The
90-Day Read
How to assess a revenue leadership hire before the numbers can.
Built from conversations with six commercial operating partners across private equity, venture, crossover and fractional models.
The 90-Day ReadAbout This Research
A revenue leadership hire is one of the single most impactful people decisions a portfolio company makes, and it is often judged on evidence that does not arrive in time to course correct. We wanted to understand what actually happens inside the first 90 days, and how the best operators form a legitimate read long before revenue can confirm anything.
Why we researched this topic. As a retained executive search firm, M Search is engaged at the point of scoping, and on a replacement search we are effectively running a postmortem on the last hire: what worked, what did not, what has to change this time. Across many searches, one pattern kept repeating. Experienced commercial operating partners can tell, remarkably early and well before the numbers move, which revenue leaders are going to work out and which are not.
Why it matters now. That expertise is scarce. Even the best-equipped funds have only a handful of these people, spread thin across a portfolio, and however good they are they cannot be deeply involved in every revenue-leadership hire.
The cost of getting this wrong is not abstract
“I estimate growth-stage companies burn roughly five million dollars on a wrong CMO hire. It’s two years lost, multiple search fees, the churn of several top performers, and most importantly, badly misallocated marketing spend. Five million, conservatively.”
It is the opportunity cost of lost momentum that hurts most, and in our own work we have seen that arithmetic play out.
So we set out to build something a CEO can use on their own: a structured, honest read at the 90-day mark, before the wrong person has been in the seat too long.
The 90-Day ReadWho we spoke to
We deliberately went looking across different fund structures: different investment theses, different operating models, different levels of involvement. Operating resources sit inside a portfolio very differently depending on who they work for. A control-oriented buyout fund can direct a company more proactively. A minority investor does not. A crossover fund does both, and a fractional operator often arrives with little structural authority at all and has to earn their pull.
Every contributor has sat in a revenue-leadership seat themselves. These are not observers. They have carried the number, built the team, and then watched these hires succeed or fail from the investor’s side of the table.
Thirty years in growth acceleration and go-to-market productivity across more than a hundred technology companies, most recently as Chief Growth Officer at a lower-mid-market private equity software buyout firm, where his team owned sales performance across a 200+ company portfolio. Previously go-to-market leadership at RingCentral and Salesforce, and before that Bain and McKinsey. Co-founder of the GTM Leader Society.
A four-time CMO who has built growth engines at Wealthsimple, Policygenius, Tiffany & Co., Live Nation and Procter & Gamble, now a Partner and Chief Growth Officer at an alternative asset manager investing across both venture and private equity, where he works with portfolio companies on growth.
Operating Partner and Chief Platform Officer, where he leads the venture platform and has worked with more than a hundred SaaS companies. Previously founded a technology advisory practice, and before that held senior marketing leadership roles at a top global enterprise software company and a security business.
A go-to-market and revenue operations leader with over a decade in B2B SaaS, most recently in the operations group of a lower-mid-market software buyout fund, running operational diligence and portfolio support across Europe. Previously in revenue and growth operations leadership at HPE, Bazaarvoice, Brandwatch and StarLeaf.
Fifteen years across revenue, customer success and operational excellence, delivering large transformation programs inside global businesses before moving to independent consulting. Works on the ground inside PE-backed mid-market technology companies across the UK and Europe.
Nearly three decades of global sales and go-to-market experience, now coaching sales executives and CEOs across the portfolio. Formerly Chief Revenue Officer of a product-analytics company he helped grow to nearly $100M in annual recurring revenue, and before that an early employee at a marketing-technology company where he ran worldwide sales through its IPO and acquisition.
The 90-Day ReadKey findings at a glance
Seven things came up again and again across every contributor. Each is unpacked in the sections that follow.
The 90-Day ReadCommon Failure Modes
When we asked contributors to think back on the hires that did not work, the culprits rhymed.
Force-feeding the prior playbook
The single most-cited failure, and the hardest one to screen for. Intent is rarely the problem. Most candidates fully expect to adapt, and say so convincingly, because they have not yet met the specific ways this business differs from the last one. The divergence only appears once they are in the seat and under pressure to produce, at which point the motion they already know is the fastest thing to reach for.
