Opening Scaling Tension
Most operators frame the hardest part of growth as a hiring problem. It rarely is. The harder problem sits one layer beneath the org chart: the senior people you’ve already identified for bigger roles are trapped underneath the work that made them valuable in the smaller ones. The succession plan is written. The names are in the right boxes. But the person who is supposed to step up still owns the migration project, the compliance files, the multi-state research, the inbox that doesn’t stop. Capacity looks like a staffing question. It is actually a sequencing question. And until that sequence gets resolved, every promotion stalls before it starts.
The Hidden Constraint
In a recent conversation on the podcast, Jessica Malone, COO of the Jimmy Simpson Foundation, described exactly this dynamic inside a small nonprofit administering a lifelong traumatic brain injury care facility. Roughly thirteen people in administration. Most of the rest of the team clinical. Every plate already full. A CFO planning to retire. A financial administrator named Nicole in line to step up. And a pile of tedious but consequential work, including a botched records migration that risked regulatory exposure, sitting on the desks of the very people who needed to move up the value chain.
This is the hidden constraint behind almost every scaling moment in a founder-led or operator-led business. The work that needs to disappear from a senior person’s desk is not the glamorous work. It is the medium-skill, high-tedium, high-consequence work. It cannot be deleted. It cannot be ignored. It usually cannot be automated. And it absorbs the exact cognitive bandwidth the organization needs back in order to grow. Leadership bandwidth is not lost to strategy. It is lost to maintenance.
The Operating Shift
The shift Jessica’s team made was structural, not motivational. They did not ask Nicole to work harder or push through. They added a dedicated, full-time executive assistant and, critically, routed her under Nicole rather than under the founder or the COO. That single decision is worth examining, because it reflects a discipline most teams skip.
When organizations bring on executive support, the default instinct is to attach that support to the most senior person in the room. It feels logical. It is usually wrong. The right placement is wherever the next bottleneck will form. Jessica’s team anticipated that Nicole would be absorbing CFO responsibilities and that her qualifications spanned both IT and financial systems. Placing the EA under Nicole did three things at once: it cleared the work blocking the succession plan, it built a working relationship before the promotion happened, and it positioned ownership of tedious-but-critical workflows in a stable place that would not need to be rebuilt later.
This is the operating principle worth extracting: leverage is placed where the next constraint will be, not where the current title is. That is a different kind of decision than most teams make. It requires reading the org chart twelve to eighteen months forward and putting support in front of the bottleneck, not behind it.
Execution in Practice
A few execution patterns from the conversation are worth naming directly, because they are repeatable.
Map the work before the person arrives. Jessica’s team sat down before their EA started and inventoried what work could move, what required physical presence, and what each team member could hand off. This is the unglamorous step most operators skip. Without it, a new hire becomes a search problem rather than an execution problem. The team that walks in knowing exactly what is going to land on the new desk in week one captures leverage immediately. The team that hires first and figures it out later spends ninety days reconstructing what they should have decided in advance.
Treat tedious work as a strategic asset, not a burden. The records migration project Jessica described would have taken years at ten minutes a day. Done by a dedicated owner, it took weeks. Multi-state workers’ compensation research that would have consumed three months of Nicole’s calendar was completed in days. The point is not speed. The point is that an entire category of work that was structurally impossible inside the existing team became routine once it had a single owner with adequate time. Capacity is not always about adding skill. Sometimes it is about adding undivided attention.
Eliminate the re-decision loop. One of the quieter signals in Jessica’s story is the moment she stopped asking “who has time to do this?” and started knowing the answer was Kaylin. That is a cognitive load reduction worth taking seriously. Every time a leader has to re-decide who owns a recurring category of work, a small tax is paid. Stable ownership of workflows removes that tax permanently. Decision-making frameworks that look sophisticated on paper often matter less than this simple discipline: assign the work once, and stop revisiting the assignment.
Underwrite the financial case honestly. Jessica was direct about the budget logic. For a small nonprofit, payroll is the largest line item, and payroll is more than salary. PTO, benefits, insurance, overtime exposure. When her team compared a part-time in-house hire against a dedicated virtual EA, the math worked in favor of the structural choice that also preserved budget for clinical staff who deliver the core mission. This is capital allocation discipline applied to a staffing decision. Most operators conduct this analysis casually. The teams that conduct it rigorously make better calls.
Leverage Outcome
The outcome Jessica’s team produced was not a faster CFO transition, although that happened. It was a permanent expansion of what the senior team could hold. Leverage, properly placed, does not make leaders work longer. It makes the organization capable of carrying more without routing every decision back through the founder. That is the version of scaling discipline that holds up over years rather than quarters.
