Thoroughpass’s Enterprise Sales Journey: From SMB to Fortune 500 Customers

Breaking into enterprise sales requires more than just a better product – it demands a fundamental shift in how companies approach everything from product development to brand positioning. In a recent Category Visionaries episode, Thoroughpass founder Austin Ogilvie revealed how firsthand experience with enterprise sales challenges shaped their path to success.

Understanding Enterprise Pain Points

Thoroughpass’s journey to enterprise success began with intimate knowledge of the challenges. At his previous startup, Austin experienced how enterprise security reviews could derail sales cycles: “If you’re a software company and you don’t take security and privacy controls seriously, not only is that a bad thing to do because it puts the company theoretically in jeopardy, but it also is really damaging to streamlined sales.”

This insight proved crucial when targeting larger clients like “Intuit, doximity, Stripe, PayPal, Johnson.” These enterprises faced a growing compliance challenge: “You take a bank like JPMorgan, who led our series B two, three years ago, they have 5000 software vendors. That’s an incredible amount of risk.”

Building the Right Team

Rather than rushing to market, Thoroughpass invested in assembling a team that understood enterprise requirements. This meant bringing in Eva, who brought crucial enterprise perspective from her role as managing director at Citigroup, overseeing cybersecurity governance and third-party vendor risk management.

As Austin explains, “Sam and I came to be commercially and intellectually interested in this space, but we don’t come from the solution side. Right? We care about these problems because we ourselves have these problems.” Eva’s enterprise experience complemented the founders’ startup perspective.

Evolving the Product Strategy

Success in enterprise sales required rethinking their entire approach to compliance automation. Austin notes, “If you’re passively collecting all of the digital exhaust that’s relevant in compliance audits, that’s great. But if you have to export all the data and go talk to a separate cottage industry audit firm, it really defeats the purpose of all of the automation in the first place.”

This understanding led them to build tools not just for companies collecting compliance data, but also for auditors to leverage that structured data effectively – a crucial requirement for enterprise adoption.

The Importance of Brand Evolution

As they moved upmarket, Thoroughpass realized their initial brand wouldn’t resonate with enterprise buyers. This led to a complete rebrand, with Austin sharing, “We did a wholesale rebrand, changed the name of the company, changed the name of all the email addresses and the website and the whole thing, all an entirely new messaging framework, totally different copy.”

The importance of storytelling became particularly crucial in enterprise sales. As Austin emphasizes, “The importance of storytelling, I think, is often overlooked, especially when you’re creating a new category or tying together categories that don’t seem to be connected in an obvious way.”

Looking Ahead

Thoroughpass continues to expand its enterprise vision, building “this single pane of glass where all software companies come to manage their IT audits across any of these standards.” This platform approach reflects a deep understanding of enterprise needs – as software companies increasingly evaluate each other’s security practices, the need for comprehensive compliance solutions grows.

Key Lessons for Founders

For B2B founders targeting enterprise customers:

1. Enterprise sales friction often signals broader market opportunities
2. Team composition should reflect both startup agility and enterprise expertise
3. Brand and messaging must evolve to resonate with enterprise buyers
4. Focus on solving complete problems rather than just automating pieces

The path to enterprise success requires more than just features – it demands a holistic understanding of how enterprises evaluate, purchase, and implement new technologies.