Building the Right Operating Cadence

Travis May

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Dec 13, 2023

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This article is a playbook for CEOs on what rituals, meetings, and processes to introduce at each stage of a high-growth tech company’s journey.

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A common theme of my posts is that operating velocity is one of the most important determinants of success for a business. Operating velocity helps you create an exceptional culture and phenomenal team, both of which are critical ingredients to moving even faster. There is one other ingredient that makes or breaks the velocity of a company: its operating cadence.

By the time you cross 10 employees, as CEO, you start to ritualize key team events. Events like the “Weekly All-Hands” become a standard way that communication occurs and culture is built.

As you get bigger, these events are the “operating cadence” of a company — they are the rhythm of an organization that shape how decisions get made and how information is shared as companies scale. Different companies have different operating cadences: some companies are meeting-heavy, and some underemphasize communication; some companies develop process too early, and others too late.

As companies cross a few hundred employees, almost all communication and decision-making needs to work its way into the operating cadence. Great CEOs build their operating cadences with intentionality, thinking about what communications are critical to whom and the best forums for the communication to take place. A few principles in process design are important here:

• Unless you are a nuclear power plant, 95% of your operating cadence should be “positive process” (process that accelerates the team by reducing steps required for coordination) over “negative process” (process that is designed as a checkpoint to prevent mistakes)
• Bias towards centralized process when there’s complex cross-team coordination, and against centralized process otherwise. Design your organization to minimize these scenarios.
• Require the minimum viable number of people in meetings to make processes effective (and encourage people to not come if the process isn’t helpful)
• To avoid meeting creep, eliminate processes with meetings unless the benefit is very crisp
• Give people access to the information they need to run their parts of the business — use emails, team meetings, etc. to curate and distribute information transparently

This post walks through the key rituals that were part of the Datavant & LiveRamp operating cadence at scale (>500 employees), and then outlines what stage we added each ritual. While each subteam had its own rituals, these were the ones that made it onto my radar as key events.

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Team-Wide Communication:

• Weekly Team Meetings. Starting when the companies were 5 employees, we set up a weekly 30-minute meeting to touch base on “what’s going on in the company” — and scaled this as we grew. We scheduled these for Monday mornings, and we had ~2 minute updates from each major function leader, as well as 1–2 “ spotlight topics” (selected by me or my Chief of Staff to curate what was important) per week.
• Win Celebrations. Rituals to celebrate company wins are extremely helpful — they focus the organization on key outcomes, and also create a morale boost with momentum. Up to 100 people, we had “Gong Time,” where every time a key deal was closed or major win happened, someone would ring a gong…and every few days we’d gather round the gong for people to talk about their wins. We also encouraged “Deal Won” emails — where the sales rep would email the whole team would outline a deal that just closed, and context on the customer’s use case. From there, the rest of the team would respond with congratulations. The last day of the quarter was especially fun!
• Quarterly Company, Team, and Individual OKRs. On the first day of the quarter, I would send the full company objectives & key results for the quarter; we would then have a “quarterly kickoff” meeting within the first week where we’d review the outcomes from the last quarter and discuss the goals for the next quarter. I generally locked on these with the management team a week ahead of time, and then team leaders would send out the teams’ goals (for teams where OKRs were the right format). And we would publicly set individual OKRs as well within the first week — so everyone could see each others’ goals and focus areas.
• Quarterly All-Stakeholder Emails. On the first day of each quarter, I sent a ~3 page recap of the last quarter to all of the company’s shareholders, as well as the team and all of our advisors. A well-written recap helps to make it clear how individual accomplishments connect to the big picture, and reiterate the big picture.
• Sharing financials. I shared all of our board decks with the team (including full financials except specific compensation information), and our monthly financial flash reports, along with some curation/explanation by the finance team.
• Weekly Digest. Once we crossed ~200 people, we began sending “weekly digests” — with key announcements and big wins. These were typically owned by a Chief of Staff with some input by me, ensuring that the most important themes are consistently highlighted.
• Lunch & Learns. Starting around 20 employees, we had weekly “lunch & learns” — optional meetings where a team member would walk through some topic relevant to the business. From guest presentations by clients to an overview of our cap table to a deep dive on policy changes impacting our business, these were usually interesting — and provided an outlet for optional, structured content.
• Bi-annual offsite. If part/all of the team is remote, it’s critical to get people together on some frequency. Up to 500 people, we made this a camping trip.
• Sunday Thoughts. Every Sunday, I would email the team an email on whatever was top-of-mind for me (often about our strategy, or a customer use case I was excited about, or something I was concerned about, etc.)
• Retrospectives. Starting at just a few employees, we had a robust culture of retrospectives. Whenever a major event happened (especially one where we made mistakes), the team involved would write a retrospective of what we learned and publish it to the whole company. This helped normalize mistakes happening and learning from them without having a culture of blame.

