Webflow and Whatnot on Hiring & Managing Leaders

Batch 4: Hiring and Managing Leaders

The best way to scale your company is to hire great people that act like founders and provide leverage. Grant Lafontaine (Whatnot) and Vlad Magdalin (Webflow) shared hard-earned lessons on hiring, promoting, and managing leaders. Their styles differ dramatically—Webflow built a polished public-ready exec team, while Whatnot favors slope over pedigree and layers internal talent aggressively. But both obsess over executive fit, context, and performance.

1. No Right Way to Build a Leadership Team

Key Observations

• It’s rare, but not impossible for executives to scale with the company. You’ll likely have to replace people as their growth slope doesn’t match the company’s trajectory.
• The hit rate on hiring is 50%. The mathematical equation on internal promotions makes sense if you can make it work because they have something new hires do not—deep company context
• The payoff on a good hire is huge. Spending time to get it right is critical. Both Grant and Vlad spend 10+ hours personally with leadership hires to ensure the right fit.

Webflow: From Founders Running Functions to a Public-Ready Exec Team

• At $20M in ARR, Webflow had no formal executives—just the three founders splitting responsibilities:
  
  • Vlad: Engineering, legal, and people.
  • Co-founder 1: Go-to-market (sales, marketing, etc.).
  • Co-founder 2: Product and design.
• The first executives were first-time VPs who had proven themselves in senior roles at larger companies but had not led those functions (i.e., still had hunger and desire to be “the leader).
• Over time, Webflow transitioned to a team where the majority of leaders are from public companies to help prepare the team for IPO. Vlad calls this his “version 2.5” of his executive team

Whatnot: A Mix of External Hires and Internal Promotions

• At 60 employees, Whatnot made their first executive hire. At the time, Logan (Grant’s co-founder) was running EPD and Grant was running the rest of the company. They hired a VP of Engineering because they lacked the experience to manage and scale large engineering teams
• They hired a candidate that previously was Head of Engineering at a few companies that went public. He had never gone as early as Whatnot, but knew what “great” looked like. He was exceptional and scaled with Whatnot for 2 years
• Today, Grant’s executive team remains light on C-level titles, with Grant personally managing many direct reports (14–15 at a time). Unlike Webflow, Whatnot hires external execs only when absolutely necessary and continues to coach internal leaders into larger roles.

2. Internal Promotions vs. External Hires

Key Observations

• Internal promotes understand your culture, speed, and expectations, reducing onboarding friction
• Promotions create strong morale, reinforcing the belief that top performers can scale at the company
• While they have proven their ability to executive, their key gap is often management skills/scale
• Scaffold internal promotions with advisors/coaching to help them scale to the next level on your team
• Don’t be afraid to layer internal promotes to help them build experience before giving them the “big” role

Tactic: Grant’s Framework for Internal vs. External hires

• He prioritizes internal promotions and only hires externally when there is a critical skill gap that cannot be filled internally to achieve a business outcome.
  
  • Example: At 60 employees, they hired a VP of Engineering because they lacked engineering management experience.
• When promoting internally, he invests in their development through coaching from advisors and third-party coaches.
• When hiring external executives, he looks for candidates who:
  
  • Have seen what "great" looks like in their function.
  • Align with the company culture.
  • Haven't yet held the top role but are motivated to prove themselves.

Tactic: How to Layer High-Potential Internal Candidates 

Context: Whatnot’s CRO, Armand, was layered twice before proving he was ready. Here is Grant’s approach:

• Transparency: Grant framed the decision as a way to support Armand’s growth, emphasizing that he had strong potential but needed to learn from someone with deeper experience because he has never done the role before
• Investment in Growth: Instead of positioning layering as a demotion, Grant made it clear that Armand was still a key leader and that the company was willing to invest in his development.
• Pair high-potential: To ensure success, Grant paired Armand with a top-tier sales advisor (Chris Payne, ex-COO of DoorDash), who met with him regularly to provide strategic guidance.
• Codify “Team First” in your principles: At Whatnot, the philosophy is “Team over ego”. If layering an executive helps the company, then it’s the right move—even if it impacts you in the short-term. Defining this principle and using it to explain decisions becomes valuable at scale
• Where layering hasn’t worked: For external exes that were brought in to lead a function. Typically, it is too much of an ego hit to be layered and these people often end up leaving. Layering has been most successful for more junior employees trying to scale

