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Illustration by Eleanor Taylor

Friends, 

Well, what a weekend! 

Coming into Friday, I can’t imagine anyone expected OpenAI co-founder and CEO Sam Altman to be punching in on Monday morning as an ostensible Microsoft employee. Nor that former Twitch founder Emmett Shear would be taking his place, at least on an interim basis. Who knows what the rest of the week has in store. 

The OpenAI schism has revealed a number of fascinating storylines that I suspect we’ll unpack in the months to come: the growing divide between “boomers” and “doomers,” shifting dynamics in the AI market, Microsoft’s fourth (?) act, and the return of “activist” VCs. 

It also sheds subtle light on today’s topic: hiring upwards. If Shear’s appointment sticks, he looks set to face an unenviable task: recruiting a slew of new talent. Though it does not always come in such dramatic circumstances, every founder and senior operator will face variants of this task at some point. 

In this edition of The Braintrust, eight exceptional founders and CEOs share their tactics and strategies for recruiting great senior talent. Their lessons apply to anyone involved in the hiring process across different organizations. They’re also relevant to investors, who will understand how remarkable founders attack this problem area and how they can help drive talent to their portfolio companies. 

Quick ask: The Braintrust is a new series from The Generalist! We’d love your feedback on it. Do you like it? Love it? What questions do you want to hear entrepreneurs answer? Help us continue increasing the value of your subscription. 

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Quick hits

If you only have a few minutes to spare, here are eight highlights from The Braintrust’s contributors on how to hire upwards.

1. Immad Akhund often hires a level below the stated position, providing room to grow. 

2. Avlok Kohli finds the top 1% in a function and uses them to identify other candidates.

3. Mathilde Collin recommends leveraging your investor network. 

4. Jack Altman suggests meeting “unhireable” people to understand what good looks like. 

5. Pedro Franceschi advocates for finding senior hires with strong emotional ownership.

6. Christina Cacioppo tailors her pitch, avoiding a “one-size-fits-all” approach to recruiting. 

7. Trae Stephens says you need to hone your storytelling chops and sell your vision. 

8. David Hsu has succeeded by hiring candidates ready to make the step up from a less prominent company.

Read on to discover the full list of tactics and strategies.

If you are a breathing human, especially one who has chosen the path of entrepreneurship, you have experienced moments of doubt. It is true that deciding to build a company requires a certain productive delusiveness, but that does not insulate you from such interludes. Nor does it protect you from the sensation that you are an imposter, the sole callow pretender in a land of competent adults. 

Among the doubt-inducing tasks an entrepreneur faces, hiring may be the most fraught. You may be willing to dedicate your own life to a dream, but can (and should) you convince anyone else to make the same bet? The matter becomes even trickier when hiring upwards – recruiting people who are more experienced and more skilled than you. While a great founder holds the vision of the company and possesses an impressive blend of skills, they cannot expect to be the best at everything. To grow their company, they need to draft operators that surpass them in one way or another – to find a VP of Engineering with 10x capabilities, a CRO that’s managed a high-performance sales team, or a COO that understands how to scale a generational business. 

Today’s edition of The Braintrust focuses on this question: How do you hire upwards? Our contributors touch on the power of storytelling, the utility of your investor network, increasing your self-confidence, and much more. 

“Hiring someone slightly below the level you are looking for can be highly effective”

Hiring upwards as a startup leader can make a big difference by bringing on a certain caliber of skill and clout to a leadership team, which helps level up and legitimize an up-and-coming organization in a lot of ways. That said, though, I generally start any hiring process by carefully considering whether hiring upwards is really the right move. While the allure of seasoned professionals from big companies might be strong, the unique challenges of early-stage startups require a specific mindset — one that thrives in the zero-to-one phase. The reality is that super seasoned professionals whose experience revolves around leading a team within more of a well-oiled machine that’s already scaled up might not necessarily have the most to bring to the table for your startup. There might be a disconnect. Startups need leaders who have more experience plugging into a grittier process of building from the ground up — people who understand the intricacies of the early stages and can lay the groundwork for what will hopefully become that well-oiled machine in the future.

I find that calibration meetings — conversations with others that can just help level set needs and expectations — can play a pivotal role in deciding how and when to hire upwards when the time is right. I like to engage with experienced professionals who've successfully navigated similar hires, perhaps a co-founder who's led a larger team. This helps in honing in on the right profile, crafting pertinent interview questions, and gaining valuable recommendations. In my experience, hiring someone slightly below the level you are looking for at your startup and affording them a stretch role in a startup setting can be highly effective. While they may not carry the official title, the opportunity to take on more significant responsibilities in a smaller team can be enticing. This approach fosters a dynamic learning environment, even if the compensation might not match that of a corporate setting.

“Build relationships with the top 1%”

Here’s a four-step process I use at AngelList:

1. Build relationships with the top 1%. Build a relationship with the top 1% within the function you’re hiring for. Ex: if you’re looking for a Head of Sales, find the best Head of Sales in the industry. Take them to coffee and understand what makes them great. This will help you calibrate what you’re looking for. 

2. Make the top 1% advisors. Once you know the top 1%, make them an advisor in your company to support you with recruiting: role design, sourcing, and interviewing. 

3. Target stage-appropriate candidates. Work with your advisor on a list of potential candidates. Ideally, they have experience working at startups that are 12-18 months ahead of your current stage. You're always hiring for what you will need in a few months. 

