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Zip and Clay on Mission, Strategy, and Metrics

Guests:
Rujul Zaparde and Kareem Amin

Table of Contents

Relevant Links From the Session

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 Kareem Leads Clay

Clay is 8 years old, has grown to nearly 300 employees, and generates over 100M in annual revenue. Clay is an AI go-to-market platform that helps businesses grow as quickly as possible. The company pioneered the concept of the “go-to-market engineer,” centered on treating go-to-market more like a product function: pulling in data on companies and people, experimenting with different growth tactics, and using software to implement and iterate on those workflows. In practice, Clay helps teams identify the right prospects based on highly specific signals and reach them with the right message at the right time. Its mission is to help businesses find and grow their best customers.

1. Zip

The Purpose of Defining Your Mission

  • 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. 
  • Zip came up with theirs in year 3 of the business, when they had 50-70 employees

Zip Uses a Small Set of Company Objectives to Anchor Strategy, Initiatives, and Metrics

  • At the start of each year, Rujul and his co-founder Lou typically write a one- to two-page company narrative that lays out the story of the year: what matters most, where the company is trying to go, and what needs to be true for the business to succeed. 
  • That narrative then gets translated into four company-level objectives, which become the anchor points for the rest of the year.
    • These four objectives are intentionally broad. Rujul described them as company-level themes that are meant to be relevant across the entire business rather than narrowly scoped to one function. 
    • In the current version he shared, Zip’s four objectives were:
      • Owning AI for procurement
      • Building the enterprise engine
      • Growing international and commercial
      • Delivering new products
  • These objectives are the top-level structure the rest of the company operates from. Every major initiative is expected to ladder into one of the four objectives, and the company’s core metrics are also organized against them. 
    • The objectives are the bridge between the annual narrative and the company’s day-to-day operating cadence.

Zip Moved Away from More Formal OKRs Toward a More Flexible System

  • Rujul said this system is somewhat like OKRs, but much more organic and less rigid than the way Zip used to run them.
    • The company previously used a more formal OKR structure, but over time that began to feel too cumbersome. The issue was not that the company no longer needed goals or alignment. Instead, the formal process made it too hard to incorporate what the team was learning in real time.
  • His view is that the business is constantly discovering new things:
    • Something that did not seem urgent last month may suddenly reveal itself as broken
    • A new initiative may need to be added quickly
    • Priorities may need to shift midstream as the company learns
  • In a more rigid OKR system, those adjustments felt too heavy and process-bound. As a result, Zip moved toward a structure where the annual objectives still provide focus, but the initiative layer underneath them can evolve more fluidly as the year progresses.

Strategy @ Zip

  • Rujul said Zip uses two distinct strategy layers that serve different purposes.
  • 1. A longer-term 5-year strategy doc
    • Zip keeps a separate 5-year strategy document with a small group of senior leaders. This is not shared broadly with the company.
      • Rujul said the reason is that getting too specific about what the company may do five years from now can confuse people and distract them from what matters this year.
    • This longer-term doc is more product-oriented than the annual company planning process.
    • It is led by a small group that includes Rujul, his co-founder, Product, Finance, and a small number of other senior leaders.
    • He said the team refreshes and revisits this document roughly every six months.
    • The way they approach it is to start with a longer-horizon question
      • In one recent version, they actually started with a 10-year North Star and then worked backward to five years.
    • Once they have the product direction more fully fleshed out, they add the distribution component afterward.
    • Rujul said the main value of this document is not that it predicts the future perfectly, but that it helps the company make better long-term product tradeoffs.
  • 2. An annual company narrative tied to four company-wide objectives
    • The main company-facing strategy layer is a short annual narrative for the year. Rujul and his co-founder write this first, and then the annual objectives flow out of it.
    • The normal order is: write the annual narrative, derive the company objectives from that narrative, then build the rest of the planning apparatus underneath it
    • The annual narrative is intentionally short — roughly 1–2 pages. Rujul said it needs to stay simple and digestible because if it gets too long, people stop reading it.
    • The purpose of this document is twofold:
      • It forces clarity of thought for him and helps with decision-making
      • It helps the team understand what the company is doing and why, which is both practically useful and motivating
    • He described it as needing to be far enough out that it makes sense for the year, but still close enough in that people can relate to it.
    • The four company objectives he shared were:
      • Owning AI for procurement
      • Building the enterprise engine
      • Growing international and commercial
      • Delivering new products
    • These four objectives are intentionally broad. They are meant to be relevant across the whole company, not just within one function. Rujul said they become the anchor points for the rest of the year.
      • Every major company initiative is expected to ladder into one of the four objectives. The company’s core metrics are also organized against them.
  • To operationalize this, Zip launched a company-wide initiative tracker that the whole company can see.
    • This became more necessary as the company scaled and cross-functional initiatives became harder to run cleanly.
    • Rujul said one of the pain points they hit as they grew was that work inside a single function could still move quickly, but anything that required coordination across multiple functions would start to bog down.
    • The initiative tracker was designed to solve that by making the most important cross-functional work visible and clearly owned. The tracker is focused on a relatively small set of company-level priorities.
    • Each company-level initiative is tied to one of the four objectives and has:
      • an owner
      • a sponsor
    • The company-level initiatives are reviewed, pruned, and refreshed monthly. That process is run by a very small group:
      • Rujul
      • his co-founder Lou
      • Zip’s Head of Finance
    • While people across the company can suggest that something should become an initiative or be removed, there is no formal bottom-up process for proposing company-level initiatives.
      • Functional teams may still run their own initiatives separately, but the centralized company tracker is reserved for the highest-priority cross-functional work.
  • Zip operationalizes the initiative tracker through a weekly written update cadence.
    • By end of day Thursday, each initiative owner sends an update email to a centralized alias using a standard template. Rujul said he gets roughly 30 of these each week.
    • He reads them on Sundays, and Lou does as well.
    • These emails also go to the Senior Leadership Team, so others can reply directly with questions, comments, or pushback.
      • Rujul said this is one of the main ways he stays on top of the company’s most important initiatives because it gives him dedicated time each week to review what is actually happening and catch areas that may need more attention.
  • In addition to the written updates, Zip uses live review time to focus on the initiatives that most need help.
    • In the Monday leadership review, the company alternates weekly between metrics review and initiative review.
    • Then in the Tuesday SLT meeting, Rujul goes deeper on the initiatives that are especially broken or materially behind.
      • The point is not to discuss everything live every week, but to use the written updates for broad visibility and then selectively pull the most problematic work into a more focused review forum.
  • Zip does not treat strategy as one single document.
    • The longer-term product strategy helps the senior team think through where the company is going over a multi-year horizon.
    • The annual narrative and four objectives provide the company-facing strategy for the year.
    • And the initiative tracker is the mechanism that turns those objectives into something operational and accountable across the business.
Example: Zip’s Weekly Initiative Email
  • Rujul showed an example of one of the weekly initiative emails that owners send in every Sunday
    • The format of these update emails has started to vary somewhat by owner, and people do not all follow the exact same structure anymore.
  • The basic purpose is consistent:
    • Summarize what happened in the last week
    • Explain what progress was made
    • Share how the initiative is feeling overall
    • Surface anything that needs attention
  • Rujul reads these on Sundays, and if he has questions, he replies directly. If he does not, he lets the update stand. This is the main way initiative progress gets fed into the operating cadence each week.

