Whatnot and Zip on Mission, Strategy, Metrics

How Rujul Leads Zip 

Zip is 5 years old, has grown to nearly 600 employees, and generates over 100M in annual revenue. Zip helps companies streamline procurement and vendor risk by enabling any employee to initiate purchase or vendor requests and ensuring they’re properly routed across finance, procurement, security, legal, and IT. The platform integrates with major ERP systems to simplify workflows, reduce security risk, and eliminate manual work. Their mission is to help businesses procure with the fastest process, the least risk, and the best value. 

How Grant Leads Whatnot

Whatnot is 6 years old, has grown to over 800 employees, and is connecting millions of buyers with tens of thousands of sellers through livestream shopping. The company generates almost a billion in revenue 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. 

1. Mission & Strategy

The Purpose of Defining Your Mission

• For Grant, the purpose of a Mission is to provide clarity on what all the work across the org is ultimately driving toward
• It also gives employees a “rallying cry” that allows them to see the impact of their work. 
  
  • Whatnot put in place their Mission statement at around 15-20 people. Zip came up with theirs in year 3 of the business, when they had 50-70 employees

Lead With Transparency and Be Candid With Your Team When Changing Course

• In cases where you have to change your company’s mission statement, Grant suggests being forward and transparent with your team about the rationale and process going into making the change
  
  • To help navigate decisions like these, Grant will write out his process, any resulting questions, and gather the smartest team members with the most context on the business to challenge his perspective until he feels as though he’s covered all his decision’s various edge cases 
• Rujul’s approach to having to change your Mission Statement is similar to Grant’s. He suggests leading with transparency and honesty to align the team and set a new direction for the team moving forward. 

2. Metrics

Driving Alignment with Vision, Strategy, and Metrics

• Vision: Whatnot uses vision as the long-term determination of where the product should be going — the future state the company is working toward.
• Strategy: Functions as the roadmap for how Whatnot plans to achieve its vision.
  
  • Grant views strategy as a way to concentrate the team’s energy on the initiatives that truly matter to move the business forward.
  • As part of defining their strategy, Whatnot is deliberate about specifying what the company is not trying to do. This is equally important when resources are scarce.
• Metrics: Play a central role in strategy by allowing leadership to audit whether the entire organization is acting in line with what matters most.
  
  • When strategy and metrics are tightly aligned, Whatnot gains a clearer, more accurate picture of progress across the company.

Whatnot

Strategy @ Whatnot

• Each year in October/November, Grant revisits the company’s strategy and sets goals for next year. The goal of this is to drive extreme clarity on what the company is trying to do
• Grant writes the document himself. When Whatnot was younger, writing the doc was limited to the founders since they’ve run or helped build the functions themselves. 
  
  • Now that Whatnot’s more scaled, once he’s finished drafting he shares the draft with a small circle of trusted, relevant stakeholders for feedback. After incorporating their input, the final doc is presented at the company’s weekly all-hands. In this meeting, they take questions and drive alignment on the team
• Grant tries to be extremely specific when drafting this doc, such as clearly defining exact the user persona they are targeting.
  
  • Being specific allows you to focus people and teams on the things that matter and move the business forward. For example, Grant believes in being very specific about the things they are not going to do, as this helps drive focus and prevents distraction from "shiny objects."
• The components covered in this review include:
  
  • Mission
  • Vision
  • Summarized Strategy 
  • North-Star Metric 
    
    • Grant would include a North Star metrics when Whatnot was younger, but no longer believes there’s always a single metrics that’s more important than the others
    • If he had to point to a North Star metric today, it would be GMV, which tracks the total value of products being transacted on Whatnot’s marketplace. This is because it captures whether both constituents on Whatnot’s platform (Buyers and Sellers) are getting value, reflected as transacting lots of goods
  • Annual Goals
  • Bets
  • Strategy 
    
    • Product Strategy
    • Growth Strategy
  • What We’re Not Doing
    
    • This is helpful to focus the team, especially for earlier-stage companies
  • Context
  • Click here for a template of Whatnot’s Annual Strategy Document 
• Grant then uses the Strategy to define OKRs. These used to be weekly and monthly goals when the company was younger. Now, Whatnot sets quarterly OKRs. 
  
  • Here is a breakdown of how this evolved as Whatnot grew from a young company to today
• Articulating Growth Strategy is important because it helps you durably invest in them over time. This is because a lot of the initiatives you want to grow, you’ll have to build teams around.

Metrics @ Whatnot

• At Whatnot, each subteam owns its own set of metrics. This ensures accountability and avoids carrying over metrics across functions where they may not be directly relevant to performance.
  
