The Revenue Leader’s Playbook: Orchestrating Teams, Winning Talent, and Building a Culture That Actually Works
Insights from Greg Leos, General Manager and Head of Payments at Weave
The role of the revenue leader has changed dramatically — and if you’re still running things the way you were a decade ago, there’s a good chance you’re leaving results on the table. Greg Leos, General Manager and Head of Payments at Weave (a publicly traded SaaS platform serving healthcare SMBs), joined us on the Rev-n-u Unplugged podcast to share his thinking on three topics that are very much front of mind for revenue leaders in 2026: the evolution of the CRO role, winning the talent war, and building a culture that genuinely multiplies revenue. Here’s what we took from the conversation.
The CRO Is No Longer Just a Head of Sales
Ask most people what a Chief Revenue Officer does and they’ll say: manage the pipeline, drive deals, lead the sales team. That was broadly accurate — ten years ago. Today, according to Greg, the job is something else entirely.
“Most revenue problems are not sales problems,” he told us. “They are orchestration problems.”
The modern CRO needs to function as an orchestra conductor, not a solo performer. Marketing owns demand generation and lead quality. Engineering influences velocity. Product drives value realisation. If a revenue leader isn’t actively engaging those functions and aligning them around commercial outcomes, they’ll struggle — regardless of how strong their sales team is.
This raises an uncomfortable but important question: are many people carrying the CRO title actually just heads of sales? Greg thinks so. If you don’t have genuine responsibility over marketing and customer success — at minimum strong influence over both — then you’re a head of sales. And there’s absolutely nothing wrong with that, provided everyone is clear on what the role actually is. Misalignment between a CRO, a CEO, and a board on what the role can deliver is where things go wrong.
Bring Finance and Legal Into the Room
Here’s the part that tends to raise eyebrows. Greg is emphatic that finance and legal need to be brought into the revenue conversation — not just consulted at contract stage, but actively included as stakeholders in the commercial strategy.
The pushback is predictable: CFOs don’t want to be salespeople, and legal teams have reputations for being deal-blockers. Greg acknowledges all of that. But his point is that in 2026, the complexity of deals — particularly enterprise deals involving price concessions, contract terms, and risk management — means you simply cannot afford to have finance and legal operating at arm’s length from the revenue function.
“The CRO’s best sale is not external — it’s internal,” he said.
The key to making this work is trust. Finance and legal have often been burned by revenue leaders who cut corners or overpromise. The moment you show up as a genuine professional who listens, understands their priorities (reducing risk, maintaining profitability), and helps them understand why the business succeeding commercially matters to everyone — that’s when they stop being blockers and start becoming allies.
Winning the Talent War Starts Long Before You Have a Vacancy
The hiring landscape in 2026 is tighter than it was in the free-spending days of 2022–23. Head counts are leaner, which means every hire matters more. Getting it right is no longer just preferable — it’s essential.
Greg’s view is that the way most organisations approach recruitment is fundamentally broken, and the problems begin earlier than most leaders realise.
Employee Engagement Starts at Interview One
Most businesses think engagement begins at onboarding. Greg argues it starts the moment a candidate enters your process. A slow, disorganised, or disrespectful interview experience sends a message — and if you do manage to hire that person, they’ll often show up with a slightly sour taste already in their mouth.
His advice: run hiring like a revenue process. Clear stages, fast feedback loops, defined decision owners, timely follow-up. You wouldn’t ghost a prospect mid-pipeline. Don’t ghost a candidate.
The Hiring Manager Needs to Be First, Not Last
One of the most common mistakes Greg sees is the hiring manager sitting out the early stages of the interview process, leaving it entirely to HR or a recruiter. He’s clear: this is a mistake.
Recruiting functions do essential work — screening applicants, running initial interviews, filtering for basic fit. But the hiring manager needs to be in the conversation early, not just at the final stage. Why? Because you’re the only person who truly understands the culture, the performance standards, and the nuance of what success looks like in that role. You’re also the one who needs to spot cultural red flags before they become expensive problems.
Practically speaking, this might mean interviewing outside of normal hours. Top performers who are curious about a role will usually accommodate a 6pm call. It’s a minor inconvenience that pays significant dividends.
