Revenue Stuck between $5M-$10M? Here's What Needs to Shift to Scale Past $20M

Most companies stuck between $5M and $20M ARR aren't failing because of one broken thing. They're failing because the team, the pricing, the messaging, and the offer all quietly stopped matching the company they've become — and nobody stepped back long enough to notice.This episode continues the Messy Middle series, expanding on the $5M-to-$20M wall conversation from a few weeks back. Today's focus: what actually needs to shift once you outgrow the playbook that got you here.Jenna Reback, messaging strategist and founder of Blueberry Creative Studios, opens with the three questions every stalled company fails to answer clearly: why this, why you, why now. She breaks down the difference between messaging that stopped landing because the market moved, and messaging that stopped landing because the company quietly moved up-market without updating how it talks about itself. Her closing point: don't outsource your differentiation to AI. She proves it with a story about her own name that no model could have generated.Victoria Chemko, executive coach and 24-year operator, brings her four-part framework — signal, state, structure, support — for why leadership teams thrash instead of pivot cleanly during a stall. Her case: the shift has to start with the leader before it can show up anywhere else in the business. Get honest about burnout and self-awareness first, or every other fix is built on a shaky floor.Shimon Perry, customer success leader, makes the case for interviewing your current team as if they were external candidates for the company you're becoming — not out of disloyalty, but because keeping someone in a seat they've outgrown does nobody any favors. He also shares a controversial move from a company he worked with: requiring customer success to sign off on deals before close, and what that structural friction actually prevented.Summer threads it together with the sales lens: why custom pricing kills a repeatable engine, why every department needs a shared, quantified goal instead of a number pulled from thin air, and why "we don't have a retention problem — yet" is the sentence that should worry every founder in this revenue range.Lightning round closes with one thing each guest says to review this week if growth feels stuck — from messaging to pricing to your own bandwidth.Jenna Reback — Founder, Blueberry Creative Studios. Messaging and positioning for scaling B2B companies. [LinkedIn]Victoria Chemko — Executive Coach, 24-year operator. Works with leadership teams navigating growth-stage change. [LinkedIn]Shimon Perry — Customer Success Leader. Builds CS functions that operate as revenue teams, not just relationship teams. [LinkedIn]Summer Poletti is the Founder and CRO of Rise of Us, a revenue architecture consultancy for growth-stage B2B companies. When revenue is flat and the old playbook isn't working, she diagnoses where the real gap is — GTM strategy, sales hiring, partner-led growth, content infrastructure, or the revenue system holding it all together — and builds what fixes it. It's never just sales. theriseofus.comRevenue Remix is on Apple Podcasts, Spotify, YouTube, Amazon Music, and iHeart.