3. Running a Great Leadership Hiring Process

Whatnot: Grant’s Approach to Hiring Leaders

• Use a search firm. Build strong relationships with a few and keep reusing the good ones
• Augment their pipeline with internal recommendations and recommendations from other operators
• Write a Mission, Outcomes, Competencies doc (MOC) to clearly outline what you want
• Meet with leaders who ran these functions or other founders who recently hired to calibrate/get tips
  
  • Today, Grant has hired in every function and knows what they need so this is less relevant
• Define interview panel, core things for each person to cover, and include the best judges of talent
• Run a weekly check-in meeting to gather feedback and review pipeline
• Always have working session, in person meeting, and dinner as part of process
• Personally spend 10+ hours with every hire, and cover each area in your MOC  
• Run a minimum of 10+ back channels
• Create hiring packet with all feedback, backchannels, and decision afterwards to ensure the why behind a decision is clear, so people believe in the process and give the person a chance to succeed
• The typical process takes me 6-12+ months

Example: Whatnot’s MOC for VP Product

Model Companies: Stripe, Airbnb, Doordash 

Could be interesting (but no knowledge of product talent/culture): Coupang, Shopify, Bytedance (non-US)

Mission:

• Consistently deliver a product users love fast that moves the business forward

Outcomes (18 months):

• Build a world-class product team
  
  • Grow product team from ~5 to over 20+ world-class product managers with strong product sense, amazing executional ability, and strong XFN skills
  • Build a user-first product culture aligned to Whatnot’s principles
  • Ensure everyone on the team is an avid user of the product and deeply understands all core components of the business
• Deliver a product that user’s love and achieves our business goals fast
  
  • Ensure the product supports and helps unlocks $700M/mo in GMV sales
  • Ensure Whatnot is a trusted brand amongst buyers and sellers
  • Deliver a world-class discovery product that ensures buyers find and discover things they’ll love
  • Generate over $100M+/mo in async sales on Whatnot
• Build the best XFN product team
  
  • Ensure the entire XFN product team is the top-executing team amongst growth-stage companies
  • Develop strong roadmaps and team visions & strategies for product pods that enable us to hit upon our business goals faster & build better products for our users
• Ensure Whatnot is capable of quickly and effectively launch into all core verticals and countries
  
  • Ensure the Whatnot product and team is capable of launching a compelling product in all core verticals we want to enter (Collectibles, Cars, Food & Beverage, Home & Garden, Fashion, Electronics, Healthy, Art, Crafts, and Beauty & Digital)
  • Enable $10M+/mo in sales in 5+ product verticals
  • Drive $100M/mo in sales from outside the US
• Drive sustainable growth through Whatnot’s product
  
  • Help develop sustainable growth channels that consistently drive 60%+ of Whatnot’s growth (sharing, SEO, referral and more)
  • Ensure Whatnot’s channels and funnel are optimized to drive strong growth

Competencies

Top 5

• Team-builder: Is adept at judging talent both for skill and cultural fit. Has built exceptionally strong product teams in the past that have executed and delivered strong product roadmaps quickly
• Strong product instincts: Can step outside of the numbers to understand what makes a great product for users, and think the product pieces need to bring this to live
• Great executer: Can cut through the noise, make swift decisions, and ensure the team is set to deliver on their roadmap with few missteps. Can do this in the product team and amongst XFN stakeholders
• Has seen a best-in-class company scale from a ~200 people to 1k+ in a product role with significant scope
• Has worked in multiple different roles and environments, so doesn’t just default to previous way of solving a problem 

Qualities (In order of importance)