Connect With the Guest
To learn more about Jessica Malone and her work: Website: https://www.safehavenjsf.org/
The Immediate Move
The real constraint inside a growing operation is rarely talent and rarely capital. It is the leadership bandwidth quietly consumed by work that should already have an owner. Before the next hire, the next promotion, or the next strategic push, inventory the tedious-but-critical workflows still living on senior desks and decide, deliberately, where they belong twelve months from now. Place support in front of the next bottleneck, not behind the current title. Assign the work once. Stop revisiting the assignment. Structure absorbs effort. Effort does not absorb structure.
Watch this before you hire your next support role.
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Today we’re joined by Jessie Malone, COO of the Jimmy Simpson Foundation, where she oversees operations, fundraising, and program strategy for Safe Haven’s brain injury care work. Like a lot of operators, Jessie reached out a point where follow-ups and scheduling and documentation and email inbox were just eating through hours for her and her team. And in this conversation, she’s gonna walk through what she stopped doing, what her team stopped doing, and what their ultimate executive assistant took over and now owns.
It’s going to be a really exciting episode. It’s great talking to Workergenics clients and hearing their testimony and learning more about their businesses and the important missions they’re doing. Jesse, welcome to the podcast. How are you today?
I’m good. Thank you for having me.
Jessica, walk us through how you came into this role, what journey led you to what you’re doing today.
Well, Jimmy Simpson, I was kind of there from day one. He was my grandfather. I’m the firstborn grandchild. I tell everyone I’m the favorite. but so when we started, when we first opened in 98, I was there sort of helping do some really light clerical work. And then I left for a little while because this was in 1998. I was 18.
And then I came back in 2011 and I came back to work part-time and just doing inventory and helping them keep up with supplies and things like that. And it kind of snowballed because I was finding that once I was done with that, I didn’t have anything to do. So I started asking for more things to do. So after a while, Vicki Hodge, our CEO,
we start talking and she said that the board had asked her to come up with a succession plan and that she thought that I would be a good fit for that. And I was a little hesitant at first because I didn’t know how, my children were still pretty young at the time. I didn’t know how much time I could invest. But I talked to my husband and we talked about this for about a year off and on. And then I finally just decided to
take the plunge. And I went back to school for two years and then went from working part-time to full-time. It was sort of pulled under her to learn how to do what she does. then eventually that led to her saying, I can’t do all of the day-to-day operations and work on expanding. And so she split it and that’s how I came into the role of COO.
Awesome. I love that story. those of our in our audience that maybe aren’t familiar with the foundation and the work you guys do, could you let us know more about the specific mission and ways you help the community?
Yes, the Jimmy Simpson Foundation, we’re a nonprofit organization. oversee the funding and day-to-day operations of a lifelong care traumatic brain injury facility called Safe Haven. We also oversee the functions and operations of a local traumatic brain injury support group called Carol’s Light.
The Carol’s Light is based on a social model we do. We focus on getting people out in the community, doing activities. We’ll go to a ball game, go to a movie. We have a lot of fun with that.
Awesome. I appreciate you sharing that. You guys have been working with a virtual executive assistant with Workergenics for some time now. Maybe you can tell us what were some of the factors that initially had you guys start thinking that maybe getting some virtual executive support for your team might be the way to go.
Well, we’re a really small organization. There are maybe 13 of us in administration altogether. The bulk of the staff here are clinicals. as we were growing, we were figuring out we have these tasks that I didn’t have time to do. And I was delegating some of my stuff already. And then everybody’s plate was just kind of overfilling.
It was about that time that we were introduced through Wade Rowan with Sandler. And you had come to speak to us about the virtual assistant. And we decided to, you know, we’ll give it, let’s try it out. Let’s see what happens. And so we really haven’t looked back. Kaylyn is our virtual assistant and she’s fantastic.
Awesome. And how did you guys think about the structure? Because I know there were like a lot of different ways you could have structured it, whether it was like direct reporting to just you or supporting your team or direct reporting to another one of your team members. What were some of the factors or decision process that you guys considered to come up with what you ultimately decided for her role?
Essentially with what we were going to have her focusing on, the tasks that we were having her working on, it was going to be a better fit for her to report to our financial administrator. our systems financial administrator, because she’s kind of got her hands in IT stuff and in financial stuff. And we knew with the qualifications that Kaylin had, we would probably be pulling her into several of those things.
That’s how we decided to kind of structure that. And so that’s who she hates us to.
Were there any challenges getting started with having a virtual team member? Because before that, of everyone was working in office in person there.
Yeah, you know, I’ll be honest, was a little, it took us, it took a little bit of getting used to because, and it was, I think it’s probably more on our end because, you know, this is someone that you, you, we don’t see and you don’t talk to, um, every day other than, know, the, check-ins, um, which can be really brief so that we know that she’s, she’s clocking in and she’s, know, she’s working on something. She, unless she has a question and, um,
to be honest, I would be like, hey, who’s working on this? And Nicole, who she answers to would be like, would be Kaylin. And I was like, yeah. So that did take a little bit of getting used to, or we would come across something and we’re like, who’s got time to do this? And so Nicole would go, Kaylin. It’s been great.
