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  • Writer's pictureZaharo Tsekouras

Why startups won't hire you (plus 3 new Chief Of Staff jobs)

The reasons why BigCo candidates are struggling to land startup jobs, hiring insights from the former Head of University Talent @ Greylock, 2 new job reqs (Chief of Staff and Sr. Associate/VP), and more

Hello, and welcome to the Right Hand Talent newsletter! I’m Zaharo, and I write about all things Chief of Staff and talent.

Every week, you’ll get 3 new CoS jobs that are on my radar, reqs I’m working on, my thoughts on growing in the CoS role and as a professional, top stories I’m following on X, and more.


But First, 3 Shower Thoughts:

  1. If your senses are telling you that something is off, you’re probably right.

  2. Your future self is watching you right now through memories.

  3. If you miss the sign the first time, don’t worry — it’ll only get bigger.


It's Not Them -- It's You (Mostly)

The inspiration for this post comes from frequently asked questions and conversations I’ve had with candidates from big companies like FAANG who want to transition to an early-stage startup. They usually go like this:

“I have a ton of great experience at top companies, but I’m having a tough time just getting a call back for interviews even though I think I’d be a strong fit for this [Chief of Staff/Head of Ops/Other] role.”

And this is true — some candidates have very impressive resumes, having enabled the sales of X million units of a new product or having launched new products entirely.

Assuming the above is relevant experience for the role, the question from the startup founder isn’t “can they do the work?”, it’s “can they do the work here?” and that’s a loaded qualifier.

Here’s what here means at an early-stage startup:

  1. Hyper speed. There’s a reason why Zuck coined “move fast and break things” in the early days of Facebook. The philosophy behind this was to encourage Facebook's devs and employees to prioritize speed and innovation over perfection. Andrew Chen, a Partner at Andreessen Horowitz, recently tweeted how “one problem for folks from larger companies is that their rate of iteration is just too slow for what a startup needs.”

  2. Low/no infrastructure. Another relevant motto for this one is building the runway while you’re flying the plane. In a lot of cases, even at late-stage startups, there isn’t a predefined path or blueprint to follow; startups often have to invent their processes, products, and even markets as they go. Need to stand up a function as a Chief of Staff? You’re likely going to do it alone. That’s probably not the case at a public company for other similarly big, hairy initiatives — you’ll have teams of people who can help you. For the record, Facebook eventually changed that old motto to “move fast with stable infra” (you can’t make this up 😂)

  3. Low/no context. You might not have access to a ton of data but you’ll be expected to be comfortable with making decisions quickly, often on the fly. As a result, learning becomes a constant, on-the-job process. And roles within startups tend to be fluid, so you’ll probably end up doing stuff that wasn’t in the original job description (has anyone ever looked at these after getting into the role, anyway? It’s like a textbook: by the time it’s printed, it’s already old and needs updating.) On the flip side, public companies have entire internal Learning Management Systems and heaps of documentation around how to do things, why things were done, etc. Things that just don’t exist at an early-stage company.

  4. Limited resources. A founder’s #1 job is to never run out of money. They already know where they’re going to spend their dollars (product & eng or GTM salaries, etc) for what (milestone X for customer growth or milestone Y for revenue) and why: so they can raise the next round (read: not run out of money!). So there’s likely not a ton budgeted for non-essential expenditures. At a startup, you have to learn how to simultaneously do way more with way less, whereas at the bigger company, funding exists for your new project. And even if it doesn’t, you likely have the luxury of time, infrastructure, and context. Assuming none of these are true, and you actually built something internally with zero support, funding, or context, you’ll still have a hard time convincing a founder because you’re battling perception.

  5. High uncertainty. While jobs at big companies are more “secure” in the sense that there’s a market for the product, the company is profitable, and the overall business is a going concern, that’s not the story at a startup. While there’s been a sane regression to valuing startups on fundamentals over the past couple of years, most of them are still highly unprofitable. Some remained so even post-IPO for a long time. There’s also no guarantee that startups at the pre-seed or seed stage have achieved product-market fit, which is a core driver as to why 70-80% of startups never make it to Series A, and one-third fail even after doing so. Can the person who operates well in a stable environment do the same in a highly unstable one? Do they have the mindset to embrace this uncertainty and rock with the extreme highs and lows of the day-to-day — nay — minute-to-minute of working at a startup? It takes a unique mettle, and frankly founders don’t want to do the mental gymnastics to try to figure out the answer to those questions. It’s much easier to hire someone who’s worked at a startup before because they’ve been through those trials already, hopefully with some success.

  6. Low-ish pay ($). You don’t join a startup because of the high base salary. You join because of the impact, steep growth curve, learning opportunities, passion for the mission, and sure, the upside potential should the company succeed (though my advice is to value equity at $0). It’s not obvious that the person who’s used to a cash comp of $250k is willing to step down to $120k in exchange for learning opportunities. There are fundamental differences between the motivations that drive people to startups versus more traditional corporate settings, and it’s hard to tease that out of candidates who’ve spent their entire career at big companies.

So when you cite an “intrapreneurial” experience like launching a product within a behemoth organization to demonstrate your fit for a startup — and I put that in quotes not because it’s an invalid example, rather because it’s a less commonly discussed initiative — these are the types of questions and thoughts that run through a founder’s head.

I had a good conversation about what big tech candidates are up against when trying to make the transition to startups with Yuliya Mykhaylovska, founder of Yuliya Talent and the former Head of University Talent at Greylock, a VC fund that has backed iconic companies like AirBnb, Roblox, LinkedIn, and many others.

At Greylock, she focused on placing early career (0-4 years of experience) technical talent (engineering, product, and design) and Chiefs of Staff (5-10 years of experience).

Here’s what she had to say ⬇️ (and PS — check out the Exclusive Deals section for a special offer from Yuliya!)

Z: What are the primary concerns startups have about hiring professionals from big corporate/big tech backgrounds?

Y: The concern isn’t so much about hiring professionals with big corporate or big tech experience, but rather about hiring the “big tech mentality” and the way they function. Their backgrounds could be an asset because people who can navigate complex organizations are able to work with lots of stakeholders and make sense of chaos.

That being said, professionals who are from environments that are far too large or overly structured might not love the chaos and ambiguity that’s inherent in early-stage companies.

So the biggest concern is not so much the background and experience — rather, it’s the mentality and EQ agility to do well at startup.

Z: What skills and qualities do you believe are non-negotiable for someone looking to be hired by a startup, as Chief of Staff or otherwise?

Y: The non-negotiable qualities are linked to soft skills — the way they do things and the way they see the world.

When it comes to placing folks at startups, I’m looking for people who want their next job to be a founder of a startup themselves! They’re hyper motivated by the learning aspect of being early-stage rather than the incentive of potentially outsized gains through an exit.

I often think “Do they have ‘future founder’ skills?” and “would this role align well with further developing those skills?" If so, then it could be a really interesting match.

Z: How should candidates highlight these skills and qualities in their applications or interviews?

Y: Humans love stories. For every single thing you’re trying to demonstrate, if it’s a soft skill, I would think of a great anecdote that goes hand-in-hand with that.

One of my favorite tools is using the Gallup Strengths talents which are unique to every individual, and then crafting stories based on those talents. This is a technique that has worked super well with my clients because the talents from Gallup Strengths tend to be hyper focused and unique.

Z: What are some strong opinions you have about hiring for the Chief of Staff role?

Y: In the beginning, the hiring manager/CEO/Founder should be open-minded about what the perfect candidate looks like. Every search always begins the same: they want a top-tier consulting firm or investment bank, but top-tier people exist outside of those institutions. Once the core skills and credentials are proven, what is the personality fit and match, the emotional fit?

Some of the hardest searches have been when founders are overly focused on looking for the GSB graduate with 3 years at McKinsey…what you really want is to focus on the human aspects. I recommend that founders are open-minded especially at the beginning so that they’re not dismissing people who aren’t “boiler plate” Chief of Staff candidates.

Also, this is a role I’ve seen benefit from strong back-channeling, so even if you like someone, make sure you find out how they do the work and who they truly are.


Search Spotlight

Leverager (Chief of Staff) @ Investment Firm

A NY-based private investment firm is hiring a Leverager (Chief of Staff) to support the Managing Partner & Chief Investment Officer across all business and investment activities.

This is a new role for the firm that offers an opportunity to partner with an industry leader to have immediate and significant impact at a rapidly-growing firm. The Leverager (Chief of Staff) will:

  • Manage projects end-to-end, offering research, analysis, and execution support for the Managing Partner & Chief Investment Officer  

  • Provide accurate, timely performance updates to leadership, highlighting critical engagement areas for the Managing Partner & Chief Investment Officer  

  • Offer tactical and strategic leadership on projects that don't have a natural owner.

  • Assist the Managing Partner & Chief Investment Officer in maintaining and developing key external relationships with investors, partners, and other stakeholders.

  • Support strategic and operational planning in collaboration with firm leadership.

Ideal candidates will have 5+ years of relevant experience, strong analytical skills, and proven expertise in project management.

