Meet Laurence
Laurence is a B2B software executive with a track record of leading cross-functional operations in high-growth tech companies. Most recently he was Chief Business Operations Officer at Contentful, helping scale the business from approximately $50 million ARR to $200M ARR. Prior to Contentful, he was Vice President of Emerging Businesses at Twilio and served as the Vice President of Revenue at SendGrid, where he helped scale the company from startup through IPO. Laurence joined Ansa’s Advisory Network earlier this year and has been active in engaging with our investments. Join us in conversation with Laurence.
Chief Business Operations Officer is a nebulous title. What did that role entail at Contentful and what types of organizations should consider this?
At Contentful, my mandate was to build the internal operating system for the company: How do we align around a strategy, and then how do we operationalize that strategy to execute it? This involved creating and running the system for the What, Who, and How of the business.
The "What" represents our strategy: What business are we in? Which customers are we targeting? My role was to help articulate this in a way that everyone, from leadership to the whole company, could understand. Then there’s the "Who"—how do we hire, develop, and engage our people to execute this strategy. Lastly, the "How" covers our operating rhythms, decision-making processes, and culture. I believe that nailing these three aspects—the what, who, and how—is critical for any scaling company.
Depending on the skill sets of the executive team, a role like Chief Business Officer or COO is a way to help integrate these elements effectively.
For a high-performing, high-growth business, what frameworks can help a founder evaluate when to bring one on?
This really depends on the specific circumstances of the company and the dynamics among the founders or executive team. I think about it in three main areas. First, where does the CEO need to focus their time? For instance, in a fast-moving space like generative AI, the CEO might need to prioritize product vision and external relationships, leaving less time for internal operations. Second, what are the CEO’s strengths and where could they use augmentation? If they excel at product strategy but find operational execution less engaging, that’s a good reason to think about bringing in a CBO. Lastly, take a look at what the executive team needs. Assess the overall skill set of your leadership team—are there gaps in data-driven decision-making or alignment? What kind of support or expertise does the team need? Perhaps it’s someone who can help align the leaders and the company around a specific direction and bring an operational mindset to the team. Or maybe you need someone who can play a facilitator role and help the other executives communicate better with each other.
Some companies see this need around $20-30 million in ARR, while others might wait until closer to $100 million. Constantly evaluating the team’s needs and driving internal self awareness is key.
For CBOs to be successful, effective communication across stakeholders is paramount. When recruiting for senior talent at the CBO/COO, how do you test for effective communicators during an interview process?
Communication is critical, especially in today’s post-COVID environment with hybrid work. It demands conscious effort. I recently heard the former CEO of Home Depot discuss how the idea of cascading communication is flawed; it suggests people wait for leadership messages, but it’s really an uphill push to make those messages resonate, requiring skill, emotional intelligence, and persistence.
To assess communication skills in interviews, I focus on two key approaches. First, observe how candidates present themselves. Can they distill their thoughts clearly and create a compelling narrative? This gives insight into their communication style. Second, I use behavioral questions on communication topics. For example, tell me about a time when you led teams through a significant change, or managed difficult stakeholders, or drove alignment between teams where it previously didn’t exist. These reveal their awareness of the criticality of communication and how they prioritize and invest in it. These insights are invaluable for evaluating senior candidates.
You've worked with many Executive Leadership Teams (ELT) to level-up leadership alignment, including some teams in our portfolio. Are there patterns in the changes these teams need to make?
There are a few patterns I’ve noticed when working with executive leadership teams on alignment. The first one is making the implicit explicit. One of the biggest gaps I see is teams thinking they’re aligned, but they’re actually talking past each other because they don’t have clear, shared definitions. For example, let’s say a company wants to focus on enterprise sales. Well, what does "enterprise" really mean? Or take a classic one between sales and marketing—everyone talks about MQLs, but do we actually agree on what an MQL is? Getting those shared definitions in place is key.
The second pattern is around goal alignment. Once you have those shared definitions, how do you make sure everyone is marching towards the same outcomes? This is where things often break down. People get out of sync, departments start operating in silos because the way goals are set is actually causing misalignment. A classic example is marketing says hitting their MQL goals, customer success says they’re hitting their activity goals, but sales is missing on their new business and expansion numbers. This is a signal that each team’s goals aren't aligned, and that creates gaps.
