Vanta and Faire on Hiring and Managing Leaders

How Christina Leads Vanta 

Vanta is 7 years old, has grown to ~1000 employees, and secures more than 12,000 customers worldwide. The company generates well over $100M in ARR and helps companies build and earn trust with their customers by helping them stand up and improve security programs through 1) their automated security and compliance platform that helps companies with SOC 2 and ISO 27001, 2) continuous monitoring tools, and 3) vendor management software.

Example: Vanta’s Senior Reporting Structure

• Christina currently has six direct reports. Three of them comprise G&A functions: 
  
  • CRO - owns all revenue functions spanning SDRs, sales, post-sales, and RevOps
  • CMO
  • Chief Product Officer - owns engineering, design, product, and analytics
  • Chief People Officer - also acts as the GC
  • CFO
  • CISO
• Christina’s EA used to report directly to her and now reports to her Chief People Officer. She feels this sets up her EA better in career-growth conversations, where before Christina didn’t have the bandwidth to meaningfully engage in those discussions
• The median tenure of Vanta’s leadership team is 2 years
• The most difficult leadership hire for her was the Chief Product Officer, which took 11 months.

How Max Leads Faire

Faire is 8 years old, has grown to 1000 employees, and is connecting 800,000 independent retailers with 100,000 brands. The company generates ~$500M in revenue and is growing 45% YoY. Faire is a B2B wholesale marketplace and helps independent retailers discover and buy from brands, while giving brands a platform to reach and grow with retailers worldwide

Example: Faire’s Senior Reporting Structure

• Max currently has eleven direct reports:
  
  • CTO
  • COO - Faire’s co-founder. Leads all GTM and Operations, and has the biggest scope
  • GC
  • Head of Design
  • 4 Pillars of Product Leads – each pillar reflects a company priority, with one PM responsible for each
  • CFO
  • Chief Strategy Officer - runs analytics
  • Chief of Staff 
• The most difficult leadership hire for Max has also been the Chief Product Officer, which he’s still actively hiring for and why product reports directly to Max.
• The average tenure among Faire’s leadership team is 3-4 years

1. Knowing When to Hire

When Do You Bring in an External Leader?

• For Max, a clear signal to bring in a leader is when you find yourself bored by the work of the function.
• He believes that between 30 and 500 employees, most companies need to bring in VPs across all major functions.
  
  • For the current CPO search, he debated doing the role himself vs. bringing someone in. He ultimately decided to hire a CPO because he found himself spending time on tasks that:
    
    • Weren’t uniquely CEO-level responsibilities.
    • Didn’t feel high leverage.
    • Weren’t energizing for him personally.
• Within this range, if you’re wondering whether to hire a leader, you probably should.
  
  • CEOs gain significantly more leverage when they place strong hires into these roles.

Framework: Bring in Leaders Once Work Becomes Repeatable

• At around 100–150 employees, Christina realized she could no longer be both CEO and the head of another function. This was the point when she started bringing in external leaders.
• Her heuristic for when a function is ready for a leader:
  
  • If the work becomes so repetitive that she could “turn her brain off” and do it.
  • When a job feels repeatable enough to document in clear steps, the function is mature enough for a leader.
• Example: the first leader she hired was a Head of Customer Support.
  
  • She opened the role in January 2021 and closed it in September 2021.
  • While the hire is still at Vanta, they ultimately weren’t the right long-term fit

When Should You Flatten Your Org?

• Flattening is a later-stage problem. Sometimes you’ll need to flatten orgs because you brought in too much structure and want to reduce the amount of management capacity in the system. Before making hires now, Max often asks himself whether certain roles at Faire should be flattened or whether they require hiring leaders

Don’t “Shop When Hungry” 

• Christina believes you only get executive hires right if you know exactly what you’re looking for.
• Waiting until the moment of need leads to bad decisions, and it’s like “grocery shopping while hungry.”
• Organizational pressure can make this worse.
  
  • Once you announce to peers or direct reports that you’re filling a role, it puts a clock on the decision and raises the company’s “hunger level.”
  • That pressure biases teams toward closing fast rather than finding the right fit.

