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Role Rundown: A Conversation with Simon de Jesus Rodrigues, Chief of Staff at Nested
Sydney Maxwell
, 2nd April 2020
8 min read

Jump to the following questions:

Can you give a quick ‘elevator pitch’ about

Nested was founded about four years ago by Matt Robinson, James Turford and Phil Cowans. Matt (the CEO) was looking to purchase a home and while going through the entire purchasing process he realised that the process itself today in the UK is broken. It's very long and drawn out with poor transparency and that there are a lot of benefits to being a cash buyer, though not many people have the option. One being, you can negotiate better, which is where the concept for the original kernel of Nested was. We wanted to promise home sellers that if we couldn't sell their home in a certain period, we would provide a cash advance upfront of 95% of the value of your property. That way they could break the chain and move onward, and then we would manage the sale for you. 

The vision for Nested today is that we want to be the redefined estate agent. Considering that estate agents, for the most part, just help you with your sale, collect their commission, and some provide some kind of sales progression service to you. Nested is bringing modern tools to the process, a sleek customer journey with a digital experience behind it and a host of other value-add services. One being a buying agent, not only do we help you sell, but we can help to negotiate tens of thousands off of your onward. On top of that, if you ever need it, we always have the cash advance, so you can break your chain and get cash fast. In the next three to five years we’re focusing on home sellers. But the vision is longer-term; five to ten years from now, we will have succeeded if when you want to buy, sell, release equity, anything when you think property, you'll think Nested. 

Can you explain a bit about your background and journey to your current role?

I’d spent nearly three years at Bain & Company in Boston when I decided to move to London for personal reasons. I was weighing up whether to continue with Bain or exit into something new. What it came down to, when I was making this big life change, was whether I wanted to make an incremental change in lifestyle and have the same job in a new city, or make a wholesale change. I knew that I was ready to make a  wholesale change and I couldn’t envision myself progressing up the consulting ladder, so I took a few months off to hike in Portugal and reflect on my plans.

After my trip, I was looking across data science and strategy focused roles, which is when I signed up to Hiperpool actually. I ended up pursuing strategy focused roles at startups, and that’s how I found my first role at Nested in Business Operations (BizOps). I think BizOps is a natural home for any ex-consultant in a startup, particularly a Series B scale-up who's ready for hyper-growth. You bring all of the strategic skills of defining problems, bringing the stakeholders along that journey and then trying to implement a solution that ideally you can remove yourself from. So for someone like me who's thinking, I have this particular strategic skillset, a commercial skillset, I'm interested in startups, I have questions about whether or not I want to be a co-founder or a CEO in the future: this is the natural stepping stone on that path.

I spent about a year in the BizOps role, and did everything from analysis, central planning, helping the Finance function before we had a full Finance team, pricing and discounting work, tweaking the proposition, to execution-oriented support to the sales and agency teams, etc. I enjoyed that for a while, but after a year I realized for my trajectory, I wanted to work closer to management and the C-suite. At the time my manager, the head of BizOps, was leaving and I was the only one in the BizOps team, which created natural vacancies. There was a lot on the BizOps side of the business that I wanted to do and there wasn't a previous Chief of Staff, so I pitched the role to my boss. 

I chose the Chief of Staff role because it's more tethered to the CEO and for my personal trajectory, I really wanted to get more of that CEO, COO exposure. Right now at Nested, we have a lot of really bright and capable managers who are in their first years of managing. Having a Chief of Staff meant that I could go between them offering support and help coach them where possible on things like communication, presentation, structuring problems, using analytics and being data-driven etc. That was a real draw for me as well. [The Chief of Staff title entails] a slightly different platform and to have slightly more authority to kind of guide the business. So when it comes to running a meeting, it’s different than just being the one who's taking notes. I'm the one running the meeting, which has been useful both for my personal growth and scaling myself across the business.

Can you give a brief overview of the core responsibilities of your role as Chief of Staff? 

When creating this role, I spent some time writing the JD and making sure everything was aligned considering it was a new role and our CEO has an executive assistant, which took any admin, diary management and logistics out of my hands. I was able to break down my core responsibilities into five areas:

  1. Conduit to the CEO: Serving as a link between the CEO, the leadership team and the broader organisation. This involves being the earpiece and listening to the rest of the business in ways that he doesn't always have time to. Being a mouthpiece, I relay important divergent opinions on things back to Matt and at the same time, I can spread his messages, design principles or operating principles throughout the business, or sometimes even directly. 
  2. Being a Lodestone: So this is being his analyst, so to speak, at times. If there's a piece of work that needs to be done and he doesn't have the time to do and I can handle it, it will fall into my hands.
  3. Being an Anchor: Being a sounding board and trusted adviser by gathering as much context as I can, running analysis, I can both listen and challenge his recommendations if necessary. A third part to the ‘conduit’, is helping him to think through ideas as much as possible.
  4. Being the Delivery Expert: Ensuring that if we have ten action items coming out of our monthly business performance review meetings, that those things get tracked and followed out within the next two weeks.
  5. Offering ‘People’ Support: The final part is more on the people side. Some Chiefs of Staff have more overlap with a traditional ‘Chief of People’ role or a ‘Head of Talent’ role, our people team today at Nested is relatively small, so I do chip in on the people and talent front. For example, I conduct one of the interviews during our hiring process focused on the values and cultural fit. I also collaborate with our Head of People on ad hoc projects like conducting workshops, aggregating the data will fit into our system, etc.

