Plaid and Whatnot on Hiring and Managing Leaders

Relevant Links From the Session

• Zach's How to Recruit Deck
• Plaid’s Culture Doc
• Grant's Hiring and Managing Deck
• Grant's VP Product MOC

How Grant Leads Whatnot

Whatnot is 6.5 years old, has grown to over 1100 employees, and is connecting millions of buyers with tens of thousands of sellers through livestreamed shopping. The company is at a ~$1.6B revenue run rate and continues to expand rapidly across new categories and geographies. Whatnot is a live shopping marketplace and their mission is to enable anyone to build a business from their passions and bring people together through commerce. 

Example: Whatnot’s Senior Reporting Structure

• Grant currently has ~17 direct reports. His leadership team and org are structured by function. He believes that once a company scales, this model is the most efficient way to operate and allows each major area of the business to be led by someone world-class in that function. 
• The median tenure of Grant’s leadership team is roughly 3.5 to 4 years. A clear tranche of leaders joined roughly 1.5 to 2.5 years ago to help fill out the leadership team as the company scaled. The rest of the team has generally been with Whatnot for about 3.5 to 5 years
  
  • The most tenured person on Grant’s leadership team, excluding his co-founder, is the CRO, who has been with the company for about 5 years
• His core functional leaders include:
  
  • Head of Product, who joined about 2.5 years ago
  • Head of Engineering, who joined about 1.5 years ago and is the company’s second Head of Engineering
  • Head of Design
  • CRO, who runs the supply side of the marketplace
  • Head of Marketing, who owns brand and much of the buyer side
  • Head of Operations
  • Head of Legal
  • Head of Comms - Grant believes this is one of the most underrated senior hires, particularly for a consumer company 
• In addition to the core functional org, Grant also has several teams working on new initiatives that report directly to him:
  
  • Logan, his co-founder, leads new markets and new categories
  • A few smaller teams working on new business lines also report directly to Grant
• Grant has intentionally kept these new initiative teams separate from the core business. He said that the mechanisms and processes required to scale the core company with rigor and efficiency are often not well suited for building new things.
• The remainder of his direct reports include his Chief of Staff and EA
• Grant also noted that many members of his leadership team were internal promotions. In several cases, these internal leaders ultimately surpassed external hires as they scaled with the company

How Zach Leads Plaid

Plaid was founded in 2013 and launched in 2014. The company has grown to a little over 1,000 employees and provides the infrastructure that allows fintech companies and financial institutions to connect to bank accounts and financial data. Plaid powers products across payments, lending, personal finance, banking, and identity, and helps developers build on top of the financial system through APIs and related infrastructure. Zach noted that Plaid has intentionally stayed more or less flat in headcount for about five years, as the company has not needed meaningfully more people and has found substantial efficiency gains over the last few years.

Example: Plaid’s Senior Reporting Structure

• Zach currently has ~17–18 direct reports. In addition to serving as CEO, Zach also acts as Plaid’s Chief Product Officer
  
  • As part of that product responsibility, he directly manages eight VPs and Directors of Product, along with the Head of Design
• He also manages a standard executive team, which includes:
  
  • COO, which Zach said is effectively a CRO-type role
  • CTO
  • General Counsel
  • Chief People Officer
  • CFO
  • President of Regulatory
  • Chief Strategy Officer
• Zach noted that some of these roles are unusually specific to Plaid:
  
  • President of Regulatory is a role that reflects how central regulation is to Plaid’s business and operating model
  • Chief Strategy Officer is a role Zach created for someone he has worked with for nine years and who he said is exceptionally valuable in a narrow but important set of areas. Zach created a title for the more bespoke role this team member plays. 
• Unlike Grant, Zach does not manage his EA directly. 

1. Hiring Leaders

Hiring Leaders is Hard and Has High Failure Rates

• Hiring leaders fails far more often than most founders expect, with the majority of hires not being successful ones. He has heard estimates ranging from 50% to 80% failure rates depending on the company.
  
  • Whatnot’s early executive hires had close to an 80% failure rate, and when he spoke with people at DoorDash, they told him their executive failure rate was also close to 80%.
• More recently, Grant feels the company has been on a better run and is now closer to a 50/50 hit rate. Even so, he emphasized that executive hiring remains extremely hard no matter how much better you get at it.
• Grant believes part of what makes executive hiring so difficult is that some failure modes are hard to detect upfront:
  
  • Some people come in and end up being bad for the culture.
  • Some tell you all the right things during the process, but do not perform the way you expected once they are in the seat.
• That being said, Grant said that despite how error-prone it is, companies that are scaling quickly have no choice but to keep hiring senior leaders
  
  • If the company is growing very fast, there is no realistic way to level up the team quickly enough through internal development alone. Your company will need leaders in order to grow and continue scaling. 
  • The point is not that executive hiring is optional, but that founders should go into it knowing the odds are worse than they hope.

Why Hiring Leaders Gets Harder as You Scale

• Hiring leaders gets meaningfully harder as a company scales because the scope of these roles expands, the consequences of getting them wrong increase, and the amount of company-specific context required to succeed becomes much harder to replicate from the outside. 
  
  • At smaller scale, a strong leader can often get by on general capability and hustle. 
  • At larger scale, leadership roles require much stronger judgment around org design, strategy, operating cadence, and cross-functional alignment.
• Grant said leadership hires get riskier as companies scale because the blast radius of a bad executive becomes much larger. 
  
  • A senior leader does not just affect their own work: they hire teams, shape culture, and influence how an entire function operates. If they are weak, the damage cascades much more broadly across the organization.
  • The cultural downside also becomes much more severe as companies grow. If a senior leader is a poor cultural fit, that damage cascades across a much larger team. 
• Another reason executive hiring gets harder at scale is that company-specific context becomes much harder for outsiders to acquire quickly.
  
  • Grant contrasted hiring a leader into a 100-person company versus an 1,100-person company operating across 10 countries. 
  • At smaller scale, it is relatively easy for an executive to build context. 
  • At larger scale, there is so much business-specific knowledge embedded in the company that strong internal people with high slope often become much better bets than outsiders because they have already accumulated years of context on the product, team, and operating system.
• Zach also noted that in some businesses, scale increases the need for external credibility in certain roles. Because Plaid works closely with banks and regulators, some senior seats cannot simply be filled by the strongest internal up-and-comer. 
  
  • Roles like CTO or General Counsel sometimes need someone whose resume will carry weight externally, not just someone who can operate well internally.

