of the 10-year plan. So what do we focus on for that 2%? Creating an intentional plan is the first helpful thing, and then communicating it to other people around me.

Annie Gilbert: This is Renee Weber. And so I met Renee months ago on - through LinkedIn. And her role is chief of staff at Gravy. I know that's not the only role that she has. That's one of her roles and the one I'm most familiar with. And so I've gotten a couple of opportunities to visit with her and so we could just share ideas and brainstorm and learn from each other. And so I would love for you Renee to just tell us a little bit about yourself.

Who is Renee Weber?

Renee Weber: Sure. Yeah. So I'm currently chief of staff. I'm also co-founder of Gravy. And so we're based out of the Atlanta area. Although our culture is virtual, we say our headquarters is Slack. And so we have a great team of about 90 people and I feel super fortunate to be a part of that. And Casey and I actually started working together about 19 years ago, which is crazy and hard to believe. And we've kind of worked in a very similar fashion over those 19 years across different organizations. And so I've always kind of served as the right hand, second - number two, I guess you would say, to him and each of the organizations. And it's looked different as we've gone along and over the years and depending on what business we were in, but that's kind of where we've - where we started and where we've come to.

Annie Gilbert: Absolutely. Well, thank you for sharing that. I remember Kade telling me, "You've got to follow Casey Graham on LinkedIn," and just reading his posts and just learning so much and have continued to learn over especially the past six months from him; lots of strategies. And so we've just loved watching Gravy grow and expand and have celebrated with you guys. Just tell us about Gravy and what Gravy does.

Renee Weber: Sure. Yeah. Gravy is a payment recovery solution for recurring revenue businesses. And so there's this little microcosm in businesses that have recurring payments called payment failure. And so we actually come alongside and serve businesses who have those recurring payments and failed payments and we recover those for them. And so it's been - we're just at four years old which has been super fun to start and grow this business. And so if you have credit cards that you have on file that get, you know, charged every month or every quarter you'll - you know that there is an issue with just those cards not going through and so there's lost revenue, and we help recover that lost revenue for those businesses.

Annie Gilbert: That's great. And tell me - you said four years. And how many employees do you have now?

Renee Weber: Yup. We have 90 team members now.

Annie Gilbert: And you've had tremendous growth just in like the past year, is that right?

Renee Weber: We have, yes. So, you know, we were one of the fortunate businesses through COVID and just the pandemic that we were able to continue to grow. And we raised some money just with our board advising us to push the gas pedal and keep going. And so we have - we've doubled since this time last year. And so we just - we're - we keep going which has been a fun new challenge. That's been something different, you know, for Casey and I, and in this business; it's just the growth rate. Not just revenue, but team and product and the whole bit has been super fun and challenging.

Annie Gilbert: Yes, as scaling business always is, right?

Renee Weber: Yes. For sure.

Annie Gilbert: That's amazing. All right. Thank you for sharing that. And then I know you have these other business endeavors as well. And so, you know, include any of that in these questions as it comes to mind; as it's applicable. We'd love to just learn all we can from you.

The Journey to the Chief of Staff Role


So one thing that I found that people are really interested in knowing when I visit with them about the chief of staff role is they want to know about the journey. They want to know, "How did you get here?" and what my story is. I mean, everybody has their unique story, right? Mine is unique, too. And a lot of educators will reach out to me and they were like, "You were a teacher and now you're a chief of staff. Like, what does that look like?" And so I know a little bit about your journey, too, but will you just share with us about your journey from where you started with career aspirations to where you are today?

Renee Weber: Sure. Well, I'm definitely not doing what I thought it was going to do 20 years ago. You know, coming straight out of college, I thought counseling was going to be my route. So my degree - undergraduate degree - is in psychology. And as I looked into graduate school, I just decided that wasn't for me. And so I started working in the nonprofit space and much, much more administrative in nature is where I began. Of just handling details and managing tasks, and just over the years that has evolved and changed. And so, I mean, honestly how I would say I started is really just more administrative assistant type role. And the more experience I got that my role has evolved and changed along with just the nature of business, too, I guess. 

