Cross Operating Partners

Communication is the Connective Tissue of Scale (Part 3 of 3) Context & Clarity Corporate commentator William H. Whyte once wrote, "The great enemy of communication, we find, is the illusion of it.” The quote critiqued the corporate management habit of high-level internal communication campaigns that lacked context and clarity. In our experience, when a leader fails to provide sufficient context or clarity, people often fill-in the gaps for themselves. The results can range from inefficiency to confusion to chaos. If you have ever given a person (or an AI Agent) an assignment with insufficient context and experienced them coming back with something completely different than what you have in mind, you have experienced the “illusion” of communication. To help ensure context and clarity, we adopted a framework from a leadership training from The Levinson Institute. In delegating work (be it an initiative, project, or assignment) you must always specify the Why (context on why we are doing this), How (the plan and how the team should work together to achieve it), and What (the specific deliverable or solution sought). Importantly, you must train your delegate on the framework so that they can ask clarifying questions and fill gaps prior to commencing work. Check-ins on progress follow the same framework. The “What” portion of the framework had another layer to ensure clarity. We trained everyone on the Levinson acronym “QQTR” – Quantity, Quality, Timing, and Resources. On Quantity and Quality, we'd clarify the scope and whether we wanted a rough draft to brainstorm against or a near-finished deliverable. Discussing Resources makes it clear how much the organization and the individual are expected to invest in the work. And Timing is critical – as our former executive coach Bruce Longshore used to say, “A task without a ‘T’ is an ask.” For us, QQTR meant fewer iterations on deliverables and fewer project delays.   In summary, product-market fit, compelling unit economics, and a repeatable sales motion are necessary for scale, but they are not sufficient. Communication is the connective tissue that helps a rapidly growing organization execute against the market opportunities that these concepts create. If you don’t build communication as a muscle, the result is slowed decision-making, inefficient work, and organizational frustration. But when a company builds a foundation for strong communication, people align, momentum grows, and growth accelerates.  Link to full blog in the Comments

Communication is the Connective Tissue of Scale (Part 2 of 3) Process & Cadence The best lesson we learned on communication processes was from another great business book – American Icon: Alan Mulally and the Fight to Save Ford Motor Company. When Mulally left Boeing to join Ford as CEO, he quickly observed that communication issues were at the center of Ford’s decline to the brink of bankruptcy. Executives were afraid to report bad news, and thus hid operational flaws, poor performance numbers, and risks to the business. Mulally launched a new, organization-wide, communication process called BPR (Business Process Review). Each team would have a BPR meeting to report on current performance against its objectives and KPIs in a Red/Yellow/Green format. Green meant on-track, Yellow meant that an issue had been identified but the team had a workable solution, and Red meant a major problem with no known solution. BPR meetings rolled up from teams to divisions to the executive leadership team. Each had the same format. And Mulally stressed that sharing Yellow and Red updates would be considered good news – a timely request for help – rather than bad news. As Revenue Analytics grew, we implemented the BPR process. At first, there was grumbling about adding weekly meetings across teams and functions to the calendar. But we quickly realized the benefits of more formal and structured sharing of key information, product and customer status, and updates on strategic initiatives. We kept the updates brief, timed, and uninterrupted, with the goal of saving at least half the meeting to discuss Yellow and Red issues. BPR also served to align each team around what success looked like for that team, backed by KPIs that drove company performance. We believe that it was a key factor in achieving a 34% CAGR, even during the “great SaaS recession.”  Link to full blog in the Comments

Communication is the Connective Tissue of Scale (Part 1 of 3) When growth equity firms talk about scaling B2B technology companies, they generally focus on concepts like product-market fit, strong unit economics, a repeatable sales motion, and product depth and reliability at scale. Obviously, these are important factors in determining the potential to scale. But one factor that can be overlooked in assessing a company’s ability to scale is having robust communication practices and processes. Any organization is fundamentally a collection of human beings. So, how those people interact, share information, and make decisions is vital to the organization functioning healthily, effectively, and efficiently. In the early stages of a company’s growth, communication happens naturally. Small teams are working closely together and develop natural communication rhythms. But as a company grows, those teams will inevitably start getting split across functions and/or verticals. As this happens, maintaining strong communication requires three things: Leadership Focus (Part 1), Process & Cadence (Part 2), and Context & Clarity (Part 3). Keeping these things in mind during the whirlwind of growth is essential to scaling successfully. Leadership Focus While How Google Works missed the cut as one of our Top 3 most influential business books, it is an excellent read full of practical advice for any operator. The chapter on communication tells the story of Jonathan Rosenberg being told by a software engineer, “You’re just an expensive router.” The remark was meant as an insult, since routers just move packets of data around a network. Jonathan replies, “If all I am is an expensive router, I intend to be a damn good one.” He recognizes that focusing on sharing information with relevant stakeholders is an essential part of leadership. The book emphasizes that strong leaders are open and transparent, know the details, and keep people informed. Being “a damn good router,” as the book implores, requires relentless focus on communication. When presented with new information or when making a decision, we trained ourselves to ask questions like “Who needs to know?,” “Who needs to know first?,” and “What is the best form of communication?” The more senior the leader, the more important the questions become, and the broader the stakeholders become. “When does the Board need to know?” “How about our customers?” “How do we ensure that leaders can answer questions from their team on this topic?” These questions sound basic, but in the hectic world of a growth company, they can be forgotten. We have recently witnessed multiple technology leaders casually mentioning important decisions in meetings prior to formal communication, which can lead to confusion and people making up their own narratives across the organization. And we have seen focused communication drive successful corporate transformations.  (link to full Blog in Comments)

