Andrea Kayal AMA: Aligning Revenue Teams at Helpscout

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,, 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.


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