And so when Casey left the nonprofit space to start a for-profit business, he asked me to come along and just help manage projects and, you know, different things like that. And so that's, that's where the business aspect of things came in. And that was about 13 years ago is when we moved into the for-profit space and started our first company. And him - he's just an entrepreneurial visionary. Like the sky's the limit, has a million different ideas a day which is super great, you know, as you're starting off in organizations. And and so, honestly, just again, moving from the administrative in nature to more helping distill down his ideas to say, "Okay, we're in a business now. Entrepreneurial visionary ideas are great at the beginning, but as you begin building an organization and a team of people, you really kind of have to rein those in. You can't have the next great visionary idea, you know, every single day. It just doesn't work on a team in an organization." And so my role evolved from more administrative things into, okay, let's take the ideas that Casey has and the ideas that he's thinking about, and let's distill it down into what actually needs to take place within the organization.


And so that's where I started to shift and change, I'd say probably seven or eight years ago, into more of the chief of staff role; into helping lead the team and really almost be a translator, if you will, for, you know, what he's thinking and what his vision and what his goals are into. Okay. This is what this means for the rest of the team on a day-to-day basis on a quarterly basis, annual basis - around that. And so it's very much been an evolution of the role from super administrative, very detailed, into as the businesses grew, as the organization grew, the needs changed in terms of just what I was doing. And so I just kinda jumped in and tried to figure it out. There was certainly no training that I went through or anything like that. So, had some good mentors along the way, but definitely just learning as we go.

Annie Gilbert: That's great. Wow. It sounds like you're very adaptable - that you kind of have to be, to be able to change and meet the needs as they come up, and working with someone like Casey, who's very high energy; lots of new ideas, lots of yeah, just really great things that he wants to do better.


I love the word translator, like just being able to translate those into realistic, actionable things that make sense for the structure and what's actually able to be supported by that. So that's really true.

Renee Weber: Yeah.

Being the Right Hand Person

Annie Gilbert: So you mentioned a chief of staff is sort of a right hand person, a number two, someone who, you know, just is really there to identify the gaps in what's needed, and fill in and adjust and adapt. So as far as just the chief of staff role, I know a lot of chiefs of staff that I have gotten to meet and interact with - a lot of them through the round table on LinkedIn, that I also was able to join through you - but what does it look like for you? You've talked a little bit about, you know, that right-hand, that number two that it's evolved into. And I know it can look different at different companies. But for you, how would you just kind of condense that role down for what it looks like for you?

Renee Weber: Yeah. Where I'm at right now and just where Gravy is as an organization, I work - I kind of have two focuses. One is making sure that Casey as a CEO stays on task and on focus in terms of just what only he can do. And so I act as a buffer, really. There's tons of requests that come in for him. And whether it's people internally on the Gravy team or externally from, I mean, private equity firms, to just outside network. And so acting as a buffer with that based on what are his current priorities and what he's looking to accomplish. And so that's number one - working with his calendar and just communication time and projects. And then number two is our work with our leadership team at Gravy to ensure that our strategic planning process is followed and that the strategic plan that we come up with is executed.


And so we look at our business - there's almost like two sides of the mountain. There's the strategy, and then there's the operations. So the operations is more of the day-to-day. The strategy is what are we doing to make Gravy better? What are we doing to make it more valuable, a more solid business, an organization that, you know, people love to be at and that people want to work with? And so I'm focused on the strategic side of the mountain when it comes to that business. And so that's really through our leadership team and working with those key team members who are running those strategic priorities.

Annie Gilbert: Oh, wow. Yeah, that makes so much sense. So it sounds like there's a lot of relational aspects to what you do because you are not only protecting Casey's time and his priorities and taking care of that, you're also serving the other leadership team members. You're serving the organization as a whole and the leaders' share. And I have a feeling that because your initial desire was to maybe become a counselor that there's that, you know, natural skill and talent and strengths in the relational area.

