M&A Science

Most buyers flood sellers with requests, ask for rollover equity, and push the target onto their ERP fast. Greg Holbrock, VP of M&A at Winsupply, a Dayton, Ohio distributor with 680+ locally owned wholesalers and about $9B in annual sales, skips all three. He runs M&A with a core team of four, has worked on 20+ deals, and says over 80% meet or beat expectations. His test is simple: if the deal can't work for the local owners, it isn't a deal.

His approach starts with trust. He explains why each diligence request matters, gets approval to sign before he sits down, and listens hard for why the seller is selling now.

In this episode, Greg and Kison cover:

• Why Winsupply pays cash and skips rollover equity (the share price counts only about a third of goodwill)

• How the model works: Winsupply owns 100% on day one, then sells down to local teams and keeps at least 51%

• Integrating at "local speed," and when a seller can stay on their own ERP

• The real reasons owners sell, from succession and family dynamics to tax worries and e-commerce gaps

• Why about 90% of his deals have no earn-out, and when one is worth it

• Why a deal gets two lives, not three, and how to spot "dealitis"

Greg also shares how the Milford deal (one his team almost passed on) grew into a poly pipe business across the company.

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Walking a seller through every request only works when the requests, their answers, and your findings sit in one place the whole team can see. DealRoom is the AI-powered operating system for Buyer-Led M&A™, with a buyer-led data room your team, the seller, and your advisors share, and diligence findings that carry straight into integration planning. Customers cut person-hours per deal by ~50%: bit.ly/4eYoRjW

Most buyers diligence a sales org by ranking the reps and cutting the bottom of the list. But if you ask John McMahon, that's usually the wrong target. In most cases, the problem is the manager.

John should know, because he's seen both sides of a sales integration. Cisco bought GeoTel, scattered its 50-rep software team across a router sales force, and lost nearly all of them. BMC bought BladeLogic, put John in charge of all of BMC sales, and took average rep productivity from $1.17 million to $2.23 million in a year.

In this conversation, John tells Kison how to read a sales org before close: Map both ICPs first, grade managers on recruiting and forecast accuracy, and spot the farmers who can't hunt. He also covers why overlay models quietly burn money, how a new-logo gate in the comp plan keeps reps from living off the install base, and why an AI-filled MEDDPICC field doesn't mean a deal is qualified.

What You'll Learn

• Diligence the managers, not just the reps. When reps underperform, check the manager first. Replacing a bad manager often turns the same reps around.

• Map both ICPs before you model cross-sell. If you sell to engineering and the target sells to finance, the cross-sell case is weak. Shared or adjacent personas are where the upside lives.

• Use productivity per rep to find weak managers. Compare each manager's per-rep average to the sales force average. Below-average quarter after quarter means no new headcount.

• Train both teams on both product lines instead of adding overlays. Overlays turn hunters into reps who wait to be invited into accounts.

• Gate commissions on new logos. Pay the higher rate above quota only once a rep hits a set number of new logos, so the team doesn't live off the install base.

• Win the undecided middle fast. After close, one group wants new leadership, one never will, and the middle is watching. Train them and help them win deals before the holdouts sway them.

• Treat forecast accuracy as a manager's real test. Accurate forecasts mean the manager knows the deals and the reps. An AI-filled MEDDPICC field doesn't.

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Grading a target's sales managers in diligence only pays off if those findings reach the team running the integration. DealRoom is the AI-powered operating system for Buyer-Led M&A™, where findings on the target's sales leadership, ICP, and go-to-market motion feed straight into the integration plan. Customers cut person-hours per deal by ~50%: bit.ly/4eYoRjW

Most corp dev teams let the banker inbox set the agenda. Michael Guptan, who has led or contributed to 120+ transactions worth over $100B across Dell, Walmart, DXC, and now The Trade Desk (NASDAQ: TTD), says that's backward. Strategy drives M&A.

