How HubSpot Trains and Retains the Best Sellers in SaaS

Few things are more crucial to a sales team’s success than having the right enablement strategy. You're searching for sales enablement tools because you know that without proper systems, your reps struggle, ramp times drag on, and top performers leave for companies that invest in their success.

The quicker new hires get to full quota, the faster they'll stop gobbling up time and money that could be better spent on building pipelines and closing deals. And that's exactly what the best sales organizations understand — enablement isn't just about tools, it's about creating a complete system that transforms average reps into top performers.

In Part 2 of Inside Sales at HubSpot, we again draw on the wisdom and experience Elanna Lalezari, Tara DiCristo-Schmitt, Katie Walsh, and Kelsey McKay—award-winning sellers and sales leaders who've helped HubSpot become the #1 fastest-growing product in SaaS.

Here's what they have to say on HubSpot's approach to sales enablement, the tools and strategies that work, how the best leaders run their teams, and the metrics that matter. If you haven't yet, read Inside Sales at HubSpot Pt. 1 here.

HubSpot's approach to sales enablement

So, what's sales enablement, really? For a top-tier sales org like HubSpot, it's not just a buzzword or a piece of software. It's the entire strategy of giving sellers everything they need to close deals faster and more effectively. Think of it as the support system that turns good reps into great ones.

This means providing ongoing training, killer content that actually helps in conversations, and coaching that's built for the real world. It's about removing friction from the sales process so your team can focus on what they do best: selling. HubSpot's success shows that when you invest in enabling your sellers, the revenue follows.

The core pillars of HubSpot's sales enablement strategy

HubSpot doesn't just wing it. Their sales enablement is built on a few core pillars that create a repeatable system for success. It's less about a secret sauce and more about a smart, structured approach.

First, there's comprehensive onboarding and training that goes beyond a one-week bootcamp. It's a continuous process. Second, they foster inspiring leadership and coaching, where managers are true partners in a rep's success. Finally, it all sits on a foundation of a strong culture and retention focus, creating an environment where top performers actually want to stay and grow. These pillars work together to build a sales engine that's hard to beat.

HubSpot's sales enablement tools and technology stack

While strategy is key, the right tools make it all happen. HubSpot leverages a smart mix of technology to support its sellers. This isn't about having dozens of disconnected apps; it's about an integrated system that makes life easier.

A big piece of this is their own internal knowledge base and resources, like the famous HubSpot Academy, which gives reps endless opportunities to self-educate. They also use internal communication tools to keep everyone connected and learning from the marketing team and sales engineers. The goal of their tech stack isn't just to track things—it's to actively help reps sell better by providing the right information at the right time.

Ramping up as a HubSpot seller

HubSpot's sales leaders work hard at reducing ramp time, because they know that long ramp times drag on both productivity and profits.

"The ramp timetable has changed over the years," says Walsh, HubSpot's Director of Sales. "But there is a period of time where you get to ramp and have a [lower] quota as you're kind of working through and developing your skills."

As that quota increases over time, it can become intimidating.

That's why HubSpot provides ongoing training throughout the process, so its reps never ramp alone.

"Right off the bat, I felt like I was wearing that HubSpot jersey and that we were better than all of our competitors…when you really believe that, it's easy to sell because you're selling something to people that's better than what they're already using," says Walsh, who achieved HubSpot's elite Founder's Club status after only 12 months on the job.

That's a million bucks in sales.

Human know-how plays a big role, too.

"We're constantly learning from our marketing team," says McKay, a mid-market AE. "We do lots of training with our sales engineers and the opportunities to self-educate are plentiful with our own HubSpot Academy knowledge base."

Even with access to the best resources, selling can be a rough sport—at HubSpot or anywhere else.

Which is a big reason why the RAM (Ramp Acceleration Managers) program was created—to give remote newbies the support and business acumen they need to become the best in the biz.

Instead of going straight to market enablement onboarding, Elanna Lalezari, Director of Corporate Sales and head of HubSpot's RAM training program says, they now get a hands-on (virtually speaking) manager to guide them through the first six months.

It's the online equivalent of having an in-person coach.

"Tara [VP of SMB Sales] brought that to HubSpot, and then we grew it," Lalezari says. "And it's been really exciting. We were trying to find a way to make sure our new hires have the best shot and can learn everything as fast as possible."

First, because ramping a distributed remote workforce is infeasible.

And also because most reps, especially inexperienced ones, fare poorly on their own without a trusted advisor to check on their progress and help them avoid—or pull out of—inevitable slumps.

HubSpot managers lead to inspire

Great managers, like the one Lalezari mentioned, are among HubSpot's most valuable resources.

"Masterful leaders bring the energy," says DiCristo-Schmitt. "They're the spark that ignites self-belief and action in people."

