Listen Here

|
Subscribe

Actionable
Takeaways

Hire to fill your gaps before you feel ready.

Andrea had no sales background when she stepped into the CRO role. Her solution: immediately hire a strong sales leader, which gave her the confidence and coverage to operate. The implication for founders: when evaluating a CRO, don't disqualify candidates for functional gaps — evaluate whether they know their gaps and can hire around them fast. "I just ended up hiring a great sales leader and that kind of gave me the confidence to say, okay, maybe I can... I feel more well rounded as a CRO knowing that he kind of solved for the gap I had there on the sales side."

AEO is the new SEO — and the playbook is mostly the same.

Help Scout uses Peak AI to monitor how they appear in LLM-generated answers. Their finding: brand sentiment and authoritative content are the biggest drivers. The content that's always worked — definitive guides, evaluation frameworks, top-five listicles — is still what LLMs pull from. The tactical shift is writing content structured as the answer, not a link to the answer. "You want to be known as the company that the LLM answers the question for... we show up as number two now, next to Zendesk."

Warm inbound is a different motion than cold outbound — treat it that way.

Help Scout uses Unify and Clay to identify site visitors who didn't convert, then re-engages them via email. Last quarter that motion produced nearly 20 opportunities and roughly $30K in revenue from automation alone. The distinction Andrea draws matters: "It's not cold outbound. It's warm inbound. Like, you knew them." Cold emailing single-page visitors is still generating some response for them in the customer support category — but she acknowledges the copy has to work hard to not feel creepy.

Design your agent org chart before you build agents.

Andrea's mandate to her director of marketing: map out a full 40-person marketing org, then decide which roles get filled by humans and which by agents. The agents become line items on the P&L — not tools, not experiments. "Plot out your digital personnel and plot out your human personnel." She's clear-eyed that agents won't replicate 40 great marketers, but the framework forces prioritization rather than ad hoc automation.

Events without a demand capture mechanism are brand spend — price them accordingly.

Help Scout ran 12 Leadership Table dinners across the U.S. in 2025, roughly $6K each, 30 attendees per event, strong NPS-style feedback. The revenue conversion never materialized. Andrea paused the program in 2026. Her diagnosis isn't that events don't work — it's that she was measuring demand gen ROI against what was functionally brand spend. "Maybe I just should have considered it brand building and left it at that." If you're running a similar motion, decide before you commit which metric you're optimizing for.

The CRO's actual job is capital allocation, not revenue.

When Andrea evaluates her own performance — and coaches founders on how to hire a CRO — she keeps returning to sales and marketing efficiency as the North Star. The question isn't what revenue did you generate, it's what revenue did you generate per dollar deployed. "Sales and marketing efficiency should be a North star for a revenue leader because they are capital allocators." She also pushes founders to ask CRO candidates how they've managed cash burn, EBITDA, and gross margin — not just top-line growth.

Conversation
Highlights

 

Help Scout: What Happens When a CMO Takes the CRO Job and Cuts the Team by 60%

Andrea Kayal sat across from a revenue organization of 33 people when she stepped into the CRO role at Help Scout two years ago. Today she runs it with 13. The math looks brutal on paper. The reality is more deliberate — and more instructive for any founder trying to figure out how to scale GTM without scaling headcount in lockstep.

Her path to the role was unconventional. Most CROs come up through sales. Andrea came up through marketing, moving into B2B tech after early agency work, then joining Help Scout’s board before stepping in as CRO. She didn’t have a sales background to lean on. She knew it. Her first move was to hire around that gap immediately. “I just ended up hiring a great sales leader and that kind of gave me the confidence to say, okay, maybe I can… I feel more well rounded as a CRO knowing that he kind of solved for the gap I had there on the sales side.”

That decision contains a transferable principle: knowing your functional gaps and closing them on day one is more valuable than months of compensating for them quietly.

In a recent episode of The Sales Front Lines, Andrea shared the GTM decisions — and one expensive failure — that have defined her approach at Help Scout.

The Capital Allocation Reframe

The most important shift Andrea made when taking the CRO role wasn’t tactical. It was how she defined the job itself. “Sales and marketing efficiency should be a North star for a revenue leader because they are capital allocators.”

