*this week we are introducing a short format roundup to our publishing schedule. 3-5 minute read, no BS. - I’d love your feedback on this type of format, or the newsletter in general. Hit reply and let me know.

Training Industry released its 2026 Top Training Companies list for Sales Training & Enablement this week. The criteria that jumped out? "Innovation in AI-driven coaching, immersive solutions, and analytics-based learning." That's not a trend prediction. That's the qualifying bar.

The take: If your training programs don't have an AI component yet, you're not on the cutting edge — you're falling behind the minimum standard. The companies getting recognized aren't using AI as a buzzword in their pitch deck. They're baking it into how reps actually practice and get coached. There's a difference between "we have AI" and "AI changed our coaching outcomes." Most of you are still stuck on the first one.

The WSJ just reported the highest price ever paid for modern art at auction.

While equities, gold, bitcoin hover near highs, the art market is showing signs of early recovery after one of the longest downturns since the 1990s.

Here’s where it gets interesting→

Each investing environment is unique, but after the dot com crash, contemporary and post-war art grew ~24% a year for a decade, and after 2008, it grew ~11% annually for 12 years.*

Overall, the segment has outpaced the S&P by 15 percent with near-zero correlation from 1995 to 2025.

Now, Masterworks lets you invest in shares of artworks featuring legends like Banksy, Basquiat, and Picasso. Since 2019, investors have deployed $1.25 billion across 500+ artworks.

Masterworks has sold 25 works with net annualized returns like 14.6%, 17.6%, and 17.8%.

Shares can sell quickly, but my subscribers skip the waitlist:

Skip waitlist

_{*Per Masterworks data. Investing involves risk. Past performance not indicative of future returns. Important Reg A disclosures: masterworks.com/cd}

A piece in WebProNews this week pulled some brutal numbers: companies spend $1,459 per rep annually on training and enablement tools, but reps forget 70% of what they learn within a week (Gartner via Yahoo Finance). Meanwhile, managers burn 60-70% of their time on tactical call reviews instead of actual coaching (McKinsey). The AI conversation intelligence market is projected to hit $4.8 billion by 2027 — because someone finally noticed the gap.

The take: This isn't a technology problem. It's a reinforcement problem. You can throw every dollar in the budget at content and platforms, but if your frontline managers aren't reinforcing what was taught, it evaporates. Full stop. The tools exist to close this gap. The question is whether your org has the coaching infrastructure to make them matter.

MarketsandMarkets research shows companies using industry-tailored enablement platforms are 65% more likely to hit revenue targets. Meanwhile, the generic crowd? B2B orgs hit quota only 47% of the time. Oh, and 65% of marketing content still goes completely unused by sales.

The take: Stop buying the "platform that does everything." The enablement market is consolidating and specializing simultaneously — Showpad merged with Bigtincan, Highspot is flexing agentic AI, Seismic locked down ISO 42001 certification. The winners aren't the teams with the most tools. They're the ones whose tools actually match how their buyers buy. If you're still running a generic content library and wondering why reps ignore it, this is your sign.

Highspot launched agentic AI features in its Winter release, designed to proactively push next-best-actions to reps mid-deal. They also landed the highest position for "Ability to Execute" in the inaugural Gartner Magic Quadrant for Revenue Enablement Platforms. Gartner's quote: "The market is shifting from episodic, generic tools to connected, insight-driven solutions."

The take: Read that Gartner line again. "Episodic" and "generic" — that's the old playbook. If your enablement program still operates in bursts (annual SKO, quarterly refreshes, ad-hoc trainings), you're playing the game Gartner just said is dying. The shift is toward always-on, contextual enablement that meets reps in the moment. Your platform should be smarter than a search bar.

Your AI Adoption Is Performative — If you're nodding along to the Highspot and Training Industry news but your team is still using AI for "summarize this email," start here. There's a maturity ladder, and most teams are stuck on the first rung.

Your Enablement Investments Are Failing. Here's the Multiplier You're Missing — That 70%-forgotten-in-a-week stat hits different when you realize frontline managers are the missing link. This piece explains the multiplier effect nobody budgets for.

Until next time... ❤️, Enablement