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.

Zip Separates Annual Strategy from Longer Term Product Strategy

  • At the longest horizon, Zip has a separate five-year product strategy document.
    • This is a sensitive document and is not broadly shared with the company. It is kept within a very small group, primarily the SLT
    • Rujul said the company revisits and refreshes it roughly every six months
  • He said they keep this document tightly held because sharing too much detail about what the company is trying to do five years out can actually confuse the broader team. 
    • In his view, the long-range product direction is useful for senior decision-making, but too much specificity on the distant “how” is often not helpful for most employees day to day.
  • Instead, the main annual strategy artifact is a short company narrative for the year. Rujul said the annual narrative is the strategy document most relevant to the rest of the company.
    • In a normal year, he and Lou start with this short narrative, then the annual objectives flow out of it. Those objectives then flow into the goals by quarter, the initiative list, and the company metrics
  • Rujul said the five-year strategy document is much more product-driven than the annual narrative.
    • They start by asking what they want the product and company to look like at a much longer time horizon
    • In the most recent version, they actually started with a 10-year North Star and then worked backward to five years
    • Once they had the product direction more fully fleshed out, they added the distribution component afterward
  • In that sense, the five-year strategy is not just a broader version of the annual narrative. It is a different tool that is more product-centric and it is primarily used by the senior team to think through longer-term product and distribution tradeoffs
    • Rujul said they have been doing some version of this long-term strategy process almost from the beginning. They had a lower-fidelity five-year document as early as about six months after

The Annual Narrative Is Intentionally Short, Simple, and Digestible

  • The annual narrative as a very short document - roughly one to two pages, and often closer to a page.
  • He keeps the document intentionally simple. It is not meant to be overly dense or intellectually complicated
    • It needs to be short enough that people will actually read it. His experience is that if it gets too long, people simply stop engaging with it
  • The purpose of the document is to create the context that sits above the objective table.
    • It explains the framing for the year
    • then flows into the objectives
    • then into the quarterly goals
    • then into initiatives and metrics
  • Rujul described this as the broader apparatus the company runs on

Why Zip Writes Their Annual Narrative

  • Rujul gave two main reasons for writing the narrative. 
  • The first is founder clarity.
    • Writing the narrative forces the founder to clarify their own thinking
    • That clarity then helps with decision-making over the course of the year
  • The second is team understanding and motivation.
    • He said it matters that people understand what the company is doing and why
    • Even if the narrative does not directly change every person’s day-to-day work, it still gives them a clearer sense of the North Star 
      • That in itself is motivating, because people want to understand the bigger reason behind the work they are being asked to do
  • The narrative has to strike the right distance between being far enough out that it gives people a meaningful sense of direction for the year but still close enough in that they can relate to it and connect it to what they are doing now

How Zip Reviews Metrics and Initiatives

  • Every Monday morning at 8:00 AM, Zip runs a leadership review meeting. This includes the broader leadership meeting with roughly 20 people. 
    • He considers Zip a relatively flat organization, which is why the group is somewhat larger
  • That Monday meeting alternates every other week between two modes:
    • One week is focused on the company’s top initiatives
    • The next week is focused on company-level metrics
    • Then it alternates back again
  • Rujul said the metrics are also organized against the four company objectives. In the view he shared, the company tracks those metrics with quarterly targets and weekly forecasting, so leaders can see how the business is progressing week by week against the broader annual goals.
  • In addition to the written Sunday updates, Zip also creates live review time for the initiatives that need the most help.
    • Every Monday, the company has two 30-minute slots where Rujul decides which initiative owners need to come present.
  • He said he generally uses those slots for the initiatives that are not going well. The presenters are usually notified about 10 days in advance, or roughly the Friday before the Monday of the following week.

How Zip Runs Their SLT Deep-Dive

  • In addition to the Monday leadership review, Zip also runs a separate one-hour SLT meeting on Tuesday afternoons.
  • This meeting serves a different purpose.
    • The Monday meeting is the broader operating review across initiatives or metrics. The Tuesday SLT meeting is where the company goes deeper on the areas that are truly broken or materially behind
    • More specifically, the Tuesday meeting is used to focus on initiatives that are struggling significantly and need heavier intervention. It is where the most problematic areas get more concentrated discussion and problem-solving from the senior leadership team

Important Metrics Are Usually Obvious - Your Time Should Go to What Is Broken Below Them

  • When asked about Zip’s “top five” company metrics, Rujul said those are always placed at the top of the metrics document and are very visible to the whole company. But he also noted that those top-line metrics are often not where he personally spends most of his time.
    •  Rujul said both the initiative document and the metrics document are open across the business. The goal is to make it easy for people to see:
      • What the company is prioritizing
      • How those priorities map to the annual objectives
      • How the company is performing against the key metrics
  • In practice, he is generally already aware of how those top-level metrics are doing. The more useful part of the review is usually lower down in the document, where the company can identify the specific areas that are breaking, slipping, or behaving unexpectedly.

