Season 2 Kickoff: AI in Annual Planning, Career Shifts, and the New GTM Reality

TL;DR: The Revenue Insiders is back for Season 2! In this premiere episode, Kelly Lewis and Tiffany Jones unpack how AI is reshaping annual planning, career paths, and enablement—and why GTM leaders from frontline managers to executives are being forced to make tough trade-offs in 2025.

We’ve been hearing it everywhere: AI is no longer a side conversation—it’s the main event. In every board meeting, planning session, and revenue strategy discussion, the same questions keep surfacing:

• How should we invest in AI?

• What does that mean we stop spending on?

• Do we need this tool, or do we need another person?

Kelly and Tiffany open Season 2 with a candid conversation about the new reality of annual planning and the ripple effects hitting every level of the org. They dig into why productivity metrics are shifting, why ICP definitions matter more than ever, and how leaders are being asked to do “more with less”—not fewer people, but fewer accounts, fewer tools, and fewer distractions.

But planning is only one piece of the puzzle. This episode dives deep into several themes shaping today’s GTM landscape:

Why AI dominates annual planning cycles and why leaders must balance automation, enablement, and human performance. We explore the difference between AI solving for resume-worthy work versus the “busywork” that should never define someone’s career trajectory.

Managers are being asked impossible questions: Do you want the tool, or the headcount? Kelly and Tiffany discuss how first-time managers can navigate these high-stakes choices, and why executive teams must enable leaders to make these calls responsibly.

Multi-year deals are rare, retention is king, and post-sales strategy is finally in the spotlight. We unpack how customer success and renewals are being redefined—and how AI can take low-value tasks off their plates so they can focus on relationships.

Enablement is undergoing a renaissance. No more endless classroom training. From AI-driven role play to SMS-based microlearning, sellers are finally being treated like adult learners. Instructional designers are stepping into more strategic roles, shaping how teams learn, practice, and perform in a modern GTM environment.

Layoffs aren’t going away, but they’re changing form. We talk about the rise of performance-based layoffs—and why they expose leadership gaps in feedback and coaching. And we tackle a new workforce trend: quiet breaking. Unlike quiet quitting, professionals today are burning out in silence, staying in jobs longer but breaking under pressure. What does that mean for career growth and team health?

Kelly shares why she’s launched discipline-specific coaching for enablement pros—and why the market needs more specialized coaching to help GTM talent grow strategically in their careers.

From the Figma IPO to the Salesloft-Clari merger, Kelly and Tiffany discuss the rapid changes in revenue orchestration tools and how definitions are shifting as AI-native players enter the market.

The conversation doesn’t stop here. Kelly and Tiffany reveal what’s ahead in Season 2:

• Deep dives into GTM engineering

• How MEDDICC is evolving in the AI era

• Guests who are redefining executive branding on LinkedIn

• Honest conversations about work-life balance as parents and leaders

• Fresh perspectives from the frontlines of enablement, sales, rev ops, and marketing

Why Listen?

If you’re a GTM professional—from early-career sellers to experienced enablement leaders—you’ll walk away from this episode with:

• A clearer lens on how AI is changing planning and budgets

• Ideas for how to protect and elevate your own career in a shifting job market

• Insights into how leading organizations are rethinking post-sales and enablement

• A preview of the conversations that will dominate GTM in the year ahead