Thank
So it took a little bit of a mindset shift of like thinking that, you do have this other resource. You’ve got this other team member that’s not in the office, but they can handle certain tasks.
It really, it really did. It did. And I think when we had other people go kind of remotely because to work remote, even, you know, I think it’s just changing your mindset for that sort of thing, because you will forget about someone you don’t see every day. You know, you’re just like, okay, I was supposed to send them that email or, you know, I forgot to send them, I forgot to send them this announcement on what’s going on with like within our administration.
Yeah, the mindset is definitely, but it’s, but it didn’t take too long.
Now, did you guys end up using any different tools or did you have tools already in place for helping with the delegation and assigning of the tasks to Kalin or other team members in your organization?
Well, we sort of just sat down and before she started and we were like, you know, what, what, what are her cases? You know, what are her, where, where are her limits at? Cause obviously she’s not here. I can’t have her really, you know, it’s not like I can’t have her come in and scan things or come in and work on their particular tasks because you have to be present for those. So we’re like, you know, what, what do we have? And we already had a few things.
So we just started kind of, you know, looking around and we’re asking everybody, what, you know, what do you have that she could work on? And we kind of just sort of structured that so that when she did start, went smoothly and we could just kind of add to as
think we lost your video. All right, John, just.
You there, Jesse?
All right, got your back. Did your browser freeze?
It just completely dropped and I was like, my gosh, no, of all the times.
Yeah, it’s all right. The nice thing about this recording service is it saves everything in separate tracks and stuff, so it should be totally fine. We’ll just keep on going.
All right. I’m really sorry about that. Sometimes a downside to working out where we do is we could lose our internet at any point. you just have to sort of reset it.
Yeah, no problem.
Yeah.
Understood, not a problem. All right, so think the question we were talking through was if you had any sort of technology tools or what your process was for managing the different tasks that were delegated to Kalin and the other team members and how you structured that.
Well, a lot of it is like, she has become a great example is that she, we have a system, which is our filing system, our electronic filing system. And that is where obviously, it’s where our charting is going to go for our patients, which, you know, there are state regulations with that. And we switched over and updated our system because we had one that was pretty outdated.
And the problem was when the migration came along to get it all the files from there to the new system, nothing went where it was supposed to. And it was like, it’s going to take us years to get this because, you know, I would have maybe 10 minutes a day to work on it. And, you know, and the others that knew the system weren’t in any better of a position. They had a little bit more time, but not a lot. So.
That was a big thing that, Kaylin was actually very vital in getting like all of our medical records straightened out and everything filed away properly so that it’s easily accessible. Because the state here could come in at any moment and go, I want to see, you know, I want to see your patient files. And we have to be able to just go, here you are. So yeah, she was key in that. And we actually have her working on some of our HR stuff now.
Nice. Were there any challenges with having the remote access to the files and your internal systems for enabling her to do the work that she needed to do?
No, the system is cloud-based, so she had no problems accessing it. We just needed to give her the permissions for it. So, and to my knowledge anyway, there weren’t any issues in accessing that system. So, and I think we’ve got her working on some other things. just kind of keep adding some things, because, you know, straightening out files is a tedious, you know, thing to do.
And we’re like, you know, she’s qualified for more than this. What else can we have her doing? And, you know, that’s why we put her under Nicole to begin with is because, you know, she had knowledge of the financial systems and backgrounds again, and that sort of thing. And it was like, okay, well, let’s have her help Nicole with some of this stuff on that end too.
Yeah. What would you say, or maybe speaking for Nicole, have you noticed any difference in her work schedule or the areas that she’s able to focus on since bringing in the executive support for her and bringing her out of some of those really tedious tasks that you’ve been describing?
Ooh, absolutely. Because maybe a year and a half after Kaylin came on board, our CFO announced she was retiring. Nicole is also part of the succession plan to step up and take over as CFO. So her responsibilities kind of jumped, you know? so, yeah, Kaylin was able to take on a lot.
that free Nicole up to be able to step into that role pretty seamlessly. So I think the timing with that was pretty lucky because she had been with us long enough that her and Nicole were familiar with each other. it worked out really well when that happened.
Yeah, so that’s the one thing too. I guess it’s been almost two years that Kaylyn’s been supporting you guys and
I think she’s been with us for three maybe three
Wow, yeah. So having that kind long-term relationship where she’s understanding Nicole’s workflow and Nicole understands her workflow and that communication, I’m sure that’s really helped with being able to kind of smooth handing off new responsibilities as they come along. Do you have any, maybe has Nicole shared examples of situations where like a new challenge has come up and she’s been able to just kind of trust Kaylin to take care of it?
