As economic caution becomes the default customer mindset and sales cycles stretch, revenue leaders need battle-tested strategies for maintaining team momentum. Few executives have navigated these waters as successfully as Ashley Hansen Grech, Chief Revenue Officer at Xero. With experience leading through the 2008 financial crisis, COVID-19, and today's volatile market conditions, Ashley offers practical guidance on what truly works when buyer urgency fades and forecasts become challenging.
What makes our current moment uniquely challenging, as Ashley noted, is that "there's no really unified enemy" facing revenue leaders. Unlike previous downturns with clear catalysts, today's landscape presents a complex mix of simultaneous challenges:
"It is an uncertain time in that there's not any one sort of unified challenge," Ashley explained. "Each and every one of our businesses will be different," requiring tailored approaches rather than one-size-fits-all solutions.
One of Ashley's most powerful insights came early in the conversation: despite changing market conditions, the core job of the revenue leader remains remarkably consistent:
"I wondered every time there's been uncertainty or a crisis, like, does my role change?" Ashley reflected. "And you're like, no... it really sharpened like are those the right jobs to be done."
Ashley's experience spans multiple leadership roles across diverse companies - from traditional financial services at JP Morgan to rapid growth at Square (where her team grew revenue from $100M to $1B in four years during COVID) to her current global role at Xero, a $3B cloud accounting platform competing with Intuit.
Throughout her career navigating downturns at JP Morgan, Square, and now Xero, Ashley has developed a consistent framework that guided her teams through difficult times:
First and foremost, revenue leaders must safeguard the business fundamentals. This means understanding the financial parameters you're working with – runway, currency sensitivity, margin requirements – and making tough decisions when necessary.
During COVID, Ashley implemented an innovative approach at Square: keeping quotas flat but providing a 50% guarantee tied to increased activity levels. This balance protected the downside for her team while maintaining appropriate accountability. As she put it, "I had a choice – I can lay off people on this team or I can implement this."
Ashley emphasized repeatedly that leading through uncertainty requires an obsessive focus on evolving customer needs. At Square, this meant quickly pivoting to highlight online ordering capabilities when in-person retail shut down during the pandemic. At Xero, it means shifting from "counting the beans" to messaging around "take control" and cash flow management.
The most consistent theme throughout Ashley's insights was the critical importance of communication – with your team, with peers, and with customers.
For teams feeling the strain of uncertainty, Ashley recommended:
When communicating with peers and the C-suite, she emphasized the need to lead with customer insights first, then connect to production impacts, and finally outline strategic actions being taken.
Perhaps most inspiring was Ashley's perspective on how challenging times have accelerated her professional growth: "I tell my team every single time there is deep uncertainty that this is also for them... It'll make them a great executive one day."
She credits navigating through economic turmoil with helping her develop:
As market volatility continues, revenue leaders who apply these principles – protect the company, support their teams, and evolve with customer needs – can transform uncertainty from an obstacle into an opportunity for both organizational and personal growth.
To quote Ashley's reminder to all revenue leaders navigating these waters: "I guarantee it."
This article draws from insights shared during Pavilion's "Leading Through Uncertainty" series, held every Friday at 11:00 AM ET. Previous guest speakers include Ian Koniak (ex-Salesforce), Kiva Kolstein (AlphaSense), and Ashley Grech (ex-Square).
This event is exclusive to Pavilion members. To attend, please register through the Member Hub.