Leadership Team Coordination:

• Weekly Management Meetings. Once you cross 30 employees, you need some form of regular cadence of meetings with a management team. I hosted these meetings weekly for 45–60 minutes and ran the agenda as a “communication/alignment meeting” rather than a “decision meeting” — decisions were made by the right subgroups offline.
• Weekly Outcomes Tracker. One of the best micro-hacks I’ve found for communication is the weekly status tracker. Each week, by Sunday evening, every member of the management team would fill out a shared Google Sheet with three columns next to each executive’s name: “Top 3 priorities for next week”, “Up to 3 positive outcomes from last week”, “Up to 3 negative outcomes from last week.” Everyone was expected to read this document ahead of our management meeting and ask questions of each other.
• Quarterly Leadership Offsites. Starting around 30 employees, we hosted a one-day offsite once a quarter for the management team (often in a conference room down the hall, but sometimes traveling if a critical mass of the team is remote). The goal was debate/discussion/alignment (NOT decision-making). We would pick 3–6 topics for the day (example: “is it time to do an international launch”), and give each topic an owner who would prepare a 1–3 page pre-read.
• Quarterly Board Meetings. As soon as we had external capital, we began hosting quarterly 3-hour quarterly board meetings (as long as 2-days for public companies, but I think 3-hours is sufficient). In between board meetings, we hosted mid-quarter sales/financial updates (30–60 minutes). The most productive board meetings I’ve hosted had elaborate pre-read packages, where each executive gave a 1–2 page update on their function, and ~30 minutes was spent on Q&A with the board, followed by 2.5 hours of “spotlight” topics.
• Weekly 1:1’s. These are nobody’s favorite meetings…but I think they’re essential parts of a healthy operating cadence at any size. I let my direct reports set the agenda, and also have a “below the line” portion of the agenda with updates I should be aware of. Most skip-level 1:1’s were ad hoc.
• Monthly Business Reviews. Once we crossed 200 employees, I began spending a day each month in “business reviews” to systematically get updates and provide feedback on key initiatives across the business. Each month, I would ask 10–20 leaders of key initiatives to do monthly, 30-minute update sessions on their initiative. To make these sessions valuable, each meeting was capped with only 2–8 attendees, and there was a 1–2 page pre-read plus 1–2 “discussion topics” for the meeting.

Customers & Sales:

• Deal Desk. As companies cross 100 employees, it can be frustrating for a sales person to get a deal done — depending on the deal, they may need legal signoff, finance sign-off, privacy sign-off, product sign-off, sales leadership signoff on pricing, etc. To make this fast (but ensure there’s adequate review by key stakeholders), we had a simple template that the sales rep would fill out and send to a “deal desk” email alias. Most deals would be approved on the same-day, but we had a standing “deal desk” meeting as a venue for escalation.
• Customer Aliases. For every customer, we created an email alias (eg. client123@datavant.com) that included all the people involved in supporting the account, as well as anyone in the company that wanted to track the account. Then, whenever we communicated with the client, we CC’d the alias, so lots of people internally could track what’s happening. This was great for quick information-sharing across delivery and sales teams, and also a helpful way for leadership to know the pulse of key accounts.
• At-Risk Reviews. Once you cross $20mm of ARR, it’s helpful to have a regularly-scheduled discussion of what accounts have churn risk associated with them. If something churns that is not on the list, that means you have an information problem. We held these monthly.
• Quarterly Sales Kick-off. The beginning of the quarter is a key moment for sales — and we used these kickoffs to discuss our path to hit the number, updates in the market, and updates in the product.
• Quarterly Partnership Reviews. Each quarter, we would try to have a check-in meeting with executive sponsors at almost all of our customers — even if there wasn’t an imminent upsell or churn event.
• Account Planning Brainstorms. Once there were more than 10 people on the sales team, it was helpful for the sales team to do deep dives with each other to know the details of key accounts. Key executives would join these and publicly brainstorm how we can grow our most important partners.
• Red Alerts. Whenever something bad was happening for an account (disappointed client, churn, etc.), we expected the account owner to email the “red alerts” alias. This went to a bunch of key leaders in the org, so there could be widespread visibility on the issue (and escalation or creating a war room if needed).

