Confessions of a First-Time CRO with Catie Ivey of Walnut
Hard won lessons from the frontlines
Building foundations in a startup is challenging enough. Doing it as a first-time Chief Revenue Officer adds another layer of complexity. In my recent conversation with Catie Ivey, CRO at Walnut.io, we unpacked crucial lessons from her first year leading revenue that every aspiring or new CRO needs to hear.
The Hidden Foundation Problem
Most first-time revenue leaders understand they'll need to build process and structure. What's less obvious is how many things get built on shaky foundations in high-growth startups.
"One of the things that surprised me was the number of things that had been built on foundations that weren't really there yet," Catie shared. "We'd bought a bunch of tech we weren't using effectively, grown teams without really nailing what 'great' looks like, and had misalignment that I'd taken for granted at larger companies."
Catie has focused on 3 core foundations that new CROs must nail:
1. Operating Rhythms
Company operating cadence (town halls, planning cycles)
Information sharing frameworks
Cross-functional alignment
Documentation and playbooks
Team meeting structures
2. Go-to-Market Architecture
ICP and persona validation
Demand gen waterfall mapping
Positioning & messaging strategy
Sales motion definition (bottoms-up vs. top-down)
Use case mapping (Catie mentioned 14 core use cases they had to organize)
3. Customer Journey Design
Onboarding experience design
Success metrics definition
Product feedback loops
Support model scaling
The Speed vs. Decision Quality Balance
The most counterintuitive challenge Catie shared was around decision velocity. While speed is crucial in startups, many first-time CROs actually move too slowly in critical areas. "I took way too long to make some decisive decisions about foundational pieces," she reflected. "There were great people and strengths, so I did too much consensus building and it took too long to decide on the basics."
Catie's approach to fixing this:
Focus on 2-3 critical priorities vs. trying to solve everything
Be purposeful about what NOT to tackle
Create clear decision frameworks
Run focused offsites with specific outcomes
Leading Through Uncertainty
Perhaps the most profound insight was about embracing uncertainty as a leader. Catie shared: "It's okay not to have the answer. You want to be decisive where you can, but very, very honest or transparent when you don't have the answer."
This connects to what psychologists call the "authenticity paradox,” which is the counterintuitive fact that showing vulnerability and being open about your gaps often increases rather than decreases trust and credibility. By admitting what you don't know, you actually build more trust with your team and partners than pretending to have all the answers.
The Product Partnership
One of the most crucial relationships for a CRO to build is with the product organization. Catie shared several key insights:
1. Create Multiple Feedback Channels
Formal product gap tracking in Salesforce
Dedicated Slack channels for internal usage feedback
Regular cross-functional syncs
Real-time information sharing
2. Focus on Your Own Usage
"We weren't using our own product in the ways we were selling it," Catie noted.
Catie endeavoured to:
Document best practices
Build internal use case playbooks
Creat feedback loops from internal teams
Drive product adoption internally first
3. Build Trust Through Transparency
Be honest about product limitations
Know where you sit in the competitive landscape
Double down on your strengths
Create clear escalation paths
The Path Forward
The transition to CRO isn't just about adding scope - it's about fundamentally shifting how you think about and approach revenue leadership. As Catie shared, "You can't do everything and you won't be good at everything."
Success comes from being decisive on critical priorities while staying honest about what you don't know. Focus on building strong foundations, but don't let perfect be the enemy of good - sometimes you need to make calls with imperfect information to keep the business moving forward.