His approach starts long before a deal. Define where the company needs to be in three to five years, find the gaps, then build relationships with likely targets 12 to 18 months before any deal talk, so culture is clear before the LOI.

Michael and Kison cover:

• The red flags that signal a culture mismatch
• When to buy instead of build (time to market usually decides it)
• Negotiating the whole package: speed, certainty of close, retention, and org structure
• Budgeting 5 to 10% of deal value for integration on smaller deals, with the integration lead in diligence
• Why he avoids compressed auctions, and the judgment calls he won't hand to AI

Kison also puts DealRoom's own strategy on the table for a live role play.

Tracking targets 12 to 18 months out only works if your pipeline lives somewhere other than inboxes and spreadsheets. DealRoom is the AI-powered operating system for Buyer-Led M&A™, with one source of truth for targets, notes, and emails, and diligence findings that feed straight into the integration plan. Customers cut person-hours per deal by ~50%: bit.ly/4eYoRjW

Most people assume the hard part of an M&A deal is getting the contract signed. However, Meg Cavanaugh, SVP of Legal at Commvault (NASDAQ: CVLT), has spent her career proving otherwise.

Meg worked in-house at three public companies, closing acquisitions almost every week during her six years at Carbonite before moving to Commvault, where her role spans legal, diligence, and integration.

What You'll Learn

• Draft the LOI in-house before outside counsel sees it. Keep the tone and structure matched to your own deal philosophy, then bring outside counsel in to review rather than build from scratch.

• Treat LOI negotiation as diligence. Every redline you get before signing tells you something real about the people and the business on the other side of the table.

• Push back on conservative lawyering. Don't let a deal stall over an immaterial closing condition or a 0.01% edge-case indemnification issue.

• Choose asset vs. stock purchase around what you need to exclude. Asset deals let you carve out debts and liabilities explicitly; stock deals mean you're taking on the whole company.

• Chase down change of control provisions early. Left unaddressed, they can let a key customer walk the moment the deal closes.

• Build a Corp Dev team that owns the deal and the integration. Once you build that muscle successfully, it gets easier to repeat.

• Train non-lawyers to negotiate commercial contracts. Give them the playbook, audit their work, and save outside counsel for the purchase agreement itself.

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Meg's in-house team reads every contract in the data room, then puts what they find on the CISO's, engineering's, and compliance's radar before close. DealRoom Diligence was built for that handoff. Each finding is logged with an owner and a mitigation plan, then carries straight into the integration plan, and the AI document analysis is built to reduce internal & external legal costs by 60%. See how it works: https://bit.ly/4BxCAb5

A partner's spouse joined a call two weeks from closing. One background check later, a PE deal was dead, along with every dollar spent on diligence and attorney fees.

Kison gathered the deal stories practitioners leave out of case studies, with the names removed. Corporate development leaders, attorneys, and advisors share deals that died at the signature line. There's also a roughly $1 billion divestiture that was unwound after a withheld forecast surfaced the morning after the wire. And a losing bidder bought the same company back 18 months later for about 80% less. The pattern across them: a late surprise kills trust faster than it kills valuation.

Most of these deals died on something that surfaced too late. DealRoom, the AI-powered operating system for Buyer-Led M&A™, keeps diligence requests, open items, and findings in one place from the start of a deal. That way surprises show up while you can still price them or walk away. See how by clicking here.

Days before closing a carve-out, Danielle Fortier's team found the seller's vendor list was off by dozens of vendors. Danielle, a partner at Cooley with four corporate carve-outs closed this year, explains why: back-office vendors are shared across every business line, and deal leads rarely focus on them early.

Her roadmap maps every entanglement, checks it against what the buyer already has, and sends only true gaps to the TSA. Cloud hosting, finance and IT security are the usual traps. Settle TSA length and pricing in the LOI. She has seen sellers assume three months while buyers assumed 18.

Her biggest warning is over-relying on the TSA. Six months in, you still go to the seller for everything.

