At 21, Emily was running $30 million auctions at Christie's. Mistakes here were final. No do-overs. No safety net. Just 300+ artworks, consigners across the globe, buyers waiting to bid, and hours to make magic happen.
"People think tech is fast," she says. "Imagine 24 hours before an auction. You have consigners all across the world. You're trying to manage them down on what they've agreed their object is worth. And you're trying to create a bidding war—because how do we really define value? Value comes from competition."
Today, Emily is the Head of Operations at Freckle, the modern AI enrichment platform for HubSpot and Salesforce users. Companies can use Freckle’s AI agents to find and enrich company or contact data across the web and 50+ data providers using natural language — keeping CRMs clean, leads enriched, and pipelines prioritized.
She's the second-in-command to a sole founder, which means she touches everything: investor relations, partnerships, marketing, product, sales support, compliance, hiring, and yes, payroll.
When Emily joined Freckle, the company was mid-transformation. Their Australian founder was relocating to the US. They were executing a full legal name change from Upbound to Freckle. They were launching SOC 2 compliance. And they were using Rippling for payroll.
"People were coming to me saying, we have the wrong benefits set up," Emily recalls. "I had to explain to an Australian founder why our American benefits look expensive but aren't actually good. And, we knew we needed to set up a 401k.”
Emily was upfront with herself: "I have never had to do payroll, but how hard can it be?"
Famous last words.
"I lost weeks with Rippling trying to debug basic things. I kept getting forced to re-authenticate mid-conversation, support was unresponsive, and the documentation didn’t match the product. There was no onboarding. Ultimately, they forgot to enroll us in health insurance because a checkbox was missed."
As you can imagine, the result was a not so happy workforce.
"There was this backlog period where everyone was like, ‘Emily, I can’t go to the doctor.’ And I’m calling our insurance brokers in the middle of the day thinking, this is a terrible use of my time."
The Real Cost of Bad Payroll Software
Emily doesn't measure software by features. She measures it by friction (or the absence of it).
"The best thing I can tell you about a product is that I don't think of problems. I index on things that aren't going well. So when I'm not thinking about it? That's when you know it's working." With Rippling, she was constantly thinking about it. And not in a good way.
"There's no part of my day where I should be blocking my calendar for an hour because I have to go try to figure out an issue. Then I have to go fight support, or email my account manager who only wants to upsell me to fix the problem."
Emily knew she had to make a move. But payroll changes feel different than other software migrations.
"We're ripping out Intercom right now. Am I scared of that? No. Are there going to be issues? Probably. But payroll is so sensitive. It revolves around your employees that you want to protect at all times."
Why Warp Is The Best Payroll Software for Freckle
Emily evaluated all her options. Rippling was cheap at scale, but the service was terrible. Gusto was a slightly better version of a bad solution. And then there was Warp.
"I usually enter conversations having made a decision. I'm waiting for something to unsell me."
Two things sold her:
Direct Slack communication: having that direct Slack communication was the most important thing for Emily, because it was where she already lived. However, she still wanted to be able to go into another dashboard and have the ability to index against that. “If I ever have a question, I know I can chat with someone in the Slack channel and know that one of my gals will respond.”
But what Emily really values is the knowledge on the other end of that Slack channel.
"I can deploy questions to a team of people who have 10x more knowledge than I do. They've probably encountered this before because they've worked with another company like us that's gone through the same issue. That type of knowledge base supporting us is massive."
Full migration support: "We’d had so many issues with Rippling locking us out of our accounts that we were like, ‘How do we do this? Do we have the right tax documents? Are we in default?’ It was so hard to figure out the state of things there. The Warp team made sure we didn’t have to worry about that, they made the experience great for us.”
Today, Emily doesn't think about payroll. Which is exactly the point.
"I go in and I'm not overloaded by options. I want to see what someone's social security number is. I know where to go. I'm not using the search functionality to find things. Through the onboarding, I was told what to do and haven't had to second-guess that."
Her founder, Nathan, barely touches the payroll channel anymore. When he does have an issue, it's solved within hours.
The Bigger Picture
Emily still goes to SF Art Week. She still evangelizes art collecting to her tech friends ("Anyone earning at our rate should be putting some money into art—it's an investment asset"). She still tries to drag her team to gallery talks instead of happy hour. They still say no.
She laughs about it. You can't win them all.
But here's what she can do: focus her energy on the things that actually move the needle. Product marketing. High-production case studies. Partnerships. Enterprise sales. Building community events. Hiring the right people, not people with fancy titles, but people who identify what's wrong, find a solution, and implement it tomorrow.
"The real unlock is ensuring people in senior leadership positions aren't spending their time doing things they simply should not be using their brain power on."
That's what Warp gave her back: her time, her focus, and the peace of mind that if something does go wrong, she won't have to fight alone.
For someone who learned to build value through competition on the auction floor, that's a pretty good deal.
Ready to join companies like Freckle and stop fighting your payroll provider and start building? Warp automates payroll compliance so you can focus on what matters. Get started with a demo today.