Interview for Character, Not Just Competence
When it comes to what to look for, Greg is unequivocal: grit is the number one trait he hires for. Not pedigree, not which competitor someone came from, not where they went to university.
“The biggest predictor of success is the ability to take passion and match it with tenacity and resilience.”
The challenge is that you can’t ask someone if they have grit and expect a useful answer. Everyone in a sales interview will tell you they’re resilient. Instead, ask open-ended questions that require them to evidence it. “Give me an example of a time you failed miserably. What did you learn and what did you do differently?” The way someone answers that question — or struggles to — tells you far more than their CV ever will.
He also coaches the people on his team who participate in interviews, giving them specific guidance on what they’re looking for at each stage. If every interviewer is just running through the same résumé review, you’re wasting everyone’s time.
Keep Networking — Even When You’re Not Hiring
Sales leaders should always be building their talent pipeline, not just activating it when a vacancy opens. Greg posts regularly on LinkedIn, cultivates relationships with strong performers in his network, and maintains ongoing conversations with people he’d consider hiring — even when there’s no immediate role available.
The payoff? Shorter hiring cycles, better candidates, and less reliance on reactive, pressure-driven decisions that often result in the wrong hire.
Culture Is Not a Poster on the Wall
The word “culture” has been well and truly hijacked. It’s been turned into slogans at sales kickoffs, reduced to free lunches and foosball tables, and used to describe almost anything a company wants to feel good about. Greg is refreshingly direct about this.
“A team will never outperform its culture. I’ve never seen it.”
Real culture isn’t a perk or a tagline. It’s a set of standards and beliefs that are genuinely lived by the team — and, crucially, by leadership first. It’s what happens when no one senior is watching.
What Real Culture Looks Like
On Greg’s team at Weave, the culture is built around high performance and genuine accountability. Everyone who joins knows the standards: strong work ethic, passion for the business, and a will to win. But alongside that, there’s real collaboration and mutual respect. People support each other. Leadership is invested in individual growth and progression.
Importantly, he resists the temptation to call the team a “family.” You don’t fire family members when they underperform. The relationship is something different — one of mutual investment, high standards, and genuine care for each other’s success.
Accountability Has to Start at the Top
Accountability is one of those cultural values that gets cited constantly but lived rarely. Greg’s view is that if you want your team to be accountable, you need to model it yourself — visibly and consistently.
That means standing up in front of your team and owning your own mistakes. It means being self-aware enough to recognise when you’re too close to something, and taking someone else’s perspective on board. It means not moving meetings you’ve booked with your team when something shinier comes along.
And if you’re mandating five days a week in the office but showing up yourself twice a week, you’ve already lost the argument — and arguably the culture.
Know Your People’s Why
One of the most practical things a sales leader can do to build a strong culture is understand what motivates each person on the team — and then actively help them achieve it. This isn’t just about commission structures. It’s about knowing whether someone is driven by career progression, financial goals, the desire to prove themselves, or something else entirely.
This starts in the interview process. Greg asks candidates directly: what does the ideal team and company look like for you? What are you hoping to achieve in one, three, five years? A candidate who can’t articulate their why is a candidate who’s likely to lose motivation when things get hard.
When you understand someone’s motivation, you can manage them in a way that genuinely lands. And when the culture is built around that kind of investment in people, it creates something that no amount of free pizza can replicate.
The Takeaway
The revenue leader’s job in 2026 is more complex, more cross-functional, and more human than it’s ever been. The CROs and heads of sales who are thriving are those who’ve accepted that their role is fundamentally about orchestration — bringing together the right people, creating the right conditions, and building teams that can sustainably outperform.
That means getting serious about how you hire (and how often you’re thinking about talent even when you’re not actively hiring). It means building genuine trust with finance, legal, and other functions who will either accelerate or stall your commercial outcomes. And it means being honest about what culture actually is — because a culture that exists only on a slide deck won’t survive contact with reality.
This article is an AI-assisted adaptation of content originally published on the Rev-n-u Unplugged podcast. Watch the full episode here – https://www.youtube.com/watch?v=dhN7BGPZ4G4
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