Balancing Strengths and Weaknesses


How do you feel like you're able to use those things and how do they apply in the chief of staff role and being able to be relational?

Renee Weber: Yeah, I think relational is definitely, you know, a key priority for me, in my role and just as a person. And making sure that people have what they need, making sure that they feel equipped and empowered; removing roadblocks and that kind of thing. I think what's interesting, and probably a key to success I would say, is that Casey have very different strengths. And so where he's strong, I'm weak. Where I'm strong, he's weak. And so we compliment each other really, really well in that. And so I would say one of the things that I'm able to bring to the table just in our organization is I would say diplomacy. Again, Casey, you mentioned super high energy. He moves really quickly. He has a billion ideas you know, in the 24-hour timeframe. And so being able to take that, again, distill it down but communicate it in a way that is going to be beneficial for the team and for the organization. He's super relational too, which is fantastic. And so he has just built a great strong culture among our team members, but when it comes down to just getting the work done and being able to diplomatically and sequentially lead the team in different ways that that's been really helpful.

Annie Gilbert: Yeah, that's great. I agree. I think having that balance of strengths is so important with a chief of staff, you know, CEO-type relationship. But also I think about our leadership team and just how all of us really, when we're all together, we cover this gamut of spaces. Whether it's execution or strategic thinking or relationship building or influencing, one of us cannot do it all. But when we work together and we bring those unique strengths together, we're so much better for it. So I completely agree.


What does a day in the life look like for you?

Renee Weber: Well, it's usually never the same. That - it - my day really flows, you know, based on what Casey's priorities are and what his schedule looks like. And so the way that he operates is not typically alone by himself. He "extroverts" is what we call it. And so he verbally is processing things. And so a lot of my day is spent just sitting and processing and working on the next big idea you know, within Gravy, whether it's a strategic direction or a new product line or a new brand message or - we've done a lot of like board decks for different firms and for our board. And so just helping create what that looks like, get it out of his brain, and then bring it to completion. And that's really where I spend a lot of my time. And then in addition to that it's really just the meeting rhythms that we hold.


So we have strategic meeting rhythms, we have leadership team meeting rhythms, and then just meeting with my direct reports every other week is kind of how that works. And then in a lot of areas in the business, as you know, one of the co-founders I do act as a consultant for a lot of different team members. So it's like, "Hey, we're looking to try this." And I'm like, "Oh, well, we tried that, you know, 18 months ago. And it didn't really - it didn't really pan out. And here's why." So, acting as a consultant as well.

Annie Gilbert: That's great. It sounds like you must be very organized and keep it all straight, all going.

Renee Weber: And to your point, no one person can do it all. So thankfully I've got some good - a good team, too, that's helping.

Annie Gilbert: So along those lines of the day in the life. And I can definitely resonate with that, that it's never the same. And that's one of the things I love about it is the variety and the opportunity to get to do different things and be creative, right? What are -what's one of your favorite, and one of your least favorite, things about your role?

Favorite vs Least Favorite

Renee Weber: One of my favorite things, to your point is just there's - I'm always learning something new. I've learned so much just in the last, you know, two years about fundraising. You know, I have a degree in psychology. I was like, I didn't do business. And so learning, you know, different sides of the business has been really fun. I just - I enjoy that challenge of always learning something new. I think one of the things that I dislike, I guess, you know, is just - people are messy. And so trying to manage expectations and, you know, what people want, whether it's from the company or from the team, or, you know, out of the product. And, so it's just - people are messy. I love it. And that's a fun part of it, too. But at the end of the day, when, you know, you're having to make tough calls that impact people's lives that, like - that's hard. And I would never want that to be easy, but just working with the messiness of people; it is a challenge.

