When Khozema Shipchandler became CEO of Twilio, the company was under pressure. Growth had slowed, investors wanted answers, and the path forward required difficult decisions.

On this episode of The BRIGHTON PARKast, Khozema joins host Mike Gregoire for an inside look at the decisions behind Twilio's turnaround—from navigating investor pressure and rebuilding confidence to balancing growth, profitability, and long-term priorities.

Drawing on more than two decades at GE and leadership roles spanning CFO, COO, and President of Twilio Communications before becoming CEO, Khozema shares why allocating talent is just as important as allocating capital, how transparency builds trust during uncertainty, and why operational execution ultimately drives financial performance.

The discussion also turns to the future of enterprise software, exploring how Twilio is putting AI to work within its own business, how AI could change the enterprise software landscape, and why reliability, security, and deep integration into customer operations continue to matter.

Hosted on Acast. See acast.com/privacy for more information.

Will AI agents replace the human enterprise seller? Nathan Rader and TJ Williams are weighing in on that debate, and not as outside observers. Early in their careers, both sold enterprise software at IBM, Oracle, and Google. Nathan later led go-to-market at a string of growth-stage startups including Parsable, HighRadius, and Karat, while TJ went on to lead sales organizations at Dropbox and Degreed. Today, they're each confronting AI's impact firsthand — Nathan as Chief Revenue Officer of Oro Labs, and TJ as an Operating Partner at Brighton Park Capital, leading the firm's go-to-market advisory practice.

In this episode, host Usman Rabbani sits down with Nathan and TJ to discuss how enterprise sales is evolving as AI agents take on more of the work traditionally done by sellers. Together, they trace the arc from Lotus Notes to AI-native GTM stacks, and what separates the shift in tooling from the shift in what actually wins deals. Their conversation spans where human judgment remains irreplaceable in the sales process, why efficiency gains from AI haven't yet translated into top-line growth, what happens to the talent pipeline as entry-level SDR and BDR roles disappear, and what will separate great go-to-market organizations once every competitor has access to the same tools.

TJ expands on several of these themes in his recent thought piece, How to Build a Sales Team That Wins in an AI World, which makes the case for investing in the SDR pipeline rather than gutting it, and for hiring sellers who treat AI tools as a core part of the job rather than a threat to it.

For anyone building, leading, or investing in a go-to-market organization, this episode offers a grounded, experience-driven view of where AI is genuinely changing enterprise sales, and where the fundamentals still hold true.

Hosted on Acast. See acast.com/privacy for more information.

What does it actually take to modernize healthcare? Dr. Mark Camel has spent decades confronting this question — not as a consultant or outsider, but as a surgeon and builder of one of the most operationally sophisticated independent physician groups in musculoskeletal healthcare.

In this episode, host Usman Rabbani sits down with Dr. Camel, co-founder of Orthopedic & Neurosurgery Specialists (ONS), to discuss the lessons learned scaling ONS from a seven-surgeon practice into a 175-physician, four-state platform. Together, they explore the operational decisions that transformed ONS into one of the most technology-forward provider groups, years before digitization and AI became mainstream healthcare priorities.

Their conversation spans the realities of building technology inside healthcare organizations, the hard-earned lessons behind buy-versus-build software decisions, why most healthcare technology struggles to achieve broad adoption, and where AI is already delivering measurable operational ROI today.

For anyone building, investing in, or evaluating healthcare technology, this episode offers an insider’s perspective on how meaningful change actually happens inside one of the world’s most complex and resistant industries.

Hosted on Acast. See acast.com/privacy for more information.