The Transition from CMO to CRO
Traditionally, the path to becoming a CRO involved climbing the ranks within a sales team. However, with the rise of data-driven marketing, there’s been a notable trend of marketing executives transitioning into the CRO role. Andrea’s a perfect example, as someone who identifies as a “left-brain marketer” that’s always been data-focused, prioritizing the impact her teams have on new revenue. While marketing and sales metrics may center around different funnel stages (ie: marketing emphasizes new trial sign-ups, while sales zeroes on conversion to net new ARR), both ultimately focus on revenue growth.
Growing in a Challenging Market Environment
In an environment where every GTM organization faces the challenge of expanding without spending more money, Helpscout stands out with over 95% of their traffic being organic. Looking ahead, Andrea envisions the key growth catalyst to be product-led sales.
Just as it’s now an industry best practice that Sales and Marketing work together with revenue as a shared metric, it’s inevitable that the same will be true of product.
AI for Revenue Teams
Help Scout is currently utilizing AI in SDR emails, a strategy aimed at reducing costs and augmenting productivity in response to downsizing their SDR organization 6 months ago. The organization is currently leveraging tools such as ZoomInfo, Make.com, and Outreach to automate the process of identifying high-intent leads and creating personalized emails. It’s allowed them to “replicate the force of 20 SDRs with just one person.”
AI in Content Creation
Andrea Kayal also addressed the potential of AI in content creation, acknowledging the challenges associated with data privacy and security. Recognizing the necessity of better tooling for data insights and reporting, she projected her optimism towards the development of advanced AI tools capable of producing high-quality content.
Help Scout, as she stated, is committed to focusing on content as a major channel, and plans to use more distribution channels in the future. Hence, the conversation reflected the importance of evolving and integrating new tools that align with a company’s content strategy.
Metrics for CROs
While revenue is a lagging indicator, leading indicators such as New Monthly Recurring Revenue (MRR), New Annual Recurring Revenue (ARR), and net expansion often offer more valuable insights.
Apart from pointing out the significance of key metrics, she also emphasized the importance of having a robust RevOps team and a sound infrastructure for data tracking and analysis.
In the early days of any company, you have to focus on building your brand and acting bigger than you are. This means investing in content, social media, PR and other channels the way a bigger company would.
We had the privilege of hosting Linh Ho, the Chief Marketing & Growth Officer at Zelros who also brings experience from companies like Condati, Optier, SAP Concur and Dynatrace.
Gong has been one of the most widely followed companies in the Go-To-Market landscape in the past few years, renowned for pioneering Revenue Intelligence as a category and for a blog that has a cult following with sales leaders.
Calendly is seen as one of the pioneers of PLG as it was bootstrapped for its first 7 years before raising $350M. In this AMA, CMO Jessica Gilmartin shares her best tips.
Sterling Snow, the former CRO at Divvy and SVP of Revenue at Bill.com, shared his insights from scaling Divvy to a remarkable $2.5B acquisition in just four years.
A playbook for 1:1 marketing in the AI era
"I take a broad view of ABM: if you're targeting a specific set of accounts and tailoring engagement based on what you know about them, you're doing it. But most teams are stuck in the old loop: Sales hands Marketing a list, Marketing runs ads, and any response is treated as intent."
"ABM has always been just good marketing. It starts with clarity on your ICP and ends with driving revenue. But the way we get from A to B has changed dramatically."
"ABM either dies or thrives on Sales-Marketing alignment; there's no in-between. When Marketing runs plays on specific accounts or contacts and Sales isn't doing complementary outreach, the whole thing falls short."
"In our research at 6sense, few marketers view ABM as critical to hitting revenue goals this year. But that's not because ABM doesn't work; it's because most teams haven't implemented it well."
"To me, ABM isn't a campaign; it's a go-to-market operating model. It starts with cross-functional planning: mapping revenue targets, territories, and board priorities."
"With AI, we can personalize not just by account, but by segment, by buying group, and even by individual. That level of precision just wasn't possible a few years ago."
This comprehensive guide provides a blueprint for modern ABM execution:
8 interdependent stages that form a data-driven ABM engine: account selection, research, channel selection, content generation, orchestration, and optimization
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Modern metrics that matter now: engagement velocity, signal relevance, and sales activation rates
Real-world case studies from Snowflake, Unanet, LiveRamp, and more
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