Can you break down your main tasks and what your day-to-day might look like? 

In terms of the tasks I actually complete, my time is spread across preparing for key meetings, liaising and coordinating with stakeholders, independent ‘IC’ work, and operating as an ad hoc advisor. 

I spend a big portion of my time, probably like 20 to 30%, in preparation for key meetings, whether that's board meetings, or monthly performance reviews, or our weekly operational KPI meetings, for example. A lot of that is organising, making sure everyone has the right materials, ready to task, etc. A good meeting for a Chief of Staff is kind of like a well-orchestrated dance, everyone knows their role, knows what they're meant to say, is efficient, effective and on topic, and ideally, most of the work has been done before. So a lot of time is spent preparing for those meetings, working with the stakeholders and managing our OKR process.

The second bit is literally just being the guy who's going around the office asking questions and listening. Typically, at the beginning of the week in my one-to-one meeting with Matt, we’ll have a shared priority list. He’ll then say, “These are the ten to twenty things that I'm thinking about this week. Can you check in with these five people about this, these two people about this, and make sure this gets on? etc.” Then it’s just a matter of checking in with each of the different stakeholders, asking how far along are they, have you hit any roadblocks, can I help by injecting myself for a little bit? Is there enough organisational resources here or do we need to get more people on it because of this ‘unforeseen roadblock’ that we didn't know about two days ago, etc. That piece is probably another 10 to 20% of the role.

Another 10 to 20% is just IC work. For example, right now, we did a holistic review of our telephony system and we found that our tracking and routing system is not up to scratch. So we need to make a migration from the existing fragmented solution into something more unified. Since there's nobody in the business who's positioned to own that, it will fall on me. I'll get it up and running over the course of the next month, and then hand it off to somebody in the tech team, and another product stakeholder and leave it there.

Finally, there's this kind of ad hoc advisor role where I'll just get questions from around the business. For example, “We need to rethink our sales associate incentive compensation package, can you help me think through what the right comp package should be?” I’ll then talk to the sales team, talk to finance about what's been done, try to get them to make sure we're on the same page to then do the analytics and present something that we all agree on, and roll it out. Depending on where we're at in the hiring cycle, the remaining allocation is doing interviews, going to debriefs, explaining how my interview fits in and what we're looking for in some of these candidates. And otherwise, just trying to bring buzz to the office, take people out for coffees, listening to what they have to say. 

One of the aspects that I find really interesting and also really motivating with the Chief of Staff role is that a significant portion of it is just hearing and listening. Trying to understand where morale may be high or low. Sometimes it feels like gossip, but there's actually a surprising amount of valuable information in that type of meeting. Let’s say we had a tough meeting and one particular person didn't necessarily present their point that well. You can tell there's some tension here or there and immediately after taking a 30-minute walk around the block, grab a coffee, debrief, come up with next steps, etc. That type of stuff is where you can add the most value in terms of it upskilling others and figuring out what the root cause of issues are.

So that's, that's probably a nicely segmented view of how I spend my time. On a week to week and day to day basis, it definitely fluctuates. But broadly speaking, those are the types of things I'm doing. You also need to be available as well to just respond and react whenever the more pressing thing arises because that tends to divert the most attention.

How does the Chief of Staff role vary by company? 

When doing research and looking on LinkedIn for the other trajectory that people take to the Chief of Staff role, I noticed and was surprised that, at least in London, the gender balance for the role was close to 50/50 if not bang on. Unfortunately, this isn’t something you typically notice with the ‘Chief’ title in technology. I was curious as to what made this role the outlier and I think there's kind of two layers to this and in terms of how the role might vary by company:

  • One track is what my role is, being a sort of consigliere to the CEO. You are the shadow, the sounding board, never seen but heard or heard but not seen, however, you want to think of it. More on the strategic and operational side of things is more about process driving and facilitation. 
  • The other track is kind of somewhere between a Chief of People with a little bit more of a strategic angle and a little bit more operational involvement than just what a Head of People or a Head of Talent might do.

So I think that the former is more of a super-powered BizOps associate, and the latter leans on the staff, part of ‘Chief of Staff’. Ensuring that people are aligned or the designs are in the right place. Because in my company, our CEO has an executive assistant, it means that my role tends to be more on the project work, meeting preparation and strategic side of things. This is the track you tend to find the ex-consultant background. Whereas in other companies, you can see the Chief of Staff will naturally pick up more of the admin in terms of determining who needs to be at what meeting, what the schedule looks like, what the meeting cadence looks like, because there's no one person who’s there scheduling what those meetings need to look like and kind of managing the CEO’s diary standalone.