Yeah, she’s learning to do, she’s definitely learning to do that. She’s giving her, my gosh, just flew out of my head what she had her working on not long ago. she needed to do like some research or some research needed to be done with work comp insurance and some of their laws. And so she just kind of was able to hand that to Kaylin and say, hey, and
I think Kayla got her the laws for all 50 states. and Nicole said there’s, that would have taken me, you know, three months to get done with everything else that she has to do. And Kayla got it done pretty quickly.
Awesome. You kind of mentioned earlier that you have a small team in the office and now some are working remotely. And being a nonprofit, I’m sure there’s budget constraints. What was the budget considerations or maybe some of the benefits of bringing on the virtual executive support to help with the budgetary constraints and maintaining your local staff maybe when there’s some tough financial times or you have to plan out in the future and make budgets for your fundraising?
talk through some of that.
Something that really we took into consideration as far as the budget goes, because, you know, yeah, with being a small nonprofit, then, you know, if you have any sort of loss in revenue that you’re looking at revising your entire budget for the year, you’re just kind of almost starting over. But something that we definitely took into account because obviously payroll is going to be the biggest chunk of your budget.
in that payroll it goes, you know, all of your benefits and any overtime. And so when we were looking at bringing on someone to help us in the capacity that Kaylin does, that is, that’s a big thing that we looked at and it was like, okay, well let’s look at what it would cost to hire somebody part-time and then actually be here or to hire some, a virtual assistant.
And honestly, the virtual assistant that was, came out that it was going to work better for us budget wise. because you do have all of your, know, you’ve got all of the things to consider PTO, depending on what the hours they work. And like I said, there’s, know, there’s insurances and there’s other benefits and that, all goes into that payroll is more than just the salary. And so that’s something that, that helps us a lot.
Yeah, it makes sense and it gives more room to make sure you’ve got the budget for the critical people you’ve got in the office already and making sure they’re taken care of.
Exactly. gives us, it leaves that open for us to have more clinical people who can do, who they do the direct care. And, you know, our mission is to improve quality of life. That’s our mission, the statements. And so it definitely frees us up so that we can focus on that.
I’d love to kind of talk about some of the next stages and looking forward for Safe Haven. What are some of the big projects and initiatives that you guys are working on today?
Right now, of course, we have the two major fundraisers that we do every year, but we have also started adding smaller fundraisers, which are kind of, they have helped out quite a bit. Or rather, maybe it’ll be a virtual fundraiser, like, know, donuts, or it’ll be a spirit night or a give back night at a restaurant where that restaurant will donate the percentage.
And that helps us out with a lot. The give back, not especially, what they do, anybody that’s raised for that goes straight to Carol’s Light, our support group. So, and I think last year we were able to do three, three, and it covered almost the entire budget for 2025 for our support group activities. So we were like, this works. This is great. People respond to it.
So we’ve been focused on that. And then of course, we’re working on expanding our admin team somewhat. cause it’s not, tell people all the time, you know, you’re not going to get less busy ever. This is not going to happen. So, you know, if, you’re a company that’s, that’s growing or you’re trying to grow, I think, I think that’s.
something that’s said for all of us. So you don’t get less busy. So that’s a focus is to sort of expand that a little bit. So, and we have in my way of, we had a lateral movement with one of my organs. She was particularly good at doing the activities and going on outings. And then we found out she was also very good.
share.
at just talking to people and telling them all about Safe Haven and Carol’s Live. So we actually created a position for her and that is her job is, you know, she kind of oversees our volunteers because we noticed we’re getting more and more of those. And a lot of that is because she’s going out there and talking to them. So those are some changes that have happened over the last year and they’ve been all great changes and we’re really excited to see it grow.
Awesome. Well, that’s exciting to hear about all those developments that are going on. And as we wrap up here, if you were talking to another director of a nonprofit or a small business operator and they’re considering, you know, feeling that stress that you guys had originally and bringing on a virtual executive assistant, what advice would you have for them for getting started in that critical first, like 30, 60, 90 day period?
Communication, make sure that you’re communicating with your virtual assistant. It’s gonna make that transition adapting to having someone who isn’t there easier on both ends. it’s gonna make sure that they feel okay if they have questions because they’re not here to see exactly what it is that you’re doing. So just keep that in mind and you’ll be okay.
Well, Jesse, I really appreciate you coming and sharing your story, sharing about the important mission that you’re doing with Safe Haven, the Jimmy Simpson Foundation. If people would like to learn more about the important work you’re doing and connect with you, what’s the best way for them to reach out and follow up?
Thank you. Thank you so much.