Twenty-five years of enterprise software, one new desk in Nashville, and a habit of starting at first principles before anyone else has finished their coffee.
On December 2, 2025, Billtrust handed Grant Halloran the keys. The Nashville-headquartered company, which moves roughly $189 million in annual revenue through its AR workflow and payments software, didn't pick a banker, didn't pick a consultant, didn't pick a McKinsey alum with a vague mandate. It picked an operator. Twenty-five years deep. The kind who once watched his parents take out a second mortgage so his startup could survive its first winter.
Halloran's resume reads like a tour of every enterprise category that mattered in the last quarter century - SaaS marketing at Orbis, ERP at Infor, planning at Anaplan, big-data visualization at Heavy.ai (back when it was MapD), and financial performance management at Planful. Each chapter rhymed with the next. He sells software that gets quietly bolted into the operating model of mid-market and enterprise finance teams, then keeps selling it for a decade. Billtrust is the logical sixth chapter.
It is also a familiar setup. Sunil Rajasekar - the outgoing CEO whose stamp is still on the company - had been building Billtrust toward AI-native receivables for years. Halloran's mandate, as he framed it himself in the appointment announcement, is to push that wave further. He is taking a $1.7 billion EQT-backed asset and pointing it at the same problem he has spent his career solving: get the finance org out of spreadsheet purgatory.
Billtrust sits inside a $189 million revenue band, with 820 employees, and a customer roster that includes the kind of mid-cap and Fortune 500 names that still process paper invoices alongside ACH. The order-to-cash cycle is a stubborn, profitable mess. Print invoicing co-exists with electronic billing. Cash application is half automated and half done by someone named Linda in Pittsburgh. AI gets a look, then a second look, then a careful procurement review.
This is the terrain Halloran knows. At Planful, he inherited a company doing financial planning at scale and rebranded it (the old name was Host Analytics) with a thesis that has since aged well: continuous planning, collaborative finance, planning as a team sport. He liked the new name's literal meaning - "rich in plans, systematic and methodical." The same instinct - put the strange-specific name on the door and explain it later - shows up across his playbook.
Halloran's official appointment release notes the headline metrics from his tenure as Planful's CEO. Revenue tripled. The customer base doubled. The employee count doubled. The company moved from a mid-pack FP&A vendor into the leadership tier. He did not get there with a single big move. He got there with a clear positioning, a long quarter-after-quarter compounding effort, and a leadership style he describes - this is a direct quote - as needing to be "a chameleon."
Source: Billtrust appointment release, Dec 2025.
Halloran graduated from the Australian National University in 1994 with a Bachelor of Commerce. Economics, marketing, accounting, and law - all loaded into one degree, in true ANU fashion. A short banking stint followed. Then, in the late nineties, he read Nicholas Negroponte's Being Digital, the MIT Media Lab book that talked about a coming world of bits, not atoms.
That was the spark. He and his brother Brett co-founded Orbis, a SaaS marketing platform built in Australia at a moment when nobody used the word "SaaS." Year one nearly killed the company. His parents put a second mortgage on the family home to keep it alive. The company found its footing, won marquee customers, and in 2006 went global. In 2012, it was acquired by Infor. By industry standards, this is a tidy founder story. By the standards of someone willing to mortgage their childhood home for a software business, it is folkloric.
After Orbis, Halloran's career flips into the operator track. He joins MapD in September 2017 as EVP and Chief Marketing Officer. MapD rebrands to OmniSci. Halloran is promoted to Chief Commercial Officer in 2019. OmniSci rebrands to Heavy.ai. Then the Planful run. Then Billtrust. Five enterprise software companies, all somewhere on the spectrum between "useful" and "infrastructural," none of them flashy.
He talks like an operator who has lost arguments and won them. Three ideas recur in his interviews. First principles thinking, which he describes as removing preconceived assumptions and starting from scratch. Situational leadership, which he calls being "a chameleon" - not in the dishonest sense, but in the sense that a senior engineer needs different handling than a Series B sales hire on day three. And relationships, which he flatly calls "the foundation of business."
On AI - the topic every enterprise software CEO is now contractually obligated to address - Halloran's position is unusually plain. "Our goal is not to displace people," he told diginomica when he was still at Planful. The point was not soothing. The point was that finance teams who get AI right will compound their leverage; teams who treat it as a headcount eraser will be out-thought by competitors who treat it as headcount augmentation. The next decade, in his framing, will rewrite what a finance professional even does.
Three things to keep an eye on now that Halloran is in the chair at Billtrust. One, branding. He has rebranded a company before (Host Analytics to Planful) with a specific philosophy about names doing work. Billtrust is already a category-defining name in B2B AR, but watch for sub-brand and product-line moves. Two, AI integration depth. Billtrust already runs Anthropic Claude, Snowflake, Gong, Outreach.io, and a serious analytics stack internally. Halloran will likely push the product side to match the operations side. Three, geographic and product reach. Planful doubled customers under him. The same trajectory at Billtrust would mean a noticeable expansion of who uses B2B AR automation, especially in the mid-market.
He is not loud about any of this. He does not run a Substack. He does not headline AI Twitter. The signal he sends is by output: companies he runs grow, exit, or step up a tier. The signal he sends in interviews is calmer than the era we're in - which, paradoxically, makes him exactly right for an era that has run short on calm.
So that is the snapshot. A Canberra commerce graduate who started a car wash before he could legally drive, founded a software company on a copy of Being Digital, mortgaged his parents' house to keep it alive, took it global, sold it to Infor, ran marketing and then revenue at the company that became Heavy.ai, tripled the revenue at Planful, and is now sitting in Nashville (and Lawrenceville, New Jersey, where he actually lives) running Billtrust. Welcome to chapter six.
The best piece of advice I've ever received is that leadership is situational. There's not one model for leadership; you have to be a chameleon.
Bachelor of Commerce at Australian National University. Economics, marketing, accounting, law.
Reads Negroponte's Being Digital. Co-founds Orbis with brother Brett in Australia.
Parents take a second mortgage to keep Orbis afloat. Halloran does not forget this.
Orbis goes global, expanding the Australian SaaS marketing business across borders.
Infor acquires Orbis. Halloran moves into senior enterprise SaaS leadership roles.
Joins MapD as EVP & CMO. The company rebrands to OmniSci, then Heavy.ai.
Promoted to Chief Commercial Officer at OmniSci, owning the customer-growth motion.
Runs Planful as CEO. Triples revenue. Doubles customer base. Doubles headcount.
Appointed CEO of Billtrust. Succeeds Sunil Rajasekar. Chapter six begins.
Before he could drive, Halloran was running a carwash and lawn service in Australia, employing other neighborhood kids as labor. Margins unknown; org chart implied.
Negroponte's Being Digital - the 1995 MIT Media Lab manifesto - is the reason Orbis exists. He read it. He called his brother. They started a company. Atoms to bits, in one read.
In Orbis's worst year, his parents took out a second mortgage on the family home to keep the company breathing. It is the rare founder anecdote that nobody embellishes - because it doesn't need it.
When he rebranded Host Analytics to Planful, he chose a word that literally means "rich in plans, systematic and methodical." A finance audience noticed.
Born and educated in Australia. Lives in Lawrenceville, New Jersey. Runs a Nashville-headquartered company with offices across the US, Europe and Asia. The commute is in his Outlook.
"Our goal is not to displace people." His stated position on AI in finance: augmentation, leverage, and a finance role that gets rewritten - not removed - by the next ten years.