“They’ve either built or been trained on a playbook, and they try to bring that exact playbook into the organization, and there’s an organ rejection. It’s one of those things I try to test for when I’m interviewing CROs, and they kind of nod their head and tell me the things I want to hear. So it’s really hard to decipher for.”
Wrong stage, or pedigree over fit
A leader who managed a thousand-person org at a category leader is often of little use building a team from scratch. Hire for roughly the next 18 to 24 months of the company’s life, not for the logo on the résumé.
“Start stage: we’re still figuring out product-market fit. Build: we have some go-to-market fit and we’re trying to create repeatability. Scale: we’re accelerating global expansion and investment. Those are three different modes. Am I hiring someone who has come out of Salesforce, spent 20 years there and managed a team of a thousand? That’s of no consequence to building a team from scratch.”
Misrepresenting the role
Another common failure mode, raised by several of our contributors: it is not uncommon for a role to be misrepresented during the interview process. Sometimes a decision made after the hire materially changes the scope of the position. Sometimes the state of the company is never fully described to the executive candidate. Both create a trust breakage early in the hire’s tenure.
“They write a spec, and then all of a sudden the CRO walks in the door and they’re like, I’m not going to give you sales engineering and rev ops right away, I’m going to have that stay reporting over here. And all of a sudden now you’re auditioning. Wait a second. You hired me for that scope and my experience. You set a job spec and now you’re changing that day one. So right away there’s a trust breakage.”
“The smart people in the company will always see it, whether it’s a VP or the best account exec. Trust is so hard to gain and so easy to lose. If you’ve started off on the wrong foot with your entire team, you start getting attrition and it compounds from there. Your best performers leave, the rest of the organization won’t trust you, you lose the trust of your peers. It’s a sinking ship from that point on.”
The 90-Day ReadThe real leading indicators
At 90 days the quantitative indicators are lagging and corruptible, and the qualitative ones are the actual tell. The trap is watching the numbers precisely when they can tell you the least.
“I’ve seen people come in sitting on good pipeline, close some good deals, and have it all attributed to them. The past gets forgotten, and now they’re the superstar, having done almost nothing. It’s like changing presidents every four years. Most projects take time to come to life, and the sitting president takes credit for work that started two terms ago.”
- ▪Their attitude toward the problems they find
- ▪Whether the CEO can answer with conviction
- ▪Whether peer alignment holds up separately
- ▪How the team shows up in their own meeting
- ▪A fact-based plan the leadership team agreed to
- ▪Closed revenue attributable to their decisions
- ▪Pipeline they actually created
- ▪Forecast accuracy and predictability
What is readable right now
Has the leader produced a fact-based assessment, validated rather than impressionistic, and a plan that the other members of the ELT have commonly agreed to?
“I’d start with their diagnosis of the business — and I’d want to be part of making it. That diagnosis tells me a great deal about their business acumen and how hands-on they are.”
Do the other members of the executive leadership team trust this person to make good decisions, and are they aligned on the strategy?
“If you spoke with your CRO and your CPO separately, would they both relay the same product strategy?”
Talk to the direct reports, and then do the thing almost nobody does. Sit in on one of the leader’s team meetings as an observer.
“I’ll tell you one nobody ever does, and it may be the best signal there is. How do they run their team meetings? Sit in as an observer and get a sense of it: do they have structure and process in how they execute the role? How well is the team showing up for them? What value are they providing their team?”
Is the CEO starting to get headspace back, handing off meetings and decisions? Every new leader takes headspace during the ramp. The transition from taking it to making it is a signal, and if it has not happened by day 60 to 90, something may be off. The most useful version of this test is to ask the CEO how it is going, and listen to the shape of the answer rather than its content.
“That’s the biggest telltale sign — the canary in the coal mine. The response of ‘they’re doing okay, we’ll have to wait and see, it’s early,’ versus ‘they’re great, thank God they’re here, we should have hired them six months ago.’”
