From PLS pioneers and OSS innovators to cutting-edge enterprises, Go-to-market mavericks is where we talk to GTM leaders about the strategies and tactics they use to drive results.
We recently talked to James Kaikis, Chief Revenue and Experience Officer at TestBox, about winning land and expand with intentionality and a whole lot more.
Here are three of the top takeaways from that conversation (check out the full recording above).
1. Acquisition starts at home
It’s no secret: Selling net-new logos is harder than ever right now.
Budgets are tighter. Buying committees are larger. And buyers can do their own homework.
James’ solution? Focus on maximizing revenue from your existing customer base via expansion.
“What we have done at TestBox is take a very deliberate approach to what is our ICP,” James said. “What companies can we deliver the most value in, and what companies would be great to bring into our portfolio where we can work on a multi-year strategy and a multi-tenant expansion?”
Intuit—TestBox’s largest customer—is the perfect example.
The TestBox team didn’t try to land the biggest possible deal on day one. It validated that there were big growth opportunities within Inuit, closed the first deal, and started working on an expansion immediately after.
“We actually closed a pretty large land deal, and we had an expansion that was double the size of our land within six weeks,” James said.
TestBox won six expansions in the first year of the contract and is working on another right now.
Reps are naturally inclined to go for the gold on the first try, but if roping in every part of the business significantly extends the sales cycle, James believes it’s smarter to start smaller, deliver value fast, and begin the cycle again.
Having full-lifecycle AEs certainly doesn’t hurt.
“They own the account in perpetuity,” James said. “So there is no, ‘Let's sit here and make sure the land is as big as humanly possible and push this deal out so that I can get my commission before it gets handed off to somebody else.’”
While this approach may not make sense for every organization’s business model, incentivizing AEs to land and expand deals has consistently helped increase expansions and renewals across TestBox’s install base.
2. Homework speeds up sales cycles
Researching accounts to make sure they’re the right fit for TestBox’s sales motion is step one. Going deeper to help stand out in executives’ crowded inboxes is step two.
For reps at TestBox, that means talking to as many in-the-field employees as possible to understand what their day-to-days are like and using it to inform outreach at the exec level.
“It takes a lot of work, it takes a lot of intention,” James said. “But if you get it right, it accelerates the sales process at the end of the day.”
AI is also a huge help here.
“We are using AI to do account research,” James said. “There's so much information out there. If I think about all the time I had to spend reading 10-Ks and getting information, wow, I've just saved so much time.”Data and signal capture agent
RoomieAI™ Capture automatically captures, synthesizes, and analyzes account-level insights from the public web and your internal data sources, all based on your custom configuration. This information is then summarized and delivered to reps in Common Room’s sales workbench.
At the end of the day, it’s human interaction that wins or loses deals. And AI makes it easier for reps to get more personalized, relevant, and responsive in their conversations.
“Every interaction matters significantly more than it ever did in the past,” James said. “[Y]ou can have the best product, but if you deliver a poor experience, poor message, don't follow up, don't put the customer at the front, you will lose that deal. The percentage of people who now buy based off experience continues to increase to an astronomical rate.”
3. Customer success isn’t a department
Land-and-expand sales strategies don’t work without one core element: happy customers.
That’s why James believes customer success is everyone’s job, not just the CS team’s.
“When you're a software company and you do not really care about your customers, it will bite you down the road,” James said.
It’s easy to get revenue tunnel vision, but as the saying goes, you can’t fill a leaky bucket.
Customer success starts with the accounts you chase in the first place. In other words: Sometimes you may need to say no to deals where you can’t deliver real customer value.
“Not all revenue is good revenue, and that is a hard thing for a lot of people to swallow,” James said. “When you focus on the customer and do right by the customer and the customer experience, the revenue, the GRR, the expansion, those things come, right? They come.”
These are just some of the takeaways from our conversation with James Kaikis.
Watch or listen to the recording for the full story.
And stay tuned for the next edition of Go-to-market mavericks!
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