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How to build trust as a Chief of Staff

A special guest post by the former Chief of Staff to the CISO at Cisco, a candidate close-up of a product leader with investment banking experience, 3 new Chief of Staff jobs, and more
 

But First, 3 Shower Thoughts:

  1. “Inbox zero” is a terrible practice.

  2. Vocalizing and naming your feelings out loud helps release them.

  3. You might think nothing of killing an ant, but to the ant, you’re its entire world.

 

Leading with heart in tech

This week’s issue features a post by Jessica Walters, former Chief of Staff of Cisco's Security Business Group. Jessica shares how understanding people (not just code) can be your biggest asset as a technical Chief of Staff, and tactical tips on how to build trust with your team.


A few fast facts about our guest writer:

  • Jessica co-built and scaled security organizations at Duo & Tessian

  • She’s wrapping up her third company acquisition experience (and starting to look for what’s next!)

  • She’s a mom to 3 tiny humans under 6

  • Jessica’s also building a hobby farm with her family in their spare time, raising over 40 animals that keep them happily busy & feeling well loved :)

 

Chiefs of Staff understand humans - this is our technical superpower.


  • “What does this type of vulnerability in our code mean for the product?”

  • “How does our product architecture protect against common threats?”

  • “WTF does that acronym stand for again?”

It’s easy to get caught up in what you think you should know as a Chief of Staff working with technical organizations and leaders. As a Chief of Staff to the CISO, I had many moments where I questioned my ability due to the fear that I didn’t possess enough technical depth.


In some cases it even prevented me from speaking up and giving an opinion out of fear that maybe I didn’t fully understand what was being discussed by the technical leaders and engineers I was collaborating with.


However, after shifting my own perspectives, I realized that as a Chief of Staff I have my own technical superpowers that compensate for any lack of knowledge I may have in real time. Mainly, we understand humans and that allows us to overcome these information barriers gracefully.  


If you find yourself feeling this way, know that it is normal.  The breadth of business knowledge that we as Chiefs of Staff encounter and consume is expansive and it is not our role to memorize every detail of the world our teams work in.


Instead, we should focus on understanding the humans we work with.  What motivates software engineers, IT teams, or our InfoSec partners?  What are their strengths and weaknesses? How does that shape the programs we are building and how we lead them?  


By taking these steps to invest in our understanding of the technical teams (and individuals) we work with, we develop trust and our teams feel an authentic interest in their well-being….so when the time comes and we need to ask questions outside of our technical depth, they’re ready and willing to help bring us along because they know we are invested in the best outcome for them.


 

Trust is the lifeblood of all good teams


In Security we talk a lot about the importance of trust. Lots of times trust is framed in the context of customer relationships and winning the confidence of those purchasing your products. However, I would argue that trust within your employee base is the most important investment to make sure you get right.


Ensuring that your teams feel confident and comfortable being their whole self at work is the first step to ensuring psychological safety in your teams.  How do we create a team dynamic where everyone can be themselves?


Here are a few areas that I think are worth embracing:


  • Lead by example.  Executives and senior leaders are humans, too.  As a Chief of Staff, encourage the leaders within your group to be transparent about who they are outside of their career-self.  You likely know their quirks and passions best, so find ways to help your teams see that side of them. I once created an entire team meeting deck filled with Pitch Perfect gifs and references knowing it would set up my CISO to share his love of the movie in a way that the entire group could giggle about. It made him more human and demonstrated to the rest of our team that we could be ourselves and have fun together despite the seriousness of our work.

  • Create team rituals that give your team space to show up as their whole selves.  Be intentional about creating space for your team to share more about themselves, if they want (we support those that don’t feel comfortable sharing, too! It’s all about giving them the choice). This can be as simple as starting a team meeting by asking if anyone has fun plans for the weekend and then showing genuine interest in what comes up in that discussion. We have also found success in establishing simple team rituals to prompt for these types of conversations.  One ritual that I have had good luck with on multiple teams is “What’s good Wednesday?” - on Wednesdays, I prompt our team in Slack to share whatever is good and top of mind!  Sometimes it’s work related, often it’s not.  Something as simple as a weekly slack message has allowed me to learn so much about my colleagues over the years and also given me the chance to share more about my interests outside of work (everyone mostly is waiting to see what creature we take in next 😅).  