The Cost of Getting Leadership Hires Wrong is Extremely High

• Grant emphasized that getting the right or wrong person into a senior role can make or break a company. The stakes are much higher at the exec level than in many other parts of the org. 
• Early on, Grant personally struggled with not being well calibrated on what great actually looked like:
  
  • Without enough repetitions and hiring “laps,” it was hard to know whether a candidate was truly exceptional or merely good on the surface. He found it difficult early on to tell where the real bar was.
  • He also found it hard to know whether a given person was actually set up to succeed in the role or whether he was rationalizing a hire he wanted to work.

Hiring Leaders Requires Time and Attention

• Zach said one of the biggest mistakes founders make is treating recruiting as something they can do casually. In his view, if you are going to recruit someone, you have to actually have the time to recruit them:
  
  • He estimated that for leadership hires, the hiring manager (you!) should expect to spend roughly 5 to 15 hours per candidate per role. Because of that substantial time commitment, he believes there is no real middle ground between “not recruiting” and “really recruiting”
• His belief is that partial effort almost always ends badly:
  
  • If you recruit only lightly, you are likely to leave the role open for six months
  • Eventually, you get tired, lose discipline, and start compromising
  • That is when bad hires happen
• He believes you should either commit fully to the process or do not open the role yet

Do Not Let the Market Pull You Off Your Own Hiring Discipline

• Market narrative today says that when you find the right leader, you should move immediately, give them a huge package, hand over the title, and do whatever it takes to close them. 
• Grant’s view was that founders should be very careful not to let that market narrative override their own judgment.
  
  • Grant said a core risk with top-tier recruiters is that they can manufacture a very compelling match around a candidate with an exceptional resume, but that does not mean the hire will work long term. In his view, those matches are often overpowered for the actual role and company stage.
• His advice was to stay close to your own principles rather than over-rotating because the market is noisy. 
• In cases where a candidate may still enter the process expecting oversized comp, immediate title, and full scope because that is the narrative circulating in the market, Zach’s advice was to address that directly and early rather than try to negotiate around it later. 
  
  • His view was that founders should decide what they actually want the role to be, what title it carries, how it can grow, and what compensation they are willing to offer, and then communicate that upfront. 
  • If a candidate is not interested in what the company is actually selling, the founder should not waste time trying to force alignment.
• If a candidate is optimizing for a company like Anthropic or OpenAI, Zach often just exits the process. He said that if someone tells him they are talking to Anthropic, his reaction is often effectively: great, you are probably not a fit for Plaid right now, and if that is what you want, go do that. 
  
  • His reasoning is that a candidate choosing among those companies is often looking for something fundamentally different from what Plaid is offering, and it is better to recognize that misalignment immediately than to get dragged into a comp or prestige battle that does not make sense.

Map Out the Best People Before Launching the Role

• One of Zach’s core practices is to start with examples before starting with candidates.
• Before formally launching a role, he tries to identify a handful of superlative examples of what great looks like:
  
  • He will call people and ask, “Who is the best CFO you have ever met?”
  • Once he gets a name, he reaches out directly and asks for 30 minutes
  • These conversations are not always meant to recruit the person directly. Often, the goal is to learn. He uses the conversation to understand what makes that person exceptional. He asks things like:
    
    • How would I hire someone like you?
    • If you were me hiring for this role, what would you look for?
• Zach said these pre-calls are extremely valuable because they sharpen his understanding of the role before the search gets too far along. 
  
  • In some cases, those people then refer strong candidates. In rarer cases, they themselves raise their hands and become interested in the role
• He also said that once he understands the profile he wants, he identifies the top one to three things he is truly looking for and then builds an interview panel designed to challenge candidates on exactly those dimensions.
  
  • That panel can include internal people or friends, board members, and other trusted external evaluators. His goal is to pressure-test candidates from multiple angles rather than keep the process narrowly internal

Some Roles Are Harder to Hire For Than Others

• Grant also said there are certain functions where the average executive is simply much weaker, which makes those searches especially difficult.
• He specifically called out:
  
  • Chief People Officer
  • CMO
  • CFO
• His view is that the average person in these roles is often not very strong, which makes the talent pool especially frustrating.
• He said part of the difficulty is that these functions are both extremely important and personally foreign to him. Because of that, those functions feel less intuitive to evaluate

Keep the Bar High in Hard-to-Hire Functions

• Because some roles can be harder to hire for, there can be pressure to lower the bar and accept someone who seems less sharp on the theory that “you are not going to find a super smart person for this role.” 
• Both Zach and Grant pushed back strongly on that idea. While the hit rate is lower, it takes more work to find the truly strong ones. 
  
  • Zach contrasted this with technical leadership roles: there are still many weak CTOs, but in his view the average quality is somewhat better than in functions like People, Marketing, or Finance. The implication was not to lower the bar, but to search harder.
• Grant believes you should never hire a weak person into any role. He said doing so will only make a founder’s life much worse. 
  
  • In his view, if someone is not genuinely strong, the company does not need to hire them simply because they carry the title. A weak leader with a prestigious title will still create problems.
• Both Zach and Grant emphasized that this is especially dangerous in People. A weak Head of People or Chief People Officer can do lasting damage to culture, and culture is much harder to repair once it has been degraded. That makes settling for the wrong person particularly costly in this function.
  
  • Zach added that one path he has seen work in People is taking a strong operator from another function and moving them into the role, as long as they have enough adjacent experience.
  • Plaid transitioned out its Chief People Officer roughly six months earlier and that he had considered two internal candidates before ultimately putting the Head of Recruiting in charge.
  • That has worked well so far. He noted that he personally prefers Recruiting to the broader People function because Recruiting tends to be more operational.

Founders Should Personally Cover Leadership Gaps Before Hiring Leaders

• Zach believes that if there’s a hole on the leadership team, the founder or co-founder should do the job until they’re confident they can hire the right person 
• Before you have hired executives, all you have are open functional gaps. He believes that means the founders should be covering those roles themselves
• In Plaid’s early days, he and his co-founder were effectively doing all of the major jobs - his co-founder was running engineering, and Zach had also directly managed engineering for a period of time early on
  
  • This matters because it gives the founders a much stronger sense of what “good” actually looks like in a function. That firsthand understanding then makes them far better evaluators when it is finally time to hire an executive into that seat

Example: Zach’s Battleship Model for Building a Sales Team

• Zach argued that founders often hire a Head of Sales too early because it feels like an escape hatch.
  
  • A founder thinks: I do not really know how to do sales, so I should go hire someone who does.
• In Zach’s view, that instinct is often wrong. If the company does not yet have a truly repeatable and scalable sales process, the Head of Sales you hire at that stage is often not the person you will want, and the probability of success is relatively low.
• Instead, Zach advocated for the founder acting as Head of Sales much longer than most founders expect. He described what he called a “battleship” model for building the sales function:
  
  • the founder is the core seller
  • then the company adds the support around that founder to make them as effective as possible
    
    • for example, someone to attend meetings, take notes, and handle follow-up
    • an implementation person
  • eventually additional “sales shadows” who sit in on calls, learn by observing, and then begin taking smaller deals themselves
• Zach said that only after Plaid had built a seven- or eight-person sales team, and only after he himself had been doing sales for about a year, did he feel comfortable hiring a true Head of Sales.
  
