Graham

headhunter - startup leadership & GTM
AI/ML+Data

[Graham @Graham_Locklear]

Here: https://t.co/5r8gVP8D0J

[Graham @Graham_Locklear]

Who you hire will dictate where you company is headed.

[Graham @Graham_Locklear]

Is this is the biggest story in PE-backed software?

Vista Equity published a report recently. Their 'AI Impact Report'. Essentially this showcases the impact of AI on their portfolio companies.

This report was stocked with a bunch of really interesting points. Case studies that showcase real portfolio stats.. outcomes, cost structures, etc. Both in product and in operations..

It also seemed like a very honest assessment of where they are and whats ahead of them.

Of all the things that caught my eye, I think their conclusion to the report is possibly the biggest story in pe-backed software right now.

And that is: The measurement of AI Impact is still in beta.

Look, lots of talk about "saas is dead" etc. However, I think that PE portfolios have shown us that they can achieve a goal that is clearly laid out.

And it is that "clearly laid out" peice that is the unlock IMO. As we develop more accurate ways to underwrite AI Impact (both in product, as well as operations), these companies will furiously charge against those KPIs. Many will achieve them.

I'm not blind to the fact that there is product that has existed for the last decade+ that will not have a place in the post-ai world. That is clear. (and anyone who knows me knows that I am sufficiently ai-pilled) But I think most people on the outside underestimate how much of enterprise spend is influenced by trust/vendor track record.

Second order impact: when PE can accurately underwrite this. So too, will the public markets, and bigger private market fish. That could have positive implications on liquidity.

[Graham @Graham_Locklear]

Here: https://t.co/XtZxPYDQy9

[Graham @Graham_Locklear]

Bain Private Equity Mid-year Report 2026:

[Graham @Graham_Locklear]

Something I'm thinking about: Young people - how will their career trajectory change? How will they learn to be valuable in the talent marketplace?

By the time the kids that are entering college now are getting their first job, more of the global data footprint will be generated by AI than by humans.
Likely by a big margin.. More books, training courses, code, blogs, video, etc etc etc.. all of it will be majority AI generated.

Some will advise youngster to just "get smart on AI".. the problem with that thinking is that the real leverage comes from marrying that technical know-how with business acumen, domain acumen, or some form of captured tribal knowledge.

Without that second piece, you are just a poor mirror of the tech itself.

How does this play out? No clue.. but I wonder: What happens when we, as a species, are learning about the world primarily through the lens of AI?

How does that change our views, our opinions, our language, our individuality, our competitive edge?

Not to get too existential but this is also coming at a time when kids are becoming less and less social, and we are taking drugs that suppress desire..

My children are small.. so I guess I've got time to figure out how to advise them. But still, strange times.

[Graham @Graham_Locklear]

Here: https://t.co/wTwQc3y0Fa

[Graham @Graham_Locklear]

Lots of hot takes about AI and sales.. but what does the real data say?

tl;dr -
pipeline grew, sales efficiency fell.. If your spamming with AI, you're losing. You're buyers are influenced heavily by a chatbot before they talk to your reps.

This week I wrote about seller performance, the AI adopter split, SaaS performance, buyer behavior, and what it all means for H2 and beyond..

[Graham @Graham_Locklear]

So, what does it actually mean to be an AI-powered CRO/CMO?

Lots of talk about this.. but what does it look like in practice? Common pitfalls, what to avoid etc..

And most importantly, what are the new skills you need to have as a Revenue Leader to build an AI-Native GTM org?

https://t.co/H3CUral8ce

[Graham @Graham_Locklear]

Every fund should be thinking about building its Operational muscle.. IMO GTM is a massive leverage point.

[Graham @Graham_Locklear]

If you find a Sales Leader that has a track record of success in environments where there have been little to no demand for the product.. you've likely found a unicorn and you should pay whatever you need to to land him/her..

This is an angle of evaluation that, surprisingly, a lot of exec teams still skip over regularly..

Ok, so they've had success.. BUT:

was there momentum before they arrived?
what was the brand recognition like?
was there competition? how much and how good?
how early was the product?
how did perform vs their peers?

And most importantly.. how closely does that situation resemble the current state at your company?

To be clear.. I'm not advising you should only look for sales talent at the worst companies you can find.. Just that you need to factor in market forces into an individual's success.

The worst seller in the world can sell bread to a starving man.

Hiring from great brands is not a bad idea.

There's many benefits of getting someone from a winning team: they've seen what good looks like, perhaps they've absorbed good habits, training could've been excellent, they likely have a network, etc..

But when certain companies hit escape velocity, the brand gravity alone makes a lot of sales leaders look very good on paper.

And that's a variable that many CEO/Founders tend to overlook.

[Graham @Graham_Locklear]

https://t.co/02u9OEbgA7

[Graham @Graham_Locklear]

I've been in exec search for a decade+ now.. And finding a company a new CRO, CMO, VP Sales, etc is a high stakes game. Something I've recognized is that the searches that are the cleanest, most efficient, and lead to the best outcomes have one thing in common..

It starts with me in a room with:
a) someone from the sponsor (usually the Operating Partner), and 
b) someone from the management team (usually the CEO).

The OP and the CEO.. a combination that is dangerous in all the right ways.

This week I write about Hiring by Committee vs. a Singular Champion.

Committee hiring gives you corroboration but it optimizes for the safe candidate and it's slow.

The singular champion moves fast and takes real swings.. the unconventional candidate a committee would've talked itself out of before the offer stage.

But, the champion gets emotionally tied to the bet. Six or twelve months in, when the signals are mixed, that same person has a harder time being objective.

Two very different approaches.. Each with thier advantages and downsides.

