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We have a fixed budget, a head count plan that’s already tight, and a product team with their own priorities. Every dollar and every hour of sales capacity we deploy is a bet. Put it in the wrong place and we don’t just waste money, we miss the quarter.

Andrea Kayal, CRO at Help Scout, thinks about this constantly. On the CRO Stories segment of the GTM Science Podcast, she put it bluntly:

“They’re giving people like me the money and they’re saying you have to allocate this capital like a hedge fund manager,” Andrea says. “You got to put it in the bets that are going to make the company more money, more enterprise value.”

Andrea shared several specific ways she does that.

In this newsletter, we’ll go over three: a budget method that’s never been rejected by a CEO or CFO; a win/loss feature negotiation system that moved Help Scout’s win rate from 25% to 29%; and a segmentation call that freed up sales capacity and lifted ACV.

Listen to the full podcast episode on Spotify here or Apple Podcasts here.

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The Budget Method That’s Never Been Rejected

Andrea mentors a lot of CMOs, and the most common complaint she hears is that their CEO or CFO won’t invest in marketing. Her take? That’s usually a problem with the plan, not the people.

“I don’t think it’s that CEOs and CFOs don’t want to invest in marketing,” she says. “They want to do nothing more than invest in marketing. But you have to be an expert at telling the story using the data and the dollars to show why this plan is going to create more enterprise value.”

Andrea has a three-tab spreadsheet she’s carried from company to company throughout her career, from her CMO days through her CRO roles. It’s never failed her.

Tab one determines marketing’s contribution to revenue. We figure out how much of total revenue comes from marketing versus sales-sourced, BD, M&A, or other channels. That gives us marketing’s number.

Tab two generates the budget. This is where she says most people get it wrong. The marketing budget isn’t marketing’s wish list. It’s derived from business facts: ACV, win rate, opportunity cost. She calls it “the business’s marketing budget,” not “the marketing team’s budget,” because the distinction matters.

“The two most important things that sometimes are not clear: the marketing budget is primarily determined by how much it costs to generate that opportunity,” Andrea explains. “And the second is win rate, because that’s the point at which marketing has handed over the deal to sales. If win rate is low, marketing budget goes up. The higher the win rate, the lower the marketing budget.”

Tab three is tactics. This is where Andrea allocates the budget across channels: events, paid search, LinkedIn, podcasts, affiliates, PR, brand campaigns. She splits it roughly 80/20, with 80% going to performance and demand capture, and 20% going to brand.

The 20% comes with a rule. “When you allocate the 20%, be like, I don’t want to talk about this. Don’t ever ask me about the 20% again. I don’t know what it’s going to do, but just trust me.”

She then closes the loop every month.

• Here’s what performed
• Here’s what we’re cutting
• Here’s where we’re doubling down

That transparency, she says, is what builds trust over time.

“I have yet to have a CFO or CEO who’s like, ‘I don’t want to spend’. Because the dollar reasoning is clear.”

This framework works because it removes opinion from the conversation. When the budget is tied to business metrics that everyone agrees on, the negotiation stops being about whether marketing deserves money and starts being about how to deploy it.

That shift from advocacy to alignment is something we see consistently in the most effective revenue organizations. It starts with getting everyone working from the same data.

Win/Loss Data as a Product Negotiation Tool

At Help Scout, Andrea runs a monthly go-to-market alignment meeting with the product team. Every month, she brings a report showing how much revenue Help Scout lost because of missing features.

Not feature requests. Dollar amounts.

“Every single month I bring the report that talks about how much revenue we did not make because we didn’t have those things,” she says. “So it just makes the prioritization efforts a little bit easier.”

Every lost deal gets logged in Salesforce with a reason. Andrea’s team tracks which missing features come up repeatedly and attaches revenue to each one. When she sits down with the CPO, she’s not saying “I think we need this feature.” She’s saying “we lost $X because we didn’t have it.”

That process led to three specific features being prioritized and built: group by company, round robin, and SLA. All three were blockers for larger customers. Once they shipped, Andrea’s team packaged them into Help Scout’s pricing tiers and the sales team started selling against them immediately.

Win rate moved from 25% to 29%.

“Every point in win rate is material,” Andrea says. “It’s actually like a 25% increase.”

She applies the same 80/20 thinking here that she does with marketing budget. Product should spend roughly 80% of its resources on what the market is asking for, and 20% on innovation. She credits Help Scout’s CPO for maintaining that balance: he has a product vision, but he’s realistic about what the commercial team needs to win.

“It takes a very mature person to understand that concept,” Andrea says. “But I’m happy I have him as a partner.”

The takeaway is that win/loss tracking isn’t just a sales exercise. When it’s rigorous and attached to real revenue, it becomes one of the most powerful tools a CRO has for influencing product roadmap priorities.

The key is making it systematic: every deal, every reason, every dollar, tracked consistently so you can show patterns over time rather than relying on anecdotes.

Reallocating Sales Capacity for Highest Impact

When Andrea joined Help Scout, sales was touching every single opportunity, including companies with just 1-10 employees. Help Scout is a PLG company. Those small accounts were signing up and converting on their own. Sales involvement wasn’t adding value. It was consuming capacity.

“I’m like, why are we doing that?” Andrea says. “I don’t think that this group needs more support from sales, and it’s not a good use of time.”

So she drew a hard line. Sales was no longer allowed to touch the 1-10 segment. Those accounts would be handled entirely through the product-led motion. Sales would focus exclusively upmarket, on deals where their involvement actually influenced the outcome.

“Our ACVs are staying low because you’re all involved in this,” Andrea explains. “If we need sales, we should really be focused more upmarket.”

The result: ACV for sales-assisted deals has been climbing because reps are spending their time on larger, more meaningful opportunities instead of spreading thin across accounts that didn’t need them.

This is a resource allocation decision that a lot of PLG companies struggle with. Where do you draw the line between self-serve and sales-assisted? The answer should be driven by the data: which segments convert without sales involvement, and where does sales actually move the needle? When that line isn’t clearly defined and enforced in your CRM and routing rules, you end up with expensive sales resources working deals that would have closed anyway.

Where it All Hits Home

Three different resource allocation problems. Three different tactics. But they all required the same thing to execute: operational infrastructure.

Andrea’s budget framework only works if you have clean pipeline data and accurate win rates in your CRM. Her win/loss reports only work if every lost deal gets logged with a reason and a dollar amount, consistently, every month. Her sales segmentation only works if you have clear routing rules that enforce who gets touched by sales and who doesn’t.

The tactics are the exciting part. The operations underneath them are what make them possible.

That’s what we help revenue leaders build at Union Square Consulting.

Whether it’s:

• Building the pipeline reporting that makes budget conversations fact-based
• Implementing the win/loss tracking that gives you leverage with product
• Building the cross-functional visibility between sales, marketing, and product

We help revenue teams put the operational foundation in place so they can execute on the strategy they already know they need.

If you’re a revenue leader in a sales-led B2B recurring revenue company and any of this hit close to home, let’s talk through it.

GTM projects stalled out?
Not after 1 hour with us.

Book a free GTM Ops Execution Workshop.

Bring your top priority and walk away with a validated approach, a phase-by-phase roadmap, and an execution timeline. All internally actionable.

Learn More