Sunil Rao’s Mission to Help Teams Win More Deals

Beyond the Brief: A marketing conversation with Sunil Rao, Founder and CEO at Tribble.

Q: Sunil, it’s great to have you with us. Before we get into what you’re building, I’d love to understand the person behind the company. Yours is a genuinely fascinating journey. Can you take us through it?

Sunil: The one constant in my life has been change. I was born in India, grew up in Saudi Arabia, and eventually made my way to Canada for university. Growing up as a so-called ‘third culture kid’ shapes you in ways you don’t fully appreciate until later. You’re never fully from one place, which gives you an instinctively global perspective and a comfort with ambiguity. I carry that with me in everything I do.

My career started at SAP, where I initially worked as an engineer, then as a forward-deployed engineer at a customer site at Colgate, in fact. That experience was eye-opening. I got to see, up close, how software actually gets used in the real world versus how it was designed. From there, I moved into consulting, spending about five years implementing SAP solutions for CPG companies. Then, in 2015, I joined Salesforce as a solutions engineer, which was my first real move to the sales side of the house. I eventually built out and led the global CPG vertical team, growing it from one person to somewhere between twelve and eighteen, and later became product owner and GM for the CPG product, growing it to $100 million in revenue.

Q: That’s a tremendous arc, from engineer to GM of a $100M product. What made you leave that position to start something new?

Sunil: The seed was planted long before I left. At Salesforce, a 75,000-person company, there were essentially only two of us who could answer a CPG RFP end-to-end. We had built this incredibly sophisticated vertical, but the knowledge was stuck in the heads of a handful of people. That’s not a people problem; it’s a systems problem. It doesn’t scale.

I had been watching AI evolve closely since 2015, when I first came across work on recurrent neural nets. I even ran a personal experiment around 2021, using GPT-2 to generate LinkedIn content and having it compete head-to-head against our junior executive writing team. The AI consistently outperformed them. That started costing me sleep. Then ChatGPT launched in November 2022, and that was the nail in the coffin for me. I knew this technology would fundamentally restructure every software category I’d spent my career in. I had to go build something.

Q: So let’s talk about what you built. For readers who aren’t in enterprise sales, how would you describe Tribble and the problem it solves?

Sunil: At its simplest, Tribble helps companies win more deals – respond faster, and close bigger deals. The product operates on two sides. The first is Respond, which automates and streamlines the process of answering RFPs, bids, and proposals. If you’ve ever been in a complex sale, you know how much time gets consumed by those. The second side is Engage, which handles real-time call coaching, context management, pre-meeting briefing packets, and automatic CRM updates post-call.

What ties them together is what I’d call constraint-based real-time personalization, or, as Sunil and the Tribble team call it, their Closed Loop Intelligence, where knowledge from calls flows into proposals and outcomes feed back. The system can operate in different modes: full automation for speed, guided automation that applies specific workflows and governance constraints, or escalation mode when a human needs to be brought in. It connects with tools your team already uses, such as Highspot, Jira, Clari, Gong, HubSpot, and Salesforce, so it fits into existing workflows across the organization rather than replacing them.

Q: Enterprise sales cycles are famously long and messy, involving a lot of different people and touchpoints. How does Tribble navigate that complexity?

Sunil: That’s exactly the problem we’re designed for. A typical enterprise deal involves 17 or more calls across multiple teams, discovery, technical evaluation, procurement, legal, the works. Most tools today focus only on a slice of that journey. Tribble captures context across the entire lifecycle: discovery calls feed into the RFP response, vendor Q&A sessions inform proposal creation, and all of that gets fed into what we call the ‘brain,’ which can then surface the right information at the right moment.

Post-deal analysis is equally powerful. We can identify patterns, for example, that answering ‘no’ to 20% of requirements in an RFP consistently correlates with losses. That tells you whether you have a product gap or a positioning problem, and each requires a very different response. The upcoming Engage launch is specifically about unlocking the full value of how the Respond and Engage functions play off each other across the entire journey.

Q: There’s been a lot of skepticism in enterprise software about AI that promises to automate sales. How do you build trust with experienced sales professionals who may feel threatened by that?

Sunil: It’s a real and legitimate concern, and we learned early on not to dismiss it. When we started working with customers, we assumed people would embrace automation immediately. What we found instead was that some users, particularly those who had built their professional identity around being the expert, the ‘proposal wrangler’, needed us to accommodate their existing workflows, not replace them.

Trust has two dimensions for us. The non-system version is simply showing up as a genuine partner capable of solving a real problem. The system version is about consistency, giving good guidance, taking feedback, visibly improving, and ultimately driving results. Our product roadmap is built around five themes: trust, automation, intelligence, governance, and compliance. Those aren’t features for their own sake; they’re the foundation of a system people can actually rely on. The goal is to bring people along for the journey, not force them to abandon the way they work.

Q: You’ve clearly got strong customer momentum, are recognized as a top performer on G2 in the RFP software category, and have been invited to three customer sales kickoffs in a single week. What does that kind of advocacy tell you?

Sunil: It tells me we’re on the right track, but it also raises the bar. One of my favorite signals right now, and a really great moment we had last week, is when a new hire at a customer company approaches one of our team members at a kickoff and says, ‘Are you the Tribble rep? I love Tribble.’ That person learned about Tribble during their onboarding. That’s the kind of organic advocacy that you can’t manufacture.

We also use the product ourselves intensively. Every call, every engagement gets recorded and flows into our own brain. We run internal competitions for the highest Tribble usage; our top sales rep recently overtook me for the number-one spot, which I love. We automatically generate a weekly CEO letter from all business data and use it to run our forecast calls. If you’re not willing to be customer zero for your own product, that’s a red flag.

Q: Looking ahead to the rest of 2026, where is your focus, and how do you define success?

Sunil: The big bet this year is the launch of Engage, which connects everything we’ve built and extends Tribble’s value across the full sales cycle rather than just the proposal stage. We’re also going deeper on verticals; logistics and healthcare are top priorities, both because they have sophisticated bid processes and because compliance and governance matter enormously in those sectors. That plays to our strengths.

As for success, I define it as extremely happy customers. If we double or triple our customer base while keeping satisfaction at today’s level, revenue and growth will follow. That sounds simple, but it’s actually a very demanding standard. It means every product decision, every support interaction, every onboarding experience has to earn that outcome. I’d rather have a smaller number of customers who are genuinely transformed by the product than a large number who are merely satisfied.

Q: Finally, tell us something about you that might surprise people who only know you as a founder.

Sunil: I think the thing that most shaped how I approach everything, Tribble included, is growing up without permanent status anywhere. In Saudi Arabia, you’re always a guest. There’s no path to citizenship. That instills a certain kind of resourcefulness and a deep appreciation for building things that genuinely help people. I’ve always been drawn to the knowledge bottleneck problem, in part because I understand what it feels like to be the person on the outside of a system, working twice as hard to prove you belong.

That perspective is baked into how I think about Tribble. The goal isn’t to replace the experts. It’s to make sure that expertise doesn’t stay locked up in a few people’s heads, that it scales, that it serves the whole team, and ultimately that it helps more customers win.

Q: For those who’d like to connect or learn more, where can they find you?

Sunil: LinkedIn is the best place to reach me (Sunil Rao), and you can explore what we’re building at tribble.ai. If you’re in enterprise sales or revenue operations and you’re wrestling with the knowledge scalability problem, I’d love to talk.