Webflow's CPO

Webflow’s CPO

Archetype

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

Technical background with deep domain expertise in web design and development
Track record of leading, hiring, and retaining teams that skew technical and craft oriented
Significant experience (or leading as a GM) in commercial growth teams of at least $300M ARR scale
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?

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Chapters