The third piece is operating cadences. You’ve got to have the right rhythms in place to stay in sync and break down those silos. At the ELT level, what are we discussing on a weekly, monthly, quarterly basis? Are we spending the right amount of time on the right topics? A common trap is that teams spend too much time on tactical stuff and not enough on strategic topics. And then when you get down to the functional level, it’s about ensuring that teams are coming together cross-functionally on a regular basis. For example, I believe Sales, Marketing and Customer Success leaders need to have some version of a Go-to-market Council where they meet regularly to share insights and make decisions across the end-to-end customer experience. Otherwise, they just end up stuck in their own silos, and communication breaks down.
What patterns and best practices have you seen around comms architectures at SendGrid and Contentful? What are some downstream implications of this?
My insights largely stem from lessons learned and plenty of trial and error. One key lesson is the importance of driving one conversation across the organization on important topics. Decisions get made in a small group, and then leaders often over-rely on cascading communication to share those decisions - I tell my directs about it, and then they tell their teams, and so on. As leaders it’s also easy to underappreciate how much other functions want to understand what’s happening in your team, which leads us to underinvest in cross-functional communication. Both of these patterns result in “telephone games” and people filling in the gaps for themselves in a way that’s ultimately unproductive. To counter this, I recommend starting with the assumption of default transparency. Make as many documents, meeting recordings, and other artifacts accessible to everyone. Have ELT members speak directly to the full company about key decisions and what’s happening in their department. One example of this is optional Lunch and Learn sessions, where anyone in the business can come hear about, say, the 2024 marketing plan directly from the CMO. You’d be surprised how many people are genuinely interested.
Another vital takeaway is embedding information into daily workflows. Many organizations have an overlooked wiki or intranet filled with information that rarely gets used because it’s not integrated into employees' routines. Think about ways you can insert content directly in the tools and platforms people use daily For example, say you’re a company that uses Slack heavily. Link to your product roadmap, team charters, and company strategy presentation in the company announcements channel. This keeps important updates top of mind and accessible. By embedding information into the spaces where people already work and directing them to the content that matters, you not only enhance communication but also create a culture where people feel like they’re informed and engaged.
A common question that comes up in growth-stage companies as they scale is, how much process is the right amount of process? What are some ways that you think about standardization in how a company operates, without creating bureaucracy and slowing down velocity?
There’s a constant tension in how we approach the process, and I focus on three key principles. First, limiting scope is essential. I call it the Small Government Principle. Basic rules are needed for a well-functioning organization, but we should only implement company-wide policies where they’re truly essential and helpful. Essential is things like compliance with the law, consistency with the company’s core values, or where lack of standardization creates a huge pain for customers or makes it impossible to run the business. Common areas where a cohesive approach really helps include metrics reporting and goal tracking at the department level, and People topics like compensation and promotions. Standardizing also has to be done at the right altitude. For example, you want a single way that each department talks about their metrics and OKRs at the leadership level. However each function might have their own way of running their day-to-day and managing progress. As long as they report up in our consistent agreed way, the way they manage things within their team is up to them.
The second principle is what I call Just-in-time Process. Many organizations fall into the trap of over-engineering processes in anticipation of future issues that may or may not arise, or future states that are still several years away. Instead, identify immediate needs and focus on addressing those now, and then develop processes over time as situations actually come up. One example here is job leveling and career ladders. It’s tempting for many HR teams to want to go straight to rolling out a comprehensive, detailed framework that is consistent across every team. But that’s overkill for a company that’s 100-200 employees, and it's a huge lift to implement. What you need at that stage is for each function to have a simple career ladder they can use to manage their teams, and you tolerate some inconsistency across departments. As you get to 500+ employees, then you’ll want to drive more coordination and less variation across the company as you have more people in more specialized roles.
Lastly, a mindset of continuous improvement is vital. Regularly auditing and removing previously installed processes that no longer serve the organization enables process balance in the organization and keeps in place what is actually providing the intended, relevant benefits. By critically assessing what works and what doesn’t— and creating rituals where you periodically identify and eliminate processes, rather than just adding more—we can reduce friction and enhance overall efficiency in the organization.