• Exhibits characteristics of Whatnot’s culture
• Team-builder: Is adept at judging talent both for skill and cultural fit. Has built exceptionally strong product teams in the past that have executed and delivered strong product roadmaps quickly
• Strong product instincts: Can step outside of the numbers to understand what makes a great product for users, and think the product pieces need to bring this to live
• Great executer: Can cut through the noise, make swift decisions, and ensure the team is set to deliver on their roadmap with few missteps. Can do this in the product team and amongst XFN stakeholders
• Oriented towards speed vs. perfection: Knows that great software is made iteratively, and not through perfection. Comfortable shipping MVPs, and moving quickly to make them better
• Exceptional communicator: Can easily communicate complex ideas, and align XFN teams on the roadmap and work we must achieve to bring the company forward
• Highly analytical: Incredibly analytical. Easily able to gain mastery of the core elements that drive a business, and has a command of business metrics than rivals anyone within any organization
• Great partner: Can easily with with a large number of XFN stakeholders and bring teams together to produce incredible outputs
• Strategic: Understands how to invest in the product and roadmap give a business increased advantage over time
• Risk taker: Willing to comfortably make bets that could change the trajectory of our business

Previous Experience (In order of importance):

• Has worked in multiple different roles and environments, so doesn’t just default to previous way of solving a problem 
• Has seen a best-in-class company scale from a ~200 people to 1k+ in a product role with significant scope
• Has managed a PM team of 20+
• Has worked in an eng-first organization
• Has built successful 0-1 products in the past (ideally, as a founder)
• Has experience in a marketplace business 

Webflow: Vlad’s Approach to Hiring Leaders

• Use a search firm. Initially, he didn’t partner with search firms initially because he was hesitant about cost. This was a mistake. They get you access to pipeline that you couldn’t normally access
• Define the archetype you want. Vlad initially used long job descriptions but found that they attracted self-optimizing candidates more than mission-driven executives. Over time, he moved to succinct, clear criteria that focused on the 3 or 4 most important competencies he wanted
• Set up an interview panel. Define what each person will cover, and test for each competency
• Always have a working session. Pick a real problem you are facing right now and provide a broad prompt to the candidate. Give them permission to ask for data and ask them to present as they would if they worked at the company. The best candidates ask for a lot of questions and data.  
• Run backchannels and references. Vlad speaks with peers, managers, and direct reports. For leaders, his goal is to ask questions that help 

Example: Webflow’s CPO

Archetype
Vlad picks 3 or 4 key priorities to guide candidate identification and focus areas. For CPO, they wanted someone with:

1. Technical background with deep domain expertise in web design and development
2. Track record of leading, hiring, and retaining teams that skew technical and craft oriented
3. Significant experience (or leading as a GM) in commercial growth teams of at least $300M ARR scale
4. Experience with expanding from a single to multi-product company; M&A track record is a big plus 

Initial Meetings
Vlad met with 25-30 candidates in the process. Vlad had 1 or 2 initial meetings before passing candidates to meet the broader team and to invest in a working session. During these initial meetings, Vlad goes deep into their background and tries to align on whether they fit the 3 or 4 key priorities that they outlined. This amounted to the following for Vlad:

• 1 hour with all 25 to 30 candidates to calibrate and see who he wanted go deeper with
• +2-3 hours with 5 to 10 candidates to go deeper on the 3-4 key priorities with Vlad

Interview Loop & Take-Home
For finalist candidates, they set up a series of onsite interviews to test for the criteria that Vlad outlined. Each of the interviewers posted their questions in a shared Google Doc and uploaded feedback directly to Greenhouse so that Vlad could review it. Vlad chose to do this instead of a group discussion, so he could get unbiased feedback.

Onsite #1

• 45 minute Meeting with Vlad on product strategy
• 45 minute Meeting with COO on operational excellence
• 45 minute Meeting with CTO on engineering excellence

Onsite #2

• 45 minute Meeting with CMO on customer and community
• 45 minute Meeting with Director of Product on coaching and development
• 45 minute Meeting with Director of Sales on enterprise sales
• 45 minute Meeting with People leader on leadership and DEI
• 45 minute Meeting with Chief of Staff on alignment and partnership

Onsite #3

• 45 minute Meeting with Vlad on core principles and relationship building
• 45 minute Meeting with co-founder on new product philosophy
• 45 minute Meeting with Head of Product Design on product design
• 45 minute Meeting with co-founder on design philosophy

Take home / Working Session

• Vlad provided an open-ended prompt on expansion from single product to multi-product company. They asked the candidate to prepare their feedback on this topic and to present during a 60 minute working session with the relevant team. Candidates are encouraged to ask for more information. Internal team members are encouraged to treat it like a normal working meeting. The best candidates go above and beyond and prepare detailed presentations or memos on the topic to lead the discussion.