  • Foster a culture of appreciation. I have to give credit to the founders of Duo for this one 💚.  In my experience, the power of sharing your appreciation for the people you work with is an unmatched catalyst for team trust. At Duo we had an organizational habit of closing or opening meetings with an open floor for sharing “appreciations”.  This is something I carry with me today and will continue to preserve space for in my future teams. When you establish this behavior, it becomes a natural place for leaders to authentically recognize growth and positive behaviors across the team. I also consciously use this space to appreciate my teammates for taking care of themselves, whether for making sure they have their next vacation time scheduled or for saying “no” to something at work that was going to bring unnecessary stress. It’s a great way to reinforce the behaviors you want to amplify within your team, including showing up to consciously support one another.

  • Make rest mandatory.  Hiring high performing, passionate individuals comes with a responsibility to make sure they avoid burnout.  At the core of this is enabling space for your team to rest and recharge.  With the unwavering support of my CISO, we set clear expectations that everyone in our teams prioritized their own rest by: 

  • Having their next round of PTO in sight and scheduled at all times

  • Scheduling regular no-meeting focus days

  • Being quick to offer coverage when someone is not feeling their best

  • Proactively working with our HR partners to understand and enable extended periods of rest for individuals who are navigating difficult personal circumstances

  • Taking breaks ourselves and truly disconnecting so our teams see that it is possible to step away and leave our work waiting

Building trust within your organization takes time and intentionality.  When done right, it unlocks an infinite amount of potential that simply cannot exist in organizations that do not value their teams as humans before employees. 


As Chiefs of Staff, we can and should hold our leaders accountable to making this ongoing investment in our people.

 

Candidate Close-up


If you’re hiring and feel like the candidate showcased here could be who you need on your team, LMK! :)


🙋‍♀️ Candidate Background

I’m a purpose-driven generalist with ~8 years of experience across banking, investing, and product management


💪🏻 Top 3 Skills

  • Empathetic leadership & stakeholder management

  • Data-driven decisioning

  • Situational agility   

✨ Proudest Achievement

Diving headfirst into the startup world as employee # 1 and successfully leading product development 0 to 1 with no prior experience! 


🔥 What’s Unique

I have a rare blend of institutional investing, early stage operating, and banking experience give me a unique ability to anticipate, strategize, and execute through an “ecosystem” lens.


🎯 Career Goals

In the short term, I’m excited to help a mission-driven seed or growth stage founder scale their operations and deliver outsized economic and societal returns. In the long term, my goal is to build a social enterprise venture studio.

Search Spotlight

Senior Associate/VP @ Venture Capital Firm

I'm so grateful that I crossed paths last year with one of the partners of this venture capital firm -- he is one of the most incredible humans I know, and this is an OUT OF THIS WORLD opportunity for a Sr. Associate/VP to join their investment team.


This is truly a one-of-a-kind venture firm that exists to wholeheartedly support courageous teams in devotion to: 🙏 Solving our greatest challenges AND doing so in ways that bring out the best of what it means to be human 🌸 Creating new models for ecosystem level change AND doing so in ways that bring us closer together in relationship ❤️ Hosting the futures that our hearts know are possible AND doing so in ways that further the flourishing of all life Each of the 4 partners has been on a long inner journey, seeking deeper meaning and asking more nuanced and fundamental questions. They are listening to the futures their minds, hearts and guts are dreaming into. They believe change in the outer world starts with change in the inner world, and their inner work is guided by decades of successful entrepreneurial/investing experience and personal transformation journeys of their minds and hearts. Some examples of their achievements: • Founded 6 technology companies • Led 2 public companies • Founded 3 venture funds, 1 private equity fund, and 1 hedge fund As a Senior Associate/Vice President, you'll be: • Preparing financial models • Crafting teasers and marketing materials • Researching & evaluating new investment and fundraising opportunities • Support in researching and evaluating strategic direction for the organization Underpinning all the above, this is truly the ultimate playground for launching an entrepreneurial career, and to receive direct mentorship from four serial entrepreneurs and investors.