  • By that point, he knew exactly what the role required, and the company could run a slower, more informed recruiting process. 
  • His broader point was that being slightly late to hire a Head of Sales is usually far better than being slightly early.
• He also warned that an early mis-hire in sales can be especially damaging because a weak sales leader tends to build process that the founder later has to unwind. 
  
  • That can leave the company in a worse position than if the founder had just kept running the function longer themselves.

How Zach Achieved an 85% Success Rate for Leadership Hiring

• Zach also noted that Plaid took a very long time to hire its first executives because the company was deeply focused on not getting those hires wrong.
  
  • Plaid’s executive hit rate has been roughly 85%
  • In his view, it is possible to have both a high hit rate and use external hires effectively
    
    • Plaid has not had much executive turnover and has had relatively few senior hires that did not work out
• This also helps in cases where a leader doesn’t end up working out. If an executive hire does not work,  Grant does not wait to remove them until he has found a replacement. He simply takes the function back over himself or asks someone he trusts internally to run it on an interim basis. 

Example: How Plaid Hired their CTO, Jean-Denis Greze

• Zach’s first example was Jean-Denis, who served as Plaid’s CTO for a little over seven years.
  
  • Jean-Denis had a highly unusual background: he studied computer science, then got a law degree, then worked as a lawyer before becoming an engineer. He later joined Dropbox, where he worked on Paper and related products
•  Zach’s broader point was that Plaid did not rush this hire. The company interviewed roughly 40 candidates for the CTO role and worked with an executive recruiting firm during the search
  
  • They were willing to let the process take a long time because they cared more about getting the hire right than filling the role quickly
  • Plaid did not allow the open role to slow the company down in the meantime. Zach and his co-founder continued covering engineering themselves and kept hiring engineers to keep the company moving
• Zach used deep off-book references to build conviction on Jean-Denis before the formal process was far along
  
  • Zach said one of the hardest passes during the CTO search was Chris Rasmussen, now CTO of Figma. Chris was extremely strong but ultimately not the right fit for Plaid at that stage because his orientation was more toward highly design and consumer-oriented product work, while Plaid’s needs were different
  • Jean-Denis came from Dropbox. Because Zach and others in the company knew many people from Dropbox, they were able to do a large amount of quiet, trusted diligence before the formal process went very far
    
    • He emphasized the importance of doing this carefully so as not to create problems for the candidate in their current role
  • The feedback on Jean-Denis was universally strong. Everyone said he was exceptional and knew exactly what he was doing
  • By the time Zach and his co-founder sat down with him, they already had extensive context. That allowed them to use the interviews less to figure out whether he might be good and more to pressure-test a thesis they already largely believed
• Once Zach finds the right executive, the process quickly becomes about closing them
  
  • Zach said Jean-Denis was a case where the early process created conviction very quickly.
    
    • Zach met him first, then he and his co-founder met him together in the second round. By that point, they already felt it was obvious he would be excellent
    • After only two or three interviews, the question was no longer whether they wanted to hire him, it became whether they could close him
  • While Jean-Denis was somewhat ready for something new, Plaid was not an obvious sell at first. He did not initially feel naturally drawn to financial services. 
    
    • Zach described this as a case where the sourcing and evaluation process identified the right person quickly, but the real work was in convincing that person to join
• Jean-Denis ultimately stayed for a little over seven years.

Case Study: How Plaid Hired their GC, Meredith Fuchs

• Zach’s second example was Meredith, whom he hired as General Counsel. This role came after a few earlier legal hires that had not fully worked:
  
  • Plaid’s first lawyer had the General Counsel title, but in practice was not really a true General Counsel. She was their first lawyer, and they gave her the GC title, but she didn’t actually operate as a full‑scope GC for a scaled, regulated fintech.
  • He then hired another General Counsel who had come from Twitter
  • While this person was a strong General Counsel broadly, they were not strong in financial services, which made them a poor fit for Plaid’s actual needs. That person eventually left for Reddit.
• By the time Meredith entered the picture, Plaid’s needs had become much more specific and much more high-stakes:
  
  • The company had just agreed to sell to Visa
  • There was extensive regulatory complexity around the business
  • Zach was regularly in Washington, D.C. speaking with regulators
  • Plaid needed someone who could operate credibly and effectively in that environment
• He described Meredith as having essentially the perfect background for that moment:
  
  • Plaid was dealing with CFPB-related issues and broader regulatory complexity and she had deep experience at Capital One. For a period of time, she had also served as director of the CFPB
• Zach believes that in most cases, the person with the “perfect resume” does not work well at Plaid. His experience has generally been that candidates who look perfectly matched on paper often do not fit the company’s culture. Meredith was one of the rare exceptions where the perfect candidate on-paper was also the right real-world hire
• Zach runs a narrow pipeline and treats the later stages as a selling process once he is confident
  
  • By the time Zach met Meredith, he had already done a large amount of preparation and had spoken to enough calibration candidates that he felt highly equipped to evaluate her. After meeting her, he knew she was perfect for their role
  • But he also emphasized that even when he reaches that conclusion early, he still runs the candidate through the rest of the interview process. The purpose at that point is less to decide whether to hire them and more to make sure the candidate becomes bought in
  • His typical pattern with a strong exec is to:
    
    • Do three early interviews
    • Reach a view that they are a 90% hire unless something surprising emerges
    • Then use the remainder of the process to build mutual conviction and close them well
  • He intentionally keeps his pipeline narrow during this process because he only wants to spend time selling and running a full process on candidates he’s already very confident about.
    