Final Onsite #4

• 60 minute Meeting with Product leadership as a debrief/continued discussion from working session
• 30 minute Meeting with Board Member #1 as close meeting
• 30 minute Meeting with Board Member #2 as a close meeting

References
Vlad spoke with ~10 people. During these interviews, his goal is to understand whether what the candidate says is reflected in their actual work. After collecting all feedback, Vlad makes the offer contingent on going through the feedback and identifying areas for development together. Below is his rough interview script.

• Background on working relationship
• [Manager and Peers] What advice would you give me to make this person successful?
• [All] In what areas and skills have you seen [X] grow most significantly when you worked together?
• [All] In your experience, what top words would people use to describe [X’s] management and leadership?
  
  • Dig into words they use to understand details behind each term
• [All] Do you have any examples of when you disagreed on something? How was it handled?
• [Directs] What was it about X that made them a great manager? What is one thing they were better at than anyone else?
• [Technical] Can you think of any examples where [X] demonstrated deep technical or domain expertise?

Interview Questions (Tied Back to Each Topic)

Operational Excellence

• Tell me about a time when you had to manage a complex operational challenge or change management in a previous role.
  
  • What was the challenge? What steps did you take to address it? What was the outcome?
  • What were the biggest challenges you faced in implementing your solution?
  • How did you overcome those challenges?
• How do you think about investments in product(s) and how they tie back to key financial metrics?
  
  • Tell me about times you’ve been able to accelerate growth with product strategy.
  • What about driving efficiencies across gross margin or operating margin?
  • How have you reduced churn/contraction with product in the past?
• Tell me about a big bet you made with product strategy. How did that impact the company? What outcomes came of it and given your experience, if you could go back, what might you do differently?
• Tell me about how you think about the organizational structure of your team as the product becomes more complex. How do you partner with your peers to design the org structure and processes to drive velocity and successful product development?
• How do you build your understanding of the customer and their needs? How does this fit into prioritization and your overall product strategy? What are the key groups you work with to build this understanding/empathy?

Engineering Partnership

• What is your strategy to come in and learn a product with the large surface area of Webflow? How do you measure success in learning the product? How do you set strategic product direction while coming up to speed?
• How do you measure product velocity? Can you give an example where you had to change the velocity of a product (faster or slower) and what was the outcome?
• When building product strategy, are you data-driven or data-informed or do you use other input? What is an example where this helped in building your product strategy?
• What are the traits of the best engineering leader that you have worked with in the past? How did those traits manifest themselves in the working relationship between you and engineering? Conversely, what was the worst working relationship you had with an engineering partner? What steps did you take to rectify the relationship and what was the outcome?
• There is the classic choice when building a product: time, features, quality, pick two. Which two do you pick? Can you give an example of a time when you struggled with this decision and what was the outcome for the product? Have you ever sacrificed quality for features?
• What is your strategy to earn the trust of your new directs and your other EPD peers? How do you measure this trust?
• What feedback do you want to receive from your EPD peers? How often would you like to receive feedback and how do you take action from this feedback?

Coaching & Talent Development

• Tell me about your approach to people leadership. What are some common tools or practices you find yourself leaning on because they’ve been really effective for you?
• How do you think about career development and coaching for your direct reports? And how does that change as companies reach Webflow’s scale and beyond?
• Can you give an example or two of senior leaders on your team who you’ve helped reach the next level?
• Can you give an example of where that wasn’t successful?
• How do you approach performance management? And can you give me an example of a challenging situation you had to work through?
• How do you balance setting direction, maintaining product integrity, and empowering your leaders? Can you give an example of where that’s gone well and an example where that didn’t go so well?
• Thinking beyond just your direct reports, can you talk about how you’ve incorporated talent development or learning & development as a key priority for your whole org?