When to Change Your Meeting Cadence

  • Rujul said the major shift at Zip happened early, when the company moved from a daily cadence to a weekly one.
    • Around 100 people or a bit before that, the company could no longer run effectively through a daily company-wide standup
    • Once that broke, Zip shifted to weekly leadership reviews and weekly or biweekly company-wide moments instead
  • Since that change, he said the cadence has stayed relatively stable.
    • Going from 250 people to 700 people did not fundamentally change the cadence again
    • The company still runs weekly leadership reviews, all hands remained regular, and Zip later added a monthly business review for the company to create more consistent visibility into core metrics
  • His broader point was that the biggest cadence change tends to happen when a company outgrows the very tight loops of the early stage. After that, the core rhythms can remain surprisingly stable for a long time.

Processes Should Emerge to Solve Real Communication Problems

  • Rujul pushed back on the idea that there is a single company size where a standard set of processes should automatically appear. Their shared view was that processes should develop in response to real communication and coordination problems, not because a company hits an arbitrary headcount threshold.
  • Rujul said Zip’s systems evolved fairly organically as the company grew.
    • Early on, when the company was around 50 to 60 people, Zip was still able to run with a daily company-wide standup
    • The whole company could stay aligned through a simple daily rhythm focused on the top problems and what needed to get done, but eventually that broke under the weight of scale
  • His point was that once a company gets larger, the issue is not that people should know less. It is that not everyone needs every piece of information at the same cadence.
  • The challenge becomes how to stay transparent without burdening people. If someone is doing support, for example, it may not be useful for them to sit in a discussion about a feature shipping in two months unless that information is actually blocking them
  • That is why his general principle has been:
    • Stay transparent
    • Give people as much information as they need, but only at the cadence that is useful
    • Make anything asynchronous that does not require live discussion
  • In other words, Zip’s processes became more structured as the company grew because the earlier default cadence stopped working. The company then had to create new rhythms that preserved alignment without forcing everyone into every conversation.

2. Clay

How Clay Uses Mission and Vision to Build Alignment

  • Kareem said Clay takes a very different approach from Zip. His view is that as companies scale, the hard problem increasingly becomes communication. 
  • Clay’s operating model is built around reducing that communication burden as much as possible by creating strong directional alignment and then trusting people to execute.
    • In practice, that means Clay runs the company with far less formal process than many companies at a similar stage.
  • There is no formal leadership team and no standing weekly leadership meeting. Leaders generally meet only when they need one another to do something
    • One reason Clay operates this way is that they did not want to create an “in the room versus out of the room” dynamic. Without a formal leadership team meeting, there is no prestige associated with being in the inner circle. Instead, the standard is simply whether someone is creating growth in their area
  • Kareem described the model as fundamentally trust-based rather than communication-heavy.
    • The company sets the objective, then trusts people to go do it. If they are not doing it, the company investigates whether the issue is the person or the system

Trust Matters More as Communication Complexity Grows

  • Kareem said his core thesis is that communication is almost always the bottleneck in a scaling company.
    • His question is therefore not “what process should we add?” but “what reduces communication overhead without losing alignment?”
  • His answer to that is trust. If people share the same high-level goal and trust one another, the company does not need to over-control every decision. Instead of building ever-heavier reporting and meeting structures, Clay tries to create enough alignment that people can move toward the same destination without constant coordination
  • He gave a simple example from his relationship with his co-founder.
    • At one point, his co-founder had brought a more formal one-on-one structure into their working relationship. 
    • They would meet weekly and go through bullet points systematically. Kareem said it was somewhat useful for a time, but eventually they realized they were already aligned and were mostly wasting time
  • So they dropped the formal one-on-one. Instead, they just text all the time. That is what works for them
    • The broader point was that companies should not keep process that no longer serves a real need just because it once sounded like a best practice

Clay Uses Mission to Define Scope and Vision to Define Approach

  • Kareem said Clay’s mission is “find and grow your best customers.”
  • He framed the mission as serving two roles.
    • The first is motivational. The company needs a reason to exist in the world and people need to feel that the company is pursuing something worthwhile. In Clay’s case, that means helping every business grow as fast as it possibly can
    • The second is practical. The mission helps define the scope of what the company should and should not do. If a decision helps a company grow as fast as possible, it is within scope. If it does not, it is out of scope
  • Kareem said they often restate this internally in another form: remove every obstacle to growth. That framing gives employees a simple way to evaluate whether something fits the company’s purpose
  • He then distinguished mission from vision:
    • In his view, mission is the enduring “why” and vision is the current articulation of how the company thinks it will achieve that mission. 
    • He described vision as “the future brought to today.” It is the current concrete expression of what the company is trying to build and why it believes that approach is differentiated
Example: How Clay Defines Their Vision
  • Kareem said Clay’s core vision is that businesses should be able to turn any idea they have for growth into reality.
    • This is not the only imaginable vision for Clay. For example, the company could have chosen a more automated vision where customers connect their systems and Clay figures out who their best customers are automatically. But Kareem said that is not what Clay is today
  • Instead, Clay’s current belief is that it is fundamentally a creative tool. The customer comes up with the growth ideas and Clay helps implement those ideas
    • He said this distinction matters because there are many companies trying to help businesses grow, but they are solving the problem from different underlying assumptions.
    • Clay’s assumption is that go-to-market teams are creative.
      • They already have strong ideas about how they want to target the market
      • The main problem is not lack of ideas but that they do not have the tools to implement those ideas quickly enough
  • For example, a team may know it wants to target companies that fit a very specific profile but actually pulling the data together across the CRM, data warehouse, and external sources takes so much time that the idea never gets executed
  • This clarity did not exist from the start. Clay originally began with a much vaguer intention: to give the power of programming to more people.
    • Over time, the company narrowed that into a more specific wedge: give the power of programming to go-to-market teams and let them use data and automation to implement complex growth ideas without needing to build everything themselves
  • He said Clay chose go-to-market because it had the largest gap between ideas and reality.
    • People had a lot of ideas about how to grow but they could not operationalize them quickly enough. That made it the best place to start
  • Kareem emphasized that some companies are already growing before they have fully articulated decisions like these. His point was that it is still important to eventually make those choices explicit, because they shape everything else the company does

