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At Carpenter Consulting Partners, we are excited to open our series of conversations focusing on the working relationship between C-Suite Executives, Founders, leaders at large and their support personnel, typically an Executive Assistant, Business Partner, Executive Operations Director or Chief of Staff. The purpose is to explore the how, the why and to inspire and educate. As technologies and businesses evolve, so do roles and responsibilities. We are interested in contributing to thought leadership on business administration and operations and are committed to showing a diversity of industries and individuals.
During our search for potential participants in the “In Conversation” series, Carpenter Consulting Partners came across Carina Ruggiero’s profile on LinkedIn with her role title of “Executive Operations Director”. As we are advocates of evolving the Executive Assistant and Chief of Staff role to the C-Suite into “Executive Operations” — she definitely piqued our interest.
Pearl Law Group, an immigration law firm and two legal tech companies, Tracker Corp and Pearl Travel Tech were founded by Julie Pearl, CEO. She and her Executive Operations Director, Carina Ruggiero, generously shared their journey of a not-so-conventional working relationship with Carpenter Consulting Partners in an interview this summer at their downtown SF headquarters.
Julie Pearl: We hired our first Executive Assistant over eight years ago. I needed somebody who could help me read emails and calendar meetings. Most of the original EA role was as a gatekeeper and pushing paper around. Since we’ve gone electronic, we no longer need that.
At the time, I had two things going on: I was CEO of law firm (with just under 50 employees) and our first software company (about 20 employees). Additionally, I had two kids at home — I needed help!
About five years ago we realized that a lot of what I was doing was communications. At that point we needed more than an employee who could do clerical work, so we hired somebody who was really good at supporting me with marketing communications as well. That employee eventually became an engineer [it was her life goal] so then we hired a marketing communications specialist to build that part of the business.
Executive Assistant is such a broad term. When you said you were an Executive Assistant ten years ago, that meant a very different thing than it does today.
At that point, we looked for someone who was not a traditional Executive Assistant, but someone who wanted to be in Business Operations. We advertised for a ‘business trainee’ and used very different keywords in the job description: tech friendly, but not a geek; somebody who was good with time-saving techniques and could become my right arm. It was at that point that we met Carina. She had been working her way through her career as an Executive Assistant and we liked the fact that she was thinking about using technology to enhance efficiency.
One of our values for all staff at Pearl Law is taking initiative and problem-solving. In our search we looked for examples of innovation in candidates; we needed to see where they could show initiative beyond responding to “hey, do this for me”.
Carina Ruggiero: I’m lucky — Julie is very open. A lot of my job is of a sensitive nature. I’ve always gravitated toward streamlining processes, project work and improving different areas of the business. My career has been a natural progression. In my first really substantive administrative role, I was interim Secretary of Diplomatic Security at the consulate in Milan, Italy. That was when I realized what the role could be and the impact that it could have on an organization. In that role, I got to touch every section of the consulate: management, security and consular activities. I had a wide overview of operations. I like having a broad vision and working side-by-side with leadership. I was contributing to the bigger picture and I was able to upgrade, streamline and standardize consular processes. It was a defining moment.
Over time, my roles kept evolving and changing: from being an English teacher and Administrative Assistant to working at the State Department, then moving into Executive Assistant roles across different industries and finally tech. I loved my time in education and the government but I prefer the fast pace and entrepreneurial spirit of tech. I’ve definitely joked about clinging to a rocket ship. When you’re moving that quickly, the executive you support is happy to have you jump in wherever needed as there’s too much for them to do in too little time. There’s opportunity everywhere.
I came to Pearl Law Group through a recruiter. She was talking to me about a different role and mentioned this one in passing: “I not sure it’s really your background, it’s a law firm.” I was skeptical at the beginning because I thought a law firm was such different thing. That said, Pearl Law Group is not your typical law firm, they also run two legal tech startups. They are at the intersection of law and technology.
When I started, Julie said “Why don’t you name the title of your role?” She didn’t want me to use the term Executive Assistant because she wanted it to have more gravitas.