    • He and his recruiter screen hard up front; only candidates he’s ~90% sure he would hire move forward.Once someone passes that bar, the process becomes mostly about selling/closing, not exploring. 
    • This narrow pipeline avoids wasting time on “maybes”, keeps him from feeling pressure to compromise because a role has been open too long, and lets him invest deeply in references, multiple interviews, and high‑touch closing for each serious candidate
• Zach’s sell process is extremely hands-on and highly personalized
  
  • Zach said the communication pattern around Meredith’s process was probably the thing that worked best to close her. He was personally very involved throughout:
    
    • He texted her every two to three days
    • Before each call, he personally prepped her on who she would be meeting and how the conversation would likely go
    • He did not outsource candidate communication to a recruiter
  • Senior candidates often need to feel unusual levels of founder engagement and conviction in order to make the leap. Especially once you know you want someone, the founder has to step in directly and make that commitment tangible
  • Zach also described how aggressive Plaid became once it was time to close:
    
    • They sent gifts to her children
    • Around 30 people on the team reached out to her
    • Many of them called her directly and encouraged her to accept the offer
• The broader lesson is that strong executive recruiting is not just about evaluating talent well. Once you find the right person, you need to run an equally deliberate and high-intensity close process

Hiring Externally vs Internally

• Zach believes there is no universal rule for internal versus external hiring. In his view, the right approach depends heavily on the business you are building and the industry you operate in.
• At Plaid, he said there are some roles where external hiring is effectively mandatory because of the company’s customers and regulatory environment:
  
  • Plaid works with banks constantly. Because of that, roles like CTO cannot simply be filled by a very young internal leader, even if that person is strong
  • Zach said that when there are “a bunch of 22-year-olds running around,” he cannot just promote one of them into the CTO seat and expect banks to take that person seriously. In those cases, part of the job is not just operating well internally, but carrying enough external credibility that important partners trust the company
  • He said the same logic applied to General Counsel and a handful of other roles where Plaid needed someone with a stronger resume on paper. 
• He believes founders should not think about internal versus external hiring in the abstract. The right answer is shaped by what the role has to accomplish and what the outside world needs to believe about the person in that seat.

2. Hiring Internally

Default to Internal Promotions When Possible

• One of Grant’s clearest rules for executive hiring is that he defaults to internal promotions whenever he can. At Whatnot, the very best internal people have had a much higher rate of success than outside hires.
  
  • He also believes this is good for culture because it reinforces that strong people inside the company have real opportunities to grow into major roles.
• Internal leaders also have a structural advantage that becomes more valuable as the company scales: people who have been in the company for years accumulate deep context on the business, the product, the team, and how decisions actually get made.
  
  • That context becomes increasingly difficult to replicate from the outside as the company gets bigger and more complex.
• His view is that when an internal candidate has high horsepower, a strong desire to succeed, and a steep learning slope, that person’s accumulated context compounds into a major advantage over time.

Example: A High-Slope Internal Leader Grew Into Whatnot’s CRO Role

• One of Whatnot’s earliest employees came in as the 10-11th hire. Before Whatnot, the largest team he had managed was ~15 people. 
  
  • He had been running podcast partnerships at a large media company, so on paper he had nowhere near the level of leadership experience Whatnot would eventually need as the business scaled.
• When Whatnot began growing extremely quickly, the company needed to build out a much larger go-to-market organization. The company went from zero to over $2B in revenue in roughly six years.
  
  • In the early years, the business was growing at extraordinary year-over-year rates, at times around 500%. That level of growth created pressure to scale the go-to-market team from something small into an organization of 50 to 100+ people.
• At that point, Grant did not think the leader yet had the experience to lead an organization of that scale. He chose to go external and hired a more experienced operator.
  
  • His reasoning was that the person had worked at Uber, which seemed relevant for a fast-scaling marketplace, and therefore looked like someone who should know how to do the job.
• But that hire failed. Grant came back to the leader and put him back in charge because even while the more experienced external hire was in place, he kept proving himself in the actual business.
  
  • The teams performing best were consistently the ones under the leader.
  • He continued learning quickly and executing well. The parts of the business he touched kept working.
• He then brought in an interim COO for a period of time. Grant placed the leader underneath her for a stretch, effectively giving him additional support and coaching while still allowing him to keep growing into the role.
  
  • She had advised the company previously, so she was a known quantity.
• Grant explained that the leader’s development was not linear, and that part of making internal promotions work is knowing when to support, layer, or coach someone rather than assuming they can do everything immediately.
  
  • For the leader, one of the biggest inflection points came when Whatnot hit growth issues coming out of COVID.
    
    • The company needed to reset its growth strategy. The leader did not yet know how to do that at Whatnot’s scale. Rather than treat that as disqualifying, Grant spent significant time working closely with him to rebuild the motion.
  • Together, Grant and the leader reset both the growth strategy and the structure of the growth organization:
    
    • They moved away from a more generalist model and shifted to a more traditional go-to-market structure, while still adapting it to Whatnot’s needs.
    • That included building clearer functions such as:
      
      • Account management
      • Sales
      • Category management
      • They also had to redesign goals, compensation systems, and leadership structure around that new motion.
    • Grant spent a lot of time with the leader during this period to get the strategy and rollout right and help him hire the right leaders around him
    • The leader also proactively closed his own experience gaps. 
      
      • He had never run a sales team before, so to compensate, he immersed himself in the topic and read every sales book he could get his hands on and listened to every sales podcast he could find. 
      • He did not rely on title or prior experience; he learned aggressively enough to grow into the role.

A Strong Internal Promote May Still Need Layering Before They Are Ready 

• Grant noted that some of his best internal promotions did require layering at different points in time.
  
  • Even when someone clearly has exceptional potential, there can still be periods where they need a more experienced person above or around them while they continue developing.
• He framed this as part of the process, not necessarily as a sign that the person is failing. In the aforementioned internal leader’s case:
  
  • Grant first went external
  • Then brought in an interim COO
  • Later brought in another COO
  • But throughout those changes, he kept compounding as an operator
    
    • Grant also mentioned that one later COO was more of a CFO/COO type and was not the long-term answer either.
  • During that period, Grant kept go-to-market under his own purview and had the leader report directly to him. That gave Grant more direct visibility into his development and allowed him to keep investing in him closely.
• To determine if the internal leader would work, Grant used the following signals:
  
  • The teams under him were already performing really well
  • He kept improving faster than expected
  • He was hungry
  • He learned quickly
  • He worked extremely hard
  • He was willing to fill in his own gaps rather than defend them
• Over time, those traits mattered more than the fact that he had not previously held a title like CRO
• By the end of the process, the internal leader had learned how to run a large team, how to set strategy, how to hire leaders under him, and how to operate a mature GTM function
  
  • Grant said that if he now looks across his executive team, his organization is the one he has to spend the least amount of time on.
    
    • That was the clearest proof point that the internal leader had fully grown into the role. It also became the reason Grant finally gave him the CRO title.

How to Know When an Internal Leader Has Reached Their Limit

• Especially with high-slope internal leaders, it can sometimes be difficult to identify when they are struggling to scale with the company and when they may need external support. 
• In Whatnot’s case, Grant felt as though a strong internal leader had reached a limit within the team when his team was no longer creating meaningful leverage within the company. 
  
  • Concretely, this looked like being able to remove half of the leader’s team without impacting the business. To Grant, that meant the team setup and the strategy was incorrect. 
• Grant emphasized that these failure modes are often less about raw intelligence and more about pattern recognition that only comes from having operated at that scale before.
  
