Data-Driven Growth: Revolutionizing Sales Performance with Brad Cross, CRO at Upflow

This week on the Revenue Insights Podcast, Guy Rubin, CEO of Ebsta, speaks with Brad Cross, Chief Revenue Officer at Upflow. In this episode, Guy and Brad explore the evolution from product-led to value-led sales, the importance of effective qualification, and strategies for improving sales team performance through data-driven insights. Brad Cross is the Chief Revenue Officer at Upflow, where he leads sales, customer success, marketing, and operations. With over 20 years of experience in sales leadership, Brad has successfully transitioned from MarTech to FinTech, bringing his expertise in customer engagement and relationship management to the financial sector.

Brad Cross is the Chief Revenue Officer at Upflow, recently promoted from VP of Global Sales. With over 20 years of experience in sales leadership, Brad has transitioned from MarTech to FinTech, bringing his expertise in customer engagement and relationship management to the financial sector. Before Upflow, Brad held leadership positions at various technology companies, focusing on helping organizations grow through scalable and effective GTM programs.

Brad Cross on LinkedIn
Upflow website
Guy Rubin on LinkedIn
Ebsta Revenue Insights Newsletter

Time Stamps:

00:00 - Introduction
01:00 - Brad's career journey and transition to FinTech
05:00 - Evolution of Upflow's sales approach
12:00 - Sales process transformation
15:00 - ICP definition and market focus
20:00 - Lead quality vs. quantity
24:00 - Sales tech stack discussion
31:00 - Sales methodology and qualification
33:00 - Future growth plans

Highlights:

Transforming from Product-Led to Value-Led Sales Brad shares how Upflow evolved from a demo-centric approach to a more solution-focused sales strategy. When he joined, the company had a strong product but relied heavily on demos to drive sales. They've since developed a more comprehensive approach, including a free AR diagnostics tool and a value-based sales process that increased close rates from 12% to nearly 50% on direct outreach.

The Power of Financial Relationship Management Brad emphasizes the shift in how CFOs think about cash flow management. Traditionally, the focus was primarily on accounts payable, but Upflow has helped demonstrate that strategic accounts receivable management can dramatically improve cash collection speeds. This has transformed AR from a purely functional consideration to a strategic priority for finance leaders.

Finding the Right Market Fit The discussion reveals how Upflow has identified its ideal customer profile in the mid-market range, particularly focusing on companies with $50-500 million in revenue. This sweet spot represents organizations large enough to invest in dedicated AR resources but not so large that they can solve the problem purely through internal resources.

Subscribe to the Revenue Insights Podcast:

Recommended Episodes: