I started this series– Curated Career Conversations– because I’ve found that job seekers– at all levels– are confused about the job search process. A job search for a leadership role at a venture-funded startup can seem even more confusing. Yesterday I sat down with Vanessa Larco, a partner with NEA, one of the top global Venture Capital firms. During our discussion, Vanessa shared strategies jobseekers can use when targeting jobs at high-growth startups, and how it differs from trying to land a position at a large company, like her former employer Microsoft.  

Let’s get started…

About Vanessa Larco

Sarah Johnston (SJ): As a partner at NEA, Vanessa focuses on enterprise and consumer investing helping founders build amazing products. She has led investments in Assembled, Kindred, Rewind AI, Cleo, Evernow, Rocket.Chat, and Mejuri, among others. She is also a board observer at Forethought, SafeBase, Orby AI, and Granica. She was a board observer at Robinhood until its IPO in 2021. Prior to Venture, she led product teams at Box, Twilio, Disney, and Xbox. 

First, I would love to hear a little bit about your work at NEA.

Vanessa Larco: At NEA, I focus on investing in companies at the earlier stages– typically at the Series A, but I also dabble in Seed and Series B financings. I’m never the first investor in the company. I typically come in after they’ve launched the product and have about 12 months of usage and revenue data. I invest in both consumer and B2B software companies. I invest in software and I only invest in high growth companies in the US and Canada.  NEA is a big firm though and I have colleagues that invest in later stages and in other sectors. 

Leadership Hiring at a Startup vs a Large Company

SJ: One aspect of your work that I find particularly fascinating is your role in helping founders and management teams make crucial hiring decisions. For our audience’s context, before becoming a partner at NEA, you gained experience at various levels, from major organizations like Microsoft to high-growth unicorns like Twilio and even small startups with just a handful of employees.

How does the hiring process differ between a startup and a large company like Microsoft?

Vanessa: Well, It’s important for me to mention that I wasn’t a hiring manager at Microsoft, but I did participate in hiring processes/interview loops. And interviewing at Microsoft and at a startup is a wildly different process. 

At a big company, they have a pretty rigid yet well organized process. They have people in HR who exclusively focus on scheduling and keeping the candidate up to date. They look for experience, predictability of performance, and ability to fit into the team. The titles and levels are well defined and they assume the candidate knows what they are getting themselves into. 

At a startup, most of that doesn’t exist. If we’re lucky we have someone in HR scheduling the meetings, but it’s really the founder and their EA trying to cobble together a process in between customer calls, engineering meetings, and everything else. The company knows what the gap is that they need to fill, but many times they are still trying to figure out what the right candidate profile looks like to fill that gap. They are trying to figure out how each candidate could fill the gap AND what else they might be able to help with. But EVERYONE is looking for a self-starter with an entrepreneurial mindset who can work in ambiguity and in a fast-paced environment. Startups are hard, you’re trying to figure out what to do and also how to do it perfectly as quickly as possible. 

So the process is less defined. The decision makers are never really well defined. And everyone really wants to know what they are getting themselves into. So you should expect a lot more “getting to know the REAL you” kind of process. Making a bad hire is just as bad for the company (arguably more detrimental to them) as it is for the candidate. No one wants to get this wrong.

Uncovering Leadership Opportunities at Venture-Funded Companies

SJ: When I talk to executives about networking, I always suggest that they try to identify the decision maker or the person who could influence or introduce you to the decision maker. At small companies, who is often the decision makers? 

Vanessa: The CEO and cofounders. Small companies are flat and can move fast. That’s the best part!

SJ: Many of my executive clients, particularly those from large corporations like Danone and Coca-Cola, have successfully pivoted to smaller, emerging brands by researching venture capital and private equity firms that invest in their target industries. For example, they’ve identified firms like BFG in Boulder, known for investing in ‘better-for-you’ food and beverage brands, and scheduled meetings with investment partners to learn about portfolio companies and explore potential leadership roles at startups.

Do you believe this is an effective strategy for uncovering opportunities at venture-funded companies? 

Vanessa: Yes AND many big firms have Talent teams which help recruit and screen pools of executive talent for our portfolio companies. They keep a CRM of “poachable” talent (folks who would be open to meeting with a startup if certain conditions are met) and we pull from that list when we open a job req within our portfolio. Our talent team is typically notified of any VP and up job openings.

SJ: What are some other creative methods job seekers can use to get noticed by startups and be considered for leadership roles?

Vanessa: Most VC firms pull and post all the job openings from across their whole portfolio. You can find the open roles you like and apply/ask for an intro to the company. 

Many candidates like to look through the list of portfolio companies from some of the top VC firms to create their wish list of companies to chat with. From there, they look for a warm intro to the CEO from a friend/connection. 

I highly recommend going through warm intros.

Aligning with the Company’s Vision

SJ: In your experience, how important is the alignment between a potential leader’s values and the founding team’s vision? What steps can executives take to ensure they are a good fit with the startup’s culture and mission before joining?

Vanessa: This is critical and what most of the time in the interview process is focused on. People want to know what the vision is. What does success look like for the company? The founders also want to know what the candidate thinks success looks like for them personally and for the company. Alignment critical for small teams. Anything that is even slightly misaligned is a huge drag on everyone. 

You want to know what the founders are striving for. You want to get a clear picture of the short term, mid term and long term goals. You want a good understanding of what their fears are and what’s not working well. It shouldn’t scare you, it should excite you. If it really scares you, it’s not a fit and move on. 

Don’t rush the interview process. With a startup and with founders, it’s going to feel almost like you’re dating. Don’t over sell yourself, be honest. Also ask them not to oversell it. The more informed and grounded the decision is, the better for everyone. 

Pivoting from Large Company to Startup

SJ: For individuals with a track record of success at large tech companies who are now looking to transition to startups, what specific skills, experiences, and mindset shifts should they highlight to appeal to both early-stage companies and the VC firms that invest in them? How can these individuals demonstrate their adaptability, willingness to embrace ambiguity, and ability to make a significant impact with limited resources, while still leveraging their experience from larger organizations?

Vanessa: The biggest concern when hiring from large companies is the perception that candidates might not be ‘scrappy’ or willing to ‘roll up their sleeves’. Startups need individuals who thrive in a fast-paced, resource-constrained environment and are ready to do whatever it takes to succeed.

Ideally they will have experience leading small, agile teams to achieve quick wins with limited resources. Highlight projects where you turned things around in weeks, not years, demonstrating comfort with rapid iteration and adaptability. Show that you are genuinely excited by the fast-paced nature of startups and share examples of how you have thrived in similar situations even within a larger organization.

Most importantly, we’re looking for an entrepreneurial spirit. The ideal candidate sees joining our startup as an opportunity to act as an owner, taking responsibility for the company’s success alongside the team. They’re motivated by equity ownership and the chance to build something truly special, not just by perks or a flexible schedule.

We value a growth mindset. The best candidates are confident in their existing skills but also transparent about areas where they want to develop. They see our startup as the perfect environment to learn, grow, and make a real impact.

Ultimately, candidates should be seeking a role where they can make a meaningful impact and contribute to building something truly special.

Embracing the Change of Pace

SJ: One of our audience members, Scott Metcalf, Executive Director & Adjunct Assistant Professor of Entrepreneurship  at Chicago’s Booth School of Business,  submitted this question:

One of the challenges of pivoting from a corporate role to a startup is that some candidates can’t keep up with the pace of change. Moving from a company with lots of structure and stability to a startup with 3-months of runway and no written SOPs is jarring for some. What’s your advice to our audience on how to do a gut check to see if they really are open to these kind of opportunities?  How can executives prepare themselves (and their families) for this shift?

Vanessa: We talk through it. I am always very honest with the candidates because we don’t want any surprises. We can’t afford to lose 3 months only to have the person leave and restart the search which will take another 6 months and then another 3 to ramp up. You lose a full year which can be the death blow to a company. 

I told a candidate we really liked once: “The company has a 200% net dollar retention. That’s going to be impossible to keep up as we scale. Your job is going to be to keep it as high as possible and that’s going to be hard. We have no processes. We have software, but it’s not set up as best as it could be. We have 2 junior people that are in over their heads. The founders work 6 days a week. This is their life’s work. It’s going to be intense. Everyone at the company is intense. On the flipside, it’s growing really fast, they’ve hired an incredible team. There is no deadweight on the team. Everyone is brilliant. You will get to experiment, you will get to move fast, there is no bureaucracy. You will have a lot of autonomy, your opinion is important, it will be highly valued and you will be treated like an owner of the company. This is what you’re signing up for. It’s okay if you’re not up for it”. I was scared that maybe I overdid it and he would drop out of the process. He went dark for 2 days, I thought the founders were going to kill me. He signed the offer and he’s doing great!

No one wins by hiding the skeletons in the closet. Some people will be excited by it. Others will be terrified. I don’t want to convince terrified people to join. I want the people that are excited to tackle the hard stuff.

Mistakes to Avoid

SJ: What are common mistakes candidates make when trying to transition into roles within PE-backed companies from more traditional corporate roles?

Vanessa: Immediately asking for headcount. I can’t tell you how often we see that and how scared it makes us that we made the wrong hire. We would rather see the person come in, do the job, get organized and figure out what the BEST use of headcount is for the company, not just their org. Being aware of the needs of the whole team instead of their own is key. Being hyper focused on your slice of it and asking for resources on day 1 is a mistake and sometimes folks never recover from that bad impression. It erodes trust with the founders and the other leaders. Please don’t do this. 

Startup Compensation Lessons Learned

SJ: Before the interview today, you and I talked about how you often get questions from friends interviewing with startups about their compensation packages.  I’d love to get your thoughts on how candidates should assess the value of their compensation package/offer at a startup. What advice do you give your friends?

Vanessa: Oh there’s so much to this one. Okay, let’s start with some basic principles:

1. BEWARE OF HIGH BURN COMPANIES.
If they are offering you a super high salary, then they probably pay everyone a high salary which means they are burning a ton of money. This means they will need to raise a lot of money and your shares will get heavily diluted. You’ll get diluted a lot at best, they will go out of business if they can’t raise a ton of money at worst (both happen often).

2. UNICORNS AREN’T LOWER RISK THAN EARLY STAGE COMPANIES.
Most people start getting excited to apply to a startup after they become unicorns (valued over a billion dollars). They think it’s a safer bet. It has name recognition. It has raised a lot of money. It has a big team. It has lots of clients. It seems like the right ingredients. What the current VC downturn has taught us is that this is actually the highest risk moment in a startup’s life. They became big and can’t move quickly. They are also burning a lot and are unprofitable so they live/die based on their ability to fundraise. Fundraising at the later stages is really hard right now. Most of these companies have had and will have many rounds of layoffs. Also, they are valued really highly which means you don’t have a ton of upside in your equity.

3. EARLY STAGE ISN’T AS RISKY AS PEOPLE THINK.
The younger/smaller the startup typically means a lower valuation which means much higher upside. They also are operating in a scrappy manner which means they won’t need layoffs. They have an easier ability to fundraise. They can move fast. Each person has a big impact on the destiny of the company. Lesson: EARLY STAGE ISN’T AS RISKY AS PEOPLE THINK

SJ: So how should one think about their package?

Vanessa: All of this context is important because your cash comp should not be what you’re excited about. It should be enough to keep a low-stress financial profile, but you want your upside to be equity. 

Your equity is likely going to be options with a strike price. You’d want to compare that to the per share price of the last financing and what the implied valuation is at your share price and at the last round. If you can’t get this (most people can’t get this info) then:

• If it’s late stage: Look at the price of the last post-$ valuation. You can typically find it on crunchbase.com. Then look at the company’s revenue this year and their projected revenue next year. If the valuation is 50x+ multiple of next year’s revenue, then your shares might not be worth much for a long time. 

• If it’s early stage: Look at the price of the last post-$ valuation and compare it to the average post$ valuation for that type of fundraise. If it is within the range of average and the company is doing well, you’re likely going to have your shares be worth more in the near future. If it’s high, talk about it with the founder and understand how they are thinking about the next round. If it is low, try to understand why they couldn’t command a higher valuation (this could be a yellow flag).

SJ: For leaders transitioning from large corporations to startups, the promise of equity and a more direct impact on corporate strategy is often a big draw. What advice do you have for them when evaluating equity offers and understanding their potential for long-term value?

Vanessa: If this is the draw, you’ve come to the right place! Seriously, this is the mentality we are looking for. I think I covered a lot of this in the previous question, but you’re basically trying to understand what the value of the company is going to be at the next round (and seeing if you believe they can actually get that value). The next level of thinking is to understand what the outcome of the company could be.

This is what I spend a lot of my time on when I do diligence on investments. I ask myself: Could this company go public? Who would they be compared to in the public markets (competitors or companies with a similar financial profile/dynamics)? How is that category of companies valued in the public markets (e.g. 2x revenue? 8x revenue? Growth? Margin profile?)? I then try to figure out what the company needs to look like to go public and see if I believe they can get there? Can they get to $1B in revenue some day? Can they get to 80% margins? If not, who would acquire this? How much would they pay for this? Have they ever acquired anything like this? Etc.

I don’t expect candidates to do this work, but you could always ask to speak to a board member/VC and then ask the VC to explain to you how they underwrote the investment and to what outcome. I get THAT question all the time!

Free Interview Guide and Opportunity to Connect with Vanessa

Vanessa Larco’s insights provide a valuable roadmap for executives navigating the dynamic startup landscape. Whether you’re seeking your next leadership role at a startup or aiming to build a winning team, her advice underscores the importance of adaptability, entrepreneurial drive, and a genuine alignment with the company’s vision.

For further insights into Vanessa’s work and the world of venture capital, be sure to follow her on LinkedIn. And if you’re ready to take the next step in your career, download my comprehensive interview guide, featuring Vanessa’s favorite interview questions and expert tips on crafting compelling answers. With the right preparation and mindset, you can position yourself for success in the exciting world of high-growth startups.