Dave Osborne, CEO at Conga – Interview Series

David Osborne, CEO at Conga is a seasoned software and technology leader with more than 25 years of experience driving growth, transformation, and operational excellence across global SaaS, cloud, and tech-enabled services companies. Before joining Conga in 2025, he served as CEO of Caseware, where he led the company’s expansion as a global leader in cloud-enabled audit, reporting, and analytics solutions, and previously as CEO of Virgin Pulse, where he scaled the world’s largest workplace wellbeing platform through multiple acquisitions and integrations. Earlier in his career, Osborne held senior leadership roles at Insight Venture Partners and Vista Consulting Group, guiding dozens of portfolio companies through successful integrations and growth strategies.

Conga is an enterprise software company that helps organizations streamline revenue operations through AI-powered solutions for document automation, contract lifecycle management, configure-price-quote, digital commerce, and billing. Its unified platform integrates with major CRM and ERP systems, enabling businesses to simplify quote-to-cash processes, improve compliance, and accelerate growth.

You have over 25 years of experience leading SaaS and tech-enabled services companies, including CEO roles at Caseware and Virgin Pulse. What leadership lessons or strategic frameworks, like your “Clarity of Purpose,” are you bringing with you to Conga?

Every team member needs to understand the company’s vision and how their work contributes to it. It is key to driving operational excellence and innovation. Additionally, I’m applying frameworks that map back to this priority, and focus on alignment, transparency, and measurable outcomes across all Conga teams and initiatives. A leadership lesson that I bring with me everywhere I go that aligns with Clarity of Purpose is following Lencioni’s principles of the 5 dysfunctions of a team. Trust at the executive level is step 1 in building a team that can lead an organization.

At Conga Connect 2025, you posed the question “Why does Conga exist?” How is that question shaping your strategic vision for the company?

Conga exists to accelerate customers’ journeys to becoming more connected and intelligent businesses. Many organizations speak to a customer’s core operational systems such as ERPs and CRMs. Between those systems lives a lot of complexity for those managing the revenue lifecycle. That complexity manifests itself in things, like manual price books and cumbersome contract processes that result in challenging handoffs, data that lives in multiple places, tedious excel work, and cumbersome contract processes. When you eliminate these manual handoffs and tasks, you are connected. When you optimize the complex variables and create new outcomes, you are more intelligent. Our “why” drives a focus on how we are operating the business, and it keeps us aligned on delivering transformational capabilities to the customers we serve.

You replaced a long-tenured CEO, Noel Goggin. How are you building on the foundation he established while carving out your own leadership direction?

Noel and the team built a great foundation. Coming in, it was important to me not to disrupt the momentum Conga had, but at the same time, we had to quickly identify opportunities for improvement. We’ve aligned our employees around our strategic plan, and we’re all focused on executing that.

Conga’s platform combines CPQ, CLM, and document automation across any ERP and CRM. What areas of this ecosystem do you believe are most primed for AI-driven transformation?

I believe the entire ecosystem is primed for AI-driven transformation. We are already working to embed AI and ML across CPQ, CLM, and document automation to drive efficiency, accuracy, and actionable insights. I’d say key areas we believe AI can have a significant impact on are price optimization, contract analytics, risk management, and predictive deal guidance.

You’ve cautioned against premature AI claims that lack strategic substance. How can enterprise software companies avoid hype and instead build real, trust-driven value with customers and employees?

I would recommend leaders prioritize substance over hype—focus on delivering real, measurable value with AI. It’s important that AI solutions are transparent, secure, reliable, and enhance both customer and employee experiences. Where possible, companies should engage customers in early adopter and advisory programs to validate and refine AI capabilities. At Conga, we’re focused on delivering AI capabilities that are grounded in business value and act as an “assistant” to business users.

Internally, how are you aligning cross-functional teams to identify AI opportunities that are realistic, ethical, and customer-first?

Our main focus is on embedding AI into our platform and solutions that can provide meaningful value for our customers. To do so, we have worked together across the organization to develop an aggressive roadmap for AI delivery. I also recognize that AI can make our internal teams more effective, and we are working cross functionally to define where AI can make significant impacts, prioritizing those projects in the immediate future.

You advocate a leadership approach of “move fast, fail smart, stay focused.” How do these principles show up in practice at Conga? 

They show up in a few ways. First, we are reducing silos that exist across the organization to improve our speed. We’re also laser focused on our strategic plan. If it isn’t part of the plan, it isn’t a priority. And finally, across the leadership team, we are fostering a culture where calculated risk-taking is supported, and lessons learned are shared openly.

How do you and your executive team make decisions quickly without sacrificing clarity and long-term alignment?

Our “why” we discussed earlier keeps us grounded as we make decisions, and it keeps our customers at the center of our thinking. I’ve worked hard to create a tight knit leadership team that collaborates well. We have a weekly meeting to make quick decisions as a team. If we are missing data or need additional insights, we’ll move the discussion to our monthly strategic session. Open and consistent communication is key for quick decisions and strong coordination. One of our strategic guardrails at the ELT level is “we won’t wait for consensus.” We may not leave the room 100% aligned on the decision, but we are always 100% aligned on defending it.

Conga serves over 10,000 customers and processes millions of quotes and contracts annually. What are your biggest growth levers over the next 12 to 18 months?

The market for our CPQ, CLM, and Document Automation solutions is large, and our current revenue represents only a fraction of the available addressable market. With the capabilities we currently have in our solutions and those that are on our roadmap, we have a tremendous opportunity to capture additional market share. Our roadmap incorporates AI across our solutions and in our platform, which is critical to solve the complex challenges our customers are facing in areas like contracting and pricing. Another growth lever for us is seeding the ecosystem with the expansion across the broader companies with CRM and ERP players using our new ecosystem agnostic Advantage Platform.

As Conga continues expanding integrations beyond Salesforce, what’s your vision for platform openness and ecosystem-driven growth?

First, Salesforce continues to be a great partner for us, and our platform will remain closely integrated with Salesforce to provide customers with a seamless experience. That said, we are embracing a robust ecosystem of partners, connectors, and APIs to support customer choice and flexibility. Our approach to delivering technology opens up connectivity across any core infrastructure. The more connected we are, the greater value we deliver to our customers and our partners, and the more informed our AI will be.

With increasing competition in the markets Conga serves, how do you plan to differentiate Conga’s value proposition in the market?

Our differentiation comes from solving a problem our competitors can’t: customers don’t want to choose between best-of-breed functionality and integrated platforms anymore. Each of Conga’s solutions is a leader in its category, but what sets us apart is how we’ve unified them with a single data model and are embedding AI throughout.

Most vendors either offer deep functionality in one area or broad integration across many. We deliver both – combining market-leading capabilities with an open platform that adapts to complex enterprise needs. When customers face rapidly changing market conditions, they need solutions that are both powerful in their domain and flexible enough to evolve with their business. That combination of depth and adaptability is where we win.

Thank you for the great interview, readers who wish to learn more should visit Conga.