  • The leader had never run a 100+ person organization
  • He had never had to reset strategy for a large team
  • He had never had to align a large org around a clear strategy, operating cadence, and metric system
• Grant said those things are not intuitive if you have never done them before. The problem wasn’t that the leader was weak, but that the company had reached a level of scale and complexity where he did not yet know how to design the team, operating rhythm, and strategy in a way that created real leverage

Bringing in an External Leader Does Not Fix the Function by Itself

• Grant clarified that bringing in someone over an internal leader is not a magic fix. Even the external person he hired on top did not immediately “get him there”. The company still had to work through the process of figuring out how to run the team properly
• Many of these issues are not solved simply by swapping one person for another. There is often a broader operating challenge underneath
  
  • The company still has to build the right planning rhythm, strategy, and management system around the function
• Grant himself is highly operational and remains deeply involved in how the company runs:
  
  • He controls much of the operating rhythm, planning process, strategy, and how those pieces fit together across the business
  • He said he still has not hired an executive who has taught him a better way to run the business than the way he has learned to run it himself

Example: How to Layer a Strong Internal Leader

• Grant says that being direct and honest is the key to layering strong internal talent without losing them. When layering this internal leader, he framed the discussion as:
  
  • He had come in having previously managed only a ~15-person team
  • His org was now around 100 people
  • He was not yet doing a great job at that scale
  • The company itself was growing around 500% year over year
  • Grant’s message to him was effectively: You are still great, but we are going to bring in someone who has done some of this before
• The reason this can work, in Grant’s view, is that if the person is low ego and highly motivated to learn, they will see the layering as an opportunity rather than purely as a demotion.
  
  • Whatnot explicitly hires for low ego and a strong desire to learn. That makes it easier to bring in someone above a high-potential internal leader if the new person is someone they can actually learn from
• While the leader was bummed out when this happened, Grant was able to retain him because he:
  
  • Was honest that he wasn’t yet where the business needed him to be
  • Was clear that he still believed he is great
  • Positioned the new layer as someone for him to learn from 
  • Continued investing in the leader’s development even after delivering the news. 
    
    • He demonstrated this by getting him get strong advisors. This showed the leader that Grant was treating him as a long-term investment
• Grant was also realistic that this approach has limits. While he has been able to do this twice with that leader, he was candid that if he tried to do it a third time he may not be able to retain him. 
• Grant says the best way to avoid churning a high-potential leader is to make the conversation about the business and their growth. 
  
  • The key is to make the conversation about what the business needs to be as successful as possible and how the person can keep growing inside that reality 
  • His framing for these conversations is:
    
    • Are we here to make the business successful?
    • Are you currently making the business as successful as it could be?
    • If not, how do we get you the support, structure, and coaching you need so you can keep compounding?
  • He said this has become easier at Whatnot over time because there are now enough examples inside the company of strong people being layered, growing, and later emerging stronger. Once those storylines exist, leaders are more likely to believe the process is real and not just a polite way of pushing them out

Example: Why Whatnot Prefers Internal Promotes for the COO Role

• Grant said the COO role sounds appealing early on because founders assume they will hire someone highly experienced who can teach them how to run the company. That was certainly his own early instinct. But over time, he has come to believe that COO is a very high-failure-rate role, especially when hired externally.
  
  • His reasoning is that the span of control is often simply too large. In a company like Whatnot, with ~1,000 employees and operations across many countries, the amount of context required to be truly effective as COO is enormous. 
  • Grant said that if someone came into Whatnot from the outside at that stage, it could take them years to build enough context to be genuinely dangerous in the role.
• That is why Grant said he would not hire another external COO. He still believes there is a world where Whatnot eventually has a COO, but only if that person is grown internally: someone who has rotated across multiple functions, deeply understands the culture, and has already built immense company-specific context. 
  
  • He said he would love to have that kind of operator because he personally still spends a lot of time on operational work and would like to spend more time on product. But he does not believe an external search is likely to produce the right answer.

3. Hiring Externally

The Ideal External Hire 

• When Grant does hire externally, his default profile is not the most experienced person on paper. Instead, he prefers someone who has seen what great looks like in a function, fits Whatnot’s culture, but has not actually done the top job before.
  
  • Zach shares the view that “perfect resumes” often don’t lead to the most successful hires. Instead, Zach looks for someone one step up into the role vs. someone who’s done the exact job before. 
• They believe the people who succeed in these roles tend to be smart, humble, and hungry. Zach specifically looks for people early in their career, with steep trajectories, and who are close to being ready but haven’t “been there, done that”
  
  • In his experience, those qualities often decline as candidates become more senior and more established.
  • As a result, he is often more excited about someone stepping into their first CFO role or first CRO role than someone taking their second, third, or fourth version of that same job.
    
    • Board members often respond to these candidates by saying they’re “not there quite yet, but could be there soon”
• First-time functional leaders are often more motivated, more open, and more driven to prove themselves. While they may be slower and less polished at first because they have not yet sat in the exact seat, he believes you can surround that person with advisors and support. In exchange, you often get someone with more slope, more hunger, and more willingness to adapt.
  
  • Grant also acknowledges that there are exceptions to this rule, but he hasn’t seen many exceptions in practice. 

The Experience Trap

• Zach said one of the deeper reasons these very experienced candidates struggle is not that they do not know how to do the job. The issue is that they often know how to do the job somewhere else, but not how to do the job for this company.
• Plaid has a concept internally called the “Experience Trap.”
  
  • This is the idea that people with a lot of experience often come into a new company and try to apply the playbook, best practices, or assumptions that worked in a prior environment. But because each company is unique, that imported pattern often fails
• Zach’s view is that every company is unique and a great leader needs to invent the right approach for this company, not simply transplant what worked at another one
  
  • That is why he often prefers someone who is learning how to do the job in this particular context rather than someone who is overconfident in a set of existing formulas.
• For example, Jean-Denis had been Director of Engineering at Dropbox. He did not join Plaid directly with the full CTO title
  
  • Instead, Zach said Plaid was very stingy with titles and had him spend time initially operating closer to the work
  • This title conservatism mattered because it gave Jean-Denis time to learn the system before fully formalizing the role

Case Study: How Whatnot Hired an External Head of Engineering

• Grant’s first external leadership hire was its Head of Engineering. At the time, his co-founder Logan was running engineering
  
  • Logan was extremely smart and capable, but not well suited to managing a large engineering organization, in part because he simply did not enjoy it
  • By fall 2020, engineering was struggling badly:
    
    • Systems were breaking
    • Reliability was poor
    • The organization was beginning to fall apart operationally
  • At that point, Whatnot decided it needed someone who had done this before. Grant hired an external VP of Engineering
    
