Kaili Linville’s Journey From Industry Novice to Managing Multi-Million Dollar Accounts

You’re new to the industry and you’re still learning your product. You lack the experience, the language, and the context. It’s just you, face-to-face with a seasoned industry expert. And you need them to buy.

How do you sell like an expert before you actually are one?

I’d ask Kaili Linville.

Kaili spends her days at Autodesk, speaking with general contractors at mid-market accounts. She’s closed deals worth upwards of $2M TCV. She’s set records for most business sold at BuildingConnected and continues to smash her annual quota.

She’s worked her way here from ground zero, mastering the art of selling while simultaneously ramping up her own industry and product knowledge.

So you may not be an industry expert just yet — but with Kaili’s advice, it won’t hold you back.

Confidence is Convincing

Fresh off an entry-level sales role at Yelp, Kaili found herself in the CEO’s office at BuildingConnected, a pre-construction SaaS start-up looking to scale their team.

The CEO himself was giving Kaili a demo of the product, showing her its functionalities and unique use cases in an effort to get her onboard.

“I had no idea what the hell he was talking about,” Kaili says, “I knew nothing about construction and it felt like I was listening to a different language.”

Was she cut out to sell this thing? Ultimately, all her doubts were overshadowed by a single fact.

“He was paying a lot better than what Yelp was paying.”

She signed the dotted line and it was sink or swim. The first thing she did was look for someone to buoy her with relevant industry knowledge she could use on Day 1. She sat down with her new manager before she even started.

“I knew this was going to be a huge uphill battle. I asked him what I could do to prepare.”

His resources gave her a head start. Along with the onboarding materials, Kaili familiarized herself with bid forms, project plans, and building permits — the building blocks of business for her new prospects.

She was absorbing new information left and right. But no amount of book knowledge prepared her for the first time she walked into a male-dominated room of C-Suite construction big wigs. Burly voices shouting words she had only heard in passing.

“Bid leveling!”

“RFI!”

“Surety bond!”

“Change order!”

It might as well have been Greek. But her quota took no heed of her linguistic dexterity (or lack thereof). 

The only thing to do was to put on confidence and sell.

“People feel confidence, your prospects feel confidence. Show that and you’re going to close more business, you’re going to earn more trust.”

But how can you sell confidently when you’re not confident? Kaili’s advice is to listen more than you speak. To support rather than lead. To take a consultative approach.

Kaili started asking non-specific, open-ended questions: How does your company handle XYZ? What’s working for you? What’s not working for you? She would listen closely, very closely, to exactly how they answered and pull out the bits and pieces to frame her next questions: How is X specifically impacting your business? What does “good” for X process look like for you?

Consultative sales became Kaili’s bread and butter, but to become the Diamond Club-winning seller that she is today, she still had a long way to go.

“I needed to get to a place where I not only sounded like I knew what I was talking about, but actually knew what I was talking about.”

Building Trust and Activating Accounts

In the early days of BuildingConnected, the company was operating off of a freemium model. 

“We were the new kids on the block,” Kaili says, “We weren’t reputable, people didn’t know our names.”

Which, in many ways, accelerated Kaili’s journey towards becoming an industry and product expert. She was encouraged to act more as an account or customer support manager, to focus on building relationships and getting folks bought into the company, rather than pushing for a hard sale.

She took the opportunity to learn the industry, hear their stories, and gather use cases, which also built a massive amount of trust between her and her clients.

“By understanding their issues, instead of pushing the product, I was able to find this really nice balance to get people to trust me.”

BuildingConnected grew. Kaili’s industry knowledge and experience grew with it. As the company rolled out solutions that needed to be sold, she was tasked with fully activating accounts.

And she had plenty of trust to leverage.

Everyone knew and loved Kaili, so asking for her client’s time was a simple request. She hopped on hour-long calls with them, not to do product demos, but to coach  them on how to use the product and how to find success with it.

“I did that over and over and over again.”

Kaili activated hundreds of accounts for BuildingConnected. She notched the most ARR in a month. Then in a quarter. Then for the year. Kaili averaged 127% to quota over her last nine quarters at BuildingConnected, and set the company record for most business sold across all teams. 

But even more important to Kaili, she built a community with both her customers and her team.

“Everyone believed in what we were doing. We saw the real problem that general contractors were facing in the industry and we knew that if we were to make this work, it was going to be something big.”

And they did.

In March 2019, BuildingConnected was acquired by the construction software giant, Autodesk.

Be the Gift That Keeps On Giving 

Kaili was an Autodesk employee now, a company with over 90 highly technical products, spanning dozens of use cases from architecture, engineering, and construction to product design and manufacturing.

It was back to square one.

“It took me 4 years to learn how to talk to our audience and be confident. And all of the sudden, I’m selling things I had never even heard of before coming to Autodesk,” Kaili says, “There was a time where I thought, ‘I don’t know if I can do this again’.”

But one phrase resurfaced repeatedly, tracing back to Kaili’s time at Yelp: trust the process. And for her, that process started and ended with community, her ultimate foothold to excellence.

She went to the PlanGrid reps (one of Autodesk’s core pre-construction tools) and pitched a mutually beneficial relationship to them: “I’ll teach you BuildingConnected’s software, front to back, if you teach me what you know in return.”

She sold them.

They demoed the product for each other. Listened to each other’s calls. Sat in on each other’s meetings. Created specific Slack channels for every project they worked on. They were a team, and Kaili became better for it.

When it was time to re-enter that room of C-suite execs, she had new strategies to handle the nerves. If she came to a dead end and her product knowledge was shot, she was completely transparent.

“If I’m doing a discovery and someone brings up a term I don’t know, I simply ask them to explain it,” Kaili says, “People love honesty.”

In one fell swoop, she uncovers important information, establishes trust, and gives the customer a little ego boost. It positions them as the ultimate expert and sends them the message that you’re there as a trusted consultant.

To her clients, Kaili is the gift that keeps on giving.

As relationships progress towards a deal closing, Kaili allows her prospects to explore the technology at low-risk with a guided, highly-structured pilot contract.

“The official signature on a contract, even if it’s for $0, tells you that they are serious about going through the process with you,” she says, “My guided pilots tend to close much, much more than anything else.”

I believe her. Kaili has a track record as master closer.

While learning the product, she scored the biggest win of career. Shortly after, she hit 120% of her quota and earned a Diamond-Club trip to Hawaii.

She emphasizes one thing about her success: she doesn’t sell alone.

She has a whole team behind her, from customer success managers and BDR technical specialists to supportive managers and team leaders, people she’s invested in and who invest in her in return.

“I know that I’ve helped so many people, and now, later down the line if I need something or have a favor to ask, I can ask for that in return.”

And she certainly will. This year, she’s selling design tools — yet another industry for Kaili to learn from the ground up.

“I’ve done this twice now,” she smiles with an air of confidence, “I could do it again.”

Nominate a Seller

Do you know a “World’s Best Seller”? Send ‘em my way! Email karli.stone[at]apollo.io with your nomination.

We’ll see you next time for the next issue of World’s Best Sellers, only from your friends at Apollo.io.