Strategy @ Clay

  • Kareem believes one of the most important things a company should have from early on is a clear strategy.
    • His view is that even a 30-person company needs some understanding of how the work it is doing today compounds into something larger over time.
  • That strategy does not need to be formal or polished. It can be as simple as a story about why one decision leads to the next and how that creates a durable advantage.
    • He said that if a company does not have this kind of compounding logic, it can eventually get stuck.
    • Beyond that, Kareem does not believe there is one single correct operating model. Founders should build processes that match how their company actually works rather than importing someone else’s system.
  • At a high level, Clay’s strategy was built around three core choices:
    • Start with a wedge that can expand into something much larger
      • Clay chose to begin with data enrichment because it was one of the few parts of the go-to-market stack that had clear customer demand and real budget behind it.
      • But Kareem’s point was that the wedge only mattered if there was a path from that starting point into a much bigger platform over time. The goal was not to become a narrow point solution forever, but to use an initial entry point to grow into a broader product.
    • Build for the most sophisticated users first
      • Clay decided not to optimize for the broadest possible user from day one.
      • Instead, it focused on more technical and sophisticated go-to-market users who wanted a more powerful and expressive product.
      • Kareem’s belief was that if Clay could make the best users dramatically better, their success would pull the rest of the market forward.
    • Take a sharper position even if it creates short-term friction
      • Clay made several choices that were less intuitive on the surface but more aligned with its long-term strategy.
      • Kareem’s view was that a company should not always choose the version of the product or positioning that feels most immediately obvious or broadly appealing.
      • Sometimes the better strategic choice is the one that creates more friction in the short term but builds a more differentiated company over time.
  • These choices led Clay to do a number of things differently:
    • Start with a specific wedge rather than trying to do everything at once
    • Orient the product around power and flexibility rather than broad simplicity
    • Invest in a user base that could become both the earliest power users and the strongest evangelists
    • Make product and positioning decisions based on long-term category direction, not just what seemed easiest in the short term

How Clay Used Agencies as their Initial Distribution Wedge

  • Kareem then described Clay’s early distribution strategy.
  • He wanted Clay to be product-led over time for two reasons:
    • He believed it would eventually make the company grow faster
    • He saw it as a forcing function to make the product better and more usable
  • But he also recognized a problem: if Clay helps companies grow, many customers will not want to reveal how they are doing it. That makes word of mouth harder than in some other categories
  • Their insight was that agencies solved this problem. They were among the most sophisticated users, they needed customers, and unlike internal teams, they were happy to talk publicly about what they were doing
  • Clay therefore sold to agencies first.
    • They became the loudest evangelists and showed the market what was possible with Clay
    • Over time, the best people at those agencies would get hired into companies, spreading Clay further
  • Kareem described this as a deliberate long-term strategy, not just a tactical customer segment choice.

Why Clay Doesn’t Maintain a Formal Strategy Narrative

  • Kareem highlighted that, unlike Zip, Clay does not rely on formal written vision or strategy narratives. Instead, Clay’s narrative emerges from a series of concrete strategic choices:
    • He and his co‑founder repeatedly talk through major decisions.
    • They align on the underlying story those decisions imply.
    • They do not feel a strong need to package that story into a polished strategy document for the whole company.
  • Kareem thinks of his job as providing “just‑in‑time” context:
    • Everyone should understand the high‑level picture of what Clay is trying to do. Beyond that, people mostly need the specific context that’s relevant when it becomes necessary for their work.
    • They do not always need a fully articulated written narrative far in advance.
  • To support this, he runs a weekly, very open‑ended Q&A:
    • He actively encourages hard, uncomfortable questions.
    • But he also pushes people to only ask questions that are actually blocking what they need to do today or tomorrow. If a question is not tied to immediate execution, he often treats it as procrastination rather than useful strategic thinking.