Customer Empathy

• How do you think about balancing multiple different personas in developing a product? How important is singular ICP focus versus not for a company like ours?
• How do you ensure deep customer insight and empathy is infused in how you develop products?
• Pricing & Packaging: How do you think about bridging what you’ve built with how we take them to market, particularly from a P&P perspective?
• As we shift our company from our historical focus on freelancers and small agencies to larger In-House Teams, how do you think about balancing investments across potentially competing segments?

Enterprise and Sales Partnerships

• Which product launch that you’ve led has most impacted top-line revenue? Lessons learned?
• “Voice of Customer”: Can you share an example of how you’ve captured prospect/customer feedback?
• Webflow competes in a mature industry: Web development/CMS/DXP. What steps would you take to create a framework for how we will win this market from a product perspective?
• PLG levers: Can you share an example of working with Sales Leadership on In-Product triggers for moving customers up through PLG offerings (upgrading from Free / Self-Serve)?
• What are the traits of the best sales leader that you have worked with in the past? How did those traits manifest themselves in the working relationship?
• Conversely, what was the worst working relationship you had with a sales partner? What steps did you take to rectify the relationship and what was the outcome?
• Example of a disagreement Product ↔ Sales on a specific feature/product prioritization? What happened & resolution?

4. Setting Up Executives for Success

Webflow: Vlad’s uses Daily 1-1s to Maximize Context Transfer

• Vlad comes up with a 90 day onboarding plan. The onboarding plan includes:
  
  • 1. Reading materials to maximize context transfer
  • 2. Important people to meet within the team
  • 3. A high-level overview of goals and outcomes for first 90 days
• He also holds daily check-ins for the first 90 days with executives to maximize context transfer
  
  • These daily-checks are opportunities to answer questions and align on approach
  • This helps validate whether they are thinking correctly about problems in your specific context
• He uses a structured daily template, where execs document on a daily basis:
  
  • 1. Urgent Topics
  • 2. Questions
  • 3. Decisions/FYIs
  • 4. Wins
  • 5. Learnings
  • 6. On Deck
• Vlad typically makes 90% of first 90 day 1-1s. It helps you clearly understand if they are working out

Whatnot: Grant Co-Runs the Organization for the First 30-60 Days

• Every new executive is by default a neutral and not a positive entity. They need to prove they can deliver since most will not. This is true irrespective of someone’s background. This isn’t evil, it’s math.
• As part of this, write a 30/60/90 plan with clear outcomes and learnings, and with peer and direct reporting chain feedback from high quality people at 60 and 90 days
• When onboarding a new exec, Grant typically continues running the org while the new hire ramps up
• For the first 30 days, Grant is in every single key meeting but lets the new exec lead discussions
• In meetings, he doesn’t speak until the very end, instead taking notes on how the exec frames problems, structures decisions, and articulates solutions.
• The most critical assessment: Are they focused on the right problem? Are they proposing the right solution? Is it based on your Whatnot’s context?
• The main failure modes is copy-pasting solutions from past companies that don’t work for Whatnot
  
  • Even top-tier hires make mistakes early—Grant’s CPO initially copy-pasted approaches from Twitch, but what set him apart was how quickly he adapted and learned from early mistakes
• Principles for onboarding:
  
  • Stay very close to the exec in the early days.
  • Assess how they think, not just what they decide.
  • Expect copy-paste mistakes—the best hires adapt fast.
  • Push company context aggressively to help them adjust quickly.