That vendor surprise happens when entanglements, gap owners and TSA schedules live in lists nobody fully trusts. DealRoom keeps carve-out diligence, open requests and integration planning in one connected platform, so gaps found in diligence carry into the post-close plan. See how Infoblox consolidated 5+ tools from pipeline through integration: Infoblox's Case Study

"Never use the word 'trust me.' It's those people you can't trust." Jerry Cedicci, Kison Patel's boss from twenty years ago, built hundreds of millions of dollars in real estate, cafes, hotels, and restaurants. This is his playbook.

For Jerry, trust is structural. Ask to run the business you're buying, let the seller fire you anytime, and hand them every card so they can't lose. He pushes the other side to name a price first so he never negotiates against himself, and he'll pay full price when the seller finances it.

Then Kison raises a competitor he wants to buy that won't share financials. Jerry works it live: skip the financials and ask how many clients, set your threshold, size what the company could become, and offer 6 against an expected 5 to 10.

In corporate M&A, Kison notes, earning a seller's trust can take a year, which means tracking targets long before they're ready to sell. Qualfon reviews 75–100 targets a year and runs that pipeline in DealRoom with real-time reporting: read more here.

"At the closing table, I left with a check of $10 million." Jerry Cedicci bought a run-down Chicago hotel for $14 million and sold it for $24 million within a year.

Jerry grew up in a French orphanage and arrived in the US in 1981 barely speaking English. Kison Patel hunted properties with Jerry about 20 years ago and learned much of his dealmaking from him. When a bank rejected Jerry's loan, he asked exactly why and got $3 million from the next bank.

A landlord warned that the average bakery does $450 a day. Jerry's first did $1,500 on day one, and he wrote a $10 million option to buy the building into the lease, exercising it 10 years later. Skipping that option on his Michigan Avenue store was, he says, the biggest mistake of his life.

Jerry's costliest mistake was an opportunity he saw and never locked in. Corp dev teams lose targets the same way when the pipeline lives in scattered spreadsheets. Jamf moved its deal tracking into DealRoom and cut deal time in half. Learn more about Jamf's case study here.

A $100 million preferred equity check with a 15% compounding floor needs $200 million back in five years, and all of it sits ahead of the producers holding common equity.

Bill Johnson grew Liberty to $250 million in revenue in seven and a half years without taking on any equity. He explains why Liberty sits out auctions and how Goldman's preferred position in the Newfront sale to Willis crammed down common shareholders.

He breaks down a pro forma move PE firms accept: cut an owner's $600,000 pay to a $150,000 salary, then ask for a 10 or 11 multiple on the difference. And he owns Liberty's mistake. After growing too fast, Liberty paused M&A in 2023 at about $150 million in revenue to build systems and upgrade leadership.

Liberty's fix was a pre-close integration roadmap, built to integrate each deal within 60 to 90 days. That only holds when diligence and integration plans live in one place. See how Liberty built a single source of M&A truth with DealRoom and recorded $200K cost savings in the first year: read the case study here.

Kim Jones, HR Director of M&A

One acquired CEO slowed his own deal by a month or two to lock down customer commitments and build relationships with buyer leadership. At announcement, employees clapped.

Kim Jones has spent over a decade as an HR deal lead at large tech companies, from single-employee acqui-hires to acquisitions bringing in thousands. The deals that integrated smoothly, she says, were the ones where leaders on both sides were enabled early. Process gets compliance. Trust gets advocacy.

Kim explains how closing fast without a plan creates integration debt, why "you'll run independent" needs a shared definition, and why integration should start at LOI. She also covers honest retention conversations, a quarterly org council for tracking talent, and an employee uprising over butterscotch Life Savers.

Integration debt builds when the deal thesis and diligence findings never become a plan leaders can carry. DealRoom keeps diligence and integration planning in one connected platform, so the plan exists before close. See how Wipfli runs both in DealRoom, where across its last three transactions not a single person from the incoming firm asked for training: here.