  • For example, the team responsible for the main metric of “Grow GMV drastically” will be responsible for:
    
    • Grow Sports GMV to $XXm
    • Grow Pokemon to $Xm
    • Grow Funko to $Xm
    • Grow Comics to $Xm
• Every two weeks, the company holds a biweekly business review. In this meeting, each team presents progress against its business goals, which are then evaluated and marked as Red, Yellow, or Green based on performance.
• The meeting follows a set cadence: the first 30 minutes are silent, with team members reviewing the metrics and adding comments directly. Afterward, each team addresses the comments and questions, explaining the steps they are taking to improve against their metric.
  
  • From Grant’s perspective, the non-operational teams are often the ones that miss their targets most frequently. In contrast, EPD (Engineering, Product, Design) and GTM (Go-to-Market) teams tend to stay closer to their functional metrics and consistently drive performance against them.

Zip

Strategy @ Zip

• Zip started out with 6 outcomes that they’ve since narrowed down to 4 since 2024. 
• At the start of each fiscal year (February), Zip holds a 3-day company-wide Sales Kickoff in San Francisco. On day one, Rujul and his co-founder roll out the company’s annual objectives and re-orient the team around Zip’s mission and vision
  
  • Zip's annual MSM doc is written by Rujul and his co-founder. They work together to draft the objectives for the year, which are then shared with the leadership team and rolled out to the company.
  • The MSM doc includes:
    
    • Mission Statement: The mission is to help businesses procure with the fastest process, the least risk, and the best value.
    • Strategy: This outlines the approach and specific initiatives that will be undertaken to achieve the mission and objectives. 
      
      • It lays out both a high-level of the company’s annual strategy, as well as specific pillars of the annual strategy with desired outcomes, inputs, and current performance today.
      • Example strategy pillars: Deliver $XXM ARR with Y+ customers, Become a true multi-product platform, Unlock TAM by establishing X, Y, Z initiatives 
    • Metrics: The document includes fiscal year OKRs that are tracked to measure progress across each quarter. 
      
      • For Zip, the four core metrics are ARR (Annual Recurring Revenue), net revenue retention, gross revenue retention, and the number of Global 2000 logos.
• Rujul previously relied on a one-page framework that mapped all outcomes and quarterly metrics on a single document. Over time, this became stale, so Zip shifted to a tracker for company-wide initiatives. The process for how Zip uses this tracker is outlined below:
  
  • The SLT tracker lists company-level initiatives, showing which objective each initiative ladders into, who owns it, and who the executive sponsor is. These list out the 10 current P0 objectives.
    
    • The P0 objectives are set during a monthly refresh process. Rujul and his co-founder review and update the initiatives each month, determining which ones are designated as P0. This process is not opened up to the broader leadership team; it is handled by Rujul and his co-founder.
  • Initiative owners are required to send a templated email every Thursday by the end of the day. This email includes updates on the initiative's progress.
  • Rujul and the senior leadership team receive these emails. Rujul commits to reviewing all the emails by the end of the day on Sunday and replies with questions or follow-ups.
  • The SLT reviews the P0 (highest priority) initiatives weekly. These are the initiatives that Rujul closely monitors.
    
    • Click here for a template of Zip’s SLT Tracker
• Rujul sees vision setting across a longer horizon (5 years) as more product-oriented than annual OKRs.
  
  • The team begins with two questions: What will the product be in five years? What will the company be in five years?
  • The vision is then broken down into actionable steps.
• Zip runs vision planning once a year to come up with a 5-year strategy memo. This is led by the Head of Product, with input from Rujul, his co-founder, CFO, and CRO.
  
  • Early on, vision planning was done by just Rujul and his co-founder
• Unlike OKRs, the vision memo is not shared broadly within the company. Rujul believes this prevents distractions, keeping the team focused on near-term OKRs instead of chasing far-off goals.

                                                                     Click above for a link to a template of Zip’s MSM doc

Metrics @ Zip

• At Zip, company-wide metrics are broken down into smaller submetrics that teams are directly responsible for. While it can sometimes be difficult to see how each submetric ladders up into overall company performance, Rujul emphasizes that it doesn’t need to be perfectly scientific for the system to be effective
• The company focuses on four parent metrics, which are tracked every week:
  
  • ARR (Annual Recurring Revenue)
  • Gross Revenue Retention
  • Net Revenue Retention
  • Number of Global 2000 Logos
• Every submetric across the business is mapped back to one of these parent metrics. This ensures clarity on how individual initiatives contribute to Zip’s top-line priorities.
• To maintain accountability and rhythm, the leadership team reviews 50% of the metrics each Monday morning in their weekly leadership meeting. By rotating through this structure, they are able to cover the full set of submetrics every two weeks.

Defining Metrics for New Bets

• When it comes to critical decisions in emerging or new areas of the business, Grant typically limits decision-making to himself or his co-founder, Logan. He believes these situations require exceptional judgment, which depends on having both a broad overview of the entire business and deep context on the company’s strategy. 
  
