When Jonas Master joined Rippling in late 2022, he inherited an enablement team of five supporting a sales org of roughly 350 to 400 people. Today, the sales org is 2,200 team members, and its enablement team is 36. The company is on pace to cross $1 billion in revenue in 2026.

That kind of growth doesn't happen by running everyone through the same playbook. Rippling sells 35 products across HR, IT, and finance to buyers ranging from three-day SMB deals to complex enterprise evaluations, with over 600 competitors on G2. A uniform approach to enablement would have collapsed under its own weight years ago.

What Jonas built instead is a highly specialized function—one in which almost every decision, from team structure to onboarding design to how AI is deployed, flows from a single organizing principle: the closer enablement is to the sales team it serves, the better it works.

➣ Dedicated enablement partners outperform horizontal programs. Once a segment hits 50+ reps, give it its own full-stack enablement partner who owns programs end-to-end.

➣ The best playbook content comes from your own reps. Find who's unusually good at a specific part of the sales cycle, codify what they're doing, and standardize it—rather than imposing a methodology from the top down.

➣ Build onboarding around deal milestones, not a content calendar. Identify the key moments in your sales cycle and build a certification for each.

➣ Managers need their own onboarding track. Not a handoff after eight weeks, but a week-by-week checklist tied directly to their new hire's milestones.

➣ Do a time-and-motion study before automating anything. Observe a rep's full day, quantify where the time actually goes, and you'll have a real number that makes leadership act.

➣ Measure behavior change, not training completion. Whether a rep is actually doing the thing on customer calls is the leading indicator. Business results are a lagging indicator.

Jonas has been doing this since 2014. He's seen every team structure, sat through every company-wide methodology rollout, and watched the pattern repeat itself enough times to have a sharp opinion about it.

The model he's seen fail most often is what he calls the "peanut butter approach"—pulling a thousand people into a crowded Zoom and telling everyone they're now a Sandler shop, or a Command of the Message shop, or whatever methodology just got the budget approved. 

You spend a million dollars. You have your episodic training sessions. And six months later, adoption is low, pull-through is lower, and the CRO is asking what enablement actually did.

The deeper failure, Jonas argues, is one of philosophy. Most enablement teams optimize for the training itself—five-star feedback scores, polished decks, high attendance—rather than the outcomes the training is supposed to drive.

At a company like Rippling, with its breadth of products and buyer types, the peanut butter model's failure would be obvious. But Jonas's argument is that it's wrong everywhere—the complexity just makes it harder to ignore.

The core of Rippling's model is straightforward on paper: every sales segment with more than 50 reps gets its own dedicated enablement business partner. That person owns full-stack programs end-to-end—onboarding, ongoing training, playbooks, certifications—and partners directly with the VP of Sales for that segment.

About 85% of all enablement work at Rippling happens at this level. The segment partner and sales leadership set the agenda together. They decide what's most important to move that particular business forward. No central committee determines priorities for segments they don't actually understand.

It's the same logic Rippling applies to its sales team—specialists for each product line, rather than expecting every AE to sell everything equally well.

When Rippling moved to that model roughly three years ago, Jonas describes it as "a massive unlock"—product lines that had been stalling suddenly had sellers who knew their domain cold.

Rippling doesn't pick a single sales methodology and install it company-wide. What they do instead is more interesting (and more replicable).

Jonas's team watches the field for variation. Who's opening calls in a way that's meaningfully different? Who's building rapport faster, setting the agenda better, multi-threading in deals where others aren't? 

Once they find a rep doing something unusually well, they codify it and bake it into the segment's playbook.

Jonas says you’re skillfully playing with a natural tension:

The end goal is sustained behavior change. For any given initiative, Rippling picks one or two outcomes to focus on for a defined period, then puts organizational muscle behind actually driving them: Gong call reviews, visibility dashboards, manager coaching, libraries of what good looks like. 

The training is just the starting gun.

Jonas is direct about why most teams don't operate this way: they're afraid to be on the hook. If you only measure sentiment coming out of a training, you can always claim the training was great—and nobody can prove the outcomes weren't someone else's problem. 

Measuring actual behavior change means your programs either worked or they didn't. 

His tool of choice for closing that loop is Gong. "If Gong got ripped away, I'm just retiring," he says. It's the only way to see, day by day, whether what you trained is actually showing up in customer conversations.

Rippling's onboarding program has 65(!) different tracks. A mid-market product AE selling IT cloud products gets a different path than an SMB IT AE selling the same products. Both get a different path than the equivalent role in Dublin. 

It becomes, as Jonas puts it, "4D Rubik's cube territory pretty quickly."

That's not complexity for its own sake. Rippling has been hiring 700 to 900 new revenue hires per year. Putting all of them through a generalist program and hoping managers fill the gaps is exactly the kind of thing that kills ramp time and pipeline at scale.

The framework that makes specialization tractable is milestone-based certification. For each role, Jonas's team identifies the five core moments in the deal that the seller will need to execute:

Each milestone gets its own certification. The entire onboarding curriculum is organized around preparing reps to pass each cert in sequence. Five checks, and they're on the phones.

The format matters too. The best training comes from having good reps model what good looks like—not a trainer explaining it abstractly—followed by a lot of repetitions. "If you can say it out loud four or five times, you're going to own it. But the first time it comes out of your mouth, it's never good."

The other piece Jonas is emphatic about: sales managers can't be passive onboarding spectators. The mistake he inherited at Rippling was managers expecting to receive a fully formed hire eight weeks later.

There's a concurrent manager learning path for every rep learning path, including a week-by-week checklist of exactly what the manager needs to do to support their new hire's milestones.

The same specialization logic now shapes how Rippling deploys AI in the sales workflow—and it started with a surprisingly old-school exercise.

Jonas had his enablement team shadow individual reps for full eight-hour days, logging exactly where the time went:

It gave Jonas’s team real data to justify their AI investment decisions.

That became a joint roadmap between Jonas's Enablement team and Rippling's RevOps team. 

Pre-call research is now 30 seconds. Post-call CRM updates pipe automatically from Gong into Salesforce. Deal briefs are auto-generated the moment a specialist AE is looped into an opportunity, pulling from Gong transcripts so they show up already oriented.

Jonas says CEO Parker Conrad's operating principle at Rippling is "go and see"—if something's broken, leaders go into the boiler room to find the actual problem before trying to fix it. 

Jonas’s entire enablement philosophy is a version of the same thing: get close enough to each sales segment to know what's actually wrong, then build something specific to that.

Watch Jonas & Alex’s full conversation on Grow & Tell.

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