Are you seeing early signs of the layer beneath the leadership strengthening and buying in?
“Have they isolated and understood the characteristics of the people they want to hire, and is that mapped to the problem they solve and the domain? Have they got onboarding right, with demonstrable evidence they can ramp people quickly? Have they thought through their ability to feed those people pipeline?”
The 90-Day ReadThe earliest tell: The new hire’s attitude toward problems
A good hire discovers issues and brings a plan. A struggling hire discovers issues and catalogues them. The strongest early green flag is a leader independently surfacing problems you already knew you had, without being told. That means they are seeing clearly. Having a productive attitude toward these problems is a key determinant of their success in the role.
“The worst-fit CMOs I’ve seen tend to say ‘we need to pay someone else to do an audit to figure out what’s going on.’ Well, shouldn’t you know how to do that? If they have a hypothesis and they want to validate it, and they have a plan on how to validate it, fine. But don’t just rely on outside support to fix a problem.”
Why the decision still takes time
Contributors were consistent that the signal is readable well inside the first 90 days. Acting on it is a different matter, and the gap between the two is not a failure of attention. Several described a delay of three to nine months, and the causes they named are human rather than negligent. An executive who has just spent six months and real personal capital on a hire is protecting a decision they own, and there can be a genuine credibility cost to reporting a miss to the board shortly after making the case for it. Almost everyone we spoke to said they had helped a CEO through this at some point, and several described it as one of the more useful things an operating partner does.
“You probably know within the first six weeks you’ve made a bad decision. I don’t think you need to wait for any kind of lagging indicators.”
“CEOs think: I lose credibility with the board if I make another change, even though I don’t love the person I’ve got. Changing a sales leader is enormously disruptive. It’s a J-curve — you see the dip before you see the benefit.”
The counterintuitive finding sits directly against that instinct. One contributor found that the companies performing best through to IPO had higher turnover of executive personnel than the underperformers. The companies that struggled were the ones that kept leaders in seat longer.
“I was looking at research on post-investment success. The most successful companies post-IPO have higher turnover of personnel, which surprised me. In the underperforming companies, the executive leaders stay longer. It seems backwards. You’d expect the opposite.”
The 90-Day Read90-Day Read in Practice
The read is not a formal, sit-down performance review. It is a lightweight loop with three beats.
Built at hire
During the search, agree the two or three things this person must accomplish in 12 to 18 months, plus what on-track and off-track look like and which signals you will watch. Set in calm conditions, before day one.
The CEO runs the read at around 90 days
It takes legwork. Talking to peers, talking to the team, sitting in on a meeting or two. It is organized around peer review, team review, the CEO’s own read, and the agreed objectives.
The honest conversation, on a schedule
A short readout, with the board or operating partner where they are engaged. Putting it on the calendar is the entire point. It forces the honest conversation to happen on a date, rather than whenever someone can no longer ignore the drift.
A key piece of all this is understanding the most important things this new revenue leader should be accomplishing. It is not fair to expect them to have completely achieved their biggest strategic initiatives. However, it is reasonable to expect meaningful movement on each one. If you do not see progress on the big strategic goals you should be, at a minimum, communicating the concern to the hire explicitly.
And if the read comes back mixed, the most practical thing anyone gave us was a way to structure the next move rather than wait for it to resolve itself.
“These are the five things I think this person should be doing now. Do you agree? We pick three, and we look at them over the next three months. If nothing changes, we meet again and we make the call.”
It works because it converts an open-ended worry into a defined endpoint, and it removes the part CEOs actually dread, which is owning the decision alone.
The 90-Day ReadOne-Page Checklist
For the CEO to fill out, roughly 90 days in. It takes legwork: talk to their peers, talk to their team, sit in on one of their team meetings.