On a more personal note, I’m not aware of any other venture capital firm in the world with such a heart-centered mission, and one that is so clearly embodied by all partners not just in theory, but in the way they live their lives and show up for themselves and others. 💰 Compensation (base salary + bonus) is highly competitive 🧿 Annual inner work budget 🧑‍🎓 Monthly coaching stipend ⚕️100% coverage for medical/dental/vision insurance 📍 Candidates must be based in the San Francisco Bay Area (hybrid)

If you're interested and want to learn more about the company, just apply here! I’ll get back to you ASAP if your experience aligns with what they’re looking for.


Know someone who could be a fit for this role? Feel free to share this blog post!


Check out our job board for the full list of opportunities with our clients!

Job Opps


📂 CoS, Rev Ops @ Hoffman — sales training in 1, 3, and 30 minutes

My thoughts: I’m starting to see more admin-type CoS job openings this year, and while that’s an overall bummer, it looks like it’s contained within certain industries or business types, namely, non-profits and solopreneurs/small biz owners.


They mention that the role “is light on general admin responsibilities (calendar, travel support, etc.) and heavy on project support”, and the first bullet on the JD is “experience in Executive Administrative Assistant and Executive Support”.


As I’ve said before, that would be an EA or Senior EA role, not a Chief of Staff.


The ultimate irony here is that I wrote down my shower thoughts about inbox zero being a terrible practice last week and am just now seeing “Nothing gives you more joy than ‘inbox zero’ and a completed ‘to do’ list” as the first bullet in the About You section of the JD…


¯\_(ツ)_/¯


My advice to companies hiring a CoS to take on admin duties: don’t! Just hire an amazing EA. I know plenty of EAs that have absolutely crushed in their prior roles who are in the $80-100k salary sweet spot and can take on back office duties and other light generalist ops work.


💰 Salary : $80-100k

📍 This role is fully remote.

📥 Apply here.


👮 CoS, Corporate Affairs @ Peregrine Technologies — powering public safety decisions


My thoughts: Peregrine provides tech for government institutions to make data-driven decisions in real-time. Customers include organizations like police departments, enabling officers to interact with data in a unified environment (e.g. combating crime).


It is notoriously difficult to sell into government institutions. There is a ton of red tape, there are long sales cycles, and you have to follow a very rigorous bid process going up against other vendors and a side-by-side evaluation. But, if you have a unique technology and are the only provider of a specific solution, you essentially win “no bid” contracts, so it changes the math quite a bit. My guess is that this is Peregrine’s edge, especially given that they raised VC.


Peregrine’s CoS will partner directly with their CEO, focusing on the company's most crucial growth initiatives in a mostly external facing role. Strong project management skills are a must.


They are looking for candidates with 5+ years of experience in building scalable SaaS organizations, preferably with exposure to government solutions and data platforms. You also need to be OK with traveling 75% of the time :)


💰 Compensation isn’t listed on the JD but given the specialized experience and leveling (Level 4 CoS, e.g. ~Director), my guess is that the salary is probably in the $175k ballpark (or should be 😊).


📍 This role is hybrid in San Francisco.

📥 Apply here.


💊 Chief of Staff at at VIVIO Health — data-driven drug selection


My thoughts: Vivio Health is a public benefit corporation, so their operations are not just focused on profit maximization but also on creating a positive impact on society. Specifically, their Precision Care™ model addresses costly inefficiencies and prescribing practices, aiming to enhance patient outcomes and save self-insured employers 25-35% in costs by prioritizing effective, data-driven drug selection.


They’re looking for a Chief of Staff to their CEO to help with strategic planning and execution, project management, data analysis, and meeting prep & follow-up.


Ideal candidates will have 3+ years of experience in strategy, product, operations, business development, finance, or similar roles (MBA is a plus and preferably you have a background in tech/product, healthcare, and PBM sectors).


💰 Base salary is $80-90k. My specific thoughts on this ↓


I assume that they need someone with more than 3 years of total experience (so maybe 5 years total, with 3 years of specialized exp) which would bump the salary well over $100k, especially given the finance/ops/strategy + MBA factors.


📍 This role is Hybrid in the Bay Area.

📥 Apply here.


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