 Clay’s Rituals to Maintain Alignment 

  • Kareem said that even though Clay runs with much less formal process than many companies at a similar stage, there are still a few core rituals that keep the company aligned.
  • Rather than building a dense operating system with many recurring meetings and reporting layers, Clay relies on a small number of high-leverage touchpoints.
  • The four main rituals are:
    • A weekly all hands
    • A weekly open Q&A
    • Quarterly planning
    • Open dashboards and planning docs that teams can access when needed
  • Weekly all hands
    • Kareem said the weekly all hands is one of the few non-negotiable company-wide rituals. Its main purpose is cultural alignment.
    • He uses the beginning of the meeting to bring to the surface what people are thinking but not saying clearly, especially places where the company may be losing momentum.
    • This is where he tries to “debug the culture” and address issues before they harden into confusion or drag.
  • Weekly open Q&A
    • Clay also runs a weekly open Q&A where employees can ask direct questions.
    • Kareem said this is another important alignment mechanism, but more interactive than all hands.
    • Anonymous questions are allowed, though discouraged unless truly necessary.
    • The goal is to give people direct access to ask about what is actually blocking them, without requiring heavy ongoing communication overhead.
  • Quarterly planning
    • Kareem said quarterly planning is the company’s biggest formal planning ritual.
    • This is where teams define what they think they should do, review those plans, and then consolidate them into a smaller number of goals.
    • Historically Kareem reviewed every team’s plan himself, though that has become more distributed as Clay has scaled.
    • Quarterly planning is the main moment where the company steps back and aligns on what matters most for the next stretch of time.
  • Open docs and dashboards
    • Clay also keeps many of its documents and dashboards open.
    • Kareem’s philosophy is not that everyone should constantly discuss everything, but that people should be able to access information when it is useful.
    • This supports Clay’s broader model of high trust and low communication overhead: people do not need to be pulled into every conversation, but they can get context when they need it.
Example: How Clay Uses the Weekly All Hands to Clarify Context
  • Kareem gave a concrete example around complaints that EPD was shipping too many bugs. His view was that the broader company was reading that situation incorrectly.
    • From the outside, it looked like the product and engineering teams were shipping broken things, but in many cases, the issues were actually superficial polish issues or final 5% details that were being fixed within a day
  • Kareem used the all hands to explain that distinction:
    • If something looks broken but is fixed in one day, that is different from a deep systemic quality problem
    • For EPD, the development cadence is fundamentally different from ops or go-to-market. They cannot always just “show up and fix it” instantly because they are often dealing with system-level causes that require more investigation
  • Part of leadership is helping the company interpret reality correctly. Otherwise teams can form narratives that are emotionally real but operationally misleading
  • He also said he sometimes uses this forum to set sharper cultural boundaries.
    • For example, when Clay was smaller, survey results showed that people were overwhelmingly happy, but there was still a background layer of routine complaining
    • Kareem said he was explicit that not every frustration needs to be escalated to leadership. His view was that people should not treat leadership attention as the outlet for every emotional reaction
  • As the company scales, his time does not scale with everyone’s desire for attention, so the company needs stronger norms around what is worth escalating and what is not.

How Clay Runs Their Weekly Open Q&A

  • Separate from all hands, Kareem said Clay also has a weekly open Q&A. He framed this as another important culture-building exercise, but one that is more interactive than the all hands.
    • Employees can ask questions directly
    • Anonymous questions are allowed, though discouraged unless truly necessary
    • Kareem actively encourages people to ask harder questions
  • This fits with his broader philosophy of just-in-time context. He does not want to over-explain everything in advance but he does want people to have direct access to ask about what is actually blocking them

Metrics @ Clay

  • Kareem said that at the company level, Clay historically looked at a very small number of core metrics.
  • In the PLG-heavy period he described, the main numbers were:
    • revenue growth
    • cohort performance
    • NRR
    • new customers
    • Churn
    • Expansion
    • Contraction
    • Restarts
  • But he emphasized that even among these, the two most important were:
    • revenue growth
    • cohort performance
  • His reasoning was that cohort performance effectively captures whether the company is getting better over time. Every product/process/retention improvement should eventually show up in the quality of the new cohorts
  • If each new cohort is at least as strong as the last, and ideally better, then the company is improving in the ways that matter. Because of that, Kareem did not care much at the company level about lots of intermediate numbers
    • He was not constantly checking website conversion metrics or other funnel details unless a team surfaced them as an issue
    • He thinks those kinds of numbers were more appropriate for departmental management than for company-level management.
Example: How Clay Used a Simple P&L and Forecasting Model Early On
  • In 2023, before having an in-house finance leader, Clay worked with an external finance person to build a P&L model and a forecasting model with base, good, and great cases
  • He said this was genuinely helpful in keeping the company on track.
    • It did not need to be overly sophisticated but it gave the company a way to understand whether growth and conversion assumptions were tracking
  • For a PLG company, he said the key inputs were relatively straightforward:
    • Website visitors
    • Signups
    • Paid conversion
    • Customer counts over time
    • Churn
    • Monthly revenue
  • Then, once Clay began layering in a sales-led motion, those assumptions could be added on top.
  • His recommendation was that companies should do this even before they have a formal finance function, because the exercise of forecasting itself is useful for managing the business.

Planning @ Clay

  • Kareem also shared that Clay used lightweight written artifacts to help keep the team aligned at different moments.
  • One example was a simple product positioning document.
    • This laid out what Clay was doing at that moment
    • How it was different and what use cases it was focused on
    • More importantly, what it did not focus on
  • He emphasized that these docs were very simple.
    • The goal was not to create exhaustive strategy decks. It was just to give people enough clarity to remember what was specific about the company’s current moment and priorities

Clay uses Quarterly Planning and Monthly Goals

  • Kareem said the single biggest planning touchpoint in Clay’s operating system is quarterly planning. He said Clay has used quarterly planning since fairly early on, once the company reached around 25 people. The process takes roughly two weeks.

Initial Plans

  • The first phase was independent planning
  • Each EPD pod/team would create its own view of what it thought it should do
  • Ops would separately create its own view of what it thought it should do, along with product feedback and requests

Second Review

  • After that first round:
    • The team would review the EPD proposals
    • Then merge in the Ops suggestions
    • Then create a consolidated plan
    • Then iterate again to clarify dependencies and expectations across teams
  • Kareem said that for a long time he personally reviewed every single team document. He would spend 30 to 60 minutes with each team. This meant four full days of back-to-back review sessions at often 8 to 10 hours per day

Final Output

  • At the end of the process, Clay would produce two major planning outputs:
    • An EPD plan
    • An Ops plan
    • Each with three overarching goals
  • Kareem or his co-founder would then present those final plans to the company.
  • As Clay grew, they progressively distributed more of this planning responsibility to the team.
  • Earlier on he presented every goal himself, reviewed every document personally, and was deeply involved in every team’s planning work
  • But as the company scaled:
    • Managers started presenting more of the plans themselves
    • Around 150 people, Kareem stopped personally presenting every team’s goals
    • More recently, product and engineering leaders now run much of the detailed review process directly
    • Kareem reviews the consolidated output asynchronously and then weighs in at the end
  • The same shift happened on the ops side:
    • Sales presents its own plan
    • Marketing presents its own plan
    • CX presents its own plan
  • In other words, the planning cadence remains central, but ownership of the detailed work has become more distributed as the org has matured.