Example: Vanta’s CMO Hires

• Christina’s first CMO search was only her second search ever, and her first major external hire.
• She over-indexed on her search firm’s confidence in a candidate and closed them quickly (in 4 days)
• Within 30 days, it was clear the hire’s strengths didn’t align with Vanta’s needs. Within six months, the company moved on. The fallout left the marketing team frustrated, and pressure mounted to hire both a CRO and an ops lead since other functions were also breaking.
• To relieve pressure, Christina recruited a former colleague and advisor respected by the team. The hire solved immediate pain but wasn’t the right long-term fit either, lasting only 9–12 months before exiting.
• This left the org needing to rebuild again. Christina analogizes this decision to “reaching for the Chips Ahoy bag because you’re starving.”

External Hires vs. Internal Promotions

• Max believes the balance between internal promotion and external hiring depends heavily on growth rate. During periods of rapid growth, he leans more heavily on external hires. In slower-growth periods, he focuses more on growing internal talent. 
  
  • When Faire was growing through rapid scaling, they almost exclusively hired externally vs. now they focus more on grooming internal talent. 
• When Max notices that internal talent isn’t working out, he begins hiring externally for the role almost immediately.
  
  • For example, he once promoted a phenomenal IC product lead into a Group PM role.
    At the time, Max was directly managing her but didn’t have the experience to properly coach someone stepping into people management. This ended up consuming a lot of his time and highlighted the gap in having experienced managers in the chain. 
  • Once Faire brought in a Head of Product with experience managing managers, internal promotions became more successful

Tactic: Max’s Framework for Deciding When to Hire Externally vs. Promote Internally 

• How mature is the function: For initial hires who are building out the function, Max finds it helpful to have someone who’s at least operated a couple years ahead of where you want to be, ideally having scaled from your stage to the next level.
  
  • Once a function is built and running smoothly, internal promotion is both easier and preferable. 
• How fast is the function scaling: If the department is scaling quickly, promoting someone too green rarely works.
  
  • For example: Promoting an IC to manager of a rapidly scaling critical function or promoting a junior manager to manager-of-managers in a fast-growing department rarely work because in both cases, the demands outpace the person’s ability to keep up.
• How excellent is the person: There are rare cases where someone is able to keep up without having a world-class leader above them 
• Can their manager coach them: Promotions can succeed if the person has a world-class manager who can train and coach them. Pairing an inexperienced leader with an inexperienced manager is especially risky – at least one layer needs to bring deep experience.

2. Running Calibrations

Calibrations Help You Understand What Great Looks Like

• When hiring your first leaders or for a function you’re less familiar with, calibrations can help you build intuition for what best-in-class looks like
• CEOs typically kick off a calibration process by asking their investors and broader network to introduce them to the best functional leaders they know. 
  
  • Christina ran ~15-20 calibration sessions for her last CMO search
• When taking calibration meetings, founders spend time learning how various leaders think about and describe their role to build a mental model of what they should be looking for in their hiring process. 

Before Calibrating for Greatness, Understand What Your Company Needs

• Only the CEO knows the business well enough to decide its priorities and the skills senior hires need. If you’re unsure whether you need to hire a CMO with a stronger background in enterprise or SMB, calibration may be helpful but won’t ultimately help you resolve the uncertainty.  
• Both Max and Christina suggest taking what is most important for the company as the “major” you want your leader to have. From there, press the candidate on whether: 
  
  • They know what great looks like in that motion?
  • They can hire talent to cover the complementary motion?
  • They value and respect the other motion (e.g. SMB/mid-market)?

• Watch out for archetypes (e.g., strong enterprise marketers who dismiss SMB as irrelevant). They may be excellent elsewhere, but not the right fit if both motions matter.