    • He said that hire was the right one for that moment in the company’s development. The new leader transformed the engineering org - he materially upgraded the team and brought in more than 30 strong engineers
  • But Grant also noted that the success of an external hire can be stage-specific rather than permanent:
    
    • About two years later, they had to part ways with that same leader. He had been effective at leading an engineering org below 100 people, but once the team grew beyond 100, his own scaling limits became more visible
    • Grant said the company increasingly needed stronger long-term planning, greater operational rigor, and a more thoughtful approach to reliability and technical architecture than this leader was able to provide
  • Grant then took engineering back over himself for about a year and only after that did Whatnot bring in their current Head of Engineering
    
    • Importantly, Grant did not initially hire him into the full head of engineering job. Instead, he gave him responsibility for only about half the team and told him to prove he could do it before taking on the entire org. Once the hire proved that he could, Grant gave him the rest of the team
  • Grant framed their existing leader as much closer to the “up-and-comer” profile he prefers. He was someone with strong slope, someone ready for more, and someone who had not necessarily already held the exact title at the same scale
  • Grant added that Whatnot has generally gotten much better at hiring in product and engineering because both he and Logan are much more calibrated in those functions.
    
    • Since they understand those domains deeply themselves, their hiring bar is higher and their ability to evaluate talent is better
    • By contrast, he said that functions like CFO and People were much harder early on because he had never personally run those functions and therefore did not know what “great” looked like
      
      • In those cases, candidates could tell a compelling story and still slip through because he lacked the underlying calibration to assess them properly

4. Interviewing Leaders

Zach’s Recruiting Principles

• Zach uses a set of recruiting principles he teaches internally at Plaid. He uses these principles broadly with hiring managers and emphasizes them even more heavily when recruiting executives
  
  • Linked here is Zach’s How to Recruit Deck
• His first principle is to hire for spikes, not for well-roundedness:
  
  • He does not want to hire people who seem broadly solid across many dimensions but are not truly exceptional at anything
  • Instead, he tries to get very specific about what a candidate is genuinely world-class at. The question for him is not whether the person seems generally impressive, but what exact thing they do at an unusually high level
• His second principle is to hire for trajectory:
  
  • Similar to Grant, he has categorically failed more often with people who had already done the exact job before. He has had much more success with people who had not yet done the job but were clearly ready to step into it
    
    • He summarized this as “slope, not y-intercept”. In other words, caring more about how fast someone is rising than where they appear to sit statically today

 Senior Candidates Are Often Very Good at Sounding Convincing

• Grant said the culture issue is something companies ideally try to detect through backchannels, references, and careful interviewing.
• But he also echoed Zach’s earlier point that many executives are extremely good at sounding convincing. Some people rise quickly because they are genuinely excellent, while others rise quickly because they are very good at talking
• As a result, some of the most important failure signals only become obvious after the person is already in the role.

How Zach Screens out “Bullshit Artists”

• One of Zach’s strongest principles is that he wants to hire doers, not polished executives who have become too detached from the actual work.
• He said Plaid has very little tolerance for “bullshit artists” in executive hiring:
  
  • If a candidate cannot explain something they personally and specifically did recently, hands-on and in the trenches, he will cut them from the process immediately. Zach wants to test whether the person can move from abstract language to concrete contribution
• The types of question he asks resemble:
  
  • What specifically did you contribute to the thing you say you shipped last month?
    
    • If the candidate cannot answer that precisely, he sees that as a major warning sign
    • His view is that many senior candidates become very good at telling broad stories about impact while obscuring what they themselves actually did. The presence or absence of specificity is one of his fastest filters

Testing a Highly-Experienced Candidate

• To assess the caliber of a “perfect resume” candidate, Grant goes extremely deep on the specifics of what the person has actually done and compares that against the real specifics of what the role will require. 
  
  • The goal here is to assess whether their actual pattern of decisions, work, and judgment maps to the real work this role needs to do.
• Zach said the ideal test would be some kind of work trial, but that this is usually hard to do in executive hiring because the person cannot realistically do the real job before joining.
  
  • In practice, his substitute is to go extremely deep on a specific initiative the candidate claims to have led. He wants to understand the whole story in detail:
    
    • How did the initiative start?
    • What were the key steps along the way?
    • What did the candidate personally do?
    • Who did they hire?
    • Who did they fire?
    • What decisions did they make?
• Grant said this was easier for Whatnot early on in functions like engineering and product because he and his co-founder came from those domains and had much stronger calibration on what good looked like there. It was much harder in functions like finance, where he had fewer reps and less intuitive understanding of what excellent looked like in practice. 
  
  • Testing experienced candidates gets much easier when the founder has direct functional understanding, and much harder when they do not.
• To build that calibration muscle, Grant talks to people at a similar company stage who he already believes are truly strong and asks them the same kinds of detailed questions. Over time, this gave him a benchmark for what strong answers actually sound like. 
  
  • He also added that there are always outlier cases: while the general advice is to be skeptical of very senior candidates, sometimes they are excellent. He noted that Whatnot has had one or two such hires work well. 
  • He also warned that if a founder is meeting ten candidates for a role and thinks eight of them are great, that is usually a sign the bar is not high enough.

5. References

References Are a Key Part of Hiring Leaders 

• Zach believes if you do not do references well you will almost certainly fail in hiring leaders. He emphasized the importance of:
  
  • On-book references
  • Off-book references
  • Doing a lot of references
  • Doing these early in the process
• He does not use references as a soft confirmation step at the end but rather an active evaluation tool. In these references, he asks questions like:
  
  • What percentile was this person among people you have worked with in this role?
  • Who was immediately better than them?
  • Who was immediately worse than them?
  • What specifically made those adjacent people better or worse?
  • If we have to fire this person in a year, why would it happen?
  • If you could only hire one person to work with you for the next two years, would it be this person?
• He also uses follow-up questions to catch inflation:
  
  • If someone says a candidate was top 25%, he asks how many people they actually worked with in comparable roles. Often, that forces a more truthful answer
  • His view is that most references become far more useful when they are comparative, specific, and pushed beyond the first flattering answer.
• If a candidate describes a major initiative, he wants to talk to people who worked with them on it and ask what they actually did, how they operated, and whether the initiative succeeded for the reasons the candidate implied.
  
  • He also pays close attention to the people the candidate has hired. One of his favorite questions is: who is the best person you have hired in the last two years? He then asks whether he himself would want to hire that person and what the executive did to make that person successful.
    
    • If the hire sounds especially strong, Zach will often reference that person directly. In some cases, he will even try to recruit them. 
    • But beyond sourcing, the point is diagnostic: the quality of the people an executive hires and develops says a great deal about their own taste, standards, and ability to build a function.
• He also asks the inverse question: who did you fire? Then, during references, he tries to understand what the team culture was actually like under that leader and whether the culture they built is compatible with the culture his company wants to build.