Accountability @ Clay

  • Clay does not run a heavy formal accountability system around those documents. Kareem’s expectation is that each team is responsible for looking at its own plan, knowing whether it is on track, and adjusting if needed. 
    • Earlier on, when the company was smaller, Kareem himself would look at those plans more directly. As the company scaled, that responsibility shifted more to the teams themselves.
  • The main formal follow-up Clay introduced was a mid-quarter check-in.
    • Each team had to assess whether it was on track or not
    • If it was off track, that was not automatically a problem
    • The important thing was to clarify whether the goal had changed because the team learned something, whether the scope had to shrink, or whether execution had slipped
  • Kareem said he generally preferred that teams reduce scope but still accomplish the core thing, rather than pretending the original scope was still realistic. What he wants to know is:
    • What changed
    • Why it changed
    • Whether the revised goal still moved the company forward
  • At the end of the quarter, Clay only does retros in a serious way if something had gone badly wrong.
    • They had tried doing retros for everything, but Kareem said that was not particularly useful. In practice, only a small number of things matter enough each quarter to dramatically move the company.
    •  If one of those core things missed, then it was worth digging in. If a team missed because of some understandable complication (like a harder-than-expected problem, the wrong hire, something external) he did not think a big process ritual was always the best response. His view was that if a team misses repeatedly, the pattern becomes visible anyway.

Explicitly Push People to Take Ownership 

  • Kareem said this philosophy is strong enough that he has banned a certain pattern of communication internally.
  • If someone says, “Kareem said to do X,” he treats that as a bad sign.
    • Either the person does not actually believe in the action
    • Or they are trying to shift responsibility upward instead of taking ownership themselves
  • Even if he was the one who originally suggested the plan, he wants leaders to restate it as “we should do X” or “I think we should do X”
    • He is not in the room for every local decision. He wants people to internalize judgment, not outsource it.

Chaos Got Your Company to This Point. Don’t Suffocate It. 

  • Kareem said founders often have an instinct to add more process and control as the company grows because chaos feels uncomfortable.
  • But he believes that instinct can go too far.
    • his view is that everyone says they want control and hate chaos
    • but the company’s best ideas often came from exactly that earlier, more chaotic stage
    • the excitement and creativity of the early company are tightly connected to that messier environment
  • He described the common progression as:
    • the company starts chaotic and full of energy
    • founders then try to control more and more of it
    • eventually they over-correct and squeeze the life out of the company
  • Clay’s answer has been to tolerate more chaos than many companies would. Kareem said they try to respect chaos as one of the ways new ideas get generated. That is part of why they do not require heavy reporting by default

Clay Pursues Speed Over Perfection

  • Kareem said Clay’s default is not to spend a lot of time trying to determine the single perfect priority or the single perfect plan before starting.
    • His view is that too many teams waste time trying to identify the exact most important thing, when in practice the company often just needs people working quickly on one of the most important things.
    • As long as someone is reasonably close to the bullseye, speed often matters more than perfect prioritization.
  • This is why Clay puts a lot of weight on individual ownership.
    • The company tries to hire strong people, make one person the DRI for something important, and then let that person figure out the best path forward.
    • Rather than over-coordinating upfront, Clay gives people room to move and expects them to exercise judgment.
  • Kareem said this works because Clay operates with what he called an FYI culture.
    • If someone decides there is a better plan than the one originally discussed, they do not need to stop and ask for permission to change course.
    • They should just send an FYI explaining what they are doing and why.
      • The expectation is not blind adherence to the original plan. The expectation is that people do the right thing for the company.
  • Kareem was very explicit about this:
    • He does not actually care whether people do exactly what he told them to do
    • He cares whether they make the best decision for the business. If someone has better information and can improve the plan, they should do that
  • He said this is also why Clay avoids heavy cross-functional prioritization exercises when possible.
    • In his view, those exercises often create communication overhead and slow the company down. Clay would rather move faster with clear ownership than spend too much time aligning on a theoretically perfect answer
  • Kareem compared it to going to the gym:
    • Early on, if a company is on the right path, many good efforts will move the needle. The goal is faster reps, not perfect theoretical optimization

Clay’s Default Is To Only Report When Something’s Going Wrong

  • Kareem’s default is not to ask people to report back constantly on initiatives that are working.
    • If someone owns an initiative, they should just go do it. They do not need to send a steady stream of updates proving that they are working
  • The only time he really wants reporting is if something is going wrong.
    • If the initiative is off track, then leadership should hear about it. If it is going well, he does not want to spend time thinking about it because his attention is better spent elsewhere
  • He acknowledged that there is a downside to this approach.
    • The feedback he has received is that he often only shows up when something is wrong, which can make it feel like he gives only negative feedback and not enough positive reinforcement

Different Functions Can Run on Different Cadences

  • Kareem said Clay’s cadence evolved somewhat differently.
  • Earlier on, when Clay was still more heavily PLG-driven, the company largely ran on monthly goals.
    • This was true for both EPD and Ops. Kareem said monthly just matched the way the business behaved at that stage
    • If one month was better than the last, that was often the cleanest signal of whether the company was improving
  • They also had a weekly release cadence initially, which later moved to biweekly, and that remained the product release rhythm even as other planning cadences changed.
  • As Clay grew and hit more meaningful product-market fit, most of the company shifted to quarterly goals.
    • This wasn’t the case for every function - marketing still ran more on a monthly cadence but sales and customer success were more naturally managed on a quarterly cadence
  • Kareem’s view was that companies should not force every function into the same operating rhythm if the nature of the work is different. Some teams need to think monthly; others can think quarterly.