Example: How Grant knew their Product Leader would Succeed

Positive signals at time of hire

• Could articulate in great detail how to build a world-class discovery experience, and they workshopped it for multiple hours. Grant had interviewed 100+ PM leadership candidates by then as this role took the team ~15 months to fill, and asked them all this question since it was our biggest issue at that time.
• Exceptional product judgement that aligned with how Whatnot thought about things, but brought experience in areas Whatnot was weak (e.g., trust)
• Had a big job previously, but hadn’t held it for a long time, so had less anchoring on prior playbooks
• Worked his way up to the job starting as an IC and was still very hungry to prove himself
• Great story teller and leadership qualities that filled known team gaps

Negative signals

• Had a couple backchannels who said they weren’t incredibly strong; some considered him abrasive.
• Whatnot backchanneled those backchannels and found that those leaders were not strong 

How Whatnot knew it would work in the first few months

• Upleveled the PM team in a few months. Brought over an incredibly strong product leader
• Dove in and did IC work to fill gaps
• When he’d copy paste from paste experience, he’d listen to to feedback, and relearn his approach
• Grant attended every product review with him for 2 months, and took note of the decisions he made. Grant would try to remain passive and let him drive, but send him feedback. He very quickly made 90% of the decisions Grant would make, and was better than Grant in a number of areas
• Existing PM team provided overwhelming positive feedback at D60 and D90 (a normally tough group)

5. Fire Fast When It’s Not Working

Key Observations on Why Leaders Fail

• They rely too much on past experience and fail to adapt to the current context.
• They operate at too high an altitude and don’t get into the details. Brex also considers this the #1 predictor of executive failure.
• They don’t set a high bar on assessing work quality and instead default to their past experiences, assuming it translates.
• They don’t want to grind or are too passive.

Tactic: How to Assess Whether an Executive is Succeeding

• Is their function hitting goals? If not, is there a clear reason why?
• Are former colleagues following them and performing? Great leaders attract and develop top talent, not just people they’ve worked with before.
• Go to the ground level in their function. For example, if it’s support, go read support tickets—does the work quality meet expectations? If not, the leader is responsible.
• Peer feedback and skip levels with top talent. What is their assessment? Are any top performers a flight risk? Great leaders retain and inspire top talent.
• Coach and give feedback. If these areas aren’t going well, provide direct feedback and an opportunity to improve—this rarely works, but when it does, it’s worth it.

Tactic: When to Fire an Executive

• Typically, it's better to fire fast before the blast radius is too wide. That said, you need to balance morale and can’t exit every bad executive within the first few weeks. Grant’s approach is the following:
  
  • He tries to not fire too quickly—he believes in giving executives a three- to six-month window to prove themselves. If the exec isn’t destructive but just ineffective, they are given structured feedback and a chance to improve.
  • If they are actively harming execution and team morale, they are asked to leave more quickly. For example, Whatnot fired their VP of International was fired within two months because it was clear they were a poor fit and slowing down execution.

Tactic: Exiting Executives

• A mis-hire is on the company. If an executive doesn’t work out, it reflects a flaw in the hiring process.
• Be fair, but not excessive. Severance should be reasonable and aligned with market norms.
• Give executives the chance to exit on their own terms. Most senior leaders are given the opportunity to resign rather than be fired. This assumes they aren’t destructive and/or extremely problematic
• Be transparent with the team. Grant ensures his direct reports understand why an executive left to reinforce the expectations of working at Whatnot.
• A clean break matters. A fair exit minimizes unnecessary tension and protects the company’s reputation in the broader ecosystem.

6. Executive Hiring Non-Negotiables

Company principles are the only true non-negotiables.‍

• Inspired by Amazon, Whatnot has 10 core principles that guide all decisions. Whatnot’s core principles are: 
  • Always listen to customers
  • Take complete ownership
  • Move uncomfortably fast 
  • Set audacious goals
  • Prioritize impact ruthlessly
  • Provide extreme transparency
  • Bet on the future 
  • Team over ego 
  • Figure it out
  • Have fun & be nice‍
• No rigid playbooks. Business strategy, operations, and team structures evolve with scale. What worked before won’t always work now. Grant has only become more malleable over time. For example:
  • Whatnot didn’t hire PMs until 100+ engineers because they wanted engineers to run product
  • As complexity grew, Whatnot had to build a product team. There were too many bottlenecks
  • Whatnot now has a product team that plans Platform/API investments 6-12 months in advance

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