Do you have any tips for people looking to pursue a Chief of Staff role?

There are two aspects to consider, one being what to think about when you’re actually looking for the role and two, if there is a role, how do you know if it’s what you want.

1. Looking for Chief of Staff roles

First, they're hard to find, typically Chief of Staff roles aren’t advertised, and if so, they're probably a later stage company. That role will most likely look different than my role today. So it's tough to find a Chief of Staff role, you might need to find the company, the segments, or a specific stage of company and then see if they need a Chief of Staff type role. Of course, you can be on the lookout, but they tend to not be very well advertised. So that's a bit of a chicken and egg situation. 

Another element in terms of finding and searching is just being very forward about what the company is looking for in that role. In the past, I've heard uncertainty around whether the team wanted a Chief of Staff or a Head of Operations or whatever what it may be. Titles can be exceptionally malleable, and Chief of Staff is definitely subject to a good bit of title dilution and inflation. You’ll want to be very proactive in asking what the role entails, which may feel weird because you think you know what it is, but it's very easy to get misaligned.

2. Determining if a role is the right one for you

In terms of choice, what I would advise the most is that this is a relationship-driven role more than any other role. You need to love the person you're reporting to and get really close to them. Your effectiveness as a Chief of Staff will hinge on your ability to shadow and absorb as much of your CEO, COO or whoever you’re reporting to’s life, thought process and all of the context that goes into their role. Ultimately, your job is to make them a superhuman, to take things off their plate, be places they don't need to be, make decisions that they would make with less information than you may like. It's kind of like if your CEO is the brain of the organisation, then you need to be the central nervous system and make sure the body is working with the brain.

If you find a role and you’re trying to scope it out, write out the JD and talk about the JD itself to be super aligned on what it is, otherwise, it's very easy to fall into ambiguity or cling to what you know. If it feels chaotic, then it's probably going according to plan, because naturally, you should be working on the most pressing problems for the business. This is a combination of fixing things before they're broken and also fixing things when they are broken. That's proactive, sometimes reactive, and that naturally just feels uncomfortable. So you have to be comfortable with discomfort and know that it's not you doing a bad job, but startups are messy, particularly earlier stages, and just defining the problem is half the battle.

3. Progression and your career track

In terms of progression, the Chief of Staff role in and of itself is a dead-end role. You need to proactively think about what your next step is going to be and what you want to get out of it.  We still live in a time where there is no natural progression from it. It's not like you're going from ‘Operations Manager’ to ‘Head of Operations’ to ‘COO’. 

There are a few ways that you can go with it. For example, If you're at a company that's scaling, and there's a new function, a new product line, a new business unit or new geography, and because Chiefs of Staff tend to be generalists, they can fit themselves into one of those roles and tend to quite well from what I've read. Otherwise, there's no way to go up, therefore, you have to go out or horizontally into one of these new roles. And if you're not proactively thinking about what your next step is, then someone else will think about it for you. And do you really want someone else to make that decision for you? I would probably recommend not. 

4. Other advice

If you’re in the role, try and find other Chiefs of Staff to talk to them about their experiences, it tends to be really illuminating. It can be helpful to find out what other people are going through and what's worked for them. I've done this a couple of times and always found it very, very fruitful, even people who are new to the role because so many of the struggles tend to be common and shared in different contexts. From what I found, most people like talking about what they do and the problems that they face, so you can learn a lot from that. 

One element I would just underscore is that regardless of the type of Chief of Staff that you are, my biggest piece of advice is just to think about the people you're working with. A lot of people that come to the Chief of Staff role, particularly from an ex-consulting background, it can be tempting to think that if you just do enough analysis in the right way, the correct answer will present itself and solve the situation. From what I found is your ability to be in the room, to have context, to have the trust in the ear of the CEO, the trust of the stakeholders whose success you can impact. Those are the things that will determine your ability to be effective.

In the Chief of Staff role, it is notoriously difficult to determine what the KPIs and evaluation criteria [for your own role] will be and that's part of the role. When the business is doing well and when others are doing well, you probably played a role in it. And when things are going badly, you're going to feel that pain. In a certain sense, it’s thankless because you don't have any KPIs to say you have 2x sales this month, or I made this change and it reduced the number of calls we missed. You have to enjoy the kind of unseen and unquantifiable aspects of the role and get a lot of motivation from that. Because you're not going to see the numbers tick up if you're doing a good job, but you might see them go down, if you're doing a good job, or if you're doing a bad job, and it's tough to know where you stand.

Finally, if I was looking for a particular resource, Scott Amenta, has written a lot about being a Chief of Staff and what it means and I’ve found his resources super useful. 


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