Case Study: How Christina Ran Calibration for Vanta’s CMO

• Process:
  
  • Nine months ago, when Vanta needed another Head of Marketing, Christina emailed all her investors asking for introductions to experienced CMOs.
  • She took every introduction and asked each leader about:
    
    • How they define the scope of their role.
    • How they structure their teams.
    • Their hot takes on Vanta’s marketing.
  • These conversations were not candidate interviews. Christina used them to calibrate her own mental model of CMO archetypes and map those against Vanta’s needs.
• Example:
  
  • Christina knew Gong had a strong marketing team after watching them win call recording.
  • As part of her calibration, she spoke with Gong’s marketing leader to understand what a strong CMO looks like, and tailored her specific questions to his experience.
• Template Questions:
  
  • How are marketing teams set up?
  • What is the point of a brand and creative team?
  • What do great brand teams actually do?
  • What is the role of a campaign in marketing?
  • Are marketing leaders always strongest in their functional upbringing (brand/PMM vs. growth/demand gen)?
  • How easy would it be for you to bring people you’ve worked with?
• What She Was Looking For:
  
  • How opinionated each leader was in their answers.
  • She gravitated toward CMOs with a strong sense of direction rather than vague responses.
• Outcome:
  
  • From these conversations, Christina formed her own opinions of what she wanted in a CMO.
  • She rejected the idea of choosing between brand and demand gen strengths. Instead, she looked for a smart, driven leader with:
    
    • High horsepower.
    • Ability to learn fast.
    • Competitive drive.
    • Willingness to go deep into the details.

Use Calibration to Untangle Real Impact and Fit

• Christina suggests anchoring calibration conversations around concrete examples.
  
  • In her CMO search, instead of asking abstract questions about “taste,” she asked candidates to define great marketing examples and explain what made them great.
  • This shifts the conversation from vague judgments (“Do you have good taste?”) to something tangible that can be compared against her own mental model.
• She cautions against simply sourcing execs from “hot” companies like Stripe or Gong.
  
  • Success always has many contributors, and multiple people may claim the same credit.
  • Christina personally knows seven different people who all claim to have invented the Facebook ‘Like’ button.
• The goal of calibration is to untangle:
  
  • What did this person actually own or build?
  • What role did they play relative to the broader team’s success?
  • What do they want to do going forward?
• Christina finds the third question especially useful in distinguishing between two archetypes:
  
  • Operators: still “in the muck,” building, and wanting to stay close to the craft and details.
  • Veterans: were in the muck 10 years ago, but now prefer to guide from the “top of the hill,” supervising others instead of rolling up their sleeves.
  • Both archetypes can be successful and have meaningful careers, but only one may fit what your company needs at a given stage
• The point of calibration is to surface these distinctions early so you can align the hire with the stage of the business.

Translate Calibration Into Mission, Outcomes, Competencies

• When hiring for a role he’s never filled before, or one with a significantly different scope, Max follows a process similar to Christina’s.
  
  • He seeks intros to the best people in those roles and meets with them to build intuition for what “great” looks like.
  • From there, he translates that intuition into a Mission, Outcomes, Competencies (MOC) document.
• He sees the MOC doc as a crisper, clearer articulation of what he needs than a traditional job description. He uses it throughout the hiring process to maintain focus and alignment.

Tactic: Max’s MOC Framework and Interview Process for Exec Hiring

• ~18 months ago, Max ran a CTO search process. His process is outlined below:
• Begin with a brief 2-3 sentence description of what the role is accountable for and, most critically, key outcomes for the next 12-24 months. 
  
  • Key outcomes should be the things that the person will be successful if they accomplish. These are ranked in order of importance
• Use those outcomes to define the key competencies needed to achieve them
• Here’s an example of Max’s MOC Document

3. Interviewing Leaders

Interview Process

• Anchor your process with calibration conversations to build clarity on what great looks like before opening the search.
• Translate that calibration into a Mission, Outcomes, Competencies (MOC) doc to guide your entire hiring process.
• Assign each interviewer one or two competencies to probe deeply, rather than everyone asking general questions.
• Structure assignments around messy, real company materials so you can see how candidates operate in practice and filter for leaders energized by the reality of the role.
• Run rigorous references to collect both formal and backchanneled perspectives to piece together a holistic picture. Expect mixed reviews, and dig deep in each call to piece together the full detail of their work 

Tactic: Max’s Interview Process for Hiring

• Interview Process: Max followed the below process to assess his incoming CTO candidate: 
  
  • Each interviewer was given a specific competency to probe that was aligned with their strengths
  • They created a take-home assignment that simulates the most important parts of the job 
  • A deep behavioral “Who” interview where they go through their background. 
    