The Committee is slow to decide and the Champion is slow to correct.

I break down the pros and cons of each, the nuance, and the exact mechanics of how to set yourself up to get the best of both.

Here’s the full read: (link in the comments)

[Graham @Graham_Locklear]

The ART/SCIENCE of Marketing..

[Graham @Graham_Locklear]

When your Exec team starts playing the game of thrones..

Look, A bit of healthy friction can be good. Keeps everyone accountable.. but if mis-managed, these feuds can reign terror on your org. Here's a story I heard that encapsulates just that:

Caught up with a CMO on a search we are running.. get this: 100% pipeline growth year over year.. and newly unemployed. They fired him.

Why?

The CMO and CRO never agreed on what the numbers were supposed to mean. One looked at pipeline growth and saw progress and the other looked at revenue and saw a problem.

Truth is.. this CMO might've had 500% YoY pipe growth and still got shot. They were doomed before they signed the offer letter.

The way this played out on the surface was a battle between sales and marketing.. but this was actually a failure of the CEO/board to create org-wide agreement on division of labor and owned outcomes.

The failure happened during the search. That's clear as day to me. The role got defined broadly, but the expectations stayed implicit and uncommunicated..

So the candidate gets evaluated against expectations that were never agreed on in the first place. CEO says I want revenue, CRO says I want pipeline, CFO says you have $100 budget, CEO says she wants you to get their top prospects a skybox at the world cup.

The blame game starts and then its every man/woman for themselves... its game of thrones and someone gets axed. This is much more common than people think.

Before you write the brief, you have to answer these questions..

- Where does accountability actually start/stop? Who owns what.. be specific
- What does success look like - specifically? Example: define what a MQL is.. please.
- What resources does this person/function have to achieve these goals?

There should be no world where you miss a qtr and can't point to exactly what the problem is and who ows that outcome.

The leadership team needs to answer those questions or the hire will be premature..

Sequence matters.

Fix the structure first.

Then bring someone into it.

And I'll close with this.. as an exec, its part of your job to build trust with your peers. But its equally the CEO/Founder's job to make your company a place where building trust is not terribly difficult. A good way to do that is by creating transparency and clarity.

[Graham @Graham_Locklear]

https://t.co/zHye8SpC7P

[Graham @Graham_Locklear]

"FDE is a cost center."

That kind of framing can kill these programs before they start.

We've placed FDEs at the most competitive AI infrastructure companies in the market.

I've seen these functions add immense value..

If you think of FDE like this you're leaving NRR on the table and underpricing a function that sophisticated buyers WILL pay for and you're building a team of talented technical people with no commercial identity. This type of thinking will cost you real enterprise value.

FDE done right doesn't stay a cost center. It moves through a maturity curve.. Four stages.

Each one unlocking more value:

Stage 1: Years 0-1

Yes, it's a cost center here. That's fine and expected. The only thing you're measuring is NRR lift.

Does FDE involvement correlate with better retention? If the answer is yes.. you have the business case to move to stage 2.

Stage 2: Years 1-2

Hybrid model. Baseline FDE gets bundled into contracts. Enhanced or specialized engagement starts getting billed as add-ons.

The function begins to offset its own cost. The commercial muscle starts to develop.

Stage 3: Years 2-4

Partial revenue generator. FDE is now contributing 5-15% of revenue at 40-55% gross margin.

This is where the conversation in the boardroom starts to change.

Stage 4: Year 3 and beyond

Full P&L owner, VP-level leadership and board visibility. Its own revenue targets, its own margin profile, its own seat at the table.

Ask the NRR question early, build the billing model in stage 2 and give the function commercial leadership.
FDE isn’t a cost center.

It can be of the highest-leverage functions in the entire company… when you choose to treat it like one.

I write more about this here:

[Graham @Graham_Locklear]

https://t.co/tdrYXMSWoE

[Graham @Graham_Locklear]

I got the call to replace a failed CRO hire.. Halfway through the kickoff call, I realized we were about to make the same mistake that they were trying to fix.

I halted the search mid-intake. Here’s what happened:

CEO was not happy.. I told him that we needed to examine what happened with the last hire in greater detail before we go live with a search.. I explained why, broke through the hesitation, and by the time we were done he was happy we did.

The cost of failed hire can be 10x+ the exec's annual comp once you count severance, lost productivity, and the team turnover underneath it.

On a $500K package, that's $5M gone before the seat's even backfilled.

Before talking to a single candidate, run the postmortem first. Or you might just be paying to repeat the same mistake twice.

Here's what that could look like:

Answer these six questions, score each one clear, ambiguous, or absent.

1) Scope and authority. Did this person actually own the full revenue engine.. sales, marketing, CS, RevOps? Or did they own it on paper only?

2) Timing. Were they hired to build a motion that didn't exist yet, or to run one that was already built? Did you hire the right profile for the stage you are actually at today (most common mis-hire mode)

3) Metric definitions. Did they inherit clean pipeline and forecast definitions, or walk into ambiguity?

4) Support and runway. Budget, headcount, time to show results.. adequate for the mandate, or was the org expecting a turnaround on a “scale the machine” timeline? Be honest

5) Peer trust. Did they establish it with the ELT, the CEO, the board? If not.. that's usually the real reason they're on their way out.

6) Who made the call. Was the org actually ready for a CRO, or did the title just sound right at the time?

Run through those six and you land in one of two places. Bad hire. Or mis-scoped role.

It took us less than a week to complete the postmortem. We rewrote the spec and went live with the search. And most importantly, we took into account the new information that we had from the failed hire.

I write more about this here:

[Graham @Graham_Locklear]

Lots of focus on implementing AI into Product.. don't forget about Ops.