In this new world of AI, being a Trusted Advisor is more important than ever. It’s true across multiple functions, but particularly for Customer Success.

Future Customer Success Managers must be Trusted Advisors. Every executive has experienced two very different types of Customer Success Managers (CSM). The first is the one you couldn't pick out of a lineup. They show up out of the blue before renewal, forward support tickets, and, if you're lucky, schedule a QBR you attend once but vow never to attend again. If they leave, you wouldn't notice. The second has their cell phone on your speed dial. They understand your business, challenge your assumptions, help you navigate change, and proactively bring opportunities and risks to your attention. If they leave, you feel it. For years, SaaS companies have called both of these people CSMs. In an AI-native world, the difference between them will become impossible to ignore. Most of the administrative work historically associated with Customer Success is rapidly becoming automated. AI can surface adoption risks, identify expansion opportunities, answer basic feature and function questions, generate usage reports, and flag customer issues long before a human notices them. That's not a threat to Customer Success. It's a threat to the droves of CSMs that never created value in the first place. A core guiding principle we taught our Customer Success team at Revenue Analytics was simple: listen to the customer, but don't obey the customer. As actor Bill Hader once said, "When people tell you what's wrong, they're usually right. When they tell you how to fix it, they're usually wrong." While he was talking about acting, the same principle applies to software, consulting, and customer success. Customers are usually very good at identifying pain. They're often much less effective at diagnosing the root cause and prescribing the right solution. A trusted advisor doesn't simply take orders. They ask questions. They challenge assumptions. They bring perspective from similar situations. They help customers solve the problem behind the request. This evolution doesn't require larger Customer Success teams. In many cases, it requires smaller and more experienced ones. As we automated more of our delivery and customer processes at Revenue Analytics, revenue per Customer Success Manager increased by 56%. Our CSMs spent less time coordinating activity and more time providing guidance. In a world where AI can increasingly handle execution, the most valuable customer-facing professionals will be those who combine expertise, accountability, judgment, and strategic guidance. In other words, trusted advisors. Read our full thoughts on this CSM transformation in the link below.

How Do You Eat a BHAG? One Bite at a Time. Early in my executive career, I hated annual planning season. Long-range plans felt like corporate theater. Endless spreadsheets. Incremental budgeting exercises. Pretending we could predict the future with precision three years out. Then we began a transformation that shifted my perspective. Our Jim Collins inspired BHAG (Big Hairy Audacious Goal) was simple to say, but incredibly difficult to execute: Transform from $20M+ bespoke consulting company to a scaled $20M+ in recurring revenue software company. At the time, less than 20% of our revenue was recurring. We wanted to flip that entirely on its head. Over time, 80%+ of revenue needed to become recurring with one-time implementation revenue supporting the product, not custom consulting. That single vision forced us to rethink everything. Gross margins needed to move from roughly 50% to 75%+. Implementation timelines had to shrink from 16 weeks to 8 weeks. We needed to move down market to expand TAM and shorten sales cycles. ASPs came down, but sales cycles dropped nearly 40%. The BHAG itself was not the breakthrough. Breaking it into measurable operational steps was. First, we introduced formal Long-Range Planning (LRP) tied directly to annual operating plans. We reviewed the LRP before annual planning discussions. Next, we moved to monthly all-hands meetings with the explicit goal of connecting the long-term vision to current execution. Finally, we shifted our weekly ELT meetings towards leading indicators, operational metrics, and accountability against targets. That enabled us to take the once almost overwhelming BHAG and break it down into meaningful chunks of change with associated metrics and measures of success. Over time, the organization stopped viewing the transformation as a future aspiration and started seeing it in their day-to-day work. That visibility mattered. For some team members, it quickly became clear the future company was not a fit for their individual goals and desires. And that’s ok. For others, the clarity created excitement and ownership. Those are the ones who became our change agents and propelled the business forward. A good BHAG should force hard decisions, expose operational gaps, and create measurable accountability between today's execution and tomorrow’s vision. The companies that successfully transform are usually not the ones with the boldest vision. They are the ones willing to continuously measure, iterate, communicate, and adapt until the organization eventually looks up one day and realizes it has in fact become something different.