  • While Grant would like to that other members of the team make these decisions, he keeps a high bar for judgement and hasn’t found other team members who meet his bar yet
• In the early stages of new initiatives, team leads often lack reliable metrics to ground their decisions. As a result, they must lean more heavily on judgment rather than data. 
  
  • Grant and Logan remain the final decision-makers in these cases since they have the deepest context and, by extension, the best judgement within the org
• At Whatnot, there are generally two different kinds of efforts the company is investing in: 
  
  • New initiatives/test areas: where they have less of/no understanding of metrics and growth
  • Areas of the business with high predictability
• For new initiatives, Grant starts by making an estimate he can justify with data or reasoning, then adjusts over time as the team learns. He sets the most ambitious goal he can confidently support, with the company aligned on the understanding that these goals will be updated as more clarity emerges
  
  • To alleviate fears about people get fired or not being promoted if they don’t hit these goals, Grant makes sure to communicate that the team will be judged on their inputs, not their outputs
• For more predictable parts of the business, Grant pushes teams to aim for ambitious but achievable outcomes. He generally expects teams to hit around 70% of the standards set
• Grant believes team members should either be focused on what’s good for the business or for users. He thinks any strong focus that’s not directed towards either of those incentives will be corrosive for the company over time. 

3. Setting Targets

Setting and Raising Targets 

• Rujul emphasizes that the ability to set precise standards improves with each OKR cycle
• Zip has different plans to manage expectations and ensure predictability in revenue, which is critical in B2B businesses with large sales teams. This structure allows each team to have ambitious targets while maintaining a more conservative outlook for overall company reporting. Zip strategizes around three different plans:
  
  • Board Plan
  • Company Plan
  • Street Plan
  • The board plan is the most conservative, with about 12-15% breakage between it and the company plan, which is slightly more ambitious. The street plan is the most aggressive, with another 12-15% gap between it and the company plan. 
  • Compensation, functional and initiative-level targets are then mapped to the street plan
• As a founder, Rujul believes the job is to continually push the company to operate at its highest potential. This requires raising targets whenever the team consistently delivers on certain metrics

Honesty and Directness is Key to Maintaining Psychological Safety with Ambitious Goals

• The key to maintaining psychological safety while constantly setting more aggressive targets is to communicate to the team that growth will be uneven, and it’s okay if there’s an occasional miss where the team meets 70% of their targets in a given quarter.
• In cases where you make mistakes, lead with transparency and honesty with your team. Rujul argues that being honest, even when mistakes are significant, allows leaders to own more missteps while strengthening trust across the company.
  
  • For example, in 2022 Rujul brought in a new CRO who tripled the size of the sales team while closing 20% less than before. This led to Zip missing targets for three quarters.
  • In response, Rujul fired the CRO along with much of his sales team and walked through the 10 things he messed up in a candid conversation in front of the whole company. After this talk, the company was even more motivated and has performed a lot better every quarter since. 

It’s Okay to Adapt Your Strategy, Especially When Things Are Moving Fast

• Grant believes that when setting goals for a young, fast-growing company, you can always: 
  
  • 1) Change the goals as you need
    
    • Internally, Whatnot defines strategy as a snapshot in time and the approach they believe will best achieve their vision. As teams execute and learn, the strategy is revisited and adjusted to reflect new insights.
  • 2) Set your target as the biggest number you can defend. 
    
    • This helps maximize the growth of your business
• At Whatnot, leaders set ambitious, hard-to-measure goals and make clear that the company won’t always hit them. This approach pushes people to stretch themselves across the org while keeping motivation high even when targets aren’t met.

4. Driving Accountability

Invest in Data Telemetry

• Building a strong grasp of your org by setting up deep, robust data dashboards helps you ground decisions in data. This helps drive clarity on what’s happening within your org and serves as a good way to make future decisions in uncertain areas. 
  
  • While this is important to set up early for both B2B and B2C teams, it’s especially important to set this up earlier for B2C companies. For B2B, you can push it until after you set up a working sales machine. 
    
    • Whatnot invested in setting up a strong data science team right after their Series A
    • Zip invested in this when they hired their sales leader, who also had a background in data science when they reached $5M in ARR. This was 3-4 years ago.
• Grant runs Whatnot with a high degree of pragmatism, dividing information into what he knows and what he doesn’t know.
  
  • Because uncertainties far outweigh certainties, he avoids making definitive statements and keeps the flexibility to change course as needed
• When you’re in a competitive space, you’ll get a lot of external input and ideas being thrown at you. What Grant believes ultimately matters is what you’re doing and whether it’s working. 
  
  • At launch, Whatnot focused on an extremely niche market: Funko Pops. Given his and Logan’s background in consumer internet, they knew the best growth path was to deliver an exceptional experience for a small set of users and expand outward.
  • By methodically growing one sector at a time, Grant developed conviction that Whatnot could out-execute its 14 competitors. Whenever feedback suggested other directions, he redirected attention back to performance metrics. This reinforced focus on results over distractions.