 Use Informal Settings to Get Signal on Character and Interpersonal Style

• Zach added that some of the most useful data comes outside formal interviews. He said he often takes executive candidates to dinner, sometimes with their spouses, and brings his own wife as well.
• You can learn a surprising amount by seeing how someone interacts in a more natural setting:
  
  • How they treat their spouse
  • How they interact with other people
  • Whether they seem grounded, warm, rigid, performative, or status-driven
• This is not a replacement for references or deep functional questioning, but another way to get signal on personality and cultural fit that formal interview settings often obscure.

6. Closing Leaders

Counter-Sell Candidates Early by Making the Hard Parts Clear

• Zach also tries to make sure candidates understand what is idiosyncratic or difficult about joining Plaid before they get too deep into the process.
  
  • He has a long culture document that explains all of the things that are surprisingly true about working at Plaid. He sends it to candidates early, asks them to read it, and comes back later and talks through how they react to it
  • Linked here is Plaid’s Culture Doc
• The point is to see how candidates respond to the actual environment they would be entering. He wants to know whether they are energized by the reality of the culture or whether there is mismatch hiding underneath the surface

Separate Selling from Evaluation

• Once a founder starts trying to convince someone to join, it becomes much easier to overlook flaws that the rest of the team later spots. This is especially dangerous in leadership hiring, where founder conviction can inadvertently overpower objective assessment.
• Zach’s advice was not to try to blend these two modes together, but to separate them intentionally. 
  
  • His own approach is to make the first conversation mostly about selling, assuming he already has enough signal that the candidate is likely strong. 
  • If that first call goes well, he then explicitly tells the candidate that the next conversation will be different: he will ask many more questions, go much deeper, and use that session to evaluate them more rigorously. 
    
    • He even tells the candidate this shift directly so the change in tone does not feel confusing or adversarial.
• Zach believes that founders can put on different hats, but they should do so consciously rather than muddling them together. If you are in sell mode, be in sell mode. If you are in assessment mode, tell the candidate that and switch into it fully.
• Grant added to not rely only on yourself to evaluate senior candidates, especially on dimensions where others may have better judgment than you. 
  
  • He said he thinks he is only average at assessing talent overall, even though he has improved over time. Because of that, he intentionally inserts “ringers” into the recruiting process. These are people on his team who he believes are better than he is at reading personality, culture fit, or certain kinds of executive signal.
    
    • For example, Grant’s co-founder is unusually good at drawing out the worst parts of a candidate’s personality, boxing them into corners, and surfacing how they actually behave under pressure. Grant said that once he himself has conviction on a candidate’s functional or technical capability, he still relies on his co-founder and a few others to get a better read on the person’s underlying personality and cultural fit.

7. Onboarding 

Onboarding New Leaders Is About Building Context and Trust

• Both Zach and Grant said the most important thing in onboarding a new leader is not a formal onboarding program. It is making sure the person gets enough context, builds trust quickly, and starts with a narrow enough mandate that they do not accidentally create damage before understanding how the company works.

Getting Into the Weeds Early Can Make a Leader Stronger Long-Term

• Plaid brought Jean‑Denis in as a long‑term CTO bet but onboarded him deliberately as an IC first.
  
  • They told him they wanted him to become Head of Engineering and that was the level they were hiring and paying him for. But they also told him they wanted to set him up to be successful over the next several years, not just hand him the title immediately
• Although he had been a Director of Engineering at Dropbox, he joined Plaid doing hands‑on engineering work for about six months to learn the stack and get deep context.
• Their view was that one of the best ways to do that was for him to get into the weeds first:
  
  • learn how Plaid’s stack worked
  • understand the systems firsthand
  • build context before taking on the full scope of leadership
• Zach said this worked because they found the right kind of person: someone humble, willing to learn, and who did not see early lack of title as an insult
  
  • He said Jean-Denis approached that period with enthusiasm and the attitude that it would be useful to go deep, understand the stack, and really learn how the company worked.
• He contrasted that with Plaid’s newer CTO, where they did not take the exact same approach.
  
  • In that case, Zach had already been serving as CTO himself for a period. When they hired the new CTO about a year earlier, they gave him an additional operating assignment as Head of Data for about six months while they transitioned that function
  • Zach believed the most important thing for the company’s success over the next five years was the Data Org. So he wanted the incoming CTO to go run that area directly for a period before fully settling into the broader CTO role

De-Risk Leadership Hires by Starting Them on Narrow Problems First

• Grant said one of his main tactics now is to avoid giving new executives the full team immediately. This is one of the main ways Whatnot has tried to control risk on executive hiring.
• Grant starts them on one narrow but important problem and waits for them to prove themselves there first.
  
  • For example:
    
    • His Head of Product did not initially get the full product team when he joined. In this case his Head of Product:
      
      • Was told directly that he was being hired to become Head of Product
      • But he had to begin as an IC. At this point, Grant’s co-founder was still running product. 
      • The implicit structure was that this person would shadow his co-founder until he had enough conviction that he was ready
    • His Head of Engineering initially got infrastructure, because infrastructure was the most broken part of the organization. In the engineering case, Grant’s instruction was:
      
      • fix infrastructure
      • get the technical strategy into a good place
      • go deep enough to prove you can actually solve the problem
      • then earn the rest of the team
    • Grant said the reason for the more cautious approach in engineering was that the function had only recently stabilized. The team had already gone through about six difficult months under leadership that he felt he had been too slow to transition out. 
      
      • That period had caused morale issues and cost the company some good people. By the time the team was finally improving, he was not willing to take another unnecessary risk

Example: How Zach Onboards Leaders

• Zach believes that many onboarding failures are actually founder failures. His view is that if an executive is not working, a meaningful portion of the problem is often about the founder - either the founder hired someone into a role they were never truly ready to give up, or the founder failed to create enough context and trust for the person to succeed.
  
  • Because of that, Zach’s onboarding process is extremely founder-intensive. He meets with a new executive every day for roughly the first two months. 
  • In each one-on-one, the executive is required to come with at least one question. His goal is to eliminate any excuse that the person lacked context, and just as importantly, to build enough trust himself that he will not end up subconsciously sabotaging them by hovering or stepping back in too aggressively. 
    
    • For Zach, these daily meetings are as much for the founder as they are for the new leader.
• This is how Zach paces onboarding in the first 90 days:
  
  • In the first 30 days, do not make big decisions. Use that time to build trust with the team through listening, coffees, and relationship-building
  • By around day 60, make the major org changes you need to make
  • In the two months after that, focus on actually accomplishing something meaningful with the team
• His logic is that if a new leader starts making major moves before they have earned trust, the team will resist them. But if they wait too long to act, they lose momentum and fail to put their stamp on the function.

