Azim Nagree almost became a trial litigator.
He grew up in Australia watching too much LA Law, went to law school with the intention of standing in front of juries, and discovered somewhere along the way that the courtroom he'd imagined wasn't the one waiting for him. He ended up in corporate law instead. Most of it was, in his words, really, really boring. Except for one corner of the practice.
M&A law was different. The deals, the structure, the strategy behind them — it was the part that actually held his attention. He read Barbarians at the Gate. The appetite formed.
From there: strategy consulting in Australia with Bain & Company, an MBA that brought him to the US (assisted by an American wife), strategy work inside Dell, and eventually a seat at Scorpion where he built the M&A department from the ground up. No playbook. No team. Just the mandate to figure it out.
Now he's head of M&A origination at Herringbone Digital, a Trinity Hunt-backed platform rolling up digital marketing agencies that serve lawyers, dentists, doctors, and the trades. Herringbone set a first-year acquisition target of two or three companies. Azim closed six, plus one more under LOI, and crossed $100 million in combined revenue.
He did not do it by throwing money at every deal that crossed his desk.
Building the Department Before the Deal Flow
When Azim joined Scorpion, he wasn't walking into an existing M&A function. He was the M&A function.
"The mandate was: you need to figure out what the strategy is, what the buy box looks like, go and build the infrastructure to find those companies, build the strategy to value them, get board approval. Very much build the entire department from scratch."
The first deal they did taught them something important: you can manage the transaction side as a team of one, but you cannot do integration alone. Legal, finance, tax, HR, IT, customer success, all of it requires time from people who already have full-time jobs. You have to borrow that capacity. And if you haven't built those relationships before the deal closes, you'll feel the consequences after it does.
Integration, Azim is clear about this, cannot be an afterthought. It has to be designed into the transaction from the beginning. Closing the deal is the easy part. Getting the acquired company to actually work inside your organization is where acquisitions live or die.
Why Stakeholder Alignment Is the Most Important Use of Your Time
Ask Azim what makes or breaks an M&A function, and he won't say deal sourcing. He won't say valuation discipline. He'll say stakeholder alignment.
"If you do not do that, you will waste cycle after cycle after cycle bringing an acquisition candidate to the table only to discover that it wasn't what the stakeholders were actually interested in in the first place."
The alignment work at both Scorpion and Herringbone looked the same in structure, even if the answers were different. What are we actually trying to achieve with this acquisition? Is it EBITDA? Market expansion? Capabilities? What does the integration look like post-close? Can the economics work? What does the opportunity set look like?
The companies they ended up buying at Scorpion reflected specific answers to those questions: the first was a technology capabilities play, filling a gap in Scorpion's proprietary ecosystem. The next two were market expansion plays, acquiring footprint in geographies where Scorpion didn't have a strong presence.
Every decision traced back to the strategy. Deals that didn't connect to the strategy didn't get done, regardless of how interesting they seemed.
The Buy Box Is the Foundation
At Herringbone, the buy box is narrow by design. They're looking at digital marketing agencies that serve a specific set of verticals — legal, dental, medical, home services — and the profile of the companies they want is equally specific.
"Really, really well means great founder, great executive team, great team, period, great product offerings. And then strong year-on-year revenue growth, strong profit margins, strong retention."
The entry point they're focused on: three to four to five million EBITDA. Not because smaller agencies aren't interesting, but because agencies that have crossed that threshold have demonstrated organizational maturity that most haven't. Getting past a million in EBITDA is hard. Getting to three is harder. The companies sitting above that line have already proven something.
What Herringbone is not looking for: underperformers they can fix. That's a different model, one that gets more headlines because it involves replacing management teams and imposing new systems. The Herringbone model is the opposite: find the agencies that are already on fire, and pour more gas on it.
"We see our role as how can we help that business by pouring more gas on that fire and helping them accelerate their growth or just be better in a way they probably haven't been able to achieve by themselves."
What the Funnel Actually Looks Like
In an ideal week at Scorpion, Azim spent roughly a third to half his time generating deal flow — prospecting, building relationships, staying in front of potential targets. A quarter on internal alignment: up, down, and sideways across the organization. The rest on active transactions.
The analogy he keeps returning to: enterprise sales. You're prospecting, following up, nurturing relationships, and eventually bringing in subject matter experts to close the analysis. You're building the financial model. You're doing diligence on customers and contracts. You're doing the legal work. And you need to be involved in every step of it, even when you're leaning on outside advisors, or you'll miss something important.
At Herringbone, the team has grown, which unlocked the deal velocity that made six closings in year one possible. Azim runs top-of-funnel prospecting and nurturing up to LOI. A team handles LOI to close. They use HubSpot for prospecting and lead nurturing, with consistent weekly communication inside the team and regular detailed updates to the sponsor, Trinity Hunt, who are looped in closely on every deal.
"There were still many long days and sleepless nights, but having that team-centric approach is the only way to unlock that sort of deal velocity."