"The difference between an exceptional leader and a mediocre one", she adds, "is [the ability] to connect with people at the highest levels, and then connect them to the company's overall vision and decision-making [process]."

"The difference between an exceptional leader and a mediocre one is the ability to connect with people, at the highest level, to the company's overall vision."

— Tara DiCristo-Schmitt, VP of SMB Sales at HubSpot

In doing so, Lalezari tries to "simplify everything and make it really clear." One example is a Monday email she sends to her managers. It includes both status updates and reminders for the week.

"A successful sales org is remembering that we're human," she says, "Sometimes we assume that people are going to be able to connect the dots, but there's no reason we can't just give them the map so they don't have to do that."

Great leaders, she says, bring "clarity and simplicity to complexity" to any project, process, or initiative.

"First and foremost, we're people leaders," Katie Walsh says. "I'm a people leader. I have a responsibility to the company, but I also have a responsibility to care about all the people in my organization, as human beings, so I can maximize the output I'm getting from them to ultimately hit that sales target."

It's a transactional take, but here's the thing: Sales is transactional.

Caring and selling aren't mutually exclusive. In fact, they complement each other. People who feel valued and supported are far more empowered, and emboldened, to succeed.

"Companies that don't have a leadership team that cares about the people who are doing the dirty work, so to speak, won't be as successful," Walsh says. "I'd run through walls for [my co-workers] because I think they're great humans and really amazing business leaders."

McKay echoes the same sentiments, "The leadership team seeks to understand things from my perspective and has been a resource to help me upskill in different areas. And they lead by example. Some of my best sales managers at HubSpot sold the product."

Retaining stellar sellers

This challenge isn't unique to sales. Plenty of companies, particularly in tech, regularly lose their best and brightest to greener pastures.

Which isn't surprising; who wouldn't pass up the opportunity to make more cash?

Among sales reps, the answer is very few. That's part of why the average turnover rate in sales is 35 percent when it should be around 10.

But it's in a company's best interest to keep their top performers from defecting. And it's not only a matter of money.

HubSpot's approach boils down to this: creating an environment that reps don't want to leave. And, of course, making sure they're well compensated.

That first one, though, is central. Toxic cultures, lack of growth potential, weak leadership, and impossible-to-hit sales targets are the main reasons reps jump ship. If they're reps who consistently obliterate quota, that's a huge blow to both the team and the company. Financially, of course, but it's also bad for morale.

It seems appropriate here to extract insight from a HubSpot blog post on the subject.

Retaining reps, it explains, requires a detailed plan that sets reasonable expectations, reevaluates employee benefits, offers more (or better) professional development opportunities, leverages the best time-saving tech tools, creates a flexible work environment, and focuses on culture.

Make sure to track your progress on all of these fronts.

For DiCristo-Schmitt, retention is all about communication, recognition, connection — including bringing her team together in person whenever possible — and staying out of the way.

"They crave the recognition. They crave the learning. They crave you seeing them. And often, managers have less tenure than some of their reps, so I'm hands-off. I'm gonna let them do their thing. I don't wanna mess anything up."

During her HubSpot career, McKay says, "I've had great support from my leadership team in pursuing a path that leads me to management. And it's a lot easier to sell a product you truly believe in.

"So it's like, Why leave?"

How HubSpot measures sales enablement success

If you can't measure it, you can't improve it. HubSpot is obsessive about tracking the impact of its enablement efforts. They don't just hope it's working; they look at the data.

Key metrics include time to ramp (how quickly new hires become productive), quota attainment rate (what percentage of the team is hitting their number), and seller retention (are top performers sticking around?). By tracking these KPIs, they can see what's working, what's not, and make smart decisions to keep improving their sales engine. It's this data-driven approach that separates them from the pack.

Building your own sales enablement program like HubSpot

You don't have to be a SaaS giant to build a world-class sales enablement program. The lesson from HubSpot is to focus on the fundamentals: a clear strategy, supportive leadership, and the right tools to make it all work seamlessly. It's about creating a system where sellers feel empowered, not overwhelmed.

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Frequently asked questions about sales enablement strategies

What are the three pillars of effective sales enablement?

While every company is different, most successful enablement programs focus on three areas: 1) People (hiring, training, and coaching), 2) Process (a clear sales methodology and workflow), and 3) Platform (the right technology to support sellers). Getting these three right creates a powerful foundation for growth.

What KPIs should you track for sales enablement success?

The most important KPIs tie directly to sales performance. Key metrics to watch are sales cycle length, win rates, average deal size, time to ramp for new hires, and overall quota attainment. These numbers tell you if your enablement efforts are actually moving the needle on revenue.

How long should sales ramp periods typically last?

There's no magic number, as it depends on the complexity of your product and sales process. However, a common benchmark for B2B SaaS is anywhere from three to six months. The goal of a great enablement program is to shorten this period as much as possible without sacrificing quality.