Example: How Grant Onboards Leaders

• Grant thinks a good onboarding process helps reduce risk substantially. 
• His first tactic is to narrow the focus immediately and get the leader to a quick win that allows them to win credibility with their team. Rather than letting a new executive take over everything at once, he tries to identify the one thing the company most needs help with, or the one problem the company is not solving well, and makes that the leader’s initial wedge. 
• Grant’s reasoning is that if a new leader cannot create demonstrable value in a narrow area first, they are unlikely to win the broader team behind them. 
  
  • A narrow wedge lets the founder see whether the person can actually operate well before handing over the whole function. 
  • It also prevents someone with little company context from trying to move too much at once and creating avoidable mistakes. 
• The second thing Grant does is stay closely involved until trust is earned. He said Whatnot’s mantra is that trust is earned, not given. 
  
  • In practice, that means he watches closely how the leader runs meetings, what decisions they make, and whether they are operating at a level that is similar to or better than how he himself would operate. 
  • Until he has that conviction, he does not fully hand over the keys. 
    
    • He said that with his incoming CFO, for example, he plans to give her the team immediately but keep her tightly focused on one core area, ask her to bring in one truly excellent person to prove her recruiting ability, and stay in the team meetings until he has confidence in her judgment.
• Grant also emphasized frequent founder contact early on. His default is more like two to three meetings per week, plus being broadly available anytime by call or text. 
  
  • The core idea is similar: spend a lot of time together, constrain the initial problem, and only expand scope once the leader has shown good judgment and earned trust.

8. Firing 

Move Faster on Weak Leadership Hires

• Grant is more ruthless on exec performance than the broader team. At non-leadership levels, he has seen people get over the hump and improve materially after a slower start. 
• But he does not take that same approach with senior leaders: his standard is that if an executive is not contributing well by day 90, and the company’s top performers are giving only lukewarm feedback on them, he is already asking them to leave.
  
  • He believes strong leadership hires need to create leverage quickly and earn strong conviction from the best people around them early. If that is not happening, he does not think it is worth waiting much longer in hopes that things will turn around.

How to Tell When a Hire Is Not Working

• Both Grant and Zach shared that the hardest part in offboarding execs is usually not identifying failure modes, but acting on them quickly enough. In both of their examples, the clearest failure was not that they missed all the warning signs, but that they waited too long after those signs became visible.
• Grant said one of the biggest mistakes he has made is letting weak executive hires sit too long. 
  
  • He gave the example of a COO who stayed roughly nine months, even though in hindsight it was already clear by around month three that the fit was not right. 
  • Part of the reason he delayed was that he was already on his second CFO and was trying to determine whether the issue was the executive or something about Whatnot itself. 
    
    • He tried to narrow the role and focus the person on a smaller domain where he thought they should be strongest, but that still did not solve the problem. His conclusion was that the original hypothesis had simply been wrong.
  • Zach shared a similar example with a CFO hire. He said the root problem began before the person even joined: by the time he made the hire, he was simply tired of running the search. 
    
    • He had run one CFO search in 2019, then the Visa acquisition process interrupted it, then another search in 2020 also failed. In one case, an outlier candidate accepted the offer and then backed out a week before starting. By the third search, he was fatigued, his board was pressuring him to hire a public-company CFO, and he said he did not have the backbone at that moment to keep resisting that pressure. He ended up hiring a more traditional public-company CFO profile even though it was not his real instinct.
    • Once the person joined, Zach saw many of the same signals Grant described. Zach said that once that happened, he knew something was wrong. But the company then had to go raise an enormous round of financing, and that created a practical complication. 
    • He said it was already clear the CFO needed to leave, but they could not realistically fire the CFO in the middle of a major fundraise. So instead, Zach isolated him from the process and ran the fundraise himself with his Chief Strategy Officer. 
• Grant said there are three signals he now pays the most attention to when deciding whether a leader is failing:
  
  • Trusted people on the team begin surfacing concerns
    
    • Grant relies heavily on a set of high-trust, high-integrity people inside Whatnot who have strong judgment and the company’s best interests in mind. When those people come to him and say they are seeing strange or concerning behavior from a leader, he takes it seriously. 
    • One challenge early on is distinguishing whether the team is simply reacting negatively to a new manager or whether the person is genuinely not good. 
  • The executive cannot attract strong talent under them
    
    • One of the strongest indicators that a senior leader will fail is if they cannot bring in strong people quickly. His standard is that within roughly 90 days, a strong executive should be able to bring in at least a couple of “killers” who clearly up-level the function.
    • His reasoning is that if someone is truly excellent, strong people will follow them. When the people they attract are not up to standard, that is often one of the earliest and clearest signs that the executive is not who they appeared to be.
  • By around day 90, there is still a lot of talking but little meaningful action
    
    • He wants to be able to point to something the person has meaningfully contributed. If there is still a lot of strategic language but not much concrete action or change, that is a bad sign. 
    • This maps to his belief that executives fail when they operate at the surface without materially improving the business.
• Grant also said that certain roles are especially dangerous to hand to outsiders. Reflecting on the COO example, he said he would never hire another COO at Whatnot. 
  
  • The scope and contextual load of that role are simply too large unless the person has grown up inside the company and already has immense context. In a business as idiosyncratic and fast-moving as Whatnot, he no longer believes an external hire can absorb enough of the system quickly enough to succeed 

Example: Plaid’s Chief Product Officer Search

• Zach’s Chief Product Officer hire failed in a subtler way. They ran a search for a CPO and, with a search firm’s help, hired someone with what looked like an outstanding resume. 
  
  • She had been Chief Product Officer at a large, scaled company for roughly seven years, and on paper the track record appeared excellent. But once she joined, Zach learned two things he had not understood well enough during the process:
    
    • She had actually been running a CEO search at the same time, which meant she wanted a bigger job than the one Plaid was offering
    • At her former company, much of new product development had been run out of another team, so the exact scope she had owned was not what Zach thought it was
• That mismatch took time to reveal itself because the failure mode was not explosive. Zach was still acting as CTO at the time and was very busy running engineering, so product did not initially get his full attention. But around nine months in, when he looked back, the signs were obvious:
  
  • The team was not making decisions
  • They had hired only one product manager in nine months
  • There was no meaningful performance management happening
• Zach eventually backfilled himself out of the CTO role and went back into founder mode on product. At that point, he said it became obvious he was effectively doing the CPO’s job while she was still there. 
  
  • In hindsight, he thinks he should have fired her more directly and earlier. 
  • Instead, the situation ended more amicably because both of them could feel that it was not working. He told her he thought she would actually be a good CEO for a certain type of company, and helped her run that search. 
  • She eventually found that path, and the separation worked out well.

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