"The next $1T company will be a software company masquerading as a services firm." — Julien Bek, Sequoia Capital It's a provocative prediction. Here's what we can say from actual experience: productization can drive a 3-5x increase in Enterprise Value for a Tech-Enabled Services firm in 3-5 years. Most Tech-Enabled Services firms trade at a discount to comparable SaaS companies, based on one-time or "reoccurring" revenue (versus true recurring revenue) and lower gross margins. Many have the opportunity for productization through: 1. Delivery Automation: Automate more delivery using AI and software. Keep humans in the loop for accountability, judgment, and relationships. 2. Recurring Revenue Model: Re-frame offerings to sell ongoing outcomes that generate multi-year contracted recurring revenue. Not "reoccurring." Recurring. It takes real work. It will be a 12-18 month effort that overhauls GTM, delivery, and team structure. Change management will be the difference between a successful pivot and one that stalls. Success means a Services company with SaaS attributes that drive Enterprise Value - higher gross margins, better EBITDA, and a higher mix of high-retention ARR. Sequoia's $1T prediction is provocative. Our 3x in 3 years is proven. That’s the power of productization. Link to the full piece in the comments.

Tired of AI Slop? Brace for a Tsunami of Sloppy SaaS… GenAI has created a tidal wave of content. Roughly 74% of new web pages in 2025 and nearly 50% of news articles contain a significant amount of AI-generated content. Some might even say those numbers are low compared to scrolling LinkedIn on a Tuesday. But nevertheless, AI slop and the Multiplicity “Xerox Effect” (slop cloning slop) are here to stay. Now, we are starting to see the next big wave on the horizon: sloppy software. Claude Code, Codex, and similar tools have changed the game. Building software has never been easier or more accessible. That will unlock incredible innovation. Faster drug discovery, personalized medicine, autonomous transportation, and agentic workflows that reshape knowledge work. The list goes on. It will also produce a lot of sh*tty software. Clunky UIs, releases that unknowingly break unrelated features, integrations that constantly fall over, and security breaches the likes we’ve never seen. Which makes this a good time to get back to fundamentals. And that starts with sound product management, a decidedly human function. A good product manager owns outcomes and drives toward a clear vision. They understand the business problem deeply, see the world through the customer’s eyes, and stay grounded in market realities. They cut through noise, define what matters, align teams, and make hard tradeoffs. If something is worth building, they make sure it’s built right. And most importantly, they are accountable for the result (another uniquely human function). Product management is a rare blend of skills, balancing long-term strategy with the ability to translate complex systems, data, and algorithms into elegant, intuitive experiences. The best understand the economics behind every product decision and build for where the market is going, not where it has been. Without good product management, we are going to live through a lot of sloppy software. The companies that win will be the ones that combine the new AI-driven speed with human judgment and discipline by investing in strong product leaders who can not only build, but also coach and develop great product teams. 

One of our proudest accomplishments as operators was hiring great people. Anyone who worked with us at Revenue Analytics would quickly cite "the people" as the best thing about working there. As we scaled, we realized that we needed to codify our hiring philosophy and approach into a playbook for the entire organization.  This case study (link in comments) tells the story of how we realized that we needed to provide guidance to the team on hiring and shares highlights of the playbook. Check it out to hear about "Hiring for non-teachable skills," "No assholes," "No hires without an advocate," and other tenets of our philosophy on hiring great people. Don't just make a hire. Make the right hire.

It’s easier to sell aspirin than vitamins. Everyone would generally agree vitamins are good for you. Longevity, prevention, performance. And yet, many of us don’t consistently take them. Why? Because “I can always start next week.” But when I have a pounding headache and a calendar stacked back-to-back, I will pay the price of 200 aspirin for a measly 2 at an airport Hudson News. Immediate pain wins. Over the past 20 years selling pricing performance solutions, we learned this the hard way. Selling future upside sounds great on paper. While some buyers will lean in, most will not prioritize benefits they hope to appear a few quarters from now. What dependably moves deals is pain. We could consistently deliver a 10x ROI within twelve months of implementation.  We even offered a no-strings-attached, money-back guarantee. It still paled in comparison to alleviating pain. As we scaled, our approach evolved to identify, understand, unpack, and apply pressure to pain. From initial awareness messaging to deep discovery and implication-driven questions, probing pain became our secret to gain. In an agentic AI world, it’s easier than ever to create new “solutions.” The questions not enough people are asking are some of the most foundational: what pain is this actually solving? How often does it occur? How much does it hurt? And what does life look like when it’s finally relieved? The promise of future benefits might get you a conversation. Solving persistent pain gets you a contract. Aspirin before vitamins.