    • In this behavioral interview, Max asks the candidate what their past accomplishments were, what their biggest mistakes were, what their relationships were like with their managers, and what others would say are their strengths and weaknesses in a reference check
    • This starts to identify patterns for where a person is really good and and the kinds of problems they can solve
    • Detail on how to run these interviews can be found in the book: Who by Geoff Smart
• References: Max runs at least five formal references with managers and another five informal backchannels
  
  • In these calls, he asks for the candidates strengths, weaknesses, and to rate their performance on a scale of 1-10. 
  • He also digs until he finds someone to say something bad about each candidate. 
    
    • Max generally thinks if you haven’t reached this point when referencing someone, you haven’t gone deep enough in your research. 
  • Max will also include his last four performance reviews in the interview packet he gives the candidate, and asks a candidate for their last four as well. 
    
    • It’s often a red flag when a candidate isn’t willing to share this during the interview. 
  • References help you weed out the 70% of candidates that weren’t going to be a good fit
• Decision Making Process: Final rounds typically include 3-4 candidates at once that are narrowed down to 2 serious contenders that you feel could do the job. Max then creates a packet with:
  
  • A spreadsheet with all the competencies listed 
  • Interview scorecards and reference notes
  • Take-home exercise results 
  • Detailed notes from the behavioral deep dive 
  • and has everyone that was deeply involved in the interview process rate each candidate on a scale. 
    
    • Each of the items in the packet are weighted to their relative importance which gives each candidate a score. 
• Max then has everyone go around and vote hire/no hire/hire both for the two candidates.
• Since implementing this process four years ago, he’s found it to be extremely effective. While the process is extremely time-intensive, Max hasn’t had a miss with hiring a bad exec candidate since then
  
  • A bad exec hire is highly damaging: they can destabilize a function by hiring poorly and replicating their mistakes. Executive hiring should be the CEO’s top priority until the hire is made, and remain the top priority for the first month to ensure they onboard well and early performance is strong
  • If there are signs that an exec you’ve hired isn’t good, react quickly to prevent them from compounding their mistakes and impacting the rest of the function

Example: Vanta’s Approach to Take Home Exercises for Execs

• At Vanta, Christina emphasizes exercises with real materials. For CMO candidates, she sent finalists a Google Drive folder with 30-40 files of real materials relevant to the CMO’s job. The purpose of the exercise was to reflect the team’s actual “chaotic and noisy” state, and the goal was to filter for leaders who are energized by the reality of the job over being intimidated by it.

• One candidate opened it and declined → good outcome (misaligned)
• Another complained to the recruiter → not a fit
• Final hire engaged deeply and found it useful because he understood what the role would be like outside of just speaking to people from the team

• The exercise both filters candidates and begins onboarding them through the interview process

• The best “try before you buy” plan for both sides is going from an advisor to a full time hire. This serves as a great way to derisk a hire for both parties

When Hiring Leaders, Make Sure You Understand Their Motivations

• Sometimes candidates express they’re excited about certain aspects of the job (like aggressively hiring a large SDR team) that may or may not be aligned with your intuition as a founder (which may say to hire when it makes sense, instead of hiring for hiring’s sake)
• In these cases, Max suggests anchoring to the Outcomes and Competencies you’ve identified. If building a big team isn’t a top outcome on your list, the candidate may be misaligned. 
• During the interview process, you should also probe further to understand the reasoning behind their excitement by asking questions like “Why do you want to build a big team?”. This can help you identify whether they’re motivated by leverage, vanity metrics, or true business need. This also helps determine whether the candidate will be dissatisfied or ineffective in cases where growth slows or the company’s plans shift. 

