How Chord Commerce Built Their First 10 Enterprise Customers: A Playbook for Operator-Led Software
Enterprise software sales typically follows a well-worn playbook. But what happens when you approach it from an operator’s perspective? In a recent episode of Category Visionaries, Bryan Mahoney shared how Chord Commerce turned their operational experience into a unique sales advantage.
The Operator’s Edge
Before becoming a software company, Chord’s team had built and operated multiple DTC brands. This wasn’t just background – it became their primary sales advantage. As Bryan explains: “We really believe that we’re operators. We had created a system as operators for other operators… we’re so enthusiastic about getting into the hands of other operators because we felt their pain.”
Finding the Right Early Adopters
Instead of pursuing any customer with a budget, Chord focused on finding brands willing to build alongside them. Bryan emphasizes: “Find some brands that are willing to build with you… we did that and having some credible logos, having some feedback, having some real life customers on the platform made it an awful lot easier for us to bring it to market.”
The Value Exchange
Early customers received special consideration in exchange for their trust. As Bryan notes, they were “willing to exchange the fact that we’re riskier and we’re early stage in exchange for having some amount of influence over our product roadmap and build with them.”
Beyond Traditional Sales Tactics
Rather than focusing solely on closing deals, Chord prioritized understanding each potential customer’s business. Bryan advises: “Be curious, offer advice, even if it means not necessarily getting the sale. It’s a long game and having a really good reputation.”
This approach often led to unexpected returns: “Sometimes you’d be surprised when people do circle back and say, you know, it wasn’t the right time for me then, but I really appreciate that feedback you gave me then. And I’m curious to hear where you are with the product, because maybe it’s the right time for us now.”
Defining the Ideal Customer
Chord developed a clear vision of their ideal customer. As Bryan describes: “The ICP are brands that want to connect with their customers and deliver these differentiated experiences… brands that want to collect first party data, that want to have all of their first party data in one place.”
The Sales Evolution
As the company grew, their sales approach evolved. Bryan notes: “Been really fortunate to have some experienced SaaS sales leaders join us recently. And just watching them really lean into what they’re exceptional at has been awesome.”
Key Strategies for Operator-Led Sales
- Lead with Operational Credibility Your experience as an operator isn’t just background – it’s your primary sales asset. Use it to demonstrate deep understanding of customer challenges.
- Build Collaborative Early Relationships Instead of treating early customers as typical buyers, position them as development partners who can influence your product direction.
- Focus on Long-Term Reputation Prioritize building trust and providing value over closing quick deals. The relationships you build early will pay dividends later.
- Define Your ICP Through Aspirations Look for customers who share your vision for the future of the industry, not just those who need your current feature set.
Learning Enterprise Sales
For operators transitioning to software sales, Bryan acknowledges there’s a learning curve: “The harder part of the transition was figuring out how to do the SaaS side of things and how you sell enterprise software. There’s a real process and a real magic to this.”
The key is combining operational expertise with proven enterprise sales techniques. While operational experience provides credibility and insight, successful scaling requires building a professional sales organization.
For founders bringing operator-led software to market, Chord’s experience suggests that the key to early success isn’t trying to immediately master traditional enterprise sales tactics. Instead, it’s leveraging your operational experience to build deep, collaborative relationships with early customers who can help shape your product for broader market success.