It is deliberately not about revenue yet. It is about whether the person and the plan are right.
| # | Section | What you are checking | Example |
|---|---|---|---|
| 1 | Strategic Planning | Have they produced a fact-based assessment, validated rather than impressionistic, that the rest of the ELT have commonly agreed to? | A real diagnosis: who we win with and why, where the motion breaks, what we stop doing. The failure version opens with “here is what we did at my last company,” or is a genuinely good plan that marketing and product are hearing for the first time in the readout. |
| 2 | Peer Trust | Talk to their C-suite and VP peers. Are the relationships genuinely working? Do they and their counterpart describe the same strategy separately? | Ask the CRO and the CMO or CPO the same question separately: who are we selling to, and why do we win? Two different stories, or a peer who hedges, means you have two strategies running in parallel and nobody has said so out loud. |
| 3 | Team Buy-In | Talk to their direct reports. Sit in on a team meeting as an observer. Real structure? Does the team show up for them? Are they adding value? | Is there structure to how they run it, or is it a status round-robin? Do the reps leave with something they did not have? Almost nobody does this, and it is the single best early signal available. |
| 4 | Your read (CEO) | Are you getting headspace back? Can you say “thank God they’re here” with conviction, or is it “we’ll see”? | “They’re great, we should have hired them six months ago” is one thing. “They’re onboarding, it’s early, we’ll see” is another, and it usually means you cannot yet tell what good looks like in that function. The hedge shows up early, well before anything else does. |
| 5 | Progress on Big Initiatives | Is there movement on the big goals you jointly set for the role or department? | You are looking for evidence it is genuinely underway, on leading indicators rather than lagging ones. “No contract closed yet, but three new conversations started with the right buyer” is real movement. “We’re building the plan” at 90 days is not. |
| 6 | Red flags | Check any that apply. | Installed a prior playbook before understanding the context · made structural changes before finishing an assessment · catalogues problems without proposing fixes · top performers disengaging · peers asking to exclude them from deals · trust with the CEO visibly eroding |
The 90-Day ReadWhat you can do before the hire is made
Almost every failure mode in this report is cheapest to prevent at the beginning, before the offer, in how the seat is scoped. This is where a good search process earns its keep.
Scope for the capability, not the title
Define the two or three things this person must accomplish in the next 12 to 18 months, then hire for the ability to do that, in this stage, this motion, this market. Clearly define what this seat will and will not own.
“You’re in a 200-person company. A PE firm has bought it and is shifting it away from founder-led. What you might need is a high-performing VP of Sales who can step up — they just don’t carry a CRO label. The misconception is that everyone ties everything to a title. What you want is the capability that gets the company from A to B in that particular period.”
Interview for adaptability, longitudinally
Rather than personality tests or situational hypotheticals, walk the candidate through their last role quarter by quarter. What did you inherit, what did you learn, what did you change, how did you scale?
“One of the best ways to interview sales leaders is to walk through their last job from beginning to end. You’re understanding how they evolved in the role, not just looking at surface-level metrics and surface-level company success.”
Have the comp plan ready on day one
Making a new revenue leader wait three months to understand how they get paid is a trust breach on arrival.
“Sales leaders are the only executive in the organization where 50% of what they earn is variable comp. Everybody else is on an 80/20 or an 85/15. Don’t come in and try to figure it out as you go.”
Design the success criteria, and the signals, at hire
This is the hinge for everything that follows. In calm conditions, before day one, write down what on-track and off-track look like at 90 days and which qualitative signals you will watch. It is far easier to have that conversation before the emotional stakes are live.
In Conclusion
The hard truth underneath all of this is that the decision rarely makes itself. The numbers will not force it in time, and the emotional gravity of a hire you fought to make will always argue for waiting. What breaks the tie is a structured, scheduled, honest read, done early, while the blast radius is still manageable.
That is the entire purpose of this instrument. It is also the discipline we build into every search we run: scoping the seat honestly, and agreeing the success criteria before day one, so that the 90-day conversation is set up to be honest from the start.
M Search is a retained executive search firm focused on go-to-market leadership for PE, growth equity and VC-backed B2B software companies.
We run revenue leadership searches from the C-suite through Director level, across sales, marketing, partnerships and solutions, most often for companies between $10M and $100M in revenue.
Graham Locklear · M Search · graham@msearchco.com · linkedin.com/in/graham-locklear/