Annie Gilbert: Yeah. I agree with that. That's a great lead into my next question, because I do think for me personally, it's one of the things I love. And one of the things that's the hardest about the role is the people aspect. I love people. I love working with people. I love getting to know all different kinds of people from all over the world. It's - I love it. But it's hard because we are so different and because, you know, there are those expectations and there's also just reality of business and hard decisions that have to be made. Sometimes things that are completely out of our control when we think about the pandemic and, you know, just the past year and a half and everything that's happened. But I think that can be one of the biggest challenges and one of the biggest joys which makes it bittersweet sometimes.

Renee Weber: Absolutely. That's right. Yeah. That's what makes it all worth it. It is, you know, seeing people's lives be better and, you know, connecting them with things that make an impact. Not just at work, but you know, in their daily life, at home, and in their careers.

Decade of Destiny

Annie Gilbert: Absolutely. So as far as just thinking about your own personal development and health. I know you wear a lot of hats, you know, like at work, outside of work, there's just so many roles that you have. You're not only a chief of staff at Gravy, you have all these other things going on. So how do you focus on that and prioritize your needs and your personal development and health?

Renee Weber: Well, that's tough. It's definitely a challenge and a battle, but I think just intentionally - one is intentionally just setting...I don't want to say goals, but just a focus for my personal health, whether it's mental, physical, or emotional relational. And so every 90 days actually within Gravy, we lead our team through something called decade of destiny, and it helps us focus on 90-day chunks. And so we say, "What do you want your life to look like 10 years from now?" And you paint just a really vivid picture of what that looks like in your relationships, financially, health, you know, just mentally and walk through the whole exercise and then you break it down. And so every 90 days is 2% of the ten-year plan. And so what do we focus on for that 2% of those 90 days?


And so just creating an intentional plan is the first helpful thing. And then communicating it to other people around me. And so whether that's to my husband or, I even tell Casey, you know, like, "Hey, here's my focus for the next 90 days. Help me make sure that, you know, I prioritize those things." And the other team members around me, too. Just communicating that so that they know, you know, "Hey, if I take a long weekend to take my daughter on a trip, it's because, you know I'm prioritizing that relationship." And so, you know, being able to verbalize that and make it really known is helpful.


And I think it just sets an example of what you want the rest of the team to do around you. And so we try and be super intentional about that. And Casey does a good job in leading out in that way. And so that's just really been a big thing is to communicate having an intentional plan and then just, you know, create the buy-in from other people around. So that there's just a respect and a mutual respect for, you know, what's needed.

Annie Gilbert: That's so great. I think it's so - it sounds so simple and I know it takes a lot of thought and intentionality like you're talking about. But, really, if we can do that and be disciplined to do it regularly; stay accountable to those things that we've identified are important to us and the direction we want to grow. And I think that communication piece, too, is so important because if we just write it down and then, you know, put it away until the next 90 day plan, you know, it's time to make that, we're not really accountable to anyone else to work on that or work toward those goals. So I think that's a really vital piece for sure.

“Are you happy and content?”


So for you, what are some goals and aspirations that you want to grow in? Are you happy and content being in this role? Do you have things that, you know, in the next five to 10 years, that you want to look a little bit different for where you're headed?

Renee Weber: I think for me, I know where my strengths lie and I'm not an out-front, number one person. I can lead a small team of people and that's great, but in terms of, you know, okay, I'm going to go off and start my own thing, or - I just know that's not who I am. I'm not, you know, this outspoken thought-leader. The fact that you're asking me to be on a podcast and do this interview is like a step out of my comfort zone, just because I value being in the background behind the scenes. And so, for me, I don't necessarily see, you know, huge, crazy aspirations to, you know, go be in a fortune 500 company or to, on the further end of the spectrum, to start my own thing. I feel like my unique ability is really to take the vision of someone or something and help make it a reality.


It's almost a problem-solving skill, if that makes sense, of here's the problem it's - we have this idea and we don't know how to make it happen. Well, I have the ability to help make that happen, whether I do it myself or I'm enlisting other people around to help. And so I think for me, I feel comfortable in my skin. I feel comfortable in what I'm doing right now. And just the role that I'm in and I don't necessarily have these huge aspirations of, you know, grandeur or publicity or, you know, any kind of huge platform necessarily.