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Julie Pearl: At Pearl Law we use approximately 30 accredited apps and software to automate company tasks. For example, I needed someone who could write well because they read my emails and sometimes respond as me so Carina uses TextExpander and labels as a time-saving tool. Just doing these things instantly facilitates a huge part of a CEO’s life. Tech tools: internally, we call it ‘business process engineering’. It’s also a huge part of what Pearl Law clients hire us to do. This is why we’re always saying: “Okay, which one of us does not need to do that?” We are constantly looking for ways to improve the paper and email trail, legal document signing for multiple parties in multiple locations etc…
Talented EAs should be looking at things with an eye towards email economy, automation and prioritizing so you don’t miss anything big. This keeps things moving forwards at a healthy pace.
Julie Pearl: In Carina’s previous employment at a well-known company, amongst her many tasks, she had the ability to brief both CEO and President prior to staff meetings. Over the years, Carina became the eyes and ears of that organization and helped them focus on important messaging. Both of her former employers confirmed that she was hugely responsible for their company culture. With that in mind, consider the importance of her role. At Pearl Law, she is known as my “Extender”!
You need someone who knows how to communicate, knows where the sensitivities lie, understands the access she has and the power of the position. Somebody who’s been in that position before and knows how to be the most supportive to their executive.
Amongst the many things we have evolved at Pearl Law are processes that enable people to collaborate more, with less waste and develop new skills. You could argue it’s just technology but actually, it’s inspiring more training. Carina runs this initiative: we give employees five hundred dollars a year towards legal and tactical training; maybe you’d like to do a negotiation workshop, a Commonwealth lecture or increase your knowledge about geopolitics. We call it Pearl University or enrichment dollars. Employees use them as they want. More importantly, you don’t even need to ask your manager. We also include a wellness budget. All of this amounts to good personal growth and even great team-building when people decide to do these things as a group.
Carina Ruggiero: It’s a very interesting time right now: my role is evolving as our organization is growing. I’m now taking over more operations, so we went with the title of Executive Operations Director. Consequently, we are looking to maintain support for Julie. The main component in the evolution of my role would be communications from the office of the Founder and CEO. As we expand our services, managing recruiting is also becoming a big part of my role. In addition, I’m running our executive searches, in partnership with a search firm. A lot of times I’ll be the first layer before they meet with Julie.
The other strategic component of my role is to always have an eye to automation. For example, saving time spent on emails: creating a system where we can have it all in one place to look things up easily and not have all the back and forth email search.
Julie and I have a really good working relationship; I’m really grateful for that. We are very open with each other and able to have those tough conversations when need be. That’s how you grow a working relationship and build trust.
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Julie Pearl: I took a lot of the functions some people use their EAs for and put them into the role of a Personal Assistant. I mention my PA, Casey, because she is different and we’ve structured a good working relationship. She has two kids and she mostly works from home in Menlo Park. We understand each other as mothers, as working women, with what little time we have available. Casey came to us with quite a few restrictions and yet, she still found a way to complete her tasks. She has access to my calendar and contacts; she does many administrative tasks for Carina and I. I have to add that I don’t understand these high-powered people, especially women, that don’t delegate their personal tasks to someone else. Casey and I accommodate each other and this frees up Carina from doing tasks that would otherwise slow her down.
It’s important to have somebody in this Personal Administrative Assistant role. Basically, you don’t force clerical work on your Executive Assistant (now Executive Operations Director); you make sure they have someone to delegate to. The more strategic Carina is, the more she is going to prevent me from making mistakes.
Julie Pearl: Before hiring Carina, I realized I needed somebody super smart. That somebody would not want to stay in a role supporting me for the rest of their career. That said, I know historically there have been some Executive Assistants who have done that and been career EAs.
I need someone who knows how to help me best spend my time: someone who is in the know. Someone who is smart enough to make a decision on my behalf — like spotting a potential business partner and identifying the importance of meetings beyond just slotting things into the calendar. They have to be strategic.