Product & Engineering:

• Quarterly Roadmapping. The roadmapping process is the single most important source of decision-making in most tech companies; micro- and macro-decisions are locked on through this process. I have never seen a company that loves it’s roadmapping process; it’s either too granular or not detailed enough. If there are more than 30 engineers, I am a fan of a process that allows for prioritizing 1–4 “big bets” at an executive level, allocation of resources across pods at an executive level, and then decision-making on the long-tail of projects at the pod level. A great product leader is critical to be able to navigate the big picture discussion with the micro-allocations that are being made.
• Annual product vision. Every year, I think it’s important to refresh the 3–5 year product vision — and either reconfirm what you’re building towards, or update the vision. I usually make this a late December project with the Head of Product and then they present it to the company as part of the yearly kick-off.
• Quarterly hackathons. There are always lots of competing priorities that make it feel like you should cancel this quarter’s hackathon. You shouldn’t. Many of the best ideas in a company are born in hackathons, and they’re a critical outlet for the innovation of the team. These are even more important as the team grows beyond 100 people.

Legal, Security, and Privacy:

• Deal desk. Outlined above…the deal desk was the key forum for ensuring there was legal/privacy visibility on all deals and an outlet to review, without unnecessarily delaying deals.
• Roadmapping. Roadmapping isn’t just for product! It’s helpful to have a moment where there can be meaningful debate about “invest in SOC-2 or HiTrust” or “tradeoffs between going deep on GDPR or CCPA expertise.” I encourage leaders of functions that touch lots of different constituencies to host quarterly roadmapping sessions to make some of these debates clear.

HR:

• Hotspot Reviews. Once you cross 100 employees, there are always several “fires” going on within the organization. I use a monthly “hotspots” meeting to track these fires systematically. Ahead of these, the People team would put together a list of hotspots/fires in the organization (eg. ABC team is low-morale right now; X key performer is probably about to resign because of tension with person Y; etc.), and rank their urgency on a scale of 1–5. At scale, there are usually dozens of fires, and it’s helpful to flip through the list; we would then use the meeting to talk through 1–5 of the issues that are most important and most solvable.
• Offer Approval Process. Starting at ~5 employees, I think it’s important to systematically think about how offers are made and approved: ensuring that you’re defaulting to no, hiring for strengths rather than lack of weaknesses, and have a high bar across the team. More on this process here.
• 9-Box Reviews. Firing people is one of the hardest things in business, and as a result, every company biases too much towards keeping low-performers. One approach to correcting this bias is a formalized 9-box review, where managers need to categorize their team as High/Medium/Low performance, and High/Medium/Low potential. With good discipline around forcing distributions, you then have visibility and a framework to encourage managers to part ways with low performers.
• Leveling & Compensation Reviews. As you cross 50 people, having “levels” for compensation becomes a helpful guide for the appropriate/default salary and equity of a new hire. I believe managers should be empowered to give raises ad hoc, but there should also be an annual process of confirming cross-team fairness.
• Pulse Survey. Once you cross 200 people, it becomes important to have a quantitative view of the mood of the company, broken down by team. We used quarterly, short (<10 question, custom designed as questions we cared about) surveys.
• Annual Performance Reviews. While micro-feedback should be given every day/week/month, meaningful, curated feedback about how employees can grow is important to do at least once per year.
• New hire onboarding. Starting around 20 employees, we were extremely focused on having a great new hire onboarding program — and making sure people walk out of their first week able to clearly articulate the vision, strategy, priorities, and culture — and know how to get things done internally. I met with every new hire cohort at the end of orientation to reinforce our culture and promote accessibility of leadership.

Financial:

• Annual Budgeting Cycle. Once you have multiple employees, you need some form of budget, and once your revenue or burn exceeds $5 mm., it makes sense to start formalizing a budget process. At <$20 mm of revenue, this should be very lightweight.
• Monthly & Quarterly Financial Results. Having quick, clear visibility on the financial metrics becomes critical as you cross around $10 mm. ARR and can no longer keep all the numbers in your head. I like to share these results with the whole organization.
• Quarterly Forecasting. Once you cross $50 mm. in revenue (and especially if you are a public company), ongoing forecasts become critical. These are important to keep lightweight, but are helpful as leading financial indicators.

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When to introduce process

As you can see above, there are dozens of processes that exist to be able to systematically have good communications and decision-making at scale. In an early stage, a lot of this is overkill. There is an art to introducing a process when it’s constructive, but not too early and not too late. This is my rough strawman for some of the processes above.

And of course…there is also an art to killing processes that aren’t adding value (and making sure the processes are meaningfully time consuming, don’t have too large of meetings, etc.).

Every company should look different. In the end, a good operating cadence is designed to help a company with a good culture and good talent to be high velocity.