Clay Intentionally Does Not Make Metrics a Constant Company-Wide Conversation

  • One of Clay’s more unusual choices is that even though the dashboards are open, the company does not make metrics a major shared conversation by default.
    • His reasoning is that most employees are not directly in a position to change a top-line metric just because they know the number that week.
      • If website visitors are down, most people in the company cannot act on that
      • The only thing that widespread visibility often creates is anxiety or distraction
  • So Clay’s default is:
    • The dashboards are available if you want them
    • The teams directly responsible for the metrics should watch them
    • But the company should not spend a lot of energy collectively staring at numbers it cannot collectively move
  • Kareem said this philosophy even led Clay to change some of its internal tooling. At one point, a Slack bot was posting daily revenue into the main company channel
    • Employees pointed out that this contradicted Kareem’s own view that not everyone should be obsessing over metrics every day. He agreed that it no longer made sense, and the bot was moved into a separate metrics channel instead
  • He used this as a broader example of how culture gets enforced. If something in the company feels inconsistent, people should surface it. Often the reason is not hypocrisy, but simply that something made sense at one stage and no one has yet updated it

3. Staying Close to ICs

Why Clay Prioritizes Check-Ins with ICs Over Managers

  • At 10 people, communication can feel ambient and effortless because everyone is in the same room. But by 40 people, once functional leaders start to emerge and the founder is no longer in close weekly contact with everyone, people begin to feel the distance and often want more direct access to the founder. 
    • A founder’s time doesn’t scale with more people, so the solution can’t just be to add in more meetings
  • This feeling is normal and persistent. His view was that even if a founder adds things like weekly Q&As or all hands, that will not fully eliminate the desire for more personal access. So while those forums are useful, they are not the whole answer.
    • He instead recommends spending less time defaulting to the leaders and more time talking directly to ICs. At around 40 people, a founder can still spend a meaningful amount of time talking directly to individuals across the company. Kareem will take walks with people, ask them what they are working on, and stay close to what they are experiencing
      • This is especially valuable before too much organizational distance hardens. If founders stay deeply in contact with individuals early, that creates a base of trust and context that continues compounding later. By the time the company is 200 people, those relationships and that information network become much more valuable
    • At Clay, they did not even hire a true product manager until around 100 people, which was partly a reflection of how long he personally wanted to stay close to that function. His point was not that every company should copy that, but that founders should consciously decide where they want to stay close versus where they are willing to introduce distance.
      • He generally assumes leads should know what they are doing and should come to him if there is an issue. Because of that, he does not feel the need to spend all his time in constant check-ins with managers. Instead, he tries to leave open space and use more of his direct time on the individuals actually doing the work
  • One reason for this is that ICs often know much more than managers about what is actually going on. When he talks to a manager, the summary may be that everything is going fine, but when he talks to ICs, he often hears the specific issues, frustrations, and edge cases underneath that summary
  • Sometimes the manager is still directionally right and the IC concerns are not all equally important, but even then, the founder still needs to understand those perceptions because they shape how the team experiences the company
  • Kareem also said there is a cultural reason for doing this. Once companies introduce management layers, people can start to associate status with proximity to the founder
    • They begin to want management roles partly because managers seem to be the people who get access. He tries to reverse that dynamic by making it feel like managers are expected to get on with their jobs, while the founder is also actively spending time with people deeper in the org
  • This kind of direct founder contact builds loyalty over time and preserves information flow from the parts of the company that otherwise get abstracted away as layers form.

Use Skip-Level Roundtables to Hear Problems Directly and Build Loyalty

  • A couple of years earlier, Rujul started doing skip-level roundtables.
    • Every other week, he spends an hour with all the people in a given team
    • Their direct manager is not in the room. It is just Rujul and the ICs or skip-level employees on that team
  • The goal is to hear directly what problems they are having and understand what is getting in their way.
  • He said that as much as possible, he then tries to go fix those problems and come back.
    • That helps him learn what is happening beneath the management layer but it also goes a very long way in building loyalty, because people can see that direct founder attention sometimes leads to action
  • Rujul noted that at a larger scale it takes much longer to cycle through the whole company this way, but when the company was smaller, it was easier to do more frequently and with more coverage

As Companies Scale, Founder Access Has to Become Intentional

  • Kareem added that if founders create more direct access, they also need to help people understand that not every issue raised will get fixed. He said one of the useful things a founder can do is tell people explicitly “this is a real problem and we are going to fix it or this is not a problem we are going to prioritize right now”
  • His view is that employees need help distinguishing between:
    • Something that is painful but temporary
    • Something that is annoying but not actually important
    • And something that is truly worth company attention
  • Otherwise, direct founder access can accidentally create the impression that every frustration should lead to intervention.

 Using Small Founder Dinners to Create Casual, Scalable Access

  • Kareem also shared one more tactic that had worked well for him: inviting small groups of employees to dinner. He said he and his co-founder each regularly invite around 10 people at a time to their homes for dinner.
    • The group is a random assortment
    • The setting is intentionally casual
    • Over time, this gives them a chance to meet a wide swath of the company in a more human and relaxed way
  • He said that even though he personally does not love dinners, this format ended up working well and being enjoyable. It creates connection without needing to frame everything as a formal feedback session and at a company in the 40–50 person range, a founder could do the same thing with even smaller groups and get through the company relatively quickly

4. B2B Sales Performance

 Building a Rigid Sales Operating System

  • Zip had hired a CRO in 2023 who looked strong on paper and then dramatically scaled the sales team under that leader. The company roughly tripled the size of the sales team but closed about 20% less business than before making that investment
  • Rujul said one of the clearest ways he diagnosed the problem was simply by watching a large number of Gong calls.
    • He saw reps not being trained properly, enablement was not standardized, and basic things that should have been fixed already were still happening in live customer conversations
    • He also did a number of skip-levels, which reinforced that the issues were systemic rather than isolated.
  • Ultimately, fixing it required much more than replacing one leader. Zip ended up firing the CRO and roughly 40% of the sales team because the hiring profiles, ramping, and standards underneath the leader had also drifted badly
    • Rujul said that experience made it painfully clear that sales does not break in one obvious place. It breaks through a large number of small inputs going wrong at once. That was what pushed him to build a much more detailed top-down sales operating system.
  • He said that in sales, things usually get worse rather than better if you wait. Bad hiring profiles, weak enablement and poor management compound.
    • He was very candid that by the time he made the move, Zip had already missed multiple quarters. At that point, he was less worried about protecting the next quarter and more focused on fixing the underlying system
  • One of the biggest lessons from that period was that sales requires much more “babysitting” than he would have liked. As a result, Zip now runs a much more hardcore operating rhythm around new rep ramp.
    • For example, every other week, the company reviews each newer AE individually. For each rep, the dashboard shows how many external sales meetings they attended each week over the last several weeks. 
    • There is a hard expectation that new reps get to at least eight sales meetings per week
      • Rujul said this is a blunt input metric, and on its own attending more meetings does not guarantee success. But if reps are not getting those reps and exposures, he knows they will not become successful, so if they are not hitting that baseline, that is a very serious issue
    • He also said managers are expected to be at those meetings too. Otherwise, in his view, they are not actually doing the job of helping reps ramp and improve

