Building Repeatable Revenue Engines at Outreach and Catalyst with Mark Kosoglow
Lessons in scale from a unicorn builder
Mark Kosoglow is a name synonymous with growth and execution in SaaS. From his early days of consultative selling at a shoe store to leading sales at Outreach and Catalyst, Mark has consistently demonstrated how to build high-performing teams and scalable sales processes. Now, as the founder of Operator AI, he’s sharing his insights on creating repeatability in go-to-market motions - a critical challenge for any SaaS company scaling from startup to scaleup.
In our conversation, Mark broke down the mechanics of building repeatable systems, hiring for success, and ensuring operational excellence. Here are the key lessons from the discussion.
1. Repeatability Starts with Process and Measurement
Mark defines repeatability as the ability to produce consistent results regardless of individual contributors. For him, this hinges on two factors: process and measurement.
“You need a process that’s standardized and measurable,” Mark explains. Without it, success becomes unpredictable and unsustainable. At Outreach, Mark developed systems that allowed his team to move from zero to $230M in ARR. The cornerstone of this success was an obsession with instrumentation—measuring every input, conversion, and output across the sales funnel.
The goal is to predict outcomes reliably based on the inputs. That’s done by instrumenting your sales process, defining each stage, tracking key metrics (ACV, win rate, cycle time), and ensuring every team member understands how they contribute to the system.
2. Great Talent Makes the System Work
Mark’s second pillar of success is people. “The right process only works with the right people,” he says. For him, hiring isn’t just about skills—it’s about traits like coachability, curiosity, and a relentless work ethic.
At Outreach, he found that coachable candidates often outperformed those with prior experience in the same role. One of his standout hires transitioned from being a middle school teacher to closing million-dollar enterprise deals within a few years.
In Mark’s opinion, skills can be taught; traits like drive and adaptability can’t. He built a hiring process that identifies these qualities and invested heavily in training and development.
3. Adaptation is Essential: Why Repeatability Ends
One of the most interesting takeaways from Mark’s experience is his observation that repeatability isn’t permanent. “Processes have a shelf life,”* he warns. As tactics become widespread and markets shift, strategies that once worked can lose their effectiveness.
For example, Mark recalls the early days of sales engagement tools, where simple email automation gave Outreach users a massive edge. Over time, as competitors adopted similar tools, the inbox became oversaturated, and the advantage diminished.
This highlights the need to agile build systems with the expectation that they’ll need to evolve. It’s necessary to regularly audit your processes and metrics to identify when performance dips, then adapt to the new market realities.
4. Instrumentation: The Key to Diagnosing Problems
A well-instrumented sales funnel can quickly reveal what’s working—and what isn’t. At Outreach, Mark emphasized the importance of segmenting data by motion (e.g., inbound vs. outbound), value, and volume. This granular approach allowed him to identify and address specific bottlenecks, such as rebooking issues or misaligned discovery processes.
“The data tells you what to fix,” he says. Without the right instrumentation, teams often misdiagnose problems, wasting time and resources on solutions that don’t address the root cause.
Mark uses both value-based and volume-based metrics to evaluate your funnel, looking for patterns in conversion rates, cycle times, and win rates by segment to pinpoint where adjustments are needed.
5. Leadership is About Enabling Change
For Mark, leadership boils down to one word: efficacy. “The job of a leader is to affect change,” he explains. This means creating systems and support structures that enable your team to improve continuously. At Catalyst, he focused on building a robust enablement function, ensuring managers were trained to conduct impactful deal reviews and that reps were empowered to execute at a high level.
He also insists on clarity in operating rhythms. Weekly forecasts, team meetings, and structured deal reviews were non-negotiable components of his leadership playbook. These routines ensured alignment and accountability across the organization.
Final Thoughts: Building a System That Outlasts You
Mark’s career is a testament to the power of combining great people with scalable systems. From crafting repeatable motions at Outreach to navigating Catalyst’s acquisition, his playbook is clear: start with a strong process, hire for traits, and instrument your funnel to evolve with the market.
For SaaS leaders, the lesson is simple: don’t settle for short-term wins. Build a system that works today and can adapt for tomorrow.