Additional key details:

  • $175k base salary + bonus

  • Medical/dental/vision insurance

  • This role is based in New York City (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!

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!

Executive Assistant to CEO & Founder

This is a one-of-kind role for an Executive Assistant to a renowned post-exit, 4x founder and builder of a community of over 14 million.

He specializes in guiding entrepreneurs to step back from day-to-day operations, focusing on growth through engaging content and automation of core systems.

This is an incredible opportunity to partner with a visionary founder who is laser-focused on building an amazing community, remarkable content, and insanely valuable experiences for other founders.

This founder is hiring an EA to:

  • Support him with various day-to-day operational needs

  • Ensure consistent and transparent communication, collaborating on current and future strategic initiatives

  • Develop and implement a comprehensive onboarding program, ensuring the smooth integration of new hires into the company

  • Enhance the effectiveness and efficiency of sales processes through systematic bottleneck reduction and organization of Notion and Asana

Additional key details:

💰 This is a contract role; compensation is flexible based on experience

📍 This role is 100% remote (must work EST hours)

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!

Job Opps

👼 Chief of Staff at Guardian — strategic comms agency for faith-driven orgs

Why I like it: Guardian is a specialized, strategic communications agency that exists to serve organizations and people driven by faith. I’m big on spirituality and I like amplifying missions that are personally meaningful to me.

While I’m not a practicing Christian, I love seeing such a niche focus. Somewhat related: I was a small but early investor in Tabella, the #1 free Catholic app for parishes, and I’m going to plug them everywhere I can because Juan Acosta and his team are just elite).

Guardian is looking to bring on a Chief of Staff to support the President in guiding decision-making processes, managing critical projects, and ensuring seamless communication across the org.

The top skills and qualities they’re looking for are 5+ years of experience with operational leadership, preferably in a consulting or advisory environment, an understanding of the faith-driven, non-profit sector, and importantly: someone who is empathetic (we love to see this called out!).

📍 This role is based in Atlanta, GA and they’re open to FT and PT candidates.

📥 Apply here.

👟 Chief of Staff at Flux Footwear — redefining minimalist footwear

Why I like it: CoS roles at CPG startups are far and few in between AND it’s fully remote. A rare combination. I also like the intentionality around adding humanized language to the job description like “what you’ll do” instead of “responsibilities” and “how you’ll do it” instead of “qualifications.

The Chief of Staff at Flux footwear will help with strategic planning, operational efficiency, and aiding the executive team with decision-making.

Ideally, candidates will have 8+ years in a leading or strategic role + management consulting experience. They must have experience at a $50M+ CPG brand that was in retail/wholesale, and preferably in the apparel/outdoor/footwear space

💰 Salary is $100k+, but they should re-evaluate this in light of the level of experience, seniority, and story they want their candidate to have lived (e.g. having had a hand in helping grow a rapidly scaling 8-figure brand). When you start getting into the 7-10 year range of experience and targeting the McK/Bain/BCGs of the world, you’re looking at $175k on the base minimum. At least, that’s what these ~Level 4 Chiefs of Staff are looking for in my network. If they come up on the salary they’ll have a better time attracting the talent they’re looking for as the role is currently scoped.

📍 This role is remote.

📥 Apply here.

🔒 Chief of Staff at TrueVault — software for privacy-conscious businesses

Why I like it: I like when startups refer to themselves as fanatical about “X”. In the case of TrueVault, they’re fanatical about building great products and making their customers successful (namely, healthcare companies that need to store sensitive patient data).

Apparently the company raised $2 million of the $2.5 million seed on YC’s Demo Day back in 2014 and count Andreessen Horowitz, General Catalyst, Maverick, and Khosla Ventures among their investors.

TrueVault is looking for a Chief of Staff to help drive key initiatives, streamline operations, and support the CEO in scaling the company’s growth.

Ideal candidates will have experience in management consulting, finance, operations, or entrepreneurial ventures, an MBA, exceptional communication skills, and an understanding of the startup ecosystem.

Strong Educational Background: Advanced degree preferred (e.g., MBA).💰 Salary and equity is P4 Level: $141,670 or P5 Level: $184,000

📍 This role is hybrid in San Francisco.

📥 Apply here.

Exclusive Deals

Career Coaching Session with Yuliya Mykhaylovska: Yuliya is a talent advisor to mid-career and early-career professionals. She has directly helped over 800 professionals get hired over the past decade and loves helping people find and land their dream role. She is offering one FREE coaching session to a Right Hand subscriber, redeemable in March 2024. If you’re interested in coaching, be sure you’re subscribed to the Right Hand Talent Substack and sign up here!


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