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

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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.

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.

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