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Stay looped in about sales tips, tech, and enablement that help sellers convert more and become top performers.
On this week’s episode of the Pod podcast, Patrick sits down with Jon Rydberg—a four-time VP of Sales, seasoned operator, and founder of Align Advisory Group—to unpack the complex transition from founder-led sales to a repeatable, scalable revenue machine. Jon brings more than 16 years of go-to-market experience to the conversation, offering candid insights on what it really takes to operationalize early traction into a growth engine that lasts.
They talk about everything from the importance of coaching and cultural fit to common missteps in hiring your first AEs. Jon also shares his thoughts on the evolving role of AI in sales, why founder energy doesn’t always translate into playbooks, and the tactical elements every GTM team needs to build real momentum.
Here are the key takeaways from their conversation.
Jon starts by addressing a common blindspot in early-stage startups: confusing product-market fit with founder-led momentum. Founders bring a unique magnetism and depth of knowledge to the table—they’ve lived and breathed the problem and can sell with a level of passion and context no new hire can match. But when a founder hires their first AE without capturing and transferring that tribal knowledge, reality hits hard.
Founding AEs often struggle not because they aren’t talented, but because the playbook doesn’t exist. The messaging isn’t codified. ICPs aren’t clearly defined. And there’s no shared understanding of what “good” looks like. The result? A painful drop in performance, high rep churn, and a six-month detour to rebuild what should have been in place from day one.
According to Jon, one of the best ways to de-risk this transition is to document just enough to be dangerous—think: new hire ramp guide, high-level GTM messaging, buyer personas, basic sales motion structure. Not a 100-page playbook, but a working doc that helps reps navigate and iterate without starting from zero.
One of the biggest traps early-stage founders fall into is over-indexing on big-name experience. Jon’s seen it time and time again: hire a rep from Salesforce or Oracle, only to watch them flame out in six months. It’s not that they’re bad reps—they’re just not wired for startup chaos.
Startups need builders, not closers. Sellers who can write their own cold emails, spin up a deck without marketing, and get scrappy with the first version of the process. In Jon’s words, you want a “MacGyver” rep—someone resourceful, self-starting, and hungry to figure it out with limited support.
That starts with aligning your hiring process to the stage you’re in. Ask questions that tease out grit, curiosity, and creative problem-solving. Be upfront about what life at your startup will look like, even if it means “selling against” the role. You’re better off turning off the wrong hire before they start than wasting six months on the wrong fit.
Jon emphasizes that structure doesn’t mean stifling your team’s energy. What it does mean is pointing that hustle in the same direction. One of his go-to frameworks is aligning the team around clear OKRs, backed by simple swim lanes and shared language.
Especially as you grow past a couple reps, this clarity becomes mission-critical. Everyone’s busy, but busy isn’t the same as productive. Without alignment, it’s easy to waste cycles chasing the wrong leads, building for the wrong personas, or cannibalizing each other’s deals.
He advises founders to avoid trying to “boil the ocean.” Focus. Double down on one or two verticals. Build a repeatable motion before expanding. The goal is to land referenceable customers in a specific segment—and then use those wins as social proof to expand further. When everyone—from sales to CS to product—is working toward the same goals with a shared understanding of your ICP and value props, scale becomes much more achievable.
If there’s one thing Jon stresses, it’s that culture can make or break your revenue engine. One of the biggest mistakes founders make is holding on to deals or continuing to “sell” long after hiring reps. Not only does this create confusion and resentment, it kills ownership and morale.
Comp plans should reflect clear swim lanes. Founders shouldn’t be competing with AEs for deals. And above all, managers need to prioritize coaching—not just pipeline reviews. Coaching, to Jon, is about removing blockers and creating space for growth. That means different types of conversations: tactical hit list calls, short pipeline check-ins, and personal one-on-ones that tie performance back to individual goals.
The best coaching environments are structured but flexible, with clear scorecards that track both metrics and growth areas—whether it’s product knowledge, discovery skills, or business acumen. And it’s not just top-down. Founders should be asking for feedback too: How can I help you better? What resources are missing?
In short: coaching isn’t a nice-to-have, it’s an accelerant.
In Jon’s view, the silent killer of early-stage GTM efforts is lack of focus. Saying yes to every deal that comes through the door feels good in the moment, but it creates a fragmented customer base, derails your roadmap, and burns out your CS team. The short-term revenue isn’t worth the long-term cost.
Staying focused means knowing what “good fit” actually looks like—and having the discipline to say no when something doesn’t align. Jon suggests doing a retro on your best customers and building a real, enforceable ICP. Sales, marketing, product, and CS should all be using that ICP to guide decisions.
Yes, it’s tempting to chase a logo, but the goal is to build a system that scales—not a one-off win that becomes a drain.
Startups live and die by their ability to transition from founder-led grit to process-led growth. As Jon puts it, “you can’t overcome a bad product, but you also can’t scale without process.” The magic happens when you hire for context, coach for growth, and build systems that empower your team to win without you in the room.
For founders navigating this tricky shift, the advice is simple: document what matters, hire like it matters, and coach like it’s your most important job—because it probably is.
You can follow Jon Rydberg on LinkedIn or learn more about his work at AlignRev.com.
And if you’re building a repeatable revenue engine, stay tuned for more conversations like this one on the Pod podcast.
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