Annie Gilbert: Yeah, I can definitely understand that. And people have asked me the same thing and I'm like, "You know, I feel like I have my dream job, so I don't know why it would change anything. I can't envision that." And so I think that's a good thing, you know, to be content with where you are. And there's still this room for growth, like you said. You love learning new things, new aspects of the business. And so it's not like being stuck and it's not like we do the same thing every day by any stretch of the imagination. Yeah, we're still getting to learn and grow and press into different aspects, and challenge ourselves and step outside of our comfort zones, you know? And so I think that that's what makes it really a dynamic position where you're able to tap into your strengths.

A Role That Depends on Clarity


I've had people ask me, you know - I'm a licensed counselor and that's one of the reasons that Kade reached out to me for this particular role. And so they've asked like, "Is that part of it? Like, is that something you need to do?" And I tell them, no, not necessarily. Like, you know, whatever your strengths are, they can be applied to this role because it's such a diverse role depending on what company it is. And so I think that that's one of the great things about the chief of staff role is it looks different everywhere. The needs are going to be different and all of the strengths that anyone has, can be applied to any role, really. So because you've been doing this for longer than I have, I would love to know: have you seen the chief of staff role at other companies, examples of like how it maybe has gone badly, how it hasn't been executed well? Or examples of, you know, other places where it has been done really well and you've seen a lot of success come from installing that type of role there.

Renee Weber: Yeah, I think success comes when, you know, you evaluate what the needs of the business are and what the needs of the executive or whoever it is that you're serving. You know, whether it's the president of a university or a CEO of a company or you know, I've seen chief of staffs for even like chief revenue officer or presidents of companies. It's definitely been a role that has become more and more popular over the years and it does - it fits in different organizations depending on the leader. And so I just think the success comes when the leader identifies where they need some complementary strengths to come in and make that happen. I would say, not just in the chief of staff role, but any role is, you know, it's super difficult to come in and be successful if there's not clear outcomes and just clarity on what's expected.


And so I think getting that really well-defined makes sense. And then in, at least in our organizations and the ones that we've done previously, like that evolves and changes constantly. And so we're consistently re-evaluating, okay, what's most important. We just did it today, you know, looking at, okay, where do I need to be spending my time over the next, you know, six to nine months. And so just making sure that there's clarity of what's expected and what does success look like because there's nothing worse than not really knowing and at the end of the day or at the end of the week, just feeling like you're not successful. I feel like that's a miserable place to be as, you know, a team member, whether it's chief of staff or wherever, that making sure that, you know, what success looks like and being able to say, "Yes, I hit it." Or, you know, "Hey, I missed it. And here's why.And so this is what's going to change next week or, you know, next month."

Annie Gilbert: Yes. I love the word clarity and it's such a silly word to love, but I was talking to someone just today about. And I'm, like, clarity and everything just provides comfort. I think it cares for people when expectations are clear. And just like you said, whenever you have identified and talked about what success means, what it looks like, and there's those measurable outcomes, I think that's so important.


So one of the things - one of my just missions that I want to accomplish is just helping people, you know, aspiring chiefs of staff who are interested in, you know, getting on the path to this type of role. Also businesses and companies who are looking to improve the health of their culture and care for their people. Well I just, you know, really am passionate about helping people understand what that looks like. And so I would love your perspective on if you were to encourage business owners or executives to consider creating a role like this in their organization, what kind of recommendations would you have?


Reading Between the Lines

Renee Weber: Well, again, I think it goes back to, you know, what exactly are you trying to accomplish through this role? And then creating very clearly defined success criteria and then there's different temperaments and different types of people that lend themselves to that. And so, you know, if we're specifically talking about helping the culture and the team of people in an existing organization feel valued and, you know, enjoy coming to work and be inspired and even be challenged to, you know, make strides in their career and career development, those kinds of things, you know this is definitely a role that can help do that. And I would say find the people-people, you know, for this role. Find somebody who cares about others, who's empathetic, who is intuitive, who can read between the lines. I think that's super important cause it's tough to get the truth out of, you know, somebody who's relying on you for a paycheck.