How They Hit 2.5x Their First-Year Target
Herringbone modeled the funnel, mapped the TAM, estimated conversion rates at each stage, and built to a target of two to three acquisitions in year one. That math felt reasonable. They were new. The infrastructure was still being built. The brand was unproven in the market.
They closed six deals plus one LOI.
The uncomfortable side of outperforming a target is that it resets expectations. Now the question is: how do you get from six to the next level without expanding the buy box in ways that compromise the strategy?
"Either we need to revise the target, or we need to revise the buy box criteria, or we rely upon improving some of those conversion metrics, or we find that the TAM is perhaps a little bit larger than we anticipated. So all of those came into play."
He's also watching the market shift. Agency owners who said no a year ago are starting to call back. Some are seeing consolidation happen around them and reconsidering. Some are watching the AI landscape and getting less confident about doing it alone. Some are just another year further into their tenure. The pipeline of willing sellers is widening, even without changing who Herringbone is looking for.
Discipline with Capital Is a Feature, Not a Limitation
Herringbone has committed capital. Unlike an independent sponsor who has to raise deal by deal, the money is already there. That's a real advantage in a conversation with a founder who's been burned by a buyer who couldn't close.
But Azim is deliberate about not weaponizing that advantage recklessly.
"We're very, very disciplined buyers. We have our own internal economic model of what makes sense for us to pay, and we're not going to budge from that."
The conversations with founders who have unrealistic expectations are some of the more straightforward conversations he has. He tells them what the business is actually worth in the market, based on real deal experience rather than what a buddy told them or what they read in the trade press. Sometimes that's a hard conversation. More often than not, he reframes it: here's what your business would be worth in twelve to eighteen months if you focus on these three things. Come back when you've hit those marks, and the number changes.
Setting that expectation early, honestly and without aggression, is part of why Herringbone's deals tend to go smoothly. Founders know what they're getting into before the LOI is signed.
The Integration Problem Nobody Wants to Think About Until It's Too Late
Herringbone's approach to integration is deliberately light — so far. The portfolio companies operate with their individual identities intact, because that's what made them worth acquiring. You don't buy a business that's on fire and immediately tell it to run things differently.
But light touch doesn't mean no touch.
The medium-term work is finding the integration touchpoints that actually create value without eroding what made each company good: getting everyone on a consolidated NetSuite instance, identifying cross-sell opportunities between portfolio agencies, and gradually building the operating model that will eventually turn a Holdco of six brands into something that functions as a single platform.
The founders themselves are a resource here. They know their markets, know their competitors, and know who else might be a good acquisition target. They're already making introductions.
"They recognize the value that can be created by doing a tuck-in. They're actually now the ones coming to me and saying, have you talked to Bill? If not, I'll make the introduction."
That's how you accelerate deal flow in year two without spending all of it at the top of the funnel.
How He Thinks About AI
Herringbone recently brought on Dan Ingley — founder of GoFish, sold to Trinity Hunt — to lead their AI initiatives. That decision signals something about how seriously they're taking the question.
Azim frames AI across three distinct levels.
The first is the one most agency owners are already working on: operational efficiency. Using AI for content, design, website builds, removing the need to hire for tasks that software can now handle. That's real, and it matters, but it's the most obvious layer.
The second is more complicated: how does AI change the product itself? GEO, generative engine optimization, is a term that's starting to circulate, but most agency owners don't yet know how to build around it. The forward-thinking ones are starting to figure out that they need both new products and versions of existing ones. Exactly which, and in what proportion, is still being worked out in real time.
The third is the hardest to model: how does AI change the end customer journey? Before AI, a consumer needing a dentist went to Google, visited a website, read reviews, and called to schedule. That funnel is stable and well understood. Nobody knows yet what it looks like in three years. Local hasn't been disrupted the way other categories have, but Azim is clear that it's a matter of when, not if.
"We are probably between the expertise we already have at Herringbone, the expertise in some of our portfolio companies, and the resources we can bring to bear. I'd be hard-pressed to think of anyone better prepared for any AI disruption."
What He'd Tell Someone Starting From Zero
Azim spends real time talking to agency founders before they're anywhere near ready to sell. Part of it is relationship building, a more informed seller makes for a better transaction down the line. Part of it is something closer to just caring about the outcome.
"Anything I can do to help someone get up the curve with respect to knowledge, I'm thrilled to do that. If you're a business owner, it's probably the first and only time you're going to go through a transaction. Kind of daunting."
The practical advice he gives founders thinking about selling: understand your business's actual worth in the current market before you take a meeting. Know the difference between what you heard at a conference and what a buyer with real deal experience will actually pay. And if the number doesn't work today, understand what levers. revenue, profitability, retention, growth rate, would move it in the next twelve months.
He's on LinkedIn, publishing content aimed at educating the market. And he's reachable directly at azim@herringbonedigital.com.
Listen to the Full Conversation
Hear Azim Nagree break down how he built M&A from scratch at Scorpion, what it looked like to close six acquisitions in Herringbone's first year, and how a PE-backed buyer thinks about discipline, integration, and the AI shifts reshaping agency M&A.
