The "Upmarket" Trap: What Actually Moves Enterprise Deals | Belkins Podcast Episode #22

Companies go upmarket, hit three slow months, and decide the strategy “doesn’t work.”

In this live episode, Yann (co-founder of Userled, former Salesforce enterprise seller) breaks down what enterprise deals actually look like up close: long stretches of silence that aren’t rejection, stakeholders who shape the decision without ever joining a call, and why “activity” can feel busy while the deal goes nowhere.

You’ll also hear the less glamorous side: what founder life feels like when momentum disappears, why some teams survive the hard quarters (and others don’t), and how hiring for energy changes everything.

Yann shares how Userled changed their ICP, survived two brutal quarters — then closed more in October–November than the rest of the year combined.

We enjoyed this conversation. Hope you will too.

🔑 WHAT WE COVER

The enterprise sales playbook Salesforce actually uses — deep discovery, the "holodeck" method, and why the best reps never feel like they're selling
Going upmarket in B2B: the real timeline — and 4 things you're probably not charging for (professional services alone adds 33% to deal value)
What ABM really is — the one question you must answer before spending a dollar on account-based marketing
The LinkedIn ABM tactic that drops ad costs from $10 to $2–3 per engagement — how to target 300 people inside a single account with messaging built around what's happening at that company right now
AI in ABM: where it cuts content creation time by 70% — and where it's still mostly hype
Hiring for energy, not just skills — why endurance and energy are harder to find than any technical skill, and the story that changed how Yann builds teams

"Startups are built on momentum. And sometimes there is none. So what do you rely on?" — Yann

About the Show

What does it really take to grow a B2B business today? We ask the people doing it. The Belkins Podcast dives deep into the strategies, decisions, and behind-the-scenes insights driving real growth at top B2B companies. Each episode features candid conversations with industry heavyweights—CROs, CMOs, founders, and seasoned operators—who've navigated market downturns, scaled teams, and mastered the realities of revenue growth. You'll hear hard truths, unfiltered insights, and actionable tactics directly from leaders who've actually done the work.

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About the Host

Michael Maximoff is the Co-Founder and Chief Growth Officer of Belkins, the #1 ranked B2B appointment-setting agency, recognized by Clutch, G2, and Inc.

Over the past decade, Michael has built Belkins into one of the most respected voices in B2B sales and marketing, helping over 1,000 companies across 50+ industries achieve predictable, scalable growth. Known for his straightforward style, Michael hosts the Belkins Podcast to speak directly with top growth leaders and uncover what truly moves the needle today.

🔗 Connect with Michael: https://uk.linkedin.com/in/michael-maximoff
🔗 Learn more about Belkins: https://belkins.io
🔗 Learn more about Userled: https://www.userled.io
🔗 Connect with Yann: https://www.linkedin.com/in/userled/