They're going to tell you what they think you want to hear. And so to have somebody who's intuitive and can see and sniff that out, you know, if there's something that maybe isn't working is important. I would say, too, having someone who understands your business is important. So whether that's someone who's coming from, you know, other business experience or maybe it's a different type of - if it's a nonprofit, you know, whatever type of organization it is that you know, is looking for this role, just finding someone who can, if they don't know it, can intuitively pick it up and understand. Because that's going to be important to make sure that the business or the organization, you know, reaches their targets and their objectives as well as just the culture and the people.

Annie Gilbert: Absolutely. Those are great that you mentioned intuitive. And it's so funny because speaking of intuition, I did my post on LinkedIn yesterday about intuition and how I feel like it's an underrated quality. But I think it's underrated because it's so hard to measure, you know, and you can't really know until you've worked with someone long enough to kind of build that intuition. But that's funny that you mentioned that. I agree completely.


Well, do you have anything else that you would like to share? I don't have any other questions for you right now, but I would love to just give you the opportunity for any words of wisdom that you want to leave with us.

Last Thoughts

Renee Weber: Yeah. I just – I think one of the things, and maybe this is just comes with age, I don't know, but for me it's been a process and a journey to be comfortable in who I am working alongside a very enthusiastic, energetic, visionary CEO. And me being the very contrast difference of low energy, very calm, you know, there's not a lot that gets me riled up. You know, there for a long time, I felt like I needed to be something that I wasn't. And again, maybe it's just age and just the hard knocks of life, but just honestly really accepting who I am. And so that came through a lot of just work of what are my strengths, what am I good at? What am I not good at? And there's some things that, you know, skill sets that you can develop to help bolster those weaknesses.


But at the same time, it's just like, you know what, I just - I can lead the way that I lead and that's okay. I don't have to be, you know, the rah-rah cheerleader, you know, upfront on this stage to have an influence and a leadership within the organization and the team. And so that's been a good just coming into my own, I guess, if you want to put it that way. But I think, you know, just taking the time to work on you and to evaluate what those are and then accept what they are and be okay with it. And there's just a lot of confidence and a lot of, I don't know, I guess confidence is the word. There's just a lot of confidence that comes in getting to that point in life and just in my career too.

Annie Gilbert: Yes. I love that. I think even peace is another word that comes to mind once you've gotten to that place of, you know, learning who you are and how you lead well, and then accepting it, like you said. There's just a peace that comes with knowing it's okay. And, and it's great, and it's a positive thing.

Renee Weber: Yeah. And just recognizing what are the things that I do want to work on? What do I - you know, what can I develop? There's - that doesn't mean learning ever stops. You know, development never stops, but, you know, I just think leadership looks different based on who you are and that's okay.

Annie Gilbert: Absolutely. It cracks me up every time I think about you're - just Casey and who he is. Or I watch one of his webinars and it wears me out because I'm afraid he's not stopping to breathe as he's talking. And he gets so excited, but he's so similar to Kade. And then, you know, just that balance that we talked about. I think that's really important to find the right balance and you know, having two really high energy people with lots of ideas and lacking the ability to organize and kind of, you know, execute and lacking a translator, can be really dangerous. And so I think that's such an important piece for sure. And it obviously has worked well for you and Casey and all of the businesses that you guys have started. And so I really appreciate you just taking the time, for stepping outside your comfort zone a little bit and, and joining us. And I know that people who are listening will benefit, will really enjoy hearing about your experience and your perspective of the chief of staff role. So thank you so much for joining us. And it was great to see you.

Renee Weber: Yeah, you too. Thank you for having me. And thanks for picking my brain about this. I love it.

<CTA: Hear more about this up-and-coming position with Annie as she discusses the Chief of Staff role with Leticia Saiid of CoNetrix.>

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