That framing changes everything downstream. Every headcount decision, every channel investment, and every program gets evaluated against the same question: what did we get back per dollar deployed? It also means the CRO’s remit is broader than most founders expect when they’re hiring for the role. “Revenue is broader than that. It includes pricing and packaging, it includes international expansion, it include M and A.”

Marketers who want to make the jump to CRO tend to underestimate this scope. The marketing remit is brand, demand, and performance spend. The revenue remit is the entire growth toolkit — and the discipline to allocate across it without defaulting to what you know best.

The Event Strategy That Looked Like It Was Working

In 2025, Help Scout ran 12 Leadership Table dinners across the U.S., covering every top market where their customers were concentrated. Andrea attended all 12. Each event cost roughly $6,000, drew about 30 attendees, and generated real brand warmth. The LinkedIn outreach supporting each dinner reached a large volume of people per market. By most qualitative measures, it was working.

The revenue attribution never showed up.

“The conversion to revenue never really… it didn’t really match in my mind. So that’s on pause for this year.” She paused the entire program for 2026. Her post-mortem is worth sitting with: “Maybe I just should have considered it brand building and left it at that because it didn’t match the experiences I was having with everybody.”

The failure wasn’t execution. The events were well-run, cost-efficient, and well-attended. The failure was measurement framing. She was evaluating a brand-building program against a demand generation standard, and it couldn’t clear that bar. The lesson for founders running event strategies: decide which metric you’re optimizing for before you write the first check. Brand spend and demand gen spend are different investments that require different success criteria.

Warm Inbound Is Not Outbound

Help Scout uses Unify and Clay to identify visitors who hit their site but didn’t convert, then re-engages them through automated email sequences. Last quarter, that motion generated close to 20 opportunities and roughly $30,000 in revenue. In 2026, they’re pushing harder on it.

Andrea is precise about how to categorize this tactic — and the distinction matters for how you write the copy and set expectations internally. “It’s not cold outbound. It’s warm inbound. Like, you knew them.” Treating re-engagement as cold outbound leads to cold outbound copy, which kills response rates. Treating it as warm inbound — because you have a real signal of intent — changes the entire approach.

She also runs outreach to single-page visitors: people who may have searched for customer support software and landed briefly on the site. She’s candid that it’s “probably still creepy,” but they’re getting responses. The copy frames the outreach around the category, not the product: “Hey, were you checking out customer support?”

The Agent Org Chart

The most structurally significant decision Andrea is making in 2026 is how she’s thinking about headcount itself. She gave her director of marketing one mandate: design the 40-person marketing org you’d want to run, then determine which roles are human and which are agents. “Plot out your digital personnel and plot out your human personnel.”

Agents now carry a line item on Help Scout’s P&L. She’s clear-eyed that this won’t replicate what 40 great marketers would produce, but the framework forces the right prioritization question. Instead of asking “which AI tools should we try,” you ask “which functions do we need covered, and what’s the most efficient way to staff them?” That’s a capital allocation question — which is exactly the question she’s defined as the CRO’s core job.

She’s also formalizing AI fluency as a dimension of how she evaluates her GTM team. “We want to measure it on impact, not effort.” The focus isn’t how much time someone spends experimenting. It’s what that experimentation produces.

What the Content Ratio Signals

Five of Help Scout’s ten marketers sit on the content team. That ratio has held through every round of cuts. It reflects a bet that’s been central to Help Scout’s GTM since the beginning: being the authority on what to look for in your category — not just promoting your product — is a compounding growth lever.

In the LLM era, that bet is being tested differently. Help Scout tracks their LLM visibility using Peak AI, and what they’ve found is that brand sentiment and authoritative content are the primary drivers of showing up when someone asks an AI assistant to recommend customer support software. The tactical adjustment is modest: “You want to write those things as the answer.” The underlying strategy is the same one they’ve always run. “We just stay tried and true to who we’ve always been.”

For founders who’ve never invested in content authority, AEO represents a new problem. For those who have, it turns out the asset they already built is exactly what the new search paradigm rewards.