Lori has spent decades leading high-growth technology and services companies, building the sales, operations, and delivery organizations behind them. Most recently, she was CEO of Caylent, a Premier AWS partner, where she grew the business more than 400% and led it to become the largest AWS-focused systems integrator globally. Before Caylent, she was President of Services at Traction on Demand, guiding the business through its acquisition by Salesforce. Earlier, she held executive roles at Appirio and Gigster, both pioneers in cloud services and crowdsourced delivery.
Why are you passionate about helping leaders of IT services firms?
This is one of the most exciting times to be in IT services. AI is changing everything about how services are sold and delivered: the technology, the financial model, the delivery strategy. And I love helping IT leaders rethink their businesses to adapt and win.
You have successfully led multiple cloud services firms through different stages of growth. Which stage do you think is the hardest and why?
Every stage has its challenges, but as a leader, the hardest is that $25-50M range. You’re balancing the need to lead a large, growing organization strategically, against the day-to-day demands of operating a business that has scaled, often without a complete, experienced leadership team in place or a fully built operational platform. It’s constant context-shifting, swinging from high-level strategy to in-the-trenches detail. And for newer leaders, it’s learning to get comfortable letting others own significant decisions. The good news: if you punch through it, you’re in rare air.
You’ve helped advise a number of firms on AI transformation. What are some of the first steps leaders need to think about when getting started?
Successfully implementing an AI operating system isn’t a contained strategic program, it’s invasive, touching every part of the business. I’d start at both ends of your operating stack and meet in the middle: understand the dynamics of your channels and offerings, look for leverage with AI tooling, and assess your organization’s readiness. Then iterate all three together, not in isolation. And balance skunkworks and experimentation against a centralized view of what you actually need to build. Otherwise the fragmentation will eat the efficiency leverage you’re counting on.
The traditional delivery ‘pyramid’ is undergoing significant changes. How should delivery leaders rethink team roles, profiles and structures in the AI era?
While I don’t believe the pyramid is completely collapsing, the org design and skillsets required are. Today’s org chart should account for both humans and agents and humans will need to be trained to partner with those agents.. As routine coding gets automated and delivery timelines collapse, you need consultants who are technically strong but can also operate up the stack, into business process design.
Most of the companies you’ve led grew quickly by leveraging channel partnerships. Can that same playbook still be used in today’s market? How does it change?
Channel relationships still matter, but for the next several years I think multiple partnerships will be more necessary as solutions become more “composed.” Single-partner systems integrators won’t deliver the value they used to, when one license got the customer the whole solution stack.