There is no traditional path for an Executive Assistant. Many women in this role have a lot more to offer businesses. Some may not have an MBA, but I know they could add a lot more to operations. Often in big companies, I see EAs going into H.R. roles or becoming Head of People.
Thinking ahead, in Casey’s case (Personal Assistant), as we grow and build our technology, [we’re building our third software company at the moment], there are many opportunities for someone like her to continue to grow. It’s a symbiotic thing. Carina and I found Casey together and we interviewed her together. We talked about what she’s doing now and what could she grow into. Carina’s job is to keep figuring out what she can delegate to Casey or somebody else. Why else would you go work for somebody? If you’re smart, care about yourself and are focused on being the best you could be, you’ll get there.
If you’re ‘that’ person, why would you work for an employer who didn’t invest in you? It’s all about people. People only stay for two reasons: First, there’s meaning in their work and second, the relationship with their manager.
In general, there are some people who are in jobs because it’s what works for them. Not everybody wants to climb up the career ladder. I think you have to provide those types of employees a good place to work. Particularly if they’re doing their job well and they meet our values, ethics and standards. You don’t throw them out. We aim to attract people who want to make their moments count, who know that their work and life has meaning.
Carina Ruggiero: Over time, I’ve worked with many different personalities and leadership styles. With each leader you form a bond and develop trust. The more trust you have in each other, the more they’re able to let you run with things. This is to their advantage and as a result, your responsibilities grow.
I’ve always had a problem with work-life balance. I am always ON. I think I can do more in less time, but I’ve never worked less! As I’ve grown, I’ve gotten a lot more efficient and I simply manage more things in less time. One lesson I’ve learned is to do quick checks and make sure you’re on the right track before you spend too much time going down one path. Constant communication is key, whether you work remotely or together. I would emphasize that open lines of communication is what it boils down to, and you constantly have to check alignment. You have to have enough EQ (emotional intelligence) to know when it’s going to matter and when it’s not.
I’d like to continue to grow my career in Business Operations. But life surprises you sometimes, so don’t hold me to it. As long as I’m driving myself to be the best I can be — to learn and grow each day — I’m happy. I love this career because it’s unique — you have the opportunity to work in every area of the company while learning from amazing leaders.
“I want to work with great leaders.” — Carina Ruggiero
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Julie Pearl: Former Deputy Attorney General of CA, she is consistently a top-ranked immigration attorney and incorrigible legal technologist. Julie founded Pearl Law Group in 1995 with the former head of the US Immigration Service (INS), growing it into one of the Bay Area’s three largest business immigration firms, with staff in Asia, Europe and the Americas. The firm’s culture is reflected in its service ethic, high retention of the most talented legal staff and awards for innovation, client service and pro-bono work. Julie also co-founded two compliance software companies: Tracker Corp (immigration case management system used by the majority of top-ranked US immigration law firms) and Pearl Travel Tech (the Permiso business traveler assessment system).
Carina Ruggiero: Carina is the Executive Operations Director across Pearl Law Group and two related tech start-ups, Tracker Corp. and Pearl Travel Tech. For the past five years, she has worked with executive teams at high-growth companies managing the Office of the CEO, executing strategic business initiatives, and developing leadership communications. Carina considers hiring A-players business priority #1 and loves this aspect of her day-to-day. Prior to her career in tech, Carina ranked as a top English teacher, serving international students from 40+ countries. She was also honored to work alongside U.S. diplomats at The Department of State in Milan, Italy in an administrative and project management capacity.
Since our initial conversation in the summer of 2018, Carina’s role has evolved to Business Operations Director. She is currently heading the recruiting function, working to scale and automating firm operations. “I focus on initiatives and processes for different areas of the company. It’s like being an internal consultant.”
If you are a Founder, C-Suite Executive or other leader who has a great working relationship with your support personnel, an Executive Operations Director, Executive Assistant, Business Partner or Chief of Staff, we’d love to feature you in our interview series. Connect with us: hello@ccpartners.co
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