References Are Often Messy and Conflict. Your Job is to Piece Together the Full Story

• Running many references requires holding multiple, sometimes contradictory perspectives in your head.
• At senior levels, everyone will have mixed references. If they don’t, it’s a red flag and likely means they’re optimizing for optics or clean references over impact. Instead of indexing on whether someone had a bad reference, try and understand why they’re getting that feedback
  
  • For example, Max was considering a leader out of a company where the CEO and the leader didn’t see eye-to-eye. His first reference call was with the CEO, and it was strongly negative. 
  • After speaking to five other people from the company, he got a clearer picture that the executive and CEO just had differing opinions that widened the gap between them over time. 
• After going deep with reference checks, Max also speaks with the candidate directly and shares the reference feedback with them. This helps him understand the full picture. 

Remote Leaders Can Work As Long As There’s Alignment Within Your Team

• As a CEO, you know what’s best for your company and whether having execs in-person will work for you and your team. Christina’s stance is that distributed teams and remote exec hires can be effective so long as both sides are invested in making it work
  
  • In cases where you know a candidate will be a great hire, location can become a solvable problem as long as both sides are aligned on visit cadences and remote expectations
  • For example, Vanta grew from 20 people at the start of lockdown to 200 two years later. They had no choice but to adapt and take on remote leadership hires.
  • Now, Christina’s direct reports are still split between the East and West Coast. 
    
    • The East Coast reports do feel somewhat at a disadvantage being remote, however

4. Closing Leaders

The Best Companies Don’t Lose Candidates

• Max learned from Brian Chesky that “elites don’t lose candidates.” He uses this as a mindset when closing top hires.
• Exec hiring requires significant time investment. Max spends 10+ hours per week on a search until the candidate signs. Early in a process that time is spent assessing many candidates, in the middle it’s spent on narrowing down to a few, and at the end it’s going towards closing the one you want
• Because of the time demands, Max prefers to sequence to running one search at a time, but has occasionally run two in parallel (e.g. Lead Independent Board + CPO) and found it extremely taxing.

Example: Max’s “Bear Hug” Approach to Closing Strong Candidates

• Once down to the top 3–4 finalists, he identifies the highest-potential candidates and spends disproportionate time with them to build trust and mutual connection. The goal is to start the relationship before the hire is in the door so that mutual trust carries into the role
• He uses structured closing steps to make the process deliberate:
  
  • A closing deck late in the process tracking candidate concerns, how they’ll be addressed, and which board members or leaders will reinforce key points. He maps out when each person on the team will meet with the candidate and what exactly each will say

Stay Disciplined on Comp, But Flex with Other Levers

• Christina tries to stay disciplined about comp bands for VP and C-level hires. This is because bands give structure and confidence in decision-making, especially once a company matures. At the same time, she acknowledges exceptions are sometimes required — and has developed a set of levers she’s comfortable using
  
  • She is more willing to flex outside the band for sales and marketing leaders by shifting comp into the variable side.
    
    • Example: a candidate had expectations above the band. Original proposal: 80/20 base-to-variable split. Adjusted to 70/30 split to meet the candidate’s target. Christina framed this as:  “If we hit our goals, I’m happy to pay that amount.” This allows her to protect comp band discipline while rewarding performance. 
• Vanta runs annual equity refreshes for all employees, including execs. This gives Christina confidence telling candidates that even if today’s grant isn’t where they want it, they’ll be topped up annually. 
  
  • The refresh program helps close candidates who otherwise might anchor on headline equity numbers.
• Christina believes if comp is the deciding factor, something else went wrong in the process. A $20k or even $100k delta should not determine whether an executive joins, and if it does, either the candidate isn’t aligned with the company’s mission, or the CEO hasn’t built enough conviction on the non-monetary side. 
  
  • Her view is that great execs aren’t playing for salary, and you don’t want them to be.
• Vanta had previously experimented with milestone grants but ultimately stopped because they created unintended resentment instead of motivation.

