Inside Sales at HubSpot: A Day in the Life

How we sell is why we win.

The refrain is a steady drumbeat from every seller at HubSpot. The driving force behind a generational product and a $20B market cap.

How they sell is why they win.

It’s something we heard from every salesperson we talked to at HubSpot, and made us wonder… 

How do they sell?

The Apollo team sat down with a VP, two Sales Directors, and a President’s Club-winning seller to find out, uncovering what about HubSpot’s team has cemented them as the leader in marketing automation for over a decade.

Join us as we go inside sales at one of the world’s best companies.

The Customer is Human

If you were lucky enough to buy HubSpot stock on the day of their IPO, a $1,000 investment in 2014 would yield you $15,000 today.

HubSpot has become synonymous with marketing automation, establishing itself as the business growth software over their decade of dominance.

In 2023, they were named G2’s #1 Global Software Company and #1 Best Marketing Product. They are also perennial honorees of Fortune’s Top 100 Best Companies to Work For.

HubSpot is great. And they’ve helped 177,000+ customers achieve greatness, too, because their sales team gets one thing right above all: 

The customer is human.

“We don’t make any mistakes about that,” says Tara DiCristo-Schmitt, HubSpot’s VP of SMB Sales, “It’s who we are, it’s what we believe, and we’ve cascaded that vision through the org.”

Direct sales at HubSpot is divided into three segments: SMB, Mid-Market, and Corporate. Each segment is led by one VP who oversees 3-5 directors. Every director manages up to seven SDR managers who then manage 6-9 reps each.

But no matter the role, every person in this massive sales org understands what many sales folks tend to forget — no one wants to be sold something they don’t need, no one wants to be pitched to, and no one wants to feel like a walking commission check.

Instead, HubSpot takes the consultative approach, learning where folks want to go and helping them get there as trusted partners.

HubSpot’s Closed-Won Playbook

Rome wasn’t built in a day — and neither was HubSpot.

Their dominance in the marketing automation space was built brick-by-brick, conversion after conversion.

Here’s how the HubSpot team gets a closed-won deal through the pipe:

The Pursuit of the Daily Deal

Some days it takes twice as many calls, others just a few emails, but the goal at HubSpot remains the same: secure one deal every day.

“It’s my job to create the opportunities that lead to that ‘deal a day’, and it’s something that I 100% hold myself accountable to,” says Kelsey MacKay, a stand-out HubSpot AE.

Every evening, Kelsey pulls together the target accounts she wants to hit the next day. Her lists are always based on some common factor, whether it’s a specific industry, recently funded companies, or recently lost opportunities.

“I know what those different buckets look like, what they require, and I try to switch out who I am targeting to give myself fresh prospecting ideas to focus on.”

Prospecting at HubSpot is diversified and caters to each rep’s strengths. Salespeople are expected to own and actively work around 400 accounts, but they aren’t handed a random list of leads — they get to choose who those leads are. HubSpot reps are encouraged to pull from a communal pool of leads, for both inbound and outbound opportunities.

“Reps have the ability to build a book that is specific to them, which we’ve found to be really impactful,” Elanna says.

From there, reps follow flow charts for engagement based on deal type and company size. 

For large, enterprise-sized accounts, sellers follow a heavily mapped-out selling motion. They’re hands-on. They get decision-makers looped in early. And they run very structured evaluations. For smaller, “transactional” deals, there’s more room for flexibility and experimentation.

But for every account, regardless of size, HubSpot reps are trained to inspire excitement and lead with curiosity.

“The first thing we do is get the customer excited about HubSpot,” Tara says, smiling ear-to-ear. “From there it’s easy to sell — because they’ve already sold themselves.”

Kelsey and her peers engage their customers with personalized Looms, interesting videos, relevant customer stories, anything that grabs the customers’ attention and leaves them wanting more.

Then, they dive into discovery, leading not with product knowledge but with genuine curiosity.

“I try to show I’ve done a bit of my own research by giving my perceived background on what they do,” says Kelsey, “Then I open it up to their 50,000-foot view. I ask ‘Why are we here today? What made you interested enough to schedule a time to connect with me?’.”

They peel back the onion, uncovering the customer’s TAM, how they go to market, what their sales-marketing hand-offs look like because, more likely than not, HubSpot has the solution.

They have five core products: Marketing Hub, Sales Hub, Customer Service, CMS, and Operations Hubs, each with dozens of tools to help teams do their work more efficiently and in one place.

“We solve a multi-faceted number of issues and we are made to support all different types of teams,” says Kelsey, “Once I uncover the impacts of a business’ issues and across which teams, that’s where HubSpot comes in.”

The HubSpot sales team runs all of its processes through its own product, and one of their favorite strategies is to pull up their personal instances for customers.

“I leverage HubSpot on a daily basis for my own prospecting, forecasting, and reporting. I love to show prospects how I’m using it on the day-to-day,” says Kelsey, “It’s really powerful — especially when you can show it to them on the fly.”

Consultative conversations and clear product walkthroughs sound simple boiled down — but behind the curtain, leadership is coaching toward perfect execution of each and every sales strategy.

Build Roadmaps and Eliminate Guesswork

Director of Corporate Sales Elanna Lalezari prides herself in being “obnoxiously organized”.

Take her deal reviews for example.

Every week, color-coded folder in hand, Elanna sits down with her managers and breaks down their ongoing deals: Where has this deal been? What’s complete? What’s left?

Taking detailed notes in the CRM, she moves into coaching, asking questions that encourage them to verbalize their strategy: What direction are you taking this deal? What risks do you foresee? What are your next steps?

Together, they build a roadmap towards closed-won.

“There’s no need to keep everyone guessing,” Elanna says, “I want to give a map to my people and watch them go even further with it.”

HubSpot leaders are intimately involved with the day-to-day operations of the sales org.

Even Tara, the VP of SMB sales, doesn’t shy away from rolling up her sleeves and diving into the trenches. She goes on listening tours, team-by-team, director-by-director, listening to the language of HubSpot sales, how reps are selling, and how directors and managers are coaching.

“I want to make sure that the training is actually reaching the reps and find out if there are any holes where we don’t have the adoption that we need,” she says.

And if one team isn’t up-to-speed? They lean into the data (with HubSpot’s data they can spin up a report on nearly anything), fix what needs to be fixed, and continue to progress.

It’s true.

Recently, the leadership team noticed an emerging trend — over-performing reps consistently closed large deals while underperforming reps struggled to close any large deals at all.

“So then it was figuring out, how do we get more of these larger deals into our pipeline and support our reps to close them?” Katie says.

The leadership team looked at specific attributes of their biggest deals and hunted through their massive CRM for similar companies. But it was more than a lead problem — it was also a skills problem. They launched a whole new training initiative, providing more product and demo training, developing business acumen across teams, and coaching their managers on how to coach.

It’s this kind of responsive action that sets the tone for the whole organization, inspiring sellers to show up to close, each and every day.

“Leadership has always sought to understand my perspective and has been there as a resource to help me scale up in so many different areas,” says Kelsey.

More to Come from Inside Sales at HubSpot

There’s just too much HubSpot goodness for one article.

Stay tuned for the next issue of Inside Sales where we’ll be diving deeper into how HubSpot ramps up and trains their world-class talent, as well as their secrets to building a globally-recognized sales culture.