Tactic: How Grant Drives Accountability Through Tracking Data at Whatnot

• Grant believes that as companies grow, employees sometimes do work that feels important but doesn’t actually move the business forward. To ensure focus on what truly matters, Whatnot invested in building a data science team just six months after their Series A
• Whatnot now maintains dashboards for every aspect of the business, spanning each team and new features
• The data science team sends a Flash Report to the entire company every day, with metrics such as:
  
  • Weekly GMV
  • Weekly AOV
  • Buyer and Seller Growth
  • Streaming Performance
  • New Account D0 Conversion Rates
  • This system has been in place since the data team was established post-Series A.
• Whatnot also uses an OKR Tracker to keep track of goal progression every week 
  
  • Click here for a template of Whatnot’s Weekly OKR Tracker
• After the Series C, Whatnot introduced the BBR to add stronger team-level accountability. Each function is split by core user segment, and project owners upload updated metrics to a company-wide deck.
• Each feature/subteam reports on:
  
  • Progress
  • Tracking to Goal (often with data)
  • Plans if they’re behind
• Their color-coded system clarifies status:
  
  • Red = not updated
  • Yellow = behind/slightly lagging
  • Green = on track or ahead of plan
• If Grant is unclear on what’s happening with a specific initiative from the BBR, he goes directly to the person closest to the project with the best context

Tracking B2B Sales Performance with Telemetry Data 

• For B2B companies, having telemetry on both pipeline health and rep-by-rep performance is critical. At Zip, Rujul institutionalized a cadence of weekly, monthly, and quarterly reviews that gave leadership visibility across every segment of the sales org
• Every Monday at 8AM, Zip holds a leadership meeting covering ~50% of company metrics across Sales, Marketing, and other functions.
• Afterward, the SLT meeting (senior leadership team) focuses on priorities and issues.
  
  • These meetings include two 30-minute slots where Rujul nominates initiative leaders to present on areas not going well. These are attended only by the owner and senior leadership team
• In addition to leadership reviews, Rujul runs forecast meetings with sales leaders of different segments. These are never skipped or moved and are attended by Sales Ops, segment leads, the Global AE lead, and Rujul. For customer segments (Commercial, Key Enterprise, Strategic Enterprise), reviews run every other week, laddering into monthly and quarterly reviews.
• In these meetings, Rujul tracks:
  
  • Pipeline creation and progression by stage (S1–S6 in Salesforce, from qualified opportunity to closed-won).
  • Pipeline by source and deal size, with week-over-week changes to spot growth or gaps early.
  • Pipeline concentration by rep – identifying whether revenue is distributed evenly across the team or concentrated in a few individuals.
  • Pipeline concentration by rep cohorts (e.g. <6 months in role vs. mature reps), to assess onboarding ramp and repeatability of performance.
  • Leading indicators for reps – hires, days in seat, meetings booked, quota attainment. These helped anticipate whether enterprise reps would be able to close deals despite long cycles.
  • Segment-level forecasts (Commercial, Key Enterprise, Strategic Enterprise) with best-case and worst-case scenarios, reviewed each week
• Zip holds separate pipeline meetings for Sales and Marketing. Rujul focuses on two marketing stats:
  
  • Marketing Pipeline Creation
  • Pipeline Influence
• They also implemented a single vs. multi-touch attribution model to reduce friction between Marketing and Sales over deal credit

Example: How Rujul Drives Accountability Across Sales Reps

• Rujul spends 10–12 hours per week with the sales team, joining calls with reps and prospects. In these sessions, the rep drives the call, while Rujul observes. He also audits Gong recordings to evaluate rep performance
  
  • If a rep underperforms, Rujul escalates to understand why and address the root issue
• To track new hires, Rujul monitors how many meetings each rep attends while still completing their certifications
• Only four people in the company are authorized to certify reps.
• If a rep fails certification once, they get a second attempt.
• If they come close to failing twice, they are terminated.
• Reps must also pass a 70-question test, which contributes to their overall certification outcome and can lead to failing out

Ownership is Key for Accountability

• Rujul’s approach to driving accountability is to have only the people responsible for an outcome in meetings when discussing issues, and to first look to the single owner of that outcome for an opinion 
  
  • He also emphasizes the importance of clarifying who will be driving an outcome when an issue is discussed
• Grant’s belief is that when accountability falters it’s usually either due to having the wrong leader in place or having a leader that’s not strong enough operationally to guide and direct the team
  
  • He’s generally also found that the external hires who don’t pick this up quickly often don’t work, and that the internal hires who are smart, humble, and hardworking can be coached to learn how to hold their team highly accountable 

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