5. Onboarding Leaders

Onboarding Is About Building Alignment and Giving Leaders Context

• Christina and Max both stress that the first 90 days for a new leader aren’t about solving every problem. The goal is to align on priorities, agree on which fires to tackle now and which to let burn, and transfer the CEO’s mental model of the team and company context so the leader can ramp quickly without guessing.
• Both Christina and Max use late-stage interviews as the first step in onboarding. By exposing candidates to real company materials, org dynamics, and unresolved fires before they accept, they filter for leaders who can handle the reality of the role and give new hires a head start on understanding the team they’ll inherit

Example: How Christina Onboards Execs

• Vanta also puts together structured comms plans to introduce new hires to the company in a coordinated way. These include a breakdown of:
  
  • Who learns what at what time
  • Who is responsible for each step
  • FAQs
  • A schedule of meet and greets

• In an onboarding packet they also include a breakdown of priorities and how “on fire” each of them are. 
• Christina also creates a team-level doc for the new exec with person-by-person notes on strengths, gaps, and unknowns. 
  
  • In their new CMO’s case, this doc was ~17 pages long. The purpose of this is to offload Christina’s mental model so it doesn’t become an unspoken “test” that new hires have to guess around

• Vanta’s People team also built a deck for the new CMO with the marketing org layout, names, and structure. This helped the new exec understand what exactly they’re inheriting 
• The goal in the first 90 days isn’t that the exec fixes everything, but it’s to align them with your priorities of which fires they’re going to actively tackle and which ones they’re going to consciously let burn. Christina says she wants to hear about every fire, and explicitly tells her team that if a fire doesn’t come up she will question if the leader is aware of it. 
  
  • From there, she’s open to letting some fires burn as long as she knows there’s alignment with her and the leader that they both recognize the fire and are choosing to deprioritize responding to it

Tactic: How Max Onboards and Manages New Executives in the First 90 Days

• Early on (first 30–90 days):
  
  • Max manages new executive hires very closely at the start, then gradually steps back.
  • This helps new leaders build alignment quickly and prevents small misses from compounding into bigger problems.
  • He believes it’s better to begin with micromanagement and reduce it over time. Giving too much freedom early, then jumping in to correct creates a “doom loop” where the exec feels undercut and mistrusted.
• Weekly structure:
  
  • Holds weekly 1:1s with the new exec.
  • Runs skip-level meetings with their direct reports.
  • Requires a 30/60/90 day plan and tracks progress against it.
  • This structure ensures visibility into priorities, alignment, and execution from the very beginning.
• Starter projects:
  
  • Assigns projects that both give the exec context and validate that they can actually do the job.
  • Manages them closely through these initial projects, only reducing intensity of check-ins towards the end of the 90-day window.
• Feedback:
  
  • At the 90-day mark, runs a start–stop–continue exercise with the exec’s direct reports and cross-functional peers.
  • Ensures the exec is on the right track.
  • Also builds the habit of receiving structured feedback early in their tenure.
• Hold pre-360s at the outset:
  
  • Shares his own expectations of the hire’s strengths and growth areas going in.
  • Establishes a feedback culture from day one, which makes future feedback less awkward and more actionable.
• End of the 90 days:
  
  • By the end of the process, the goal is for the exec to be fully aligned with the company’s priorities, have a track record of validated performance, and be accustomed to continuous feedback loops.
• Sometimes someone on the team may feel like they’re “managing” the CEO.. Max sees this as often helpful (especially for more junior founders) because it provides added perspective and balance.

6. Managing Leaders

Why Layering Happens

• When companies scale quickly, you may have team members that either can’t grow with the pace of the company or may need additional management guidance
• Layering becomes necessary when the company needs a more seasoned operator to unlock the next phase of growth without losing the original leader’s contributions.

Be Transparent When Layering and Involve the Team

• Vanta’s first CSM came in wanting to manage the team. As customer growth outpaced CSM hiring, Christina assumed she had the same drive and appetite as herself and pushed her hard.
  
  • Eventually, the CSM admitted she didn’t want the role. Christina realized she had been projecting her own ambition onto someone excellent but uninterested in management.
• Vanta’s first AE, by contrast, was extremely ambitious and wanted to become CRO. When the team reached ~30–35 AEs, Christina hired a CRO over him because both she and the AE were stretched too thin.
  