 Early Sales Leaders

  • For early sales leaders, bias towards people who are 80% operator and 20% manager
  • The profile for a good early sales leader entails:
    • someone closer to a strong number two than a classic “executive CRO”
    • someone still willing to do the work directly
    • someone who can sell, demo, train, and ramp reps themselves
    • someone who is still 80% operator and only 20% manager
  • The failure mode is hiring someone too senior, too removed from the work, and too under-contexted on the product and motion, then giving them broad control before they have proven they can actually run the system.

Tracking Pipeline Generation

  • Rujul said the first layer of the system is simply tracking pipeline creation and conversion through the funnel.
  • He walked through the terminology Zip uses in Salesforce:
    • S0 = meeting set
    • S1 = qualified opportunity
    • S6 = closed won deal
    • stages in between are governed by qualification criteria, including MEDDIC-style definitions
  • At the top of funnel, he looks at how many meetings the team is generating against target. The dashboard then showed current pacing against that target and it could be broken down by segment and geography to identify where generation was weak
    • For example, in the March view he showed, Zip’s target was 780 net-new sales meetings for the month
  • He then looks at how those meetings convert into qualified opportunities. The point is not just whether pipeline exists in the abstract, it is whether each stage is converting at the rate the company expects

Looking Ahead To Assess Sales Engine Repeatability

  • Rujul said that as the company scaled, it became increasingly important not just to understand the current quarter, but to see whether the engine was getting healthier over time.
  • One of the most useful views for him is a dashboard that looks two quarters out. For a given segment, he can see how many opportunities are sitting two quarters from now, then compare that against where the company was on the same day one quarter ago and two quarters ago
    • He said this is especially useful for understanding whether the company is getting stronger or weaker before the revenue outcome shows up. 
      • If the opportunity count two quarters out is improving, the engine is likely getting stronger
      • If it is weakening, that is an early warning sign that something will break later
  • He prefers to look at opportunity count rather than ASP in these forward-looking views because ASP forecasting hygiene can vary too much to make those numbers trustworthy enough.

Zip’s Biweekly Segment Reviews

  • To operationalize this, Zip runs biweekly segment reviews.
  • These are attended by:
    • Rujul
    • the relevant sales leadership
    • RevOps
    • Sales Ops / Enablement
    • the relevant segment leader
  • The meeting itself is run by RevOps every other week, not by Rujul personally, but he attends. The meeting is designed to review a specific set of inputs in a highly repeatable way
    • These reviews cover both the top-of-funnel pipeline views and the deeper leading indicators that help the team understand whether each segment is actually scaling properly.
  • In these meetings, they review, at minimum:
    • Top-of-funnel pipeline creation
      • S0: net new meetings set per segment (vs monthly targets, pacing)
      • S1: qualified opportunities created (conversion from S0 → S1)
      • Breakdown by segment (e.g., NA key, EMEA, commercial) to see where they’re behind
    • Forward‑looking pipeline health
      • Opportunity count by future quarter (e.g., current quarter, +1Q, +2Q)
      • Quarter‑over‑quarter comparison of “two‑quarters‑out” pipeline to see if they’re building enough for future quarters
      • View by segment to spot where future quarters are underbuilt
    • Rep‑level productivity / scaling
      • Pipeline and “mature pipeline” held by each AE, sliced by tenure cohort
      • Whether new AE cohorts are consistently ramping to expected pipeline levels by quarter and two quarters out
    • Activity/behavior inputs (for new reps)
      • Number of external sales meetings per AE per week (with an expectation of ~8/week)
      • Flags for reps and managers who are below activity thresholds

Tracking New Rep Cohorts’ Productivity

  • Rujul said that once Zip started hiring more AEs, one of the most important questions became whether new cohorts of reps could be made productive in a repeatable way. That is what determines whether a sales team can actually scale.
  • He looks at:
    • He looks at mature pipeline by tenure cohort to see how much “real” pipeline each cohort is holding based on time in seat.
      • If a new cohort has been hired into a segment, he expects to see them holding meaningful pipeline two quarters out, even if not immediately in the current quarter
    • He tracks overall opportunity count by segment over time at every stage of the funnel, not just S0 and S1.
      • He compares “two‑quarters‑out” opportunity counts day‑by‑day against prior quarters to see whether forward pipeline is stronger or weaker than it should be.
    • He looks for segment-level patterns: segments that are repeatedly underbuilt two quarters out, or where close rates / ASPs are shifting.
      • He uses these patterns plus rep‑level meeting and pipeline metrics to diagnose whether problems are in segment strategy, pipeline generation, or individual rep execution.
      • This lets him assess whether ramping is working, not just whether individual reps are busy.
Example: 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

Do Not Use “Quota Capacity” as a Crutch If the System Underneath It Is Broken

  • Rujul also pushed back on the idea that more headcount automatically creates more sales output. His point was that quota capacity only matters if the system underneath it is working.
    • If the sales process, hiring, training, and management are broken, adding more reps just increases cost without increasing output
  • His view was that founders should not let capacity math or pressure to fill the org override what they know to be true operationally. If the engine is broken, fix the engine first. Otherwise all you are doing is expanding the cost base and worsening CAC payback

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