4. Articulate a clear, ambitious vision. When contacting these candidates, emphasize the mission and ambition of your startup. This vision should be compelling and something they would be proud to be a part of. Counter-intuitively, it’s easier to hire top talent for a bold, ambitious vision. They will choose this over a stable company any day.

“You can’t just wake up one morning and decide you’re now confident”

The most important thing is to convince yourself that you CAN get these people. But building confidence is hard! You can’t just wake up one morning and decide you’re now confident. What I’ve found most impactful is to surround myself with people who believe in me and Front. For example, Patrick Collison was one of our investors. He’s always been good at telling me why he believed I was a good CEO and why Front is a great company. Hearing this from someone you respect and admire has such a high impact. As a leader, you’re always in the weeds and aware of the 100+ problems that need to be fixed, so asking people like your investors and mentors why the opportunity is great is a good way to build confidence and showcase your unique strengths to compel someone to work with you.

The second most important thing to do is to leverage your investors. For these senior candidates, having top VCs (for us: Sequoia) tell them why they’re excited about the company will help tremendously. I leverage our investors for a lot of candidates, but not always at the same stage. Sometimes, they’re the first person to talk to the candidate (to convince them of a first meeting); sometimes, they’re at the very end of the process to sell them. 

And lastly, what I found is that the more candidates get a glimpse of what it’s like working at Front, the more interested they become. Here are some of the tactics I have used:

• Inviting them to have lunch at Front. Finding a job where you enjoy the work you do is great, and enjoying the team that you get to do that work with is even better. We have been very intentional about the culture we’ve built at Front, and this is a great opportunity for candidates to experience that firsthand. 

• Sending them the recording of Last Quarter at Front (LQAF). LQAF is a company-wide meeting that covers learning and results from the previous quarter, a preview into the quarter ahead, and a reminder of Front’s mission and strategy. I aim to be very transparent and share things like revenue numbers, our runway, hiring updates, things we’ve shipped, and our goals and things to be excited about. I strongly believe that LQAF is a vital way to maintain and increase employee engagement. By bringing everyone together and reminding them how their work impacts our ability to deliver on our larger mission, they feel like they’re a part of something greater. LQAF builds excitement for employees and candidates as well. (More information on LQAF can be found here.) 

• Once the offer is made, having Fronteers reach out. We ask Fronteers from the interview panel and broader org (for example, for an Engineering role, we’d have members of engineering, product, and design) to email the candidate, sharing how excited they are for them to join. It’s a personal touch that helps build a sense of camaraderie before they even join. 

“Meet unhireable people”

One of the best pieces of advice I ever received on the topic of hiring was: Make sure you meet with at least 5 “unhireable” people for each role you’re looking to fill so you really understand what good looks like. If you’re looking for a VP of Finance and you’ve never hired for that role before, tap your network, engage with other founders and teams you respect, and meet with 5 VPs of finance who are operating at the top of their game – but are also just outside the range of hireable for your company. This shouldn’t be a recruiting exercise but an educational one. Inevitably, this exposure will teach you how a great candidate will think and speak, the depth of their expertise, what things they prioritize, and how they problem-solve. 

The other really key concept for me – and this applies both to the hiring process and to management and leadership best practices – is that you always have to strike a balance between having the humility to know that this is someone who is far more experienced than you, but the confidence to be firmly rooted in your own expertise and sense of your business, especially with someone you are managing. It can be a slightly paradoxical tension, but getting comfortable with that tension is key to being an effective leader.

To me, the ideal recruiting process is one where, by the end, the step of discussing and signing the offer is basically just down to logistics and feels very natural. So, backing into that vision for the conclusion of the process…how do you get there? There are lots of components to this, but among the most important for me is getting to a place where communications move from periodic and formal to frequent and informal, where you are discussing potentially tricky bits early and often with your potential hire, and spending enough time together to have a firm grip on what matters most to the candidate.

“Make sure they have emotional ownership”

Brex has only been able to scale the way it has because we’ve hired extremely talented people with expertise that Henrique and I do not possess. For many of these people, Brex is compelling because they get to build out their function almost from scratch and have true ownership over the team, something they may not get at a bigger or older company. 

Our initial two hires were quite senior. We brought in Michael Tannenbaum as our CFO and Vince Cogan as our General Counsel. This may have been unusual for a startup, but given the regulatory and financial hurdles of working in the fintech space, these hires were critical. My advice when looking to hire senior leaders is to make sure they are sold on the opportunities that come with working at an early-stage company AND that they have emotional ownership and buy-in to the strategic vision for the company. Financial upside is great, but getting to build something lasting that didn’t exist before is often even more motivating for the best and brightest leaders. 

Beyond the challenges of convincing someone to join an early-stage company, there are also challenges in finding hires that are the right fit for the stage of the business. One consistent trait across our successful senior hires at Brex is their ability to operate at all levels (I wrote a blog post about this here). They have to be able to be strategic but also highly operational when needed, and they must be able to work without the amount of support they may get at a larger company. Additionally, it’s equally important to ensure that there is value alignment between the company and who you are hiring. Even if you do end up hiring someone with a high level of expertise or seniority, you need to ensure you have a shared language of success. For us at Brex, impatient optimism and growth mindset are core values of how we build and execute, and it requires that all employees - at every level - be operators and lifelong learners.

“There isn’t a one-size-fits-all pitch”

Start with the foundation to hire senior colleagues: potential hires need to believe in what you’re building. Whether they’re motivated by the mission, the product, the customers, the business growth, or the opportunity to build a team, figure out why they’re interested in talking to you first...