  • The AE was angry at first but stayed, is still doing well, and ultimately acknowledged he didn’t truly want the job of running a large sales org
• Christina assumes that in the small tech world, people will quickly find out if you’re layering someone. She believes it’s better they hear it directly from you rather than secondhand.
• When layering, Christina includes existing leaders in the interview process. While she doesn’t give them blocking votes, she involves them to:
  
  • Signal respect and transparency.
  • Expose them to the incoming leader and hear their opinions.
  • Help set the new leader up for success with the team.

Normalize Layering with Expectation Setting

• During scaling, Max tells people upfront they will likely get layered. He frames it as natural and okay given the company’s growth rate.
• When he’s betting on someone, he’s explicit about what must happen in the next 3–6 months. 
  
  • For example, he will say: “Here’s what needs to happen. If it doesn’t, I’ll kick off a search.” About 80% of the time he ended up kicking off a search to layer them. Setting expectations upfront made the process less painful and more transparent.
• An example of when this approach worked was with a senior leader who needed to hire well and build a hiring machine. Max’s expectations were that they needed to:
  
  • Double the size of the team within a year.
  • Fill key leadership roles to create leverage.
  • Consistently bring in high-caliber ICs.
• Because they hadn’t done it before, Max supported them through the process. The leader delivered and successfully avoided having to be layered. 

Delay Titles

• Christina and Max believe in delaying title inflation as long as possible. Titles set precedent and create pressure, so they prefer to hold off on them until they can’t do so credibly anymore.
• At Vanta, many early leaders carried Lead-level titles (Lead of Finance, Lead of People, Lead of Design).
• When the pressure finally broke, she promoted several Leads to Head-level titles all at once. Doing it in a batch avoided messy one-off promotions that could create unfairness or politics.
  
  • This allowed her to reset the standard broadly.
• Titles are cheap to hand out but nearly impossible to take back. Having discipline upfront pays off.
  
  • The Lead → Head transition happened around $15M ARR.
  • The Head → VP transition came later, once the company reached roughly 55–60M ARR.
  • The first C-level title appeared at around 62M ARR.
• In Max’s view, you don’t really know what a true VP looks like until the company is at 300–400 people. Until then, VP and C-level titles should be avoided unless it’s absolutely obvious.
• Max saw the downside firsthand at Square: Square gave out VP titles too early and when the company later needed to hire real VPs, they had to “take titles back,” which created resentment and politics and a status-oriented culture

Firing Leaders

• With mis-hires, it’s important to move fast once you reach conviction. Dragging out a mis-hire at the exec level is one of the most damaging things a company can do, as it gives them more time to replicate their mistakes within the team 
• Allowing leaders some control over timing and narrative shows respect, reduces resentment, and makes it easier for more empathetic managers to take action on mis-hires

Example: Vanta’s Glide Path Approach to Fire Leaders and ICs

• At Vanta, Christina uses a glide path to transition leaders out of a role gracefully while still removing them from the company. The Glide Path involves the following steps:
  
  • Let the leader know it’s not working and this is the end of the road
  • Allow them to craft their own exit story with the CEO having veto/approval rights. This can be whatever narrative feels natural to them.
  • The speed at which you remove them from the company’s daily operations depends on how disruptive they are:
    
    • If they’re highly disruptive, remove quickly
    • If less urgent, they may stay “in” the company but with no real responsibilities
    • Sometimes keep them on payroll so they can job search while saying they’re still employed. This is typically used for long-term ICs. The bet here is that if you treat your leaders like adults, they will act like adults in return, and that giving people as much control in a situation where they otherwise have very little makes an unpleasant situation slightly easier and helps empathetic managers move faster towards removal

Use Your Intuition to Know Which Fires to Let Burn

• Max leans on intuition and a rough mental sizing of the problem to decide which problems matter most. The key is identifying where the highest leverage is (what’s most broken, and what will free up the most time or impact customers most directly)
  
  • For example at Faire, his top two priorities are: hiring a CPO and fixing selection growth. He arrived at these two because:
    
    • The PM function consumes a huge share of his bandwidth, and product is the company’s most critical function
    • Through customer interviews